Finding Our Way

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Booking.com’s VP of Product and former VP of Design Che Douglas joins us to talk about the cultural and functional relationship between product and design, what it’s like to lead both as an integrated team, and the necessity of driving alignment in order to drive change as a leader. Peter: Well, hi, Che. Thank you for joining us today. Jesse and I have been talking to a bunch of design leaders over the last well, five or six months, and so we’re excited to have you join us. In particular, we’re excited to have you join because, at least looking at your LinkedIn profile, you’re not simply a design leader. And so I’d love to learn just, like, what your role is, what you do, and how did you end up there? From VP Design to VP Product Che: Great question. So right now I’m working with Booking.com as their Vice President of Product. I joined Booking in end of late 2019 just before the pandemic started. Good time to join a travel company, during a pandemic. Um, I joined as their first Vice President of Design. They’d had kind of director-level designers previously, but no one at the executive level overseeing the community. And with about 300 designers across the organization at the time, they were very interested in bringing someone in that could kind of make sense of all of that and define a strategy globally for the company and set a vision and help point everyone in the right direction. So I came in as a VP of Design. My role transitioned through the pandemic into also running product development. Whole host of reasons for that. I had previously led part of products with The Wall Street Journal towards the end of my role there in New York. So I had experience, and then previous to the Wall Street Journal, I ran a business in Australia doing brand and digital work for about 10 years. So I think my experience of building products, you know, physical and digital environments, branding, all of those things combined, and running the company that I’d started, I think gave me a fairly good grounding to move into what we call product development or software development these days. So, you know, the people that I employed in my business before I joined The Wall Street Journal came from all sorts of disciplines. And, and that’s kind of how you needed to make up a company to do any kind of digital product development or branding work. So, that experience kept following me through my career when I moved to New York, work for The Wall Street Journal and also into the role with Booking as a first Vice President of Design. And, and that evolved quite quickly into, like I said, running product and, and parts of it anyway. The time I joined there was a Chief Product Officer. He was my boss. And he was running basically the program to start building what we call the connected trip, which has been there since even before I joined. So we were still three years into that mission, recently bringing in all of the other things that Booking Holdings has. So supply of flights, everything outside of hotels, so you know, ground transportation, insurance, attractions, you name it, and, and building them into our existing app and website. And I was leading the design side. Through the pandemic our CPO left. I also ended up picking up a lot of the pieces of the product organization as a result of that. We’re a two-sided marketplace, so there’s another VP of Product. The partner and supply side, which is more commercial. I would, I would say, to try and keep it simple for our audience. And I look at all of the traveler side, so all of the traveler touchpoints, customer-facing in that sense. Particularly our web and our app platform, which is where all of our bookings come through and all of our travelers come and book on our platform. So now I look after that, you know, it’s a big team. It’s around 500-plus, 550 people, 50-plus product teams that look after that on the experience and platform side from software engineers, data scientists, researchers, UX writers, designers product managers, and everything in between. So that’s where I am today and that’s what I look after. And yeah, hopefully that helps give a bit of context. Peter: Yeah. Correct me if I’m wrong, my assumption is that as VP of Design, you were responsible for overseeing all designers on both sides of the marketplace. But it sounds like as you’ve become a product leader, you’re responsible for only one side of the marketplace. So are you still responsible for the designers, all the designers, or did that change? Che: Great question. So that’s still the case. So we, through the, also through the kind of pandemic and some of the changes that we needed to make, and looking at how we wanted to set the business up for the future, there was a big push for the, what we call crafts disciplines, whatever you want to call ’em, so a designer, a researcher, a writer, to report to someone of their craft rather than up into technology or up into product. So I worked with our VP of Engineering to basically orchestrate that with our works councils and all the different labor laws in the Netherlands and everything else, and put together a big plan, that took, you know, the best part of a year to roll out, functional reporting for all of our crafts. So all of design, research, writers across the entire organization, except for a couple of small pockets in marketing, still report up into a UX leader, a senior director that reports to me. So that’s kind of the structure of everything. Engineering reports into our VP of Engineering and, and vice versa. So we have, you know, a data leader similarly for the data and analyst crafts as well. So very much now in functional reporting mode. There’s still some pain points, growing pains and things like that as we mature and we’ve rolled it out, ’cause we’ve always been quite siloed in the way that we’ve done work in terms of product teams and everyone being embedded, now with the craft management structure. That’s kind of a view of both ways of looking at it, right? So, there’s a few things that we need to kind of iron out over time, but the response has been great and the feedback’s been great to date, from, particularly the smaller crafts in design, writing, and research, so being managed by someone of their own craft. We also opened a bunch of director and senior manager roles and more principal level roles at the same time as we scaled that all, ’cause there wasn’t enough in the senior kind of management levels to kind of make that structure work. So we actually had to open and fill those roles before we could actually roll out functional craft reporting too, because they were typically kind of getting stuck at the director level when rolling into either directors of tech or product at that point. Jesse: I think there’s an interesting intersection between culture and craft, in that you can have groups within an organization, practitioners of the same craft that will develop their own culture around that craft, around the implicit values of that craft. I wonder what the implications of that are for your entire organization as you have these distinct crafts within it, with their own distinct cultures, that you are also trying to integrate with a product organization as well. Che: Yeah, there’s so many ways you can slice this. The one that comes to mind, maybe it’s a little bit off track, but it’s kind of the information knowledge transfer in an enterprise company is, is quite challenging. We have over a hundred product teams across the entire landscape. Designers and writers and all of those research and stuff are still embedded. So those crafts now report up into their craft managers. I think it’s, you know, there’s overlaying strategies. There might be a design strategy, a writing strategy, a product strategy for, even for a particular area. Some of them need to more global. So connecting the dots, as a lot of people probably like to say it, from a UX point of view is actually incredibly important. But how you do that through the lens of each of the crafts and execute on it with, in our case, a product-led organization that is moving from being transactional to very much traveler, partner-centric in the way that we think, all the way up. So we are also going through a cultural shift that I think gives more of a voice to that UX community that hasn’t felt like they’ve had much of a seat at the table because it’s been very data, transactional, product-led to date. So I think we’re moving to more of a, much more kind of cross-functional. The voices are there, the, the right leaders are kind of in place to be able to bring that information and knowledge transfer and collaboration together to build great products. I mean, I think, I hate the idea of any of them doing anything in isolation. I, it is always feel like the best things that you make, particularly in big companies, are when you get the right people together and give ’em the space to go and do it. Whatever their skillsets might be that are needed for that particular thing. So yeah, the craft bit kind of, it’s, it’s unlocking it, right? It’s finding the best way to not feel like they’re stifled or cornered or aren’t able to bring all of their knowledge and skills and the information, like I said, to the right places and make the right decisions. From Transaction to Experiential Peter: So I’m familiar with Booking.com because I was supporting OpenTable when Booking or Priceline Holdings acquired them. And I remember hearing about Booking having these very of atomized product teams. It was very A/B oriented and very transactional, very kind of inspired by Amazon or Spotify. It sounds like there’s an evolution though now happening. I don’t know if it’s away from that transactional model, but let’s say towards something that’s rooted in customer types and their experience. What was the impetus for that? Is, is that something that was happening before you joined and you were brought on to help make that happen? Was that something that you recognized and were able to help others realize the opportunities? What was the, yeah, the instigation for, for that shift? Che: I was certainly kind of one of the voices. It felt like one of the few when I joined— a, a smaller group. But I think that has kind of grown over time. It’s certainly from repeating the same messages. I also, you know, I’m senior enough in the organization to get the attention of the right people and have trust with the right leaders to be able to build that. The statement of transactional to traveler-centric or, and partner centric is not necessarily… it’s not black and white either, because everything we’ll do, we’ll still have data that we look at behind it. But I think it’s that we want to actually put some kind of standards and quality around some of the things that we’ve done in the past and be able to do mid- and longer term thinking. Everything has been much more short-term driven. So when we look at you know, what people will talk about lifetime value, metrics, equity, how you measure that of a customer, all those things over a much longer period of time so that the things that we are doing and shipping to travelers , more in the mid and long term thinking, not just the short term. So it’s basically expanding the way our toolkit and the way that we build product. That’s the best way that I could probably articulate it. And then how we instrument things and measure them is not purely based on how many bookings per day we get, but a whole range of other metrics, like that lifetime value, but also based on priority actions and behaviors of customers through different journeys of our products rather than based on like small parts of a screen or a screen itself. So that’s, you know, that’s a huge collaboration, a huge shift in the way that I would say we work. We’re still on that journey, but it’s gonna be, it’s a long way, too. We’ve also articulated a product vision around how we will develop what we’ve talked about for three-plus years, the connected trip, and how that will then come together over a period of time, the commercial side, but particularly from the traveler side. Peter: Did you have to make a business case? Like how did you, you mentioned building trust and because of your seniority, you, you had the relationships. But in a, in a company that can be so data-driven or metrics-driven, what was the language you needed to frame this evolution in, such that others would be receptive to it? Che: Right… So very early on there’s a whole host of things that I did and other people did as well, but the things that I did that I had control over, so when we were looking at, let’s say, let’s just take something design and kind of engineering-centric, like a design system. So as we’d scaled some of our new products, like flights and things into the Booking app and website, we’d basically done that intentionally quickly to validate where the customers wanted those products within the Booking.com brand and Booking.com products. But at the same time, the teams that went and did that built them in different ways. So different technology stacks, different front-end frameworks, new design systems emerge. ‘Cause it’s just such a big company and everyone’s moving so quickly. But we didn’t have a strategy to pull those things back. So I think one of the things that I did early on was actually a presentation to Glenn, our CEO and a few senior leaders, and said basically, here are all of our supply verticals. But there’s a bunch of horizontal things like the customer experience that you want to get to this connected trip. If you look at each of these verticals, within each one of them, you can see that we’ve built a whole bunch of things in different ways. Now that was great to get us to market really quickly, but now as we scale ’em, we’re gonna have to unwind a lot of that. There’s a lot of technical debt. It’s stopping us from like, our velocity is reducing, we are having to maintain five different design systems, et cetera, et cetera. Right. So then I was able to, through the way that the company operates, through planning, you know, get into the practicality of it and the planning cycle, which has a financial component that is the kind of key driver of the cadence and timelines built. You know, I listened to the kind of motions of the business, so to speak, and then came in at the right times and said, here’s what we need to do. Basically put objectives with senior leaders across the entire company that were outside of my remit, to wind back some of the design systems and consolidate them into one. And we did that with a number of different programs. So it was kind of multi-pronged. You know, some other examples, and now as we roll out, example, kind of a much more kind of inclusive design. ‘Cause we, you know, our mission is to make it easier for everyone to experience the world, needs to be more accessible, all of our product landscape. There’s a compliance side of that with our holdings company. So we’re roll– rolling out a big accessibility program at the moment, which is around not just kind of making things compliant, but also doing the right thing and the way that we build that into the DNA of the organization going forward. It’s not a program that someone’s running, it’s actually just the way we do product development as a whole. So, those things are changes in the way that people develop. It feels like another thing on their backlog to do, but like, you’ve actually gotta build it in a way that everyone understands it, values it, and then it becomes part of the way that they work going forward. So that’s changing the way that we work as well. Jesse: I’d love to hear more about going back to that transition that you made from leading design to leading both design and product. And I wonder, although you had clearly had previous experiences that prepared you, qualified you for the role, I wonder what surprised you when you came into the role? What was the biggest shift or adjustment you had to make as you were transitioning from being a design leader to being a hybrid design and product leader? Che: I think knowing in a product, more product-led company that whatever I ended up articulating as a vision or a mission, direction, strategy, it was actually, there was a lot less fighting. It was like, oh, that’s it, okay! Let’s all go and… Jesse: do you think that is? Che: Because we’re already kind of product-led. Like that was the way that everyone worked. They followed what product did. So if you laid out a roadmap and you worked with your technology partners and things, then, whereas if you’re design, you kind of constantly felt like you were always trying to convince someone to, to get something done and build it into a plan. So that was a big shift in terms of the way I had to think about things. Almost, you have to be careful kind of what you’re doing, more deliberate and you kind of end up wielding a bit more power in that regard. So as a shift I think, yeah, it’s an interesting one. I guess I didn’t feel like I operated too much differently. I, I felt like I probably had to be less biased to my design roots as well. Because I’m a very visual person. What I mean by that is when I joined Booking everything that I received in my inbox was financial reports. And I was like, don’t we have like 200 product teams? What are we shipping to customers? What do we ship? Everyone’s like, I’ll go into the experiment so you can kind of see things. And I was like, but that, like, I don’t even know what’s changed between that A and that B test. Like, like what? I was like, and we’ll probably run a thousand experiences. I was like, but what are all the kind of like big moments of like a big release or this or that, and it was very hard to make sense of that. So I really like what design brings when you look at something through the interface. And so I’ve always been very big on seeing that. So when we’ve articulated a product vision and things, even though it’s not super prescriptive, it’s enough of a north star for people to kind of lock onto and have something tangible to work towards rather than you just get lost in conversations and people debating words. And I’m like, but we’re building software. Like what’s the actual end interface? Like, what’s the experience that we’re even talking about? and I think that was a change for me as well, is like, how can I bring that lens to product without everyone thinking I’m the designer wearing a product hat. So that’s what I was getting to and, and I think that that’s been a bit of a shift for me is how I can make sure that Jesse: Mm-hmm. Che: I’m still visible as the product guy, but then there’s a component I , think of my background in design that I think is very useful. You know, I run a business too, so you know, the different components of my experience I think help kind of, I guess help me in my current role, so to speak. And I also think I bring something different to building product that is certainly kind of probably more tangible. You know, there’s a data component, the kind of business component. But then, yeah, I, I think it’s a super valuable trait to be building products is to have that kind of design view anyway. Peter: Well, of course. Who, Who do you report to? Are you reporting straight into the CEO or somewhere else in the C-suite? Che: So I report to James Waters, who runs our accommodation business, which is, you know, basically most of the company. And he reports the CEO. Peter: Okay, Che: So he’s a, he’s kind of our business leader. Yeah. Peter: Got it. Even though you support other businesses… Che: Correct. Yeah. So we have other obviously smaller products that we’re integrating in. What happens to the organizational landscape over time, and how you would do that is kind of, certainly not up to me. But the, that’s kind of where we’re at the moment. There’s kind of the incubator of like bringing in the flights, attractions, ground transportation, insurance, et cetera. And my teams, all the designers, research, and everything are embedded in all of those teams that report up to me. And we have a product vision that we articulated this year that I drove forward, which looks at the entire traveler experience to build the connected trip. So I work for the biggest business unit, logic being that it’s already got huge scale, right? Like, you know, we nearly got to a billion bookings pre-pandemic. So through that lens it’s accommodations plus the others, right? And that’s how you kind of get to get to a point where you build a connected trip. Peter: And was James your boss before or was it the Chief Product Officer? Che: Chief Product Officer before, and he was basically the incubator for the other product verticals. Earning Credibility as a Product Leader Peter: I’m curious… to go from being the head of design to now being the head of product with design is still a significant part of your remit, how did you earn the credibility or demonstrate the credibility? What was that thing that allowed them, especially such a product-oriented company like Booking, to say, you know what, Che yes, you are ready to be in charge of product. ‘Cause that’s, that’s a pretty big shift. Che: Right. I think, I think it’s that I just generally have a kind of liking for, and I guess common sense for like, that I work for something bigger. So that, what I mean by that is that there is a business, there are shareholders. It’s listed, it’s the biggest, you know, online travel company in the world. So I have that kind of grounded reality, I guess. And I think I always brought that to every conversation I had. So, and I think designers typically, and I’m generalizing obviously, but will really just care about the design piece. And I always cared about every other role in the company, whether I could help the people department with something around employee experience and onboarding or service design for our customer service team and all the different, like, things that make up the business and help it run in a healthy way, but also like what should that look like in the future? What are the things that might disrupt it? So I, I guess I, for me, that’s been a designer, but I think once people are in an organization at a certain level as a designer, they’re very much focused on their area and kind of us versus them like design versus product or engineering. And I’m like, we’re all in it together. We’ve gotta build this whole thing. I think it’s just my mindset is different. And I ground everything back to like, we’re all just working for Booking.com. I was like, calm down. Like it’s, we’re not like this team versus that team or whatever it might be. It’s, and I know that’s hard because, you know, that that can come down to different relationships with managers and, and you kind of, like I said, your mindset going in. And that doesn’t downplay struggles and things that people have within organizations at all. That’s just my experience and I think that’s the thing that has allowed me to transition into product quite seamlessly is that I looked at everything from different points of view and I saw, like, what product had struggles with or where they could evolve a bit more and what technology needed from a product partner that I could maybe bring that was different. And, you know, design and engineering play a really close, tight-knit role. And I think for engineering, having a design leader come into a product role can actually be quite powerful to strengthen that relationship. Same with kind of bringing research in that might have been kind of more central and on the outer and bringing insights and things into how you plan and build roadmaps. All of those things I think sometimes just get a little bit lost when you’re just driving a product. So they, they were the things and the signals that I was, messages I was probably sending that allowed me to move pretty easily into it. Jesse: You mentioned that on moving into that role, you found yourself wielding more power or maybe wielding power differently than you did when you were in a pure design role. And I think that for a lot of design leaders, there’s a certain amount of envy of the product leader that sets in, this sense that uh, we just kind of have our noses pressed to the glass and, and are, on the sidelines watching all the big decisions get made. Understanding the value you bring Jesse: What advice do you have for a design leader who wants to be on the other side of that glass? Che: Who wants to move into product or just wants to have… Jesse: well, is it who just wants to be in those… Peter: …in those conversations. Yeah, I, I, I hear this all the time as well. Che: I think until product, whoever their product and tech counterparts are, understand what value they can bring, it’s hard, and it doesn’t mean going and proving it. That just means finding the time with them and working through their problems with them, asking, asking them kind of what motivates them, all of those things. So, and that can be very much like just a core designer and a PM relationship as well. Some of the best products I’ve built have been in that vein at that level of the organization as well in my past experience. So I think, yeah, that’s my advice is just, just build those relationships. They’re not always gonna work though. You have to have kind of lower expectations, ’cause someone might just like the way they’re doing things, it’s not always a guarantee, and then you kind of have to go on. But depending on how big the company is, you can go and find other people that are doing great things within the organization and product or tech and go and talk to them about what they’re doing. And maybe, you know, if there’s good internal mobility, then you can kind of start positioning yourself to go and work on something elsewhere. And, and work through that point of view. Figuring out where to work Peter: I wonder how you chose these companies to work for, and if that played a factor, right? Like… Che: Yeah, yeah. Peter: As you were looking for opportunities, you know, new roles or whatever, Che: Mm-hmm. Peter: How did you navigate those opportunities? And did you have conversations with companies where you’re like, oh, this isn’t gonna work for me because they want to put me in my little design box. They want me to wear the black turtleneck, and I want to be more involved. Or like, were there signals like that that you were able to pick up such that you’ve been able to choose companies that had this more inclusive, broader view of how product and design could work together? Or did you have to create those conditions once you came into these organizations? Che: I’m smiling ’cause it’s the right question. So I, I certainly was intentional. I like the cultural challenges ’cause I feel like that’s the first step to then making a great product. So I kind of saw products that I wouldn’t want to share with my family and friends, so to speak. And I felt like there’s obviously some underlying cultural things that you’d need to change before you could make them great. ‘Cause there’d be a lot of, you know, whether it’s empire -building silos, politically charged landscape, all of that stuff. Right. And that’s what I enjoy, I guess. ‘Cause I think I have the depth of experience in design and kind of patience to be able to go and do those things. So what I mean by that, with Booking all of the interviews and everything I had were all about data. How many experiences I ran, how data-driven they were, and I thought I’d failed it all. ‘Cause I basically was saying the opposite things and challenge them on everything. And I think that’s what they were looking for. They were looking for someone to come in and maybe balance their viewpoint a little bit. And not from a kind of one-size-fits-all, or black-and-white approach, but, you know, I don’t think data and design or product are at odds with each other. I think they work really, really well in harmony, but it can take a while to get that humming along nicely. So I saw a lot of cultural challenges, lot of opportunity. I spoke to Airbnb and Apple, you know, places I’d probably wanted to work. Particularly Apple. And had amazing opportunities at both, arguably even bigger potentially. And both were, yeah, probably a little bit boxed in. And I was like, so what do you want me to do ? I was like, I don’t think that’s a challenge. I think that’s just like doing beautiful design. I’m like, you got it. You’ve already got it. So I think there’s an opportunity. That’s what I saw in both the other, my previous roles where New York Times is an example against, you know, The Wall Street Journal. You know, there, there was kind of already the, it was established in that sense. Peter: An opportunity for change, but also, uh, interest in changing, right? ‘Cause I end up working with design leaders who find themselves in organizations where they want to make change, but the organization isn’t accommodating to that. Right, and so it’s… Che: That’s it. But that was it. It’s both, right? So I, I found, like, the organization didn’t, so like, they might say they do, but they never do because when change actually starts to happen, everyone starts rejecting it and that it, it’s a kind of a groundswell and then you give up. But I like not giving up and, and I think also in that process you learn a lot. So I’m also one to, like, change if I need to. I might have come in and particularly with Booking, like I’ve learned so much where I’ve reverted some of my original kind of blanket statements around all sorts of things that work from doing, whether it’s A/B, multi-variant testing and the designers and things might balk at. But I, what I’ve learned in going through that process is there’s a lot of knowledge that’s been built up over a period of time and, there’s a ton of stuff there that’s super valuable, and now I’ve kind of been able to add that to my toolkit alongside other things that I’ve built up over time. So it’s, it’s, it’s been super valuable. So it’s, I didn’t just come in and change everything. I also like changed a lot, is probably the biggest takeaway. As much as I felt like I’ve made an impact, it’s probably had an even bigger impact on me and all the people that have done amazing stuff there for a really long time. So it wasn’t terrible when I got there at all. It was working incredibly well and for good reason. I just looked at it through a different lens. Cultural change Jesse: To what extent do you see creating that kind of change as the leader’s role? Che: I, yeah, I think it’s obviously easier particularly when you have direct control, so to speak, with hierarchy and structure. I think cultural change needs to come from leaders ’cause they’re the ones that send the messages throughout the organization. If it doesn’t come from the top, those behaviors, the kind of authenticity of it, then people pick up on it very quickly. Jesse: Well, I guess I wonder about, you know, you called out the distinction between taking on a real challenge and simply stepping into a role where you’re running the design delivery machine. Che: Yeah. Jesse: And I wonder If there’s an element in how you define leadership, that involves questioning the way that things are done, re-engineering things, re-imagining the way that things are done. Che: Yeah, I mean, I think there’s a huge role to play. I would just argue that you need to be really open with how you do that. So my philosophy is you, you don’t do that in isolation. You can kind of build your theories on things, but then start testing them with people you trust in the organization. You know, preferably your counterparts in product and tech and other things. And then that’s what I’ve always done. I haven’t kind of been a single player. I’ve kind of managed to get a lot of people on board before I start driving anything significant. And make it as much as possible if you’re okay with not getting credit, make it feel like other people’s idea. Jesse: What’s your favorite go-to method for driving that kind of broad alignment? Che: I, there’s kind of probably two phases, maybe the first one is just really talking it through with people you trust that you know have influence. And really listening to their feedback. So taking that on board, but not losing sight of things. So if there’s kind of a crisp idea that you want to drive, but there’s some feedback you can take that doesn’t kind of dismantle it, so to speak, then, and you can keep the integrity of it. And you can get them on board and there’s a very explicit, explicit ask for them to help and what they would do and when they would do it, and all of those kind of things. And then the next phase is kind of going through, not just being the kind of messaging of it through an organization, but like making it real for people, like I said before, like understanding the kind of rhythm of an organization through financial planning and objective setting, roadmaps, whatever it might be. Make sure that you have a very clear tie into that process. You work with whoever’s driving that process through the organization. You find all of the moments you’re in, all of the meetings, you drop everything else you’re doing to get the, the work, that… the idea kind of seeded and then baked into plans. And then depending on what you’re doing, whether it’s proof of concepts, whatever, iterations, learnings, yeah, that, that’s kind of where I would typically kind of drive things through. Driving change throughout the organization Peter: I’ve seen some attempts at change from on high, particularly around new ways of developing product, and what I’ve seen is the leadership articulating a vision for how they want things to work. And then as change starts rippling, kind of, deeper and deeper into the organization, it becomes more and more diffuse. And at the point where the work is actually happening, the change doesn’t hit them. And they continue to work the way they always have. And I’m wondering what you’ve put in place to try to really, kind of, get change to make it something that happens at the, the, those points of delivery and not just something that’s talked to. “Look, we have this journey map and we have a North Star, and isn’t that exciting everyone?” But then when you find out designers are still being just kind of told what to do and everyone’s just moving tickets on a Jira board and they’re working the way they always have. What were those mechanisms to really drive change it at a detailed level? Che: Well, typically there’s like an incentive structure in any organization, so I guess you need to understand how that operates, whether it’s tied to bonuses and equity and pay rises and performance. So that cycle’s typically deeply tied to planning and performance reviews. So I think you have to understand that and the mechanisms that drive it and what people are motivated by. And if you understand that, then you can show value to different layers of the organization. Design systems, like the early kind of piece that we drove through and were able to consolidate, that felt like it was an impossible thing to do. Where we were able to basically set objectives across other business units that I didn’t have direct control over through leaders getting on board with the plan and understanding the value and doing it, and then driving that through the organization. And at the same time, the design community were kind of talking about how they could do it, working with engineering. And working through pain points and problems in parallel so that it didn’t just get stuck and engineering said, no, this is, doesn’t make sense. So you know, obviously there’s a lot of depth and detail to the hands-on approach of how that works, but yeah, there was kind of two layers to it. It, it doesn’t always have to be top-down either. I think a lot of these things can feed both ways. So in that case, it was a bit of both ways. Like there were problems and pain points and things that needed to be surfaced and resolved. But it didn’t mean that we couldn’t kind of have a very crisp vision, which was like one design system for all of Booking.com that expressed the brand identity worked for the engineering community on the, you know, stacks, frameworks and everything that they were moving, technologies they were moving towards across the board. So it took into account kind of a multitude of all those different things and had the right things in place to be able to do it. And then we drove it through the planning process and had it in people’s objectives. So it was incentivized, it wasn’t like a separate thing that if something were to happen with their top priorities, that, that they would drop. It became one of their top priorities. And that’s always key. That’s hard. That doesn’t always work. ’cause I think depending on kind of what level you’re at and where your influence is to drive what the business cares about and what the kind of top strategic priorities are, if it doesn’t fit within one of those, then you’re still gonna struggle for that year or period of years. So, I think it’s always important and it depends on how the company runs, but you know, if we have five strategic priorities for the business, if it doesn’t ladder up to that, you are gonna really struggle where, you know, if you have attrition throughout the year or whatever it might be, the one team that was driving it has some people out for a while, stuff that’s naturally gonna get dropped ’cause it’s newer, it’s not as tangible. So yeah, there’s no guarantee, but I think that’s, that’s all you can do is kind of really bake it into that process. Then performance planning cycles, et cetera. Jesse: You have this whole big diverse group of people under your care. These different crafts within design, each with their own areas of focus and their own, you know, values associated with those crafts, cultures associated with those crafts. You also have a product organization that has its own culture. Balancing autonomy and cohesion Jesse: Everybody is running in a million different directions, doing a million different things. How do you create a sense of cohesion in an environment like this? How do you make it actually feel like we’re all on the same team? When people are focused on different things, using different language, working in different areas? Che: I think we’re still on that journey, to be honest. Like it’s really hard in such a big company and they’ve been able to be autonomous and there’s been a lot of value in these autonomous teams to date, but there’s also a level of autonomy that’s still good, and there’s another layer, which I believe and other folks believe that you can do kind of big coordinated efforts around that. So as a business, we released last year an articulated product vision that’s really tangible, that gets broken down to journeys, customer problem statements, you know, all based on data that we have in research that we’ve done. So we have now something that everyone can ladder up to, and that’s been tried in the past and it’s failed. But this time there’s very, there’s very little to no pushback from any part of the organization. Everyone’s really inspired by it. Everyone’s really engaged with it. It’s actually motivated a lot of people, teams have come forward to say, how can we contribute? How can we help? So some of it’s organic, but then there’s also now a need of like, if we want to do these big coordinated efforts and we do want to have more of a portfolio view, how do we go about doing that? So we have a north star, we have some tangible concrete work around it. And the next step for us is, I think laying out a set of kind of principles. Like you could argue that different product teams still have different ways of how they would make decisions and trade offs. I think we’re kind of at a point where we need to be able to say, look, this is how, you know, our ways of working principles from a technology point of view, from a product point of view, end up all laddering up to a set of like consistent principles in the way that we want to work and how we make decisions, how we make trade offs, and then give people a lot more space. I think there’s still a bit of that still going on in, in kind of the microcosm and people making their own principles, you know? But I think this is kind of a cultural thing, like people, like teams. So is your team Booking.com or is it like a level down, or is it at a group level, like product area? Is it a single team? You know, with so many teams, it’s like, at what point do you kind of, and kind of ladder it up and say, that’s the team that I’m part of. I’ve always struggled a bit with this and it, and like teams create their own brands. Like in a, in a blank canvas world, I’m like, maybe we can just have like 150 teams and it’s like, Team one through to 150. And then, like, as a leadership team, we can be, like, here are the strategic priorities of the business. And then everyone can kind of, we understand the skillsets and we can pivot and we can be like, we’re gonna go after that this year. And everyone can, but you know, these are theoretical. And, but I think some people want a sense of belonging in that. But I also think those things are dangerous ’cause people get stuck on the thing that they care about, that they’re delivering at a certain part of the organization. That if the strategy changes the environment, the business landscape, the travel market, they’re kind of stuck. And, and that can be really hard. And so to pivot or create more mobility and go after certain topics and things that are more coordinated, then, that’s where I think is a big challenge, like for, for us, but also a lot of companies do that, and I, I think that’s just a natural way that people work. They want to feel part of something and they go over and work for team, you know, ABC and that’s the one that kind of is, it’s the thing they care about at that particular time. Jesse: Right. And as much as you want to give people a sense of identifying with their work and identifying with the particular piece of it that they are delivering, at the same time, there is still this need to raise their awareness of what’s going on outside of their individual tunnel vision within their teams. How do you do that? Che: There’s lots of mechanisms. I mean, there’s just like the standard kind of communications and all hands, and we use, you know, Facebook’s Workplace. Groups have open channels that they share updates and all sorts of things. There’s not a consistent way that we do it, so everyone kind of communicates differently in different layers. But that, that, that kind of works. Maybe as a leader you’d probably like sifting through a few things to figure it out. Cause it’s not as standardized, so it could be possibly a bit better. Yeah, but I, I also kind of, back to the other point, there’s, there’s domains and there’s capabilities and services and things that people also still need to really own. So you want that institutional knowledge for those kind of things to be, to be really, really well looked after and platforms, et cetera as well. So there’s that part. But yeah, I don’t think there’s like a specific way to kind of communicate out and get everyone on the same page when there’s so much going on. The planning cycle helps a bit and that kind of opens up at a company level all the different things that are going on and how people are prioritizing things. And a lot of those things are continuations from years prior, so you can kind of see that’s where things start to come together and glue and ladder up, and you get a better view. Through the year, you typically don’t get that as well, depending on kind of mailing lists and, and your activity on Workplace or all hands or… Jesse: Mm-hmm. Che: …or whatnot. Jesse: Mm-hmm. I’ve heard you talk a lot about aligning people to a vision that kind of comes down from above, so to speak, but you’ve also talked about the importance of giving your teams and the leaders of those teams autonomy. How do you maintain that balance between the directive from above and giving people the freedom to explore and come up with solutions creatively at a lower level? Che: Yeah. So I think people need that kind of tangible vision of the future. I think it’s then how you articulate how you get there and that it doesn’t necessarily need to look like that at the end of it. So it’s okay. There’s gonna be things that change along the way. That’s the nature of it. So this thing that they’re working towards they have all of the opportunity to shape that or completely change it and throw it out the window. But you need something to start, and that’s the starting point. . And then through particularly our culture, it’s a way of releasing things, trying things, experimenting, iterating, getting feedback, talking to customers, partners, et cetera, and, and building on it over time. So all of the good stuff comes from the teams making it, not the leaders kind of defining a direction. Peter: I’m now thinking about feedback loops. What, if any, mechanism is there from the learnings that’s happening on the ground that might feed back and inform the vision and actually change that north star, or does that happen? Or once a north star’s created, it’s, it’s set and then maybe five years from now you’ll go back and change it in a, in a big push? Or is that, is a north star something you can iterate on? Che: No, north star’s absolutely something you should iterate on. Cause I think that’s where companies can go to the graveyard if they get too fixated. I think, you know, you always need to be looking at the future and the entire landscape and being really conscious of what’s happening and being okay to pivot and adjust. So I think, yeah, those learnings need to come back into product and the business and, and all the teams in between that need to actually understand it. You know, like I said, we’re kind of very much on that journey. We’ve done this with lots of other things in the past, but we’re now on it for the entire, entire company. So we’re, we’re in that process. I think it’s at the right levels. It’s now what things you measure, how you measure them, what metrics from the different proof of concepts and things like that. Now we’re kind of biting off chunks and driving forward with, with pieces of it. So we can kind of start understanding how we build certain things and if they’re valuable. ‘Cause if we go all in on building a capability for a year or two and the functionality to then be able to build experiences on top, and by the time we get there, the whole thing’s changed. That’s very dangerous. So there’s certainly an iterative approach because our products are alive and, and operating really, really well. We kind of have to be, we have to tread fairly gently, but it doesn’t mean we can’t kind of make those learnings, consolidate them to release larger than life features that we’ve struggled a bit with, I guess, in the past. It’s more smaller improvements, and I think we’re getting to a point where we’re able to actually do some bigger shifts. Peter: You mentioned earlier about how you have changed, particularly in the last, what is it, I guess a couple years, year and a half since you’ve been in this role. But I don’t think you shared some specifics. So I’m curious, like what were some of your preconceptions or, you know, tenets that you used to hold, that now in this role, with a broader mandate, you’ve had to let go of and embrace new, new ways of, of thinking, new mindsets. Che: Probably the main one is that I felt like, with all my experience, I was probably a little bit of over the top in terms of what I would think and how confident I would be with what would work with running certain experiments or making certain changes. And the data can often tell you otherwise, and it’s, it’s just a really interesting thing and, and sometimes you want to be bullish and be like, no, no. That’s just a kind of like, that’s part of the pain of like the initial change. It’ll kind of get better over time, but maybe it doesn’t get better over time. So it, it is actually, the main thing I’ve learned is, you know, I, I think you should measure everything. I don’t necessarily, I, I wouldn’t have come into Booking thinking that you do. But we literally measure absolutely everything because it, it’s, it surprises you more often than not. And that feeds into how you make decisions. People can obviously, depending on how you set up, kind of game that a little bit in terms of what they do. But I think the more disciplined you are, the more you kind of look at it and as a team understand it and try more things and iterate. It’s, it’s incredibly valuable. I just, I never thought I would be quite in that head space. I probably came in more leaning on my experience of what has worked in the past, and now I’m a little bit more balanced. I would say Booking was probably over the top. It was like if it hasn’t been proven at Booking, like even if you’ve done it at Amazon or whatever, you still had to come and prove it at Booking. That was kind of the mindset. I’m not, I’m not fully there at all. I think I’m still in between. I think there’s some things that you can apply that certainly work from other, other places that have learned a lot as well. Peter: You haven’t let go of design. It’s just less of your, it’s less of your focus, given that you have these product responsibilities, and as you’ve embraced these product responsibilities, I’m wondering what did you see, if such a thing exists, standard issue product management practice, that you’re, like, stop doing that. Like, we have, you know, maybe we have five product managers listening to this podcast ’cause it’s primarily a design podcast, but for those five product managers, what would you say to that audience? That community, like, you all seem to keep doing things this way and I’m here to tell you now that I’ve seen more, like, stop doing that. What are, what are some product management practices that maybe should be sunsetted or that could be informed by smart designerly approaches? Che: Right… Can I start with one thought that’s somewhat on topic of, and then I’ll, I’ll jump. Peter: Take it where you will… Product needs to bust their siloes Che: So the thing that I’ve observed that’s worked well, I’m kind of flipping it a little bit. It feels like a very obvious one, but as a product manager, really lean on the other skillsets around you. So don’t think that as a product manager, you know everything and you just go out and gather data from the research team, the data scientists, and then the designers help you kind of build that. Like, and it’s, it’s leaning on everyone’s, if you’re building plans and I mean that like, in detail and really listen to them. So that’s kind of, I, I think that’s the key thing that makes PM successful is, is gathering all of that and being the kind of orchestrator of it. And having all of that at their disposal, but also just it should really feel like a team at equal, kind of, seat at the table. So the PM, while they might make the final call on the roadmap to be able to do that, I think they have to operate as a team and listen to everyone really well. Then they can push back on certain things and be the decider. So I’m kind of flipping it. In terms of like standard stuff, I think it’s that PMs typically look at their area and just drive that and struggle a bit more with how they can actually open up to things going on elsewhere in the organization and make sense of it. So if they’re doing something in their particular area, it’s like how could that affect something maybe in a more negative way, in a different area? I see that a lot in, in big organizations. So, and there’s concrete examples where the experience can really take a big hit because one team’s going down one path and that’s just the way they operate. So it’s, it’s, it’s towards that kind of silo thing where I think you get a lot out of the lens of UX and design from thinking about how everything works together as a system and all the different touchpoints and experiences that people have. So, as a PM, that’s the one thing I would kind of upskill is how you work. You know, whether it’s more horizontally, whether it’s how you contribute to the larger strategy and always kind of be thinking about how you do that. And if there’s technologies that are kind of more centralized and standardized across the company, how can you embrace those so that the whole thing runs more smoothly? ‘Cause at some point they’re gonna rely on them whether they like it or not. And there’s just too many independent decisions would be my way of putting it. And I think to kind of release that a little bit and look to kind of how you make more joint decisions as a PM. Peter: Research is going through an evolution. You have UX research aligned with design or UX teams. You have market research in marketing. You have data and analytics. You’ve got customer service and what they’re learning. And I’m curious what your best guess is in terms of how organizations can best take advantage of research. And now that you’ve shifted from a design to a product role, where I’m guessing you’re exposed perhaps to a wider array of information and, and evidence that you’re now making decisions on, how, how has your thinking about research maybe changed over these last few years? Che: Yeah. So many of these things are people dependent, like a lot. Everything I think about in the conversation we’ve had really depends on the people I’ve worked with a lot. So it’s just like a caveat for everything I’ve said. You know, I’ve worked with some great people. I’ve worked with some difficult people and everyone… Peter: Who, who are the difficult people by name? Che: No, no, no. We’re all friends now, so it’s fine. It’s more just to start that kind of grounding in the reality that it’s, it’s, it’s so people dependent and they obviously drive the culture, too. But in the kind of theoretical space, and what I’ve seen work and not work, you know, I think research in particular, like design, needs to be at a certain level in the organization that it can look at everything and be able to not have control over it necessarily, but at least influence it. And so I don’t think you need a Chief Design Officer, a Chief Research Officer, a Chief UX Writing Officer. Like I, I think at some point everyone has to understand that it’s still a business and there’s kind of certain levels and then where you can have influence is kind of at what level the, the most important then aspect. And it also comes down to the person a bit. So in that leadership role where I think research plays a big role in the future for us particularly, is bringing in those insights at the right moments. There’s two layers. One at the kind of planning phase for the medium long-term stuff that I talked about that is kind of coordinated and strategic and helps inform the whole company strategy. It’s one of the components. It’s not the thing that does it, but it’s one of the components. And then the other layer is, I think it needs to be embedded in product teams and at certain levels if there’s groupings of teams. But I think you have to then have really good workforce planning because there’s times you might not need it in one area and the macro view says you need it in another area and you don’t want teams hoarding people that they don’t need and then having decision making power, it’s to switch a research role to an engineer or whatever, ’cause their roadmap dictates it. You need a holistic view. Workforce planning needs to be in the hands of those particular disciplines or crafts. So research or design or writing. But I think particularly in, in, in research that’s super important. Particularly because of the size. So if you look at the size of an engineering organization versus product versus design versus writing versus research versus data, you often, like, you’re talking about research and writing, probably being, in particularly our case, the smaller ones where there’s like 60 to 80 people versus thousands. So if engineers are yelling really loudly, they’re probably gonna get what they want. If the research 80 researchers are yelling really loudly, they’re gonna have to yell really loudly. And that’s kind of the, the, the way a lot of software development works now, right? And it’s, it is very engineering focused. Maybe that’s okay. Maybe it’s not, who am I to say? But I think the smaller crafts, like research, need to have that voice. So they need to have a point of influence in the organization. They need to be embedded, but they need to be in control of their workforce planning and they need to understand the company’s strategy deeply enough to be able to align the right people against the right things. That’s my kind of common sense view of it. And that’s where they can have the most bang for their buck. And that’s certainly where we are now. It’s taken us a while to get there. There’s a bit of stuff to still continually do. And Molly Stevens, who joined us from Uber, kind of similar time that I joined, she was director of research there is now our Senior Director of UX. So we have all of design, writing, and research reporting in to Molly. And she’s been fantastic. Shout out to her in kind of instrumenting that and having a voice at the right senior level. So I think we’re, I think we’re in a really good spot, to be honest. But that’s, that’s how I would, that’s my experience from where I am now. And it might change over time, but that’s what I think works well. Jesse: I have one last question for you because I know that this is a question that a lot of design leaders have on their minds as they are sitting across the table from their counterparts in product. Che, is the grass actually greener on the other side? Che: Uh, No? I, I, I don’t, no. Um, um, I want to, I, I, It’s so early. Like I feel like our industry’s so young, you know, software engineers have been doing it for a little longer. But it’s so young. I think we need people to kind of also not, not just do what I’ve done, but like a mix of both. So don’t feel like you have to move to product. That organically happened for me. It wasn’t an intentional thing. Like I’d almost happily kind of run all design again, or, or what, like it’s not a so I don’t think it’s a one or the other if I’m me. Um, But it’s a, yeah, look, it’s a super exciting space right now. I just think there’s still a lot of maturity and evolution that needs to happen. Peter, you talk a lot about this and yeah, I think we need, there’s still a long way to go and so I think there’s a lot of stuff that we can still shape it. The whole industry’s still young in my opinion. We need to kind of be aware of that and be conscious of it, be okay with it. I think sometimes we’re trying to find, fight something that doesn’t even exist and that people that they’re fighting against don’t even care about. So it, it’s kind of almost a lost cause from the beginning. You’re wasting energy instead of just kind of going about it. Jesse: Che, this has been great. Thank you so much. Che: That’s okay. I loved it too. I enjoy talking about it. Nice to have my brain picked occasionally. Peter: Is there any way that you like people to keep up with you out there on the internet? So are you writing or speaking or whatever, or do you have channels that you’d like folks to engage with you? Che: I, once I start at businesses and I’m doing these big, what I feel like changes, I’m so all in that I’m absolutely useless on every social media platform known to man. But if anyone wants to reach out, LinkedIn’s probably the best way if they want to connect me. But yeah, I’m, I’m sadly a bit useless on them. Peter: It’s all good. That’s why, that’s why we’re here to fill those voids. Che: Thank you for helping I appreciate it. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Jehad Affoneh, Chief Design Officer for the restaurant point of sales system Toast, joins us to talk about driving an experience strategy across functions beyond design, dealing with tricky executive stakeholders, and how his background in engineering informs his work now as a design leader. Peter: Hi Jehad, great to have you here. Thank you so much for joining us today. As you know, we’ve been talking to folks who have a title of Chief Design Officer, SVP of Design, SVP of UX trying to better understand just what this role and responsibilities entails. So that’s what we’ll be digging in with you today. So thank you for joining us. Jehad: Thanks for having me. Peter: Awesome. So the first question we’ve been asking everybody, and we’ll ask you, might as well start on the top rope: How do you define the role of Chief Design Officer? That is your current title at Toast, I believe that was your title at Splunk. What, what does that mean? What are the responsibilities? How are you held accountable? What does your leadership want from you? All of that. Defining the Chief Design Officer role Jehad: So first of all, thanks for having me. I’m excited to chat with both of you.  If you think of the role of any kind of executive team member, there are three main things you’re doing.  One is your discipline’s contribution to the business. So if you’re the chief, you know, technology officer, you’re leading technology for the company. If you’re the chief people officer, you’re taking care of culture for the company. So your discipline’s contribution to the company.  The other one is how you’re building your team and how you’re building that organization that drives that work, and bringing talent, hiring, growing talent, setting up the right culture for that team to, to bring the right culture into the company. And then how are you uplevelling that discipline or the contribution of that discipline to the, to the company continuously? You can track that with metrics, you can track that qualitatively with, with feedback. You can track, you know, there are multiple ways to track that, but that’s, that’s a third piece. So if you think about it that way, and obviously any executive team member is looking at strategy, helping define strategy for the company on, on vision, feedback from customers and so on. But that’s really just comes with the role. Like, if you’re at an exec role you’re helping drive strategy and execution for the company. But if you think of these three areas, the role of a Chief Design Officer is to build, hire, and grow talented designers, user researchers, design ops folks, roles and disciplines required to operate a healthy organization. Build that culture where around, you know, skills and, high quality work and hold customers feedback and voice of customer as, as core to that story, they’re responsible for upleveling that conversation at the executive level and having conversations not just about customers in general, but about the way experiences help shape the product strategy. And then provide language for the executive team to talk about design and user experience. So internally for a team, it’s easy for us to get stuck into, you know, the details of how user research operates and how design operates, and all the language and words that we can use in order to understand how our work is happening externally. Externally, meaning within the rest of the company, outside of the design team. The role of a, whether it’s a CDO or VP of design, is to provide that language where the company can now talk about experience in an intelligent way that helps the company deliver more to it. And this is, by the way, where the conversation, I don’t know if we’re gonna get there, but this is where like most conversation gets stuck on design metrics, but design metrics or experience metrics end up being a shortcut to, we don’t really understand what you do, so could you please, you know, translate it to the way the business operates. But it’s really common language of the business.  Peter: You mentioned operating at an executive level. To whom are you reporting? Are you reporting straight into the CEO, into someone else in the C-suite? What’s your relationship with that highest level of leadership in the organization? Jehad: At Toast, we’re still, you know, founder led to some extent. We, we have a CEO, but we have two key founders that lead R&D and Go-to-market. So I report on the product side of the R&D organization. And I’m part of the, what we call the RD exec team, which is the triad CTO, CDO, and the Head of Product. In addition to, you know Chief Security Officer, you know, and other disciplines that are related to R&D, but we operate as that key triad of CTO, CDO, and head of product or SVP product. Peter: Last organizational question, how, what is your responsibility, if any, for like marketing or brand design? Obviously you’re working on product design and UX research. Are you also working on the marketing and brand design, or is that handled separately? Jehad: No, we collaborated very closely with them, but that’s handled as part of the marketing org reporting to the Chief Marketing Officer. Jesse: And are you the first Chief Design Officer they’ve had. Jehad: Yeah, the first Chief Design Officer. They’ve had design leaders in the organization before at different levels. Jesse: Right. What led to the leveling up of design to a C-level function for Toast? Jehad: Yeah, that’s a good question. I obviously have a different part of that story having, having been on the other side, but I think a couple things.  One, which usually is the case in organizations, there is usually a believer on the C-Suite that believes in, okay, we, we’ve gotten this organization as far as we can, and sometimes by the way that CDO, sometimes even CTO or other disciplines, but we’ve gotten this organization far enough with what we have. It’s now a moment for us to uplevel that discipline and both bring someone, either, either promote someone internally or bring someone externally to make a clear point about where design now stands or where engineering and other discipline stands. And two, it’s, it’s oftentimes driven by, and I, I think that probably was the case of Toast, too, driven by the market change. Like if you want that level of talent, there is now a, a specific expectations of, that level of talent on what the role will be in the organization. That’s somewhat taken for granted in other disciplines. Like having a CTO is kind of pretty typical thing to have. That change is happening in design now, which is why like, it’s, it’s a novelty to have a CDO in some companies, but it’s, you know, you wouldn’t be surprised that a company is hiring a CTO, for example, Peter: I’m curious what the difference though is between a Chief Design Officer and a VP of Design, who is the senior most design leader, whose boss is the head of product, who reports into the CEO it sounds like you’re in a very similar context as quote, VP of Design. Is Chief Design Officer simply kind of, like, good branding for otherwise a VP of Design or do you see it as actually, “No, they’re asking me to do something interestingly different than if I were called a VP of design?” Jehad: Yeah, it’s actually interesting. It, it really depends on the company. So like, there are times where it’s branding and, and you hear about different roles, by the way, at the C level that have C-level, like chief I don’t know. I, I don’t wanna mention specific roles, but like, I was at a hospital the… Peter: Chief Customer Officer, Chief Data Officer. Every, I mean, there’s chief everything now. Jehad: Exactly, and obviously not everybody can report to the CEO and by the way, sometimes that’s not what you want either. Depending on the maturity of the org that you’re leading, and the, your place in the organization and so on.  But I do think– so, so there are places where, hey, chief is a way to, to attract talent. It’s only one part of the equation. If we give that title, we’re able to bring someone in. But really it’s, it’s, it’s internally not a big change.  Partnering with other “C”-level leaders Jehad: And there are times when it’s actually not the case. It’s actually, part of the senior leadership team. Part of the executive team. Only people at that level have that, you know, being part of that team. And that means you have, you have responsibilities to the company, owning the actual end-to-end experience and, and sometimes customer experience end-to-end. You are actually accountable to metrics, company-wide metrics, that’s the case at Toast. Accountable to company-wide metrics around experience, around product satisfaction, around customer satisfaction and so on. And the other piece is we, we have been working a lot at Toast to drive, which is part of the hiring of this role, to drive the partnership in R&D around design, engineering, and product. So this role was not just about a single person, but about having triads from the top-down across the whole organization, starting with CTO, CDO, or you can think of it by the way, if you remove C titles, SVP of Engineering, SVP of design, and SVP of product, down to product teams that are operating at a designer, product person and, and an engineer. I think that there’s a lot of debate in design about who reports to who and how reporting works. My opinion is that debate is sometimes misguided around, to do a hot take, to be controversial about, around more about ego of the person versus the actual value that the role can bring to the org. I think the most, most important thing is, are you a partner to your product and engineering partners, or are you or are you a member of one of their teams? Like, are you a true partner to the engineering and product org, and obviously other orgs, and marketing and customer success and so on. Two, do you have the autonomy to actually execute for your org things that might not be popular at the time, but you believe are true? Do you have the autonomy to execute alongside product and engineering versus for product and, and, and/or engineering?  And three, are you accountable for true company-wide metrics or, or, or outcomes? Or is that accountability held by someone else? Like are you actually accountable to the company? Obviously everybody’s accountable to the company, but is part of the company’s key experiences or metrics part of your accountability, or are you, you know, delegated that accountability through someone else? As long as you have those three, then where you report to, what your title is, obviously, you know you know, you, you get different access points, having these different areas, and there are extremes, like if you’re reporting 16 levels down, but you have these things, obviously autonomy is not there. But in my mind, it’s less about that and more about do you have these three pieces that make you a true leader in the org. Jesse: The first of those you mentioned is being a true partner with product and with engineering. It’s interesting because we hear so much about the need for better partnership there. And I think that in a lot of cases, the elevation of design to the C-level is intended to kind of enforce that partnership because a lot of people really, they don’t know what a good true partnership actually looks like here because nobody in the room has had that experience. What do you think makes for a good true partnership between product, design, and engineering? Jehad: Yeah, I think obviously every discipline brings something else to the room, but I think a true partnership means true ownership of the overall outcomes of that triad. So, you know, if, if you’re a, if you’re a partner in that team, you’re involved in and, and you have ownership over, how do we come up with the strategy? So, like, what are we gonna go actually achieve next year at any level, by the way, even if you’re leading a team, what ways in which we’re gonna actually go and measure the success of that strategy, and then owning the outcomes of the execution of that strategy, even when it’s not necessarily the execution of your team. So, like, if you’re having a conversation that says design has shipped, but engineering hasn’t, you’re not really a true partner. ‘Cause at the end of the day, yes, you might not be the head of engineering, but you have responsibility as a true partner to figuring out how do the three of us sit in the room and, and drive that level of accountability. In my mind, shared outcomes and shared metrics is, is, is the north star way you materialize true partnership. ‘Cause if you’re responsible for, Hey, look, your metrics as the head of design or leader of the design team or the design discipline is, you know, as long as you ship these three metrics, you ship on time, you deliver a great experience, whatever that means, and you, your team is happy, you’re good if those are the metrics you’re tracking.  Notice that none of these metrics talks about actually shipping the product. None of those metrics talk about product market fit. None of those metrics talk about revenue. None of those metrics talk about you’re staying in business. So if, if you don’t really feel accountable for the other metrics or quote unquote other metrics that truly form triad accountability, then you’re not really a true partner. The, the opposite is true if, if, if your engineering and PM partners don’t feel accountability towards experience metrics, they’re, they’re not true partners. True partnership is often formed, together. It’s a partnership. So like if you’re not coming up with the metrics together, if you’re not building the metrics together, if you’re not building the strategy together, if you’re not accountable together, if your rituals are separate, then you know, you might be a great collaborator, but that’s not necessarily the same as a great partner. Jesse: Mm-hmm. That makes so much sense to me. And at the same time, I also hear from design leaders that they want unique metrics for design because they need to provide pro of of design’s unique contribution to the organization and that these blended or shared metrics actually make it easier for design’s contribution to be kind of swept under the rug. Metrics and organizational maturity Jehad: Yeah. And it’s very fair, and it depends on the kind of maturity of the org, but the way I think about it, and I’ve been there too, there are metrics that prove your worth and there are metrics that are actually valuable. And those two are not always the same. Sometimes they are, but they’re not always the same. So as an example, if you’re early on in your design leadership role and the company is early on in their design maturity, maybe the metric that proves your worth is the opinion of engineering and product of you. And that’s not gonna stay the same. And I know that like to many designers or design leaders who are hearing this conversation, this might be like an allergic reaction to that statement.  Peter: Let me interrupt ’cause I’m curious if that’s something you’ve had in prior jobs. You’ve worked in very engineering heavy companies, very tech driven companies. Was that something you needed to do to build that maturity muscle? Is that, is this born of your experience? Jehad: Yeah, it is. And, and sometimes if you step aside and say, let’s say it’s not a mature design team and not a mature organization from the way design is viewed, if you step out and say, I gotta invent my own experience metrics, that I’m now gonna build the whole thing around them to measure them and I’m gonna report on them, but the organization’s not even ready to talk, to have that conversation, instead of proving your worth, you’re seen as like, you know, vanity conversations around things that we don’t care about. So like, you’re spending so much time building these metrics that we don’t even care about versus, I’m actually gonna work very closely with my engineering and PM partner. Doesn’t matter if they see me as one yet, but I’m gonna work very closely with them, have ownership over what we’re shipping and not shipping, talk the language of that team, which by the way, could be, most teams have an experience language that is not up to our standards in design maybe, but most teams talk about experience in one way or another. They talk about it in adoption. They talk about it in customer qualitative feedback. They talk about it in NPSs. So there is a bunch of different language in the business that exists. How do you capitalize on the existing language and say, I understand it. I’m accountable to it. I’m gonna help you get there. Could be a great starting point for someone in engineering and PM to say, I could have not gone in there if this, if, if it wasn’t for this person or if it wasn’t for this team.  And then capitalizing on saying, now that we’ve had that credibility, let me tell you how we can do this better. Like, let me tell you this one other metric that if we track, we can provide such a, you know, a much better experience there. But taking the leap of faith from, you know, we don’t know what design does to let me tell you the exact metrics I’m gonna invent and then hold myself accountable to is sometimes too, too big of a gap to be effective. Again, depending on the org. That’s by the way, not the story at Toast, for example, but that was the story in previous roles earlier on. Jesse: You’ve touched on organizational maturity a couple of times, and I wonder how you see that tracking with the age of the company. ‘Cause you’ve worked for some older, much more sort of established companies, as well as companies that were much, much earlier in their life cycles. And I’m curious how you see the organizational life cycle affecting the way the design is received and the way that design is done in these organizations. Jehad: I think it plays a factor, but I think structure of the team you’re immediately having an impact on is likely far more important. So like, if you think about, you know, our roles in different organizations, there is probably a role you don’t understand. Like, we talk about design a lot because we’re designers and that’s our thing. But like, if, if I ask you what do you think a business analyst does and what is their value to the organization? And there… Peter: They analyze business. Jehad: It’s, I mean, it’s very clear. I understand, but uh, but you know, like there are so many roles in every organization and, and there are roles within roles, right? Like in design, in, in the, in the big umbrella of design, there is product designer and user researcher and design ops and blah, blah, blah. And two things are true. Not everybody needs to understand these roles. Like it’s just impossible for, for like a CEO, for example, as the top of the umbrella, or the board, to understand every single role that makes this organization tick.  And not every role deserves a full discipline and team and, you know, a large umbrella of a C-level role or, or something like that. It’s just, just not scalable as an organization. So if, if you think about it from that perspective, and then think about the next step of, okay, and then how do we make the decision for what gets a larger umbrella versus what doesn’t? There are two paths to that.  There is the path of advocating for, I’m gonna start at the C-level and I’m gonna convince every single executive in the organization that design is the most important thing under the sun. Or there is the path of saying, I’m gonna actually make impact in a circle that I can actually influence. Depending where you are in the org, that could be media team, that could be the VP team, that could be you know, the engineering team. You know, it depends where the org is and what’s the center of influence. And a lot of the time the center of influence is not where you think it is.  Like if you’re an engineering-heavy organization, individual contributor senior engineers hold a lot of weight. So collaborating closely with architects ends up being such a huge impact on how design is seen across the org. One, because they’re thinking at a high level. They’re not bogged down by the daily details of what they need to ship every day. Two, they have systems thinking already. They apply it differently, but they’re actually very close to the way we, we operate in design. And three, they’re generally at the level of maturity where they have the company’s hat on, versus their individual team, even though they’re attached to a specific team, but they’re still thinking, how can I make this company better? And they have a ton of influence. They have influence on the executive leadership team. They have influence, and this is just an example, not saying always start there, but if you’re an engineering-heavy organization collaborating with these senior engineers may be a far more effective path, than let’s build design metrics across the org that’s gonna convince the CEO that C-level role is needed. And then how you deliver in collaborating with these architects on, you know, whatever their goals are, ends up being a huge ticket to, ” Wow. Like imagine if every architect in this organization had a, had a designer working with them. Now imagine if every engineer in this organization had a designer working with them. Now imagine if every team had a senior level person working with them. And then take it from there into, into, you know, into that story.  But that, but you have to understand the organization and the way it operates. And that’s less about the age of the team or company and more about like what tools and, what does the environment give you. Peter: I wanna kind of follow this thread, but specific to Toast, where you’ve been there, if LinkedIn is accurate, about seven months. So still pretty new. Jehad: Six months. Yeah. Peter: Six months. Yeah. And I’m curious what you found when you joined, how much was already set in place? I.e., your product peer and your engineering peer, had they been there, had they developed a relationship that you now had to find your way into, or was everyone new and you were all figuring it out together? You know, as you’re talking about relationships and navigating organizations to understand how to situate yourself to be effective, what was that experience like for you six months ago as you assumed this, this role at Toast? Jehad: Yeah. So it, it’s kind of mixed. As an example for my triad, like the immediate triad, the SVP product has been there for a few years– two, three years. But my partner in engineering, our CTO, joined I think a month after me, if I’m not mistaken. So we, we had like a chance to set up the triad together. Two of three members of the key triad joined recently. The person, Steve, who leads R&D, is one of the co-founders. So he has been there since the early days of the first line of code. So there is a mix of that.  Managing change Jehad: But on that note, which kind of gives me just quick something to think about, there is no organization that’s not changing. I think one of the key things a design leader can do is figure out what change that’s happening and how you tie in the change you wanna drive into it. Like in my case, for example, a new CTO joined, the product leader was there, and he was, he’s, he’s an awesome partner to work with, working together and, okay, what, how do we wanna shape this relationship, was, was the change that you can tie a lot of stuff into. We want to build triads across the org. We want to drive change across the org. Here’s how it’s going to work. In other organizations, the change could be, people have been there for a very long time, but the team is going through, I don’t know, some change management process around… process. We want to change planning. Okay, let’s change planning together. Let me tell you how I can help change planning. Whatever it is, there is always something to tie into. Jesse: And when you think of the change that you see yourself driving, as a design leader, the change that you want to weave into the change that’s already unfolding in the organization, what guides your choices? Jehad: Yeah. That’s a good question. I think like looking six months back, like maybe three or four things that influence this.  One is conversations with a team. So spending time and the listening tour, and I, I use team as a larger kind of umbrella. It’s not just the design team, the, the, the R&D organization. Spending time with the team to understand, first of all, how do we see the quality of what we’re shipping? Like, are we happy with the experience we’re shipping? And if not, why not? Obviously you develop your own opinion, but listening from the organization tells you a lot about how much bar raising you need to do. Listening to, How is designing versus shipping? Many good experiences die in Figma graveyards where like, you know, “yeah, yeah, let me tell you this experience that we’ve designed six months ago that never shipped and never will ship because, you know, because,” and sometimes it’s not because of engineering. Sometimes it’s because it was designed in a way that cannot be shipped. Sometimes it’s engineering is not shipping and sometimes product doesn’t believe in it, but listening to these stories is really helpful. So that listening piece is one piece.  The corporate strategy and company strategy is the other piece. Where do we actually want to go? And most companies have a three-year strategy at a minimum. So understanding that longer term strategy, not just next year.  There’s the piece of digging deeper into the team dynamics for design in particular. Do we have the right talent? Do we have the right people? Do we have the right skill sets? Do we have the right organizational structures that enable that to happen? And then the last piece is process. Do we have, you know, is this, hey, we actually have the tools in the toolbox and we’re just not using them effectively, or we are using them effectively and can use them better. Or is this like, actually, there is more change management to happen process-wise? Understanding those four were the key pieces to kind of setting up, but okay, here’s our experience strategy. Developing an experience strategy Peter: And when you set up an experience strategy, is this your own n-month plan? 12 month plan, 18 month plan? Like you mentioned the three year strategy. Are you doing kind of your own version, probably not with this distance to horizon line, that you start to work towards? How, how explicit does that become? How broadly shared? Is it, does everyone understand it? Explain kind of how that strategy gets operationalized or manifest. Jehad: So about three to four months in, so two, three months ago we kind of developed that experience strategy working with the design leadership team, our general managers of each one of the lines of businesses that we have, as well as the R&D executive team. I own the experience strategy, so I’m the single threaded owner that’s accountable for that, for delivering on that strategy. And the strategy has two pieces to it.  Here is how we think of experience as Toast, which impacts every single person’s job in R&D. So for example here’s how we’re gonna measure our experiences before we ship them. Here’s the level of quality we expect from every product that ships across the organization. Here is how we’re gonna work closely with support on our customer experience. So this is every single team, here’s the framework by which experience is gonna work at Toast.  So that’s one piece.  And the other piece, and here are very specific projects that I’m accountable for that will lead experience on product, customer, and end-to-end experience. So on, on customer experience, here’s the work that specifically Design will own in working with our customer success team to improve our customer experience on product. Here are the specific two or three product leverages that we think our experience is a very important piece and we’re gonna own the metrics on. And, you know, I’m accountable for both, I’m accountable for experience metrics across the org. But obviously you can’t be accountable for every product experience. Your, your teams are and your triads are. But personally that, that’s not the role. But accountable for that framework being implemented, measured, tracked, and part of our quarterly business reviews. And then on the other side, here are specific projects that design will be the, someone from design will be the single threaded owner in, in driving. Obviously also tracked by metrics, but specific outcomes that we’re gonna drive next year. And that timeline is 2023. Peter: So what you’re explaining feels quite mature, quite robust. And my sense is most of the design leaders that I know and work with wouldn’t know how to build a strategy like this, right? Because they’re not thinking about things always from that business lens or have that understanding. And so I’m curious how, how much of this was something that you created, that you said, this is my playbook, this is, this is how I make sense of things. How much was asked of by the head of R&D and your peers? Like how did you know that this was the shape for this strategy to take? Jehad: Yeah. That’s a good question. I think it’s a kind of combination. So we, we, the product team and, by product I’m using the bigger umbrella of product, you know design, engineering and product. The product team is accountable to deliver a strategy for, like, the way it works at Toast before we do planning. Like, here’s what we wanna go do next.  And the expectation was, and that’s part of the work we did as a triad, the expectation was there are product strategy pieces that cross everybody’s work. Like, how are we gonna go ship Product X and product Y is, is a combination and triads in that product area need to go and tell us what they wanna do. There are pieces though that are horizontal across the org or pieces where we wanna lean in more on either engineering or design in particular. So on engineering, think about scalability, reliability, engineering effectiveness, so on, so forth. On design, think specific rethinking of, of areas of the experience. You can think of design system and other things, but there are areas where, hey, we’re gonna take a lead on reshaping this specific experience.  Trying my best to say it without giving the specific example for 2023, not giving away strategy. But, that design saying we wanna do horizontally. That ends up being for, for engineering and design, what, what we’re sharing that are specifics, and then a point of view on how we’re gonna track across all of these different products, how we’re gonna track that we’re delivering good experiences in a reliable, scalable, secure, et cetera way.  So it’s, it’s a combination. Like there was an expectation that the triad would deliver that product strategy with specific horizontal deliveries, but also that expectation was more of, we need an experience strategy. There wasn’t really an expectation and here’s how it’s gonna look like. And I think that’s the role of a CDO, like that’s, that’s a huge part of the role of the CDO.  And by the way, that’s shared. Like it starts with, you know, we presented it to the executive team, the whole executive team. Tons of great feedback because the marketing team looks at it from their perspective. And if that’s good enough, the customer experience team looks at customer care. Service team looks at it from their perspective. The CEO looks at it from their perspective. We took that feedback, shared it with the rest of the organization. We shared it with the R&D team first, and then with all of Toast, as this is Toast’s experience strategy. This is not the design team experience strategy.  And by the way, we call it experience strategy on purpose. This is not a design strategy. This is Toast’s experience strategy. This is how experience is gonna happen at Toast moving forward. A big part of that strategy is, is the frameworks by which we know we’re gonna, we, we will, and we, we will ship a good experience and we know we’ve shipped a good experience. Calling it design strategy, in my mind, limits it to, here’s what the design team wants to do, or here’s the, you know, it’s like saying you know, here’s our…  We use business analysts, but like, “here’s the business analysts’ strategy.” If, if I tell you that’s true and then I tell you, here’s a 30 minute of it, my reaction at least would be like, “good for them. Glad they have a strategy, but I don’t really need to know,” versus here’s our Toast analytics strategy. I’m like, oh, okay. I need to, I need to learn a little bit more about that because I, I need to understand how the metrics I’m driving are gonna fall into that. So experience is the ownership of everyone. Design is the team or discipline.  Jesse: So then you are carving out a space for design within these conversations.  Jehad: Yeah.  Jesse: Yeah.  Jehad: Yeah. Design has specific ownership over key deliveries, both in terms of the frameworks, how we deliver, operationalize these frameworks. But also actually, you know, like we, we proposed and got funded for specific deliveries that will enhance our experience in, in 2023, that design owns.  By the way, these happen across the org, so like the engineering… teams that will deliver these experiences report to engineering, but design actually owns the, the, the budget and, and, and metrics for actually having these deliver and actually impacting the experience.  Handling company founders Jesse: You were talking about engaging people across the org, and there’s one relationship within that that I’m curious about because in my experience, there is a particular kind of senior executive that needs special handling in this kind of process, and that is the company founder. And I should know because I’ve been one. So I’m curious about, as you’re doing all of this strategy work and all of this visioning work, how does that work when you’re engaging with the people who came up with the idea for the thing in the first place? Jehad: Yeah, that’s, that’s a very good question. I, I think I mean, obviously it depends on the company and the founders, but at least at Toast we’re lucky that both founders are still very deeply involved and deeply care, but also recognize the scale at which the company operates now, that, that, that might not be the scale at which the company operated, you know, 10 years ago or, or, or even five years ago. That said, I think founders hold a lot of keys to not just the product or strategy, they hold a lot of keys to culture. A lot of culture gets formed by the founders and, and what they care about. And most founders, at not just Toast, most founders, you know, I’ve worked with, have deep care for experience. They might materialize those words differently, but they have, they deeply, deeply care. And they, partially, deeply care because they’ve been in the trenches selling the product, hearing from customers, getting the customer support call late at night to do something early on in their career. And that’s in, in, you know, imprinted in their, in their brains of how like, you know, the empathy is, is core to building a company. You can’t really build a company without talking to customers. And that’s really powerful because it’s also, you know, it’s also important to translate that empathy into why you’re doing the things you’re doing. So I worked closely with our founders on the experience strategy, but one of the first things I shared as an example in the experience strategy, when we went through it, the first 10 minutes out of the hour or 10, 15 minutes were three specific customer stories. Like we ran through, here’s a restaurant, the name of the restaurant, here’s the problem they’re facing. You know, Kate at the following restaurant, not to mention a restaurant name on here, but Kate at the following restaurant, here’s what happened when she used Product X, here’s how that product looks like. It is a real story of what happened. And by the way, that story represents X percent of our customers. So like, this is not an anecdote but starting with these stories was really powerful in bringing back that, you know, this is about people. This is about restaurants, this is about the, the people we care about and you care about and we all deeply care about. And these are statistically significant things for us to be, you know, paying attention to. But those stories, I think working with founders resonates a lot because again, it, it brings back the deep empathy they have for customers and the deep care they have for, for individual, you know, customers they’ve worked with, and by the way, some still Toast customers or many are still Toast customers that, you know, call the founders by name. Bridging that empathy they have to, okay, and here’s how that translates into business and here’s how that business translates into action or what we’re gonna do about it becomes really important. Like that, telling that story in that perspective. Peter: So you’re now hip deep, neck deep in restaurants and your prior jobs were much more technical. VMware, Splunk, your audience were developers and engineers, and now your audience are people like me who like to order from Cholita Linda down the block and the people who run those…  Jehad: Hopefully using Toast by the way. Peter: Oh, yeah,  Jehad: yeah. yeah.  Peter: Cholita Linda’s on Toast. That’s why I’m mentioning Cholita Linda…  Jehad: yeah.  Peter: and the people who run Cholita Linda, and I’m just gonna keep saying their name ’cause they’re, they provide my favorite both fish tacos and Cubano sandwich in the Bay Area, but I worked at Groupon and I know that the people who run restaurants are terrible business people who don’t have I.T. Functions, right. And so, so you’re, you’re dealing with a very different audience now in terms of level of savvy, the challenges they’re facing, the role the technology plays in their lives. And I’m wondering how you’ve had to change, if at all, how you approach your job as a Chief Design Officer serving these very different audiences than the very technical, very savvy ones that you might have worked with before. Jehad: Yeah, I think so. I wouldn’t call them very terrible business people. I would call them very passionate, hospitality oriented people who need to figure out the business to continue to provide that service… Peter: They might be naive business people, right? That’s not what they’re getting into it for, right? They didn’t get into it to run a business. They got into it to serve food. They recognize that in order to do so, they need a business that survives, but they don’t have MBAs. They don’t understand a lot of kind of core business stuff, that, that’s not their passion. I was being a little facetious, so that aside, how, is it just transferable, like how you led at Splunk is how you lead it Toast? Or are you having to change how you show up in the things you’re doing to accommodate now a different audience that, that your products are serving? B2B vs B2C; tech-savvy vs tech-naive  Jehad: Yeah, a lot of the lessons you learn are transferable. So, you know, for example starting from how you lead your team, how you hold yourself accountable, your team accountable, how do you build processes that enable teams to execute these things? And, and they don’t look the same at every company, but these things become lessons. You learn about what could work and what might not work. But I think you know, moving to B2B2C and specifically around small businesses at Toast, there are a lot of, lot of lessons that I’ve learned over the last six months. And a lot of advantages that you can start applying previous lessons faster to. So for example, like, speaking to customers. I’m now the guy at a restaurant, at dinner with my wife who like, you know, just gimme a few minutes and walk to the kitchen and talk to the people in the kitchen and talk to the GM of the restaurant. And, you know and when a waiter comes in, the weirdo who says, “Do you like, do you like this device? What do you like about it? What could be improved?” for five minutes. So access to customers is a lot, is very different. When I worked at VMware, Splunk, you know, you’re working with an admin who’s at a company who you have to get access to who you, you need to plan an hour of their busy day to be able to talk to them. So it’s, it’s a lot different. So getting a pulse is a lot easier than it was before. But also the audience you design for is very different. So how you think about the experience you’re delivering and the quality, the experience is very different.  In enterprise, people are willing to go through walls to get to the value. Like, as long as you’re delivering value to some extent, and that value is entrenched into how people operate, you can get away with a lot. That’s not obviously true for, you know, someone who’s trying to operate their business effectively and they’re run a small business and they’re run on thin margins and they have to get things done quickly. Like, that’s a very different set of expectations that you have to design for or, or guests or consumers that have a different, you know expectations of the consumer experience. But I think the muscle of how you deliver good experience, the intuition and muscle of how do you build a good team that can deliver these good experiences, the muscle of taking ownership of the customer experience that’s delivered, that muscle is very transferable, even if the toolbox is different. So, you know, like I think about it, if, if you’re, if you’re, I don’t know, I’m not into gardening, but if you think of gardening, planting different trees takes different types of work, but a lot of what you learn from gardening in general applies. Like, you don’t just water all your plants the same way. You don’t all, you don’t plant all of them the same way. You don’t cut the leafs in the same, you know, different seasons require you to do different things, but if you get into gardening, you know, once you’re, once you’ve learned the basics, the, the foundations and you’ve gotten good at it, then learning how to plant a new tree is a lot easier than if it’s your first. And, and every company, every role, even by the way, VMware versus Splunk, even though they’re both in enterprise, was, was a very different role.  Jesse: Speaking of those roles and what you learned from them, you’re a little bit unusual among the heads of design that we’ve spoken to in that you really sort of came out of this world of design systems and firsthand experience in spinning them up and building them from scratch. And I wonder how you feel that experience has informed you as a design leader.  Background in design systems Jehad: Yeah. So I started my career in engineering and I know most, by the way, most design leaders I know started their career elsewhere, like in, in a different function. Doesn’t have to be engineering, but somewhere else. And I think by the way, if used correctly, that’s very powerful. Like being bilingual in two things is, is like I, I joke that I’m bilingual in engineering and design. It’s a very powerful way of being able to empathize with someone else in the org but also push on them in certain ways. I think working on design systems, when we set up uh, Clarity, which is the design system for VMware, we started with, I think, at the time, two, three people, or three, four people including the engineering team. And we, we grew Clarity from nothing to the design system for VMware across 35,000 people and, and, you know, 130, 140 products. That journey teaches you a lot about what’s possible with a small team. What’s possible, you know, having to actually, and you can learn the journey in different ways by the way, but selling teams on owning a piece of their work with very little influence over that work. So you’re owning their UI layer, you’re owning their engineering implementation components. You’re, you know, without a top-down mandate. So that was, that was very interesting. But it also teaches you a lot on, on, on the, on the challenges of the details, like things that may seem very obvious, you now understand how difficult they may be, but also you understand how to balance them. Just an example, every designer at a certain point in their career implements a date picker or is around a team that implements a date picker. And you know, date pickers are very simple. If you think about it, like just from a consumer experience, like you, you go pick your flight. It’s very simple. You, you choose the date, you choose the time you’re good to go. Like if you go to, I dunno, Kayak or, or Expedia or something, but they’re actually quite complicated. Making them accessible is very hard. Ensuring that they’re easy to use for the use case you’re looking for is very difficult. The balance of that though is, you know, you hear stories about teams that have been, that spent eight weeks building a date picker from scratch. Even though their product includes like two date pickers in a workflow that like 1% of users visit. And it teaches you about value, like what matters to spend time on versus not. And you also hear about teams where, you know, if you’re a travel site, that’s actually very important piece of your business and every small improvement makes a huge difference. But that systematic thinking about the layer of who uses it, how do you build it in ways that different use cases can use it? And how do you build it in a way where engineering teams can actually use it? Like engineering productivity matters a lot. It changes your perspective about how organizations operate. ‘Cause it exposes you to all these layers of different choices you have to make on, on such a simple thing as a, you know, quote unquote simple thing as a date picker. Peter: What led to your shift from engineer to designer to design leader. Why? Why that path? Jehad: I don’t know if you have time on, this podcast, but, but I, I really wanted to be a journalist by the way. Like that was my dream growing up and that’s what I really wanted to do. Peter: Well, now you’re talking Jesse’s language. Jehad: Yeah. So when I started kind of reporting on news stories, I’m originally from Palestine, so I started reporting on news stories there. This is very, a long time ago. It was a time where you had to set up your own website. You had to set up your own thing and you have to, you know, we used to rent servers from Softlayer and you had a server every time few thousand users show up. That got me from like, oh, actually as much as I love writing, I also love writing code. So I really enjoyed the process of building that, that experience. And then I really loved being able to analyze consumer behavior and build that experience around it. Like the ability to have data very, I don’t know if you remember the, like server data. You, you actually get what the servers logging exactly, like, you, you, you’re really analyzing what server data is giving you and you’re trying to understand why people are going to this, this thing versus this other thing. That was real helpful. So as, as I started as an engineer, I always kind of stayed close to customers and that was really, was really powerful to me. And that translated into, okay, how can I better write better code to do it design systems? Before design systems I worked on a product, I was, you know, this ui slash ux role where you lead both teams. And that was kind of a transition point to me. If actually, you know, there is a ton of impact to do when you systematically improve the experience, which was through design systems and then from there, okay, like I actually really enjoy the, the impacting experiences at scale role, which is how I think about my role. Still a journalist at heart. Not a career though.  Leading in difficult times Peter: So you, you started at Toast six, seven months ago. The past six, seven months have been strange, to say the least, in any number of vectors. And I’m wondering what it’s meant for you, in terms of how you show up as a leader, given both the uncertainty that we’re seeing inside companies with the economic conditions and companies having layoffs and stock prices going mostly down, but also sideways.  But then also with your customers, particularly the restaurants who are probably also feeling a lot of anxiety and concern and, and yeah, because of the uncertainty. And just like, what, how, how do you help? I mean, you’ve gotta figure out your own way of navigating through it, but then how do you help the people that you’re responsible to on both sides, both in-house and externally? How do you see your responsibility helping them all navigate through this? Jehad: Yeah. we’re, we’re lucky in a couple ways to Toast. Restaurants are surprisingly resilient to, to, you know, I don’t want to say the word recession, so I’m trying to think about a different word. So I don’t jinx this call, but, you know, recession related things. And obviously that doesn’t remove the uncertainty and it doesn’t remove the, like, nobody could have predicted a pandemic two years ago. So, you know, like, you never know what happens. But I think the one thing that stuck with me early on in my career, I, I worked with a leader who, who was a very transparent about sharing what they’re able to share. Like, there are obviously always things that you can’t share, like, you know, financial numbers or something. But they were very transparent. And you always knew that you had all the information that you needed to have, good or bad. And it really resonated with me that there was never, like, if there was, if there was bad news, it’s not because they knew it and I didn’t. It’s because they didn’t, which is fine. Like there’s always uncertainty in any job, any time, any place. And that really resonated with me and I try to do it at work where, for example, as part of our rituals, I have a weekly all hands we call T G I T, Thank God it’s Thursday. Where we, you know, we have half an hour where I do top of mind and update the team. I do Friday thoughts every single week on Slack. What I publish here is what I’ve done in my week on Friday. Here are thoughts on things happening around the economy, the business, the, the team experience. This is, you know, where I share my thoughts, but also updates happening around the team. I have an anonymous feedback form in my email signature and Slack signature that says any question, all questions are okay. And then I answer them on Slack publicly. But basically it’s the goal of here’s all the information I know. And that that still might not be enough, by the way. Doesn’t mean I know everything or I know what’s gonna happen next week, but I know as much I’m telling you as much as I, I know. And I think navigating it with the team, versus navigating it for the team makes a huge difference. Like the team feeling involved in that, Hey, we’re navigating this together. Nobody can predict what’s gonna happen in three months, but I’m gonna tell you what I know and how we’re thinking about it makes a huge difference in folks feeling like, okay, I’m included in this journey. And being transparent about the good and the bad. Like, I’m, I’m not a fan of the term, you know, being a, I don’t know what we can say or not say on the podcast, but like an s-h-i-t  Peter: You can swear,  Jehad: umbrella. Yeah. Peter: if that’s what you’re wondering. Jehad: You know, I’m not, I’m not a huge fan of being a shit umbrella. I’m a big fan of, helping shield the team from distractions. That’s totally fair. But I think sometimes by being a shit umbrella, we hide the reality of how things operate. Which in my mind does two things: prevents a lot of good people who have good ideas from being part of that conversation; does not prepare leaders for the next step.  Because all of a sudden, once that umbrella is removed in their new role, they realize like, holy crap. Wow, okay. Like, I gotta learn this from scratch. And the team feels like, oh, you know, I’m, I’m learning. ‘Cause once you leave the umbrella, there is always more information elsewhere. So I’m learning these things not from my leader, but I’m learning it from the rest of the organization or maybe the external market. So I’m a fan of like, shielding your team, but also telling them what you’re shielding them from. If, if you are, and then being transparent just about what you know.  But for customers, I think it’s very similar, like being transparent with customers, with, with what you can, but also thinking about, you know, like, we think a lot about how Toast is gonna help you be more profitable. How Toast is gonna help you increase your margin, how Toast is gonna help you, like, we impact real people’s lives, and real, real people’s businesses and we take it very seriously.  And I think having that sense of urgency always to put, you know, their businesses first is, is really, really important. Internally, we talk about it at least, you know, one of the principles for design is customer, business, team, self in that order. Every decision you make, customer, business, team, self in that order. So we talk a lot about the impact to customers and every decision we make, whatever that decision is.  Design executives are here to stay Jesse: So you’ve worked in a bunch of different kinds of organizations and you’ve touched several times on the notion of maturity, and I wonder, as you have seen everything becoming more mature in recent years, I wonder where you see all of this going.  Jehad: That’s a very fun, that’s like the meaning of life. So, I think you’ll start seeing more design leadership positions and more design leaders for two reasons. One, you know, every CDO position now, or every VP of design or SVP whatever, you know, your choice of design position, when that person leaves, if they’ve done a good job, it’s very hard for the organization to go backwards. So you’ve just created a new role. And, if you think three years with movements, you’ve, you’ve now have a ton of organizations that might have had their first VP, their first CDO, their first SVP, but now they will have their second and third as that person goes, opens, hopefully a door elsewhere. So you’ll see more design leadership roles. But I think you’ll see more design leadership roles than design leaders. So like the funnel will open up where companies start realizing, okay, like if I’m a competitor to, I don’t know this other company, I’m a competitor to Toast and Toast has a CDO, maybe we should start thinking about it and like, you know, what does that mean for us? So even though it’s one role in some place, it starts opening it up. And growing design leaders to get there is gonna be a, a big deal. And, and then I think you’re gonna start seeing a lot more companies go back to basics of like, how do we make customers happy, and make, keep them engaged and have them, you know, stick on the whatever platform that you have. You know, we had a, I dunno, was it a 10 year run of infinite VC money and infinite, you know, stock growth, where you could have experimented with a ton of stuff and enjoyed your, you know, having 70, 80 people on the problem that, you know, to its essence is, is, is 15 people, now you’re gonna get back to like, how do we do this effectively? How do we do this efficiently? How do we do this well?  Where design can contribute a lot in how we de-risk experiences before they ship. How we dis- risk experiences after they ship. I think that’s gonna be a huge part of the conversation. And then overall I think, like, the flip side of that is if you look a little bit farther, you’re gonna have a lot more CTOs and heads of product and product directors who have a lot more experience in design. So, you know, a lot of, a lot of us been in areas where design thinking or the way design works or whatever is our specialty. I don’t think that’s gonna be good enough anymore because the product leader you’re working with will probably now know the basics to get by and knows, knows them well, or worked with a designer or design leader that was really good and they’ve learned a ton from them. You know, the bar will go higher, in my opinion, for what a designer needs to bring to the table, which is a good thing in my, but, but also means for designers just simply coming in and saying, I can help you figure out the workflow as an exam– oversimplifying, but as an example is, is not gonna be good enough. And that would change the dynamics.  Peter: Yeah, I hadn’t thought about it this way, but the, the late nineties to early two thousands were great for establishing whatever user experience became, before the bust happened, like we had gotten enough of a foothold that through the bust we were able to to emerge. And perhaps these last two or three years, we’ve seen something similar now at the highest end of design leadership, where these companies, as they scaled and started hiring CDOs and SVPs of design over the last two or three years, ’cause they were, every company has a team of 60 to 80 designers. That’s a little bit of an overstatement, but way more. And, that’s provided an opportunity of figuring out what this role is and maybe introduce this role to peers that hadn’t been exposed to it. That even if we’re retrenching, which I’m seeing across the board with my various relationships, there’s some, some flavor of retrenching happening, but there’s a general elevation of, of savvy and awareness because of what’s happened the last couple years. Jehad: Yeah. A– as an example, this is, this is a slightly, like, exaggeration on purpose or going the extreme and purpose. But if you’re a design leader, like the moment of maturity for a design leader, in my mind at any level is when you have a conversation that says, I’d rather have an engineer more than I want one more designer. ‘Cause I care so much about what we ship, that I’d rather, like, I’ll take one designer away from my funding and give it to the engineering team. ‘Cause I feel like that’s where we can make impact.  Or I wanna be involved in an interview for the UI engineer, you know, and I’m gonna care that about, I’m gonna care about that as if it’s my top hire this year. ‘Cause I know that the quality of the shipping is actually handled by the code, not just by the Figma. These conversations where you’re starting to think about, and I think they will happen more, they will be forced to happen more often in, in a bad economy, because, you know, it used to be, oh, no, no, you don’t have to say, I’d rather have, an engineer, we’ll have both. We’ll have a designer and an engineer.  That goes away now, like, we can have one. What do you wanna do? And if you’re part of that triad or part of that team, and you’re not thinking, I’d rather have an engineer because you know, I wanna ship more, I wanna like, I’ll figure out how to optimize my team, then, then if you’ve never had that conversation as a design leader and by leader I mean, you know, manager, IC leader then you should think about it. Like, you should think about why not? Because then you’re, maybe, you’re still thinking downwards on your team versus across and above on, on how can I help this product mature and especially in an economy like this. Jesse: This has been great. Thank you so much.  Jehad: Thanks for having me. Love the conversation.  Peter: Thank you. This has been awesome. How can people engage with you across the Internets? Jehad: I’m on Twitter, kind of interesting to say that now, but , It’s @jaffoneh on Twitter. Or if you search for my name and on LinkedIn as well. Those are the two places I hang out the most. Peter: I, I’m gonna give you a plug, I’m trying to remember the name of your website is, my name is Jehad Jehad: Yep. mynameisjehad.com. Peter: Okay, we’ll make sure that’s clear. I’m gonna plug that just because I’ve found it as a, a helpful resource. The writings you’ve had, not just around design leadership, but design organizations, design operations, in particular, I think you wrote about chief of staff once, that when I was doing some research, so we’ll point people to that as well. Thank you so much for your contribution today. This was great. Jehad: Thank you so much for having me.  Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Chief Design Officer for PayPal, Daniela Jorge joins us to talk about leveraging the superpowers of a designer to tackle the challenges of a leader, the leader’s role in developing the skills of their team, and leadership lessons from her time spent, both inside and outside Silicon Valley. Peter: Daniela, welcome to our show. Thank you so much for being here. Daniela: Thank you for having me here. I’m really, really excited. It’s lovely to see you both as well. Peter: Jesse and I have been talking with a bunch of what I sometimes label true design executives, meaning senior, board- facing, hundreds of people in their organization, because we’re getting more and more of them in industry. There’s still not a lot, but there are more and more, and it’s definitely a trend that we’re seeing as these design organizations evolve and as companies continue to understand the impact that design can have. At PayPal, your role is, at least according to LinkedIn, Chief Design Officer, I’m wondering how do you define that role? What are the responsibilities of the role? How are you held accountable? How do you spend your time? Just what does a Chief Design Officer at PayPal, at least, what do they do? Daniela: It’s probably not too different, I think, than some of my other colleagues who are chief design officers, right? First and foremost, I’m responsible for the holistic experience of our customers, and at PayPal we have many segments that we serve, so that also spans all of the segments. Consumers, small businesses, large enterprises, developers. We even work on some employee experiences too. So, and really thinking about those experiences from acquisition to obviously using our products all the way to online customer support and, you know, as the functional leader, for design or ux, I’m responsible obviously for the craft for how we’re delivering on all of these experiences with cross-functional teams. And then equally as important, nurturing the culture, right? And making sure that we have an environment where folks can do their best work and where they feel like they’re growing and learning. So that’s what I’m, you know, largely responsible for, in terms of where I spend my time. It maps, you know, closely to those responsibilities. The Four Components of Daniela’s Role Daniela: So the first thing is on the strategic end, is really working with partners and with the team on defining vision. So we do quite a bit of, you know, where possible, like, working backwards exercises where we get everyone in a room and we think about what could the experience be for a PayPal developer? What could it be for a PayPal consumer? And then helping to shape that and visualize that so that it can help drive alignment and excitement for what it is that we’ll be delivering for customers. So that’s number one is, almost that sort of facilitation of vision, right? Vision in my mind is a team sport. So we spend a lot of time facilitating those types of workshops. We have a few actually happening this week. The other piece, which was something that we started two years ago, our customer experience reviews. So I’m part of a two- person customer experience council, and we review almost every experience that goes in front of our customers. There are weeks when we have two or three sessions a day, where we’re looking at all of these customer- facing experiences. We’ve done, I think, over a thousand since we started. So, and our role is, is twofold. One is to bring in that, that sort of fresh perspective, right? We, we obviously know what the company’s trying to do, we know what the customer needs are, but we’re not too close to the actual work product. So we’re coming in somewhat with fresh eyes. But more importantly is also connecting dots. Right, Right. So we, we might observe areas where perhaps we’re showing up, like our org chart, which we all know is something that I, I think design is oftentimes trying, trying to address. So we connect those dots, we mind those seams in between teams and solutions. And then also connect teams that should be talking to each other, for various reasons, either because they’re creating redundant work, or again, not necessarily thinking of how one plus one can equals three, if they join forces and how they’re thinking about a customer problem. Then obviously I spend a lot of time, you know, focused on growth and development of the team, so, so running the organization, investing on individuals and their growth and, you know, spending time with my direct reports. And then the last thing is just non-UX or product work. So for instance, I’m one of the co-executive sponsors for Aliados, which is our employee resource group for Latinx, and allies. I participate also in the employee resource group for, for women at PayPal. I’m an ambassador for PayPal’s leadership principles. I do quite a bit of mentoring outside of just UX as well. So these are things that, I spend time on that are outside of what you might think a chief design officer might be doing. Jesse: Mm-hmm. Where Design sits organizationally Peter: There’s a lot there. A lot to unpack. I think we might just be spending our time going through each of these and understanding it. An organizational situational question. And then a metrics question. The organizational situation question is like, where are you in this organization? Right? A lot of even senior design leaders report up through some product function. Is that true of you or do you have a different organization? And then given all of these areas that where you spend your time, what does your leadership hold you accountable for? Are there metrics or numbers or outcomes that they’re expecting you to drive towards? Daniela: Yep. We sit in the CPO organization at PayPal and CPO at PayPal includes product, engineering, design. So it’s, you know, more expansive than just product management. So part of that three legged stool. Though, we, and then we also work very closely with legal and risk and compliance. But we sit in the CPO organization in terms of metrics. We don’t have necessarily hard metrics that I own from an experience standpoint, but we define those per project, right? So if we have a specific project that’s around helping customers achieve a specific goal, those are defined at the initiative level. That’s where more of the hard metrics live. So for us, it’s just really the quality of our experiences. Are we seeing customers call into customer support because perhaps things are not as clear as they should be? How are these experiences testing with our customers? And then are we able to influence roadmaps to make sure that those are being prioritized and that are part of, of a team’s delivery plan. So it’s a bit more qualitative in that regard. And then organizationally, of course, there are metrics, right? Things like attrition and whether or not we’re hiring within a specific timeline. Engagement scores for annual surveys, et cetera. So, in the people area, I would say I obviously have hard metrics. On the UX area, they sit more at the initiative level. And then I think that there’s always that qualitative feeling of whether or not right, the experiences are where they need to be. Vision Jesse: I noticed there’s just a lot of vision work in the description that you laid out. And it’s interesting because I see a real challenge for leaders as they get more and more removed from the roll-up-your-sleeves, do-the-design-work kind of work. Product vision starts to get to be kind of a distant thing for those leaders as their concerns become more business-oriented, more operational, more around the orchestration of the design engine, rather than being oriented around the outcome. To what extent is this an element of your style that product vision is so central to how you perform this role? Daniela: That’s a really good question. You know, as you’ve probably experienced yourselves, I think that there’s always this separation of, of design leaders who are either visionary or operational. And I actually consider myself much more on the operational side, right? What I’ve done is like, I’ve really figured out how to lead at scale, how to work well within, within large companies. I don’t consider consider myself a visionary leader, however where I think I, my strength is, is on the people side. How do you drive alignment? Jesse: Mm. Daniela: How do you drive excitement? And, and to me that’s where vision is really helpful. It doesn’t mean that I’m the one crafting the vision or even that design is the one completely defining the vision, but it’s about how do you get everyone together in a room on calls you know, whatever the, the forum might be, and then have a framework that helps to tease out that vision and package it in a way that’s accessible to everyone, right? That whether we’re showing it to the person who might be leading customer support, to someone in sales, I think that that’s where design has a real strength. And, and where we can really help is to drive that alignment and to also make it feel real so that everyone can get aligned around that same outcome and that same end state in terms of this is the North Star, it may not be, again, that detailed execution plan, but then teams can come up with their own execution plan aligned to, to that north star. Peter: What degree were you the initiator of the importance of vision? Was that something that you helped others around you realize that vision can be a tool for alignment? Or was that something that was realized prior to you, and you’ve been delivering on that? ‘Cause I’ve seen design leaders want to do vision work, but their, their partners are like, we don’t need that. We just need to ship things. And so I’m, I’m just, I’m wondering where the impetus for vision is generated… Jesse: The cultural permission almost. Peter: Yeah, yeah. Daniela: Yeah, it, you know, it, it varies and I would say that it’s probably varied for each situation and also depending on the altitude of the vision that, that we’re driving. Sometimes it might be that there’s a product area, and I might notice that teams are swirling. And people are coming in and it feels like they’re at odds, right? Or, or maybe the team is aiming too low and you’re like, ah, if we could just get in a room and think a little bit bigger and that’s where, not that that I think, you know, workshops, design sprints, whatever it is you wanna call it, not that those are always the silver bullet, but that’s where I found it’s really easy to convince people to just dedicate like three days, five days, to get in a room to, to go dream little bit bigger and to get to that alignment. And every time we’ve been able to then convince people to do that, they’re sold, right? They never wanna want to work another way. They don’t want to kick off planning a different way. So, so that, that’s what’s worked mostly, especially when it’s like at the, that product level, that initiative level. And then of course there have been times, you know, maybe there’s a very senior executive who has a vision and who comes to us saying, “Hey, can you just help us visualize this?” And through that process, you kind of influence the, you know, it a little bit more so that we’re not just the, the ones coloring in between the lines, but again, we bring in an approach where we can also help shape that narrative and, and shape it a little bit more, bring in that customer lens into the thinking. And then of course, help visualize it, right. Since that is a, a key skill that we have. Jesse: Mm-hmm. . Peter: And then how, how do you operationalize a vision, right? One of the concerns around visions is you get these very pretty concept cars. You get these very pretty imagery and videos of some future state experience that then people lose sight of over time and they just go back to doing whatever they were doing. Do you have mechanisms to turn these, this vision work into something that gets metabolized within these teams. Daniela: Yes. And, and again, it, it’s, it’s varied over time. So one of the things that, even though I’ve participated and, and driven even exercises where it was like a five year vision, I, I much prefer to drive shorter term vision activities. I feel like those are, right, much more achievable to, to the point that you’re making. I, I have found that five-year visions are very inspirational, but don’t always translate into action. So one is just picking the right timeframe for, for defining that vision. And then the other piece, which I think is really critical and important is your vision is a rough blueprint. so then you can actually work backwards from it and actually saying, if this, if these are the outcomes that we want to achieve or what we want to eventually deliver for customers, right, what’s the first step? What’s the first version of, of what we’re building, right? Are we going to build a living room, a kitchen, maybe one bedroom and one bathroom, even though eventually we want to have this amazing mansion? So, so I think it’s then that, that discipline of being able to work backwards from that vision and having that first step defined. And then to add to it also not being super precious about the vision, because I think one of the beauties of, of the work that we do is, is what you learn in the process, right. So I think it’s helpful to have that north star, but you also need to leave that open, as for learning as you go and, and for having customer input shape where, where it should go because, and what you may end up in version three may not be exactly what you had figured out and, you know, for that full vision two years ago. So I think it’s about then working backwards for the V1 and then iterating your way towards that end state. Jesse: You said earlier that defining that vision is a team sport. I’m interested in who the players are. And how you call those players to the table when, you know, sometimes the, the interest isn’t there, sometimes the motivation isn’t there sometimes the belief in what you’re doing isn’t there. How do you bring the right team together to create a successful product vision? Daniela: You know, at PayPal we’re really lucky that, that I feel like everyone wants to be included and participate and when, I mean everyone, right, we’ll have legal in the room. We’ll have risk and compliance in the room and, and it’s, those are always the best, in my opinion is when you actually have, not only in terms of what comes out at the end of that five day session, but in terms of then how the project itself plays out, right? Because people were included upfront and they actually have that, that sort of buy-in and that motivation and they understand who the customer is, they understand what, what we’re going to be delivering, what the outcomes are. And then they’re part of solutioning throughout because they were part of, of that inception phase. So, so to me, the more cross-functional, the better, and at PayPal it hasn’t really been a challenge in terms of, of engaging others. When I think about other companies where perhaps that, that has been more of a challenge we’ve been really thoughtful about thinking about the activities and then figuring out, like what’s, you know, how can you make it more accessible so that someone can maybe come in for, like, two hour kickoff on, you know, immersion on customer insights, and then maybe they just come in for like a couple of checkpoints so that they’re not from the get-go saying, “Oh yeah, I have to commit five days” to something that, you know, feels very fuzzy and feels like a, a big time commitment. So, so that really helps. It’s just really thinking about your audience and thinking about how do you close that gap between where they are and where you are. So that has worked well in, in other contexts. Facilitation and customer-centricity as design leader superpowers Jesse: Yeah. You know, it’s interesting. As you were talking, I noticed that it’s hard for me to imagine a different C-level role in most organizations, being someone who claims workshop facilitation as a core part of their skill set and their value. And I’m curious about how that plays out, how your designerly sensibility plays out among the other senior executives that you have to engage with. Daniela: So first of all, I think that that’s awesome, right? That we can claim that I think that those differentiators or, like, superpowers and things that you should lean into. So, so I think that’s a great observation. And if anything, again, I think that that’s something that we should highlight. And I think that that’s how it’s viewed by my counterparts. They appreciate that, that we actually have that skill. I’ll give you an example. We sometimes do these workshops for contexts that are entirely outside of, of product. We’ve done it with, done it with finance, we’ve done workshops around like pricing strategy, right? So, so I actually think that they see it as a very unique skill that most people actually don’t have naturally. And, and, and they, you know, it’s, it’s usually welcomed and sought after. And, and perhaps, design thinking aside, right, but perhaps it is a unique skill that we haven’t necessarily always leveraged and celebrated ourselves to, to position ourselves differently from, from our counterparts in, in senior executive roles. Jesse: What are some of the other design superpowers that you think are especially important that especially come into play at the executive leadership level? Daniela: One of them is obviously, you know, this will sound very obvious, but I think it’s being customer-centric. One of the things that, that I often hear is that everyone knows that I’m always acting on behalf of the customer. So they see me as being very neutral. So when you have teams that might be at odds or have conflict, they feel like if they bring me into the conversation, I’m going to be there with no agenda other than doing what’s right for the customer and the business, of course. But I’m a neutral party. I think being a horizontal leader also helps in that regard. You know, I’m not claiming that this is just a design thing. I think that there’s other functions that, that might be horizontal, that have a similar leverage. So, so I think that that’s a key one, is I always bring the conversation back to the customer. It’s how I’m wired. It’s how many on my team are wired, right? So we think that way and we can bring the conversation back to that. And oftentimes, I think, cut through things. that perhaps, you know, would be a little harder if you weren’t centering the conversation around the customers. If, if folks are just more concerned about ownership or what their specific products are, what their specific, you know areas of responsibilities are. So, so I think that that’s a, a key, a key strength. Connecting dots. We talked about this already, right? I think most designers and design leaders are able to zoom in and zoom out. So we’re able to zoom out, zoom way out, and figure out how to connect dots and think about the, the holistic experience that others may perhaps not be, be able to do so easily. And then the zooming in part, which is like you’re able to do that and yet you’re able to zoom in and talk about a word or a pixel on the screen, right, And care equally about the craft and the fit and finish. Jesse: mm-hmm. Peter: Given what I assume to be the size of your organization and the, and the surface area that design covers across PayPal, customer experiences, merchant experiences, you mentioned internal employee experiences, all that, just how detail oriented can you get? Or do you, do you have like themes, like, this quarter I’m all about this audience and I’m gonna kind of dig deep and I’m gonna let the other one slide. Just because one of my concerns and, and let me, let me pose it as a little bit of a provocation. Daniela shows up at my meeting and swoops and poops about something that she doesn’t actually have a lot of context. I’m trying to figure out how do you not overstep, not claim that you understand something that you don’t in an area, but still maintain that level of depth that you need to provide credible meaningful context and feedback to these teams. Without working 120 hours a week to try to keep on top of everything. Daniela: Yeah. Which I don’t do by the way. I, PayPal is really good that way and I’ve also learned that over time. So, so in a couple of ways, and you alluded to one of them first, they’re every quarter or so and timeframe may vary, I do have a couple of priorities that I’m closer to, right, that I’m involved much more beginning to end. And then myself and my leadership team, we sort of also look across to figure out like, you know, who’s focusing on what, so that we have coverage on, on the highest priorities. And, and that seems to work really well. And then the experience reviews that I mentioned are really helpful. So that is how I then look at everything else, which is these daily, you know, sometimes two, three times a day, we have different project teams coming in and sharing work, and they’re doing it at different phase in, in their project. So we’re seeing it again, also beginning to end. And in those sessions we sometimes do get it, you know, we, we go all the way to discussing product strategy policy all the way to, to a pixel on the screen. And it’s, you know, it’s helpful in the sense that we have a dedicated forum where we can do that. So, so teams are coming into these sessions expecting to get feedback at varying levels. And as we know, right, that that can be sometimes hard for teams because you’re right, I don’t have all of the context. So they do have to spend some time usually giving us context. Even if it’s a team that we’ve seen before, if three months have gone by, right, they have to reset context oftentimes, or even remind us about all of the details and intricacies of, of their specific project. But hopefully we still, you know, add enough value in terms of, not being so close to it, that, where I think that’s one of our values is that we’re not so close to it. That, that we don’t, you know, we’ve all been in teams when we were designers and, and you’ll make trade offs and you’ll make decisions because you’re so close to it and sometimes you miss that you’re doing that when you’re so close to it. So we’re able to challenge some of those things. We’re able to remove roadblocks for teams. That’s another benefit of, of these forums. And then again, just look at how, how is everything coming together? Right? How are all of these experiences hanging together because we’re looking at, at so many touchpoints. The CX Council Peter: Let’s unpack the CX Council. You, you mentioned it as part one of your core areas at the outset, and I’m, I’m very intrigued by it. Who’s on it? You know, what, what’s the, makeup of it? What, Jesse: Who’s the other person on it? Peter: Right. I think you said it was only two people. And then, what teeth does this council have? Is it, is it more like, so I have behind me the book, Creativity, Inc. By Ed Catmull from Pixar, right? And they talk about the brain trust, where there’s this group of people who know a lot and give you notes, but it’s up to you, in this case as the director, to take those notes or not. But you probably, you should probably listen to the, you know, some of the best directors who’ve ever done this work, if they’re giving you feedback. Are you giving it in in more of this spirit of mentorship and guidance and hey, did you think about or is it a bit more directive? So help, help unpack this CX Council for us. Daniela: Sure. So, So the CX Council, John Kunze, who is my manager now, wasn’t when the CX Council got set up. So when, when the CX Council was established, John was responsible for our consumer segment, and I was running design. So we were asked to, to form the CX Council by, by the CPO at the time. And then John was, John’s role became, essentially to look after CX for PayPal. So he now is in a different role that’s much more dedicated to this notion of actually looking at CX horizontally. And, I report to him now. So, so we’re the CX Council, if we will, if you, you know, had the chance to meet John and, how I am, like we, we don’t carry that label around. I’m not like big on hierarchy and labels. So, but so we’re the, the ones who were always in these sessions and the consistent sort of reviewers, right, in, in the experience reviews. And then we bring in all of my direct reports. My peer in the CX group who, who runs project enablement is also part of, of these and you’re right, 99% of the time, we’re primarily giving suggestions. If there’s something that we think is a absolute showstopper, we’ll call that out and actually say, Wow, no, we have to, to reconsider this. That rarely happens. It’s maybe, you know, only happened a couple of times, so it’s usually much more suggestions and we’re very clear with the teams that it’s up to them to actually figure out how they want to prioritize the feedback and, and what they want to take away versus not. Peter: I think the most obvious question is, what’s the difference between CX and UX? What, what does CX encompass that UX maybe doesn’t? Daniela: That’s a really good question. You know, so in John’s remit, his team works with customer support. For instance, looking at things like top call drivers and you know, how should we be thinking about prioritizing experiences to address those. So it’s, it goes beyond I think, some of the pro–, and not that we’re not involved, of course, UX is involved then in doing things in the product that might, might help with, with customers having to call because they’re having issues. But, but it will include things like policy and, you know, it’s, it’s a bit broader than, than just UX. Working end-to-end Peter: I’m trying to understand the, end-to-end here in terms of engaging with the customer experience, right. You know, you’ve got, if you look at a standard customer lifecycle from, let’s start at the beginning, marketing, customer acquisition, there’s some conversion experience, you’ve got the product experience that your teams are probably most responsible for, and then there might be some type of service and support experience. Sales might be involved there, I suppose. Given your, your enterprise orientation, do you and John cover most of that end-to-end customer experience? Are there others that get brought in? Daniela: It varies per segment. So, so let’s talk about the consumer segment ’cause that’s probably the, the easier example to follow through. And before I, I do that, I’m also responsible for our paypal.com website as an acquisition channel. Not just from a design perspective. So I am actually, I have a team of product managers. We’re responsible for the platform, the channel. We work very closely with marketing on, on that and also SEO. So not something perhaps you would typically find under a chief design officer. But it was an expansion of my role a couple of years ago and I have really enjoyed taking that on. So on consumer, we’re responsible for SEO. We’re responsible for all of, you know, for the pages that a, a customer might land on when deciding whether or not to sign up for PayPal. Then once they sign up, or if they’re logging in, that’s where all of the product experiences start and we work on with all of the teams that, that are responsible for those logged in experiences, if you will. And then we work with our customer support platform team that is responsible for online help, chat, etc. So we work also on, on those experiences and some agent experiences. So if someone calls in the tools that the agents are using, we also work on, on those experiences. So it is fairly end-to-end in, in terms of how we work. And then of course, there’s, you know, differences if you’re looking at large enterprises primarily where the experience might be a little bit different because obviously there’s a big sales component on the acquisition. Jesse: You know, you have so many different experiences that you’re responsible for, this whole diverse array, and I wonder where you choose to personally invest yourself. Where do you get hands-on in all of this, versus having a group of trusted lieutenants that you give guidance to, but otherwise really let them have autonomy over some segment of that vision. Daniela: So it’s probably not a versus, right. I, I’m very fortunate that I have a group of trusted lieutenants that hopefully have autonomy and, and who are, who are driving the work and partner with, with others. So it’s really much more around key initiatives that, that are high priority for the business that where, you know, it’s helpful for me to be involved, for our VP of Design to be involved and to stay close to it. Just, just because of its importance and because it might require, for instance, a little bit more orchestration between the acquisition part of the journey or the support part of the journey where, we can be that glue and provide that level of, strategic input, if you will. So, so it really varies. It’s usually not like one area where I would say in this area, I’m always spending my time. It changes, you know, pretty much on a quarterly basis I would say. Driving alignment when you’re not there Jesse: You talked earlier about the importance of driving alignment. And these kinds of interventions and course corrections are a great way for you to be able to drive alignment across your teams as a design leader. But it is very hands-on and very intensive. And I’m curious about the mechanisms that you’ve developed for driving alignment when you can’t personally be the one to provide the guidance to every team. Daniela: That’s a, a, a great question. I think, I mean, part of it is just having an awesome team, right? That I, that I know that they’re going to be there asking the right questions, setting the right goals with, with their partners, et cetera. So I think that that’s number one. Without that, there’s no way that I would be able to scale myself or trust that, that we were doing the right things as, as a UX organization. We’ve talked about the, the customer experience reviews. We encourage teams to come in as early as possible into those… Jesse: mm-hmm. Daniela: …right, because it’s much easier for us to figure out if teams are thinking about the right customer problems, are they considering other aspects of the experience, other teams that they need to be engaging if they come in earlier than, than if we’re already at the sort of like, here’s the solution. And then, then now we’re saying, Wow, you really need to go talk to this other team because it’s really important that what you’re doing works with, with what, you know, this experience that, that they may be responsible for. So, so some of it is just figuring out these channels for having visibility at the right point in the process on our most critical initiatives. Leadership skills Peter: In your job as kind of bringing up this team and helping them be their fullest selves, what are the kinds of things that you find that you often need to help them better understand now that they’re operating perhaps at a level that they hadn’t operated before? Daniela: They’re probably, they are a lot more, I think, around just leadership skills, right? And so, for instance knowing that, yes, we may have a vision, but we may have to make tradeoffs in terms of what we’re able to do in the short term. And that that doesn’t mean that you still can’t be pushing and challenging the team to continue to deliver more, more better experiences for the customer. So, so a lot of it is that we talk about is perspective, patience, right? Figuring out how you’re influencing, figuring out how you can sometimes measure progress in small increments. Because I, because the job that we do is hard, right? And especially because I think we are able to see what it should be and what it could be. And that isn’t always what is happening in that moment or in the short term. So, So a lot of the time that we spend is actually, I think just talking like regaining perspective so that folks don’t get discouraged. And so that we, you know, so that everyone collectively as a leadership team can do the same for our teams. And, and have them feel excited and, and sort of get the perspective that like, yeah, but if we look at where things were six months from now, look at how much we have actually achieved, then yes, yes, maybe there’s like, you know, so much more that we could be doing, but do we feel like we’re marching in that direction and do we feel like what we’re doing today, if we look at it six months from now, we’ll be like, Wow, that was pretty awesome, right? So, so I think a lot of it is just, like, perspective, patience, having a bit more of an optimistic, in terms of how we are having impact and, and not necessarily, I think getting discouraged if it doesn’t feel like you’re not getting to the end state overnight. It feels like a lot of conversations are centered, you know, much more on that. And, and, and just using each other, I think, as sounding boards and then recognizing the progress and impact. Peter: There’s this concept that comes from executive team dynamics around the first team. And typically the first team is not your or your functional organization, right? It’s your peers. And I’m wondering, one, does PayPal practice first team, do you consider product and engineering and customer experience, your, peers? And then, two, you know, this, this sharing that you’re talking about that happens amongst your leadership team, is that similar to maybe conversations you’re having with your peers or, or is the tenor of those discussions different? Daniela: So I love that you brought that up. The Five Dysfunctions of a Team is my very favorite leadership book. Highly recommend it. I bring it out at every leadership offsite I have, and talk about that concept with, the team, especially because in design I feel like we have two first teams, which, which just makes things a bit more complicated. We’ll get to that in a minute. I think PayPal is very cross-functional and very collaborative. So even though we don’t necessarily use that term of a first team, we behave that way. And then I certainly behave that way, right? I spend just as my much time with my cross-functional counterparts and building those relationships potentially even more time than, than with my direct team. And I do believe that it’s critically important for, the, you know, the UX team to lean on each other. When I was at Intuit, which was when I was first introduced to this book, I had a manager that actually said that he would consider it a success if he found out that we were all meeting without him. And that really stuck with me, Jesse: Hmm. Daniela: and that that’s been one of my goals, right? It’s always to get to that point where my direct reports are meeting with each other and excluding me from conversations. I think that that’s a really good sign of a healthy first. So, so, yes, a hundred percent, subscribe to that. Peter. Peter: And then you mentioned the dual first teams, right? And is there something different about design, maybe from other functions, where we can’t let go of our design first team the way maybe other functional leaders can? Daniela: I think that that’s true for most functional… Peter: Okay. Daniela: …organizations. I’ve, I’ve never double-checked this with product management, but I would assume it’s the same, but I, but I definitely know talking to engineering, marketing, et cetera, it’s true, right? Which is you have to balance the fact that you have your functional first team and then you have your cross-functional first team. So, so for instance, when a designer introduces themselves on a team, they may say, I’m a Venmo designer. They’re leading with usually, right, the cross-functional team that they’re part of, and then like their functional team that they’re part of. And you have to balance the two. And I think, you know, in a centralized partnership model for, for that to work well, the reality is you’re actually spending a lot more of your time with your cross-functional team. I use this, I hate to use family analogies in the context of business or work, but I, I do use one that I think is quite effective, which is, right, you’re, you’re sort of born into design, but then you marry into the cross-functional team. So that means you’re spending most of your time with that family, but you’re still having Sunday dinners and your DNA is part of the family that you were born. Peter: Mm-hmm. Daniela: And that, that usually is what I’ve seen, you know, be more effective is when you can strike that balance. Compare and contrast Silicon Valley with more traditional companies Jesse: To take a step back from PayPal for a moment. You’ve been a designer for a very long time. You’ve been a design leader for a very long time. And almost all of that experience, as far as I know, has been in Silicon Valley, which has its own unique culture, which people outside far and wide look at and speculate about and have their curiosities and their envies and often try to emulate. And I wonder, in your experiences of Silicon Valley culture, what are the aspects that people should seek to emulate and maybe not seek to emulate based on your experience? Daniela: You know, it’s actually interesting. I’ve worked in some very traditional companies as well. So I started my career at Kodak. I worked at Kaiser Permanente, and then I worked at AT&T. So I have had, I think almost like the two sides, right? Very tech, Silicon Valley companies, and then some companies that have been around for you know, more than a hundred years. So, what was interesting to me, and AT&T just being the more recent one, was that yes, AT&T wanted to emulate and learn about, like what was the, you know, the magic secret sauce that that was happening in Silicon Valley. And, and when I got into the company, I, aside from obviously the sheer size and scale of the company, there were many more similarities than differences in how we approached product development. Between the two companies, there were many more similarities in terms of the caliber of the talent. So, so I found more similarities than differences. There were some things, obviously, right, being in these companies, I think the thing that always was the most different was that the core of the business isn’t necessarily, right, the digital products that you might be working on. So that’s a significant difference in terms of just the level of importance given to it and the fact that not everything revolves around those experiences. Like there’s a whole other business that, that the company is, running, right, And that, that at the end of the day is, is most important. So it’s more of a support function in some ways. And even the way that you work, it might be that you might be in the CTO or CIO organization and the BUs have to actually fund those digital projects and you don’t get started on projects until they’re funded. So those things are obviously fundamentally different than when you’re in a company like PayPal or others where software is the business. The other thing though, that was remarkable at AT&T and then at Kodak and at Kaiser was the caliber of leadership. So in Silicon Valley, I think functional background is really important, right? And that’s how all of us rise through the ranks. It’s like you’re an amazing engineer and then one day you’re a VP of Engineering. Jesse: Right. Daniela: Same for design. And in these larger companies, that’s not the case, right? They usually groom people to become GMs. And the way that you do that is that by actually rotating through a bunch of different functions and, and you don’t necessarily have like a very clear, functional background. So, so what was interesting there is that perhaps that functional background in some cases was missing and, and should have been there, depending on the role that they were doing. But on the other hand, they were amazing leaders, because they had been selected and groomed to be amazing leaders. Jesse: Mm-hmm. And what did you feel that they brought as leaders? Daniela: Some of it was just, you know, obviously on the, on the sort of like running a business side. It was just the rigor and the discipline and the structure… Jesse: Mm-hmm. Daniela: …right, of, how you run a business, like the operating mechanisms and, and, and I think the clarity, et cetera, it was just, I think that there was just a lot more rigor and discipline. I think the, the people side, I was perhaps for- fortunate enough where I think that they, they also just had much more experience in training in how to lead people, how to lead large organizations, how to motivate people, how to communicate, how to ensure alignment of, of you know, large groups of people, where I think if you’ve only done, like, if you’re an amazing designer and all of a sudden you became a leader, like you’ve got no training in how to do that, right? It was just because you were really good at your craft. Jesse: Yeah. That’s definitely a recurring theme that I’ve been hearing among my coaching clients for sure. I’m curious about how you’ve seen the relationship between design and other functions evolve over the course of your career. Because as we’ve been talking to other design leaders and we’ve been hearing about the march toward the executive level, that design has been undergoing over the course of the last 20 years. What is the most dramatic difference between being a design leader now versus when you started out as a design leader some number of years ago. Daniela: You know, it’s funny, I, was really fortunate. Where I feel like in the companies that I worked at Design had an opportunity to work across a broad set of, of areas in the company. So for instance, you know, working closely with marketing, working closely with product, working closely with engineering and, and other areas. But I feel like that if I just look, more broadly, I feel like that that’s probably the biggest difference is more than just the traditional sort of product and engineering functions. Realizing the power of design and how to partner with design and design realizing how to partner, right, with, with more functions than the typicals, product and engineering functions. So as I talk to other leaders as well, many of us get involved in designing office spaces back when the world was very, you know office space focused. Or we might again get pulled into HR programs. So I think it’s that expansion of, of where design can play a role that, that I have observed, that, is a great, great thing to see so that we’re not just boxed into, we’re the people who design screens on the product, and that’s the only place where we add value. So, and I think it’s, it’s both ways, by the way. I, you know, my advice to people is always be curious about every function in the company and figure out, like, how they operate, what matters to them, how you can add value, how partnering with them can add value in terms of our agenda of delivering better experiences for customers or employees. leadership growth and development Peter: You mentioned one of your areas of focus was the growth and development of your team, and then we were talking also about developing leadership skills, the, the conversations you’ve had with your leaders and helping them reflect, but then also what you saw when you were outside of Silicon Valley in these, in these contexts where leadership is seen, you know, almost as a function in and of itself, distinct from your delivery functions of product or engineering or design. What have you instituted to really help the development of the people in your organization? How much have you had to do on your own versus maybe aligning with HR, you know, firm-wide learning and development function? You know, how, how have you invested in it? What kinds of things have you done that you found are effective, maybe more effective than, than people might realize? Just kind of curious how you think about that, that growth and development activity for your organizations. Daniela: Yep. So on, on the more formal side, right, of HR programs, we do get access to, to things like coaching and development 360 programs and make use of all of those, right. I find those hugely helpful, so that folks can be getting feedback and actually getting feedback from, from coaches that, that, like, that’s their, their expertise and their full-time jobs. So we have that in place for, for most of, of the leaders on, on my direct team. And, and then as possible also for, for other levels. Aside from that, I, I’m definitely someone who, you know, coaches much more in the moment. So I find that it’s really important to actually have those direct conversations about what I’m observing or seeing, and then also creating the space for them to bring in, here’s a challenge that I’m encountering, how, how might you go about it? So those conversations are always part of every interaction that we have. and they’re happening at all times. And again, I think that it’s that sounding board, you know, model that we were talking about or, or approach, which is part of it. I go to them as well for advice on things. So, so just creating that safe space, I think for having these conversations. Being really open and, and clear about, like, what each of us are working on, including what I’m working on. And then we support each other, right? So if someone might be working on, I dunno, presentation skills, to senior stakeholders, right? I’m– they’re presenting, I’m in Slack and being like, Wow, the way you just said that thing, that was amazing. Do more of that going forward, right? So that, it’s that sort of like real time feedback loop. And so that it’s also not like this big thing or like once a year thing where you’re coming in with like a list of things that they should be working on and, you know, and, and, and you don’t wanna be surprising. So it, it happens, I think, much more ad hoc, but also much more regularly throughout the week, I’m having these, these conversations with, with folks on my team. Peter: How much do you stress that, kind of, at all levels of the organization? Like, do you make sure that all of your managers are coaches as well, and how do you help everybody tap into that kind of coaching awareness so that when you’re not in the room , you feel confident that people are getting that kind of helpful feedback. Daniela: We’ve done a number of things. I would say this is a focus area for us now, just because we have scaled so much and also have a lot of new managers, and we have fantastic managers, but we also have folks that are new to being managers. One of the things that, that we’re hoping to bring back was something that when Dorelle Rabinowitz was on the team, she introduced this and it was really effective, which was manager circles. So we created these manager circles where managers were co-coaching each other, if you will. So folks would come in and they would speak about different challenges that they had and, and it would be a safe space with folks that, you know, of the same level, a couple who were more experienced. And these, these were just a great way of, of ensuring that folks were getting support from each. And as, as they were getting into managers, sharing best practices, et cetera. So shout out to Dorelle ’cause that was a really effective program and something that we’re, we’re looking to, to bring back as well. Jesse: As all of these practices and processes continue to evolve the challenges that we’re taking on are evolving as well, as you touched on. And I’m curious about what you’re excited about for the future, for the future of design broadly but also for the future of design and its ability to have a meaningful impact on business. Daniela: The first one we already touched on, which is right, how can we help businesses center decisions on the customer? Jesse: Hm mm-hmm. Daniela: And I’m someone who, perhaps because of my time at Intuit, I, I truly believe that you don’t have to, you know, make a tradeoff between business results and delivering for the customer, right? If you put the customer at the center of business, results will generally follow. So, so that’s what always gets me excited. What’s, it’s what gets me, me out of bed in the morning. The other piece is product inclusion or responsible design. So this is a program that we started at PayPal, believe it was early last year. Benjamin Evans joined us to, who had been leading similar programs at Airbnb, joined us to, to lead this at PayPal. And, and to me, maybe it’s more of a duty, right? I feel like it’s, it’s truly important for us to make sure that we’re putting our powers to action for good and that we’re not necessarily overlooking how we might be creating experiences that may exclude certain groups of people that may actually cause harm intentionally or unintentionally in, in many ways. And again, making sure that, that that’s front and center for how we actually deliver product and, and create solutions. So that’s something else that I personally am, am very excited about, Leading through difficult times Peter: Following a little bit on what you were just mentioning around matters of inclusion, and not just in the United States, but, but globally, things have been fraught for at least a couple years, pandemics, et cetera. And there’ve been some challenging times to, to lead through. And more specifically, there’s a lot of news around layoffs and so folks are starting to get anxious, right? Either they’ve lost their job or they’re wondering if they’re gonna lose their job. What have you found that works to help the people that you’re responsible to, see forward and acknowledge the very real challenges they’re facing, but also maybe be able to, I don’t wanna say move past them, but, not allow them to overwhelm them. How do you do that at your level? Keep a whole org buoyant, when things can get challenging. Daniela: It’s a, it’s a really good question, right? And I don’t think that any of us had playbooks to that, that helped us figure out how to lead through a pandemic or lead through, you know, high inflation. I think all of the challenges that, that are part of, of just being a human. In the world right now. But I think that there’s definitely certain things that as, as a leader, you can do to, to help. The first one is just acknowledge what is happening, right? And acknowledge that things are difficult. Acknowledge what, what, what is happening externally. None of us can completely like just section that off and say, Well, I’m leaving that all behind and now I’m in this meeting and none of that is impacting how I’m doing my work, how I’m showing up as a human. So acknowledging it, being transparent whenever possible, and, and that’s something that I always aim to do as a leader, is providing as much transparency and context, right? It’s, I think it’s very easy when, when you’re in a leadership position to forget that you have access to a lot more information and context that a designer on the team might not. So even if you have to deliver difficult news or difficult updates, I find that people can process that much better if they actually have context about why that decision was made, right? And why we have to, to take a certain direction. So providing context, being transparent. And then lastly, providing safe spaces for people to share how they’re feeling, how they’re doing, how that’s impacting them, whether it’s at work or at home. So those are three things that throughout. I, I would say the last two, three years we’ve really aimed to do, I have aimed to do as a leader and we have aimed to do as a leadership team. And that I think are also very true for how PayPal is and the kind of company we are. Jesse: Daniela and thank you so much. Peter: This has been great. Thank you. Daniela: Absolutely. Thank you. I really enjoyed the conversation. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s peterme and I’m JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Global Head of Design for Expedia Group Rachel Kobetz joins us to talk about staying connected to the work while keeping sight of the big picture, getting past zero sum thinking in building partnerships, and the importance of intentionality in leadership. Peter: So Rachel, thank you so much for joining us today. Jesse and I are talking to a lot of truly senior design leaders. And even though we don’t know you directly all that well, you’re working with my co-author Kristen, who Jesse worked with extensively at Adaptive Path. Defining the role of Global Head of Design Peter: You’ve been building a really impressive design organization at Expedia, and we wanted to learn more about that process and unpack that. So thank you for joining us. The question that we’re asking everybody to start, the conversation with, we’re just diving right into the deep end, you’re an SVP and global head of design at Expedia. How do you define that role? Like, what are the responsibilities, to what are you held accountable? What’s that job? Rachel: All right. Well, thanks for having me first off. And you know, the role is rather interesting. It’s a transformation role. So if I think about, you know, setting the vision and the organizational leadership for getting us to become an experience-led company, that’s essentially the bulk of what I do and that’s across three areas. So my charter is to transform the experiences, transform the function, and transform the company, small task, you know. Jesse: Mm. Peter: No, no, no big thing. How– so. So that’s a big definition of the role, how well did they understand that when they brought you in ,that, that this is what they were looking for, was someone to do this kind of transformation, versus you, through engaging them as they were looking maybe just for some design leader, through some engagement with them, you helped them identify this transformation opportunity? Where was that conversation when you started? And I guess now almost two years in, where is that conversation now? Rachel: Yeah, I think it was both, right? So, in conversations I had, even when I was, you know, starting to explore the opportunity, talking to our C-level, our, our CEO and, and all the leadership across the company, there was a hunger, right. To… what is the type of company we’re gonna be on the other side of this thing, right. You think about COVID and all the stuff that was happening at the time, and space for innovation. And space to define what is the DNA of the company, what is gonna be the culture of the company? And there was an understanding that customer experience is our competitive advantage or should be our competitive advantage. And in order to get there, you have to become an experience-led company. Some people call it design-led, but you know, I, I definitely go out the door, calling it experience-led. And in those conversations, when someone says, I wanna become this thing, they have to understand what that takes, right? It’s not just something that you kind of like slap on a poster. It requires transformation of the culture of the company and the way that you work and the way that you operate to get to that point. And so that’s the type of conversations I started having. And so part of it was them having an understanding and a growth mindset of what they wanted to become and how they wanted to transform as a company, moving from transactions to relationships and what that takes. And then the other piece was me having conversations, starting to talk about what that could look like. And so for me, it’s very important, no matter what environment I’m in, that people know what they signed up for. Number One. And, and, Two, that we’re creating the environment for strategic design and we’re setting up the role for success. And so there was a lot of conversations about, well, what does it take to do that? Because just bringing in an executive in itself, if you don’t create the conditions for that executive to be successful, you’re not gonna have the outcomes that you’re looking for. You’re gonna have kind of the, the hero mentality where this one person is going to change the world, versus being able to have the entire environment foster and nurture that type of strategic design culture, essentially. Peter: How long were you talking to them before you joined? Was this over many months, were, how many conversations were there? It sounds like, and, and this is something I encourage, but rarely happens, it sounds like there was a long kind of courtship to make sure this was the right fit. Just, you know, practically what did that involve? Rachel: It was over the span of a couple months, because, you know, I had to make, you know, we all wanted to make sure that it was the right thing, right. Bringing in the right person, making sure the environment was right and making sure that you’re setting the role up for success, as I mentioned. And because the charter is, it’s a large charter, but it’s also for the first time ever, it was to build a centralized function for the entire company. And I’ll, I can talk a little bit about what that looked like, because we were separate brands for the longest time and we were operating that way. And it was the first time ever, they were bringing all the design groups underneath one leader, right. So that’s a major shift. So there was a bunch of conversations we were having. And what that allowed me to do, though, is to get to know everybody, right, to understand what you’re walking into and who are gonna be your partners, and then to also set the stage and create the runway. So the leadership at the company was setting the runway for people to understand what’s the charter of this person coming in, in the role, what are they here to do and how can we best support them and partner with them. And so that, that amplifies or accelerates the level of impact you can have in the first year, cuz as you know, the first year is usually foundational work. And so that accelerated the amount of impact I was able to make in the first year in that foundational work. Stuff that would’ve taken probably a year or a year and a half was like the first six months. And so that, that to me was major. That sets the, you know, sets the ground for awesomeness in my, in my mind. And because this, this centralized function works across the entire company that is, you know, you know, creating and defining experiences for travelers, partners, agents, developers, and employees. And so there has to be this, this galvanized support or this, this, this like coalition of the willing, right, across the company that is, you know, not just interested but aligned to what that means. Establishing relationships with your existing leadership team Jesse: It seems to me that one of the most crucial groups of partners for you to recruit, to achieve these kinds of outcomes so quickly, are the people who would be your direct reports, the people who were the leads of these individual brands, who previously had, you know, their own domains entirely, never had to think about anybody else’s problems. And I’m curious about how you went about establishing those relationships and establishing a way of engaging them, engaging with them and engaging them with each other at this larger scale. Rachel: Great question. So definitely, when you wanna build a world– world class organization, it starts with bringing in world class talent. It, it’s a mix at my table of people that are subject matter experts and have been in the company for a while, and, you know, kind of people that have been there a couple years and people that are net new. And I think that’s a great mix to bring in so that you’re not just like completely flipping over the table, but you’re bringing the, the best-in-class individuals for the specific roles that you need. And so I did a couple things. I identified what are the needs for each of the roles to be successful? These are pivot roles, right? To your, to your point. Like these are crucial roles and they have to operate as a first team, right? They cannot operate… they can no longer operate just in their domain and just their group. They have to actually operate as a first team, together, in order to get the best possible outcomes, and also to be able to work across and up, across the company. And so that was really important to me. So it, part of it is the dynamics at play, of, like, the expertise, the personality, how they show up, what is their, you know, what is their presence? Who are they gonna face off with in the company and how are they gonna be successful in those environments? And then what are the embedded capabilities that I needed to build? What do we have today versus where do we need to get to, to be strategic design, right? As far as like, what, what, we didn’t have design operations, right? So that was one of the first things I went after to build. We didn’t have service design, you know, you think about all these different capabilities. We had to be able to build them and, and start those practices from scratch, the ones that we didn’t have. So it was very important for me to bring in the right leaders, bring them together and have them start to have the mindset and behaviors of operating as a team, not just a bunch of high performance individuals that happen to work together. Jesse: Mm-hmm mm-hmm. Peter: While all these designers now are reporting up through a single centralized design organization, have you maintained teams that are brand by brand, or did that all get kind of shaken up as well? Let me start with that question. Like what are are, because, well, actually let me not start with that, just that question, because you mentioned service design, right? And so I’m wondering with service design, is that looking across brands, like in some broader holistic experience, what is the interplay with some of these more strategic, centralized design functions and what I would imagine in a company like Expedia, and you have Expedia, and you have VRBO and you have all these distinct brands that I would imagine there’s teams specific to them. How does, how does that interplay work? Organizing by customer and their journey Rachel: Yeah, that evolved. So, we instead organized by customer. So, when you think about the traveler, you think about the journeys for the traveler. There’s a lot of similarities across those journeys and you’re designing for those journeys, right? So instead of just having a VRBO team and just having a brand Expedia team, even though we’re building out those brand experiences, we’re actually looking at it more holistically. So we’re looking at the end-to-end across the different phases of the journey. And those things are very similar, right? You think of, you know, I am in discovery mode, I’m in dream mode. I am shopping and I’m booking, right. You’re working across those journeys. And so it was it was a shift in mindset to be able to then look at things crosscutting and look at things more holistically instead of looking at them either only by brand or only by specific function or feature, which was a, which was a shift in the company. And so being able to start having conversations about end-to-end, allowed us to start to shift that mindset from product roadmaps to experience roadmaps. And, and that makes it so that we’re talking about, well, what are we delivering? What value are we delivering for our customers or for our travelers? And, and then what are the things that need to be true? What are the services and capabilities that need to be able to light up that experience? And that’s a different way of working. Jesse: Mm-hmm.. Peter: Is is that end-to-end specific to design or did product and engineering also adopt this structure? Rachel: They’re looking at it the same way. And I think, I think that’s required. None of this stuff is done in isolation. It’s so important to have very strong partners in the different functions so that you can be doing this together. You know, we, we talk about it as not just three in the box, talk four, box– four in the box, sometimes five in the box to be able to get this done, ’cause we’re working with, you know, data science. We’re working with ML, we’re working with marketing and brand, right? So they’re at the table as well, not just product, design, and engineering. And so being able to look at things more holistically, everyone’s at the table and caring about the quality of the experience. And I think that’s where you get success. Jesse: So in engaging these partners, it seems that you must have gone through a process of some education, some evangelism, some reframing of design, its role, its value to shift it toward this more strategic emphasis. Tell us a little bit about how that went for you. Rachel: Yeah, sure. You mean the road show? Jesse: Yeah, sure. Rachel: yeah, Peter: If that was part of it, yeah. Rachel: Yeah. I mean, it depends on the level of maturity in organization, right? So if you have an environment like like Expedia, where you had a world where there were multitude of brands underneath one umbrella, and they were all operating as separate companies. You could imagine that when you bring all of that together and you’re looking at it and delivering as one company, you’re gonna have different levels of maturity throughout the organization. And so we had some parts of the organization that were already operating, like, operating like mini Frogs and IDEOs, right. And then we had other parts of the organization where design was an execution arm, right. Or operating a completely different way. And so because of that, it was a– it’s, it’s mixed. I always talk about when you’re going through change management, it’s gonna be mixed maturity across the board. You’re gonna have some people that just get it and wanna drive with you and, and they’re ready to roll. And then other people have to be educated and brought along in order to get to that place. And so, it was a mix. It was a mix of finding the people, when I mentioned coalition of the willing, it was a mix of finding those people, and those people that could be champions with me, those people that could be the, the beacons. It’s really important to find, not just the individuals, but the projects or programs that can be the beacons to showcase how a new way of working yields better outcomes. And so that’s part of what I did. So part of it was a little bit of a road show talking about, like, what does being experience-led mean? And what does that mean for the company and how does that translate to how all of us show up every single day to deliver a better customer experience? And then part of that was bringing people along and using programs themselves to then become those, those proof points or those case studies of this new way of working. And then you get to a point where you’re leaning into operating models, right. And, and codifying those operating models. And then, you know, part of my job is delivering for the business, right. And so becomes a measure what you’re doing. So benchmarking what you did before, and then measuring the, how you’re moving the needle is critical to be able to also then bring up people along that don’t have that same mindset initially, where they’re already in it. Like they already get it. They, they actually need to be convinced. Usually the data is what can do that. Communication strategies and tactics Jesse: Hmm. You mentioned creating these beacons that showcase what’s possible and kind of can lead the way for the organization, and one of the challenges in an organization of your scale and of your complexity is just getting the message out about your successes, especially in these environments where people have historically been isolated, blinders on, focused on their own sort of corner of the kingdom. How did you make sure that people knew about these– how did you make sure that these beacons got in front of people? Rachel: I used any vehicle possible. Jesse: Hmm. Rachel: So, you know, and it, it’s not, it’s not, I’m definitely not always looking for perfection, I’m looking for that progress, right. So you know, you think you’ve said something a couple times, you think you’ve talked to people and they understand, but you have to overcommunicate so that the, the, the essence of it is just overcommunication. So all the different vehicles at my disposal, leveraging every single one. So whether that is in a conversation with another executive in a meeting, and being able to have that moment to talk about the great work that the team is doing, or that our two teams are doing together, right. Being able to highlight that. Creating a newsletter. Doing my own writing and, and pushing it out across the company. Whether it’s in town halls or, you know, showcases, quarterly events, all of the different avenues you can take, you have to use those as opportunities to get the word out. And, and, because also people absorb information differently, right? Some people are gonna love watching the town hall on video, or being there in person. Some people are gonna love being in the process with you and learning by doing. And then some people are gonna love seeing that, that readout of the impact that’s been created and they like the newsletter. So it just depends. But it’s, you’re essentially, you know, you have to develop a communication strategy, and I’m still going, we’re still going through it as a team, like as an organization, it never ends, because you can have created, you know, the best possible thing that went out the door for the company, and it has huge impact, and the very next day you’re like, okay, what’s next? So you’re not, you know, you’re never done with that communication. Peter: As you’re trying to make this transformation, as you’re trying to shift people’s mindsets towards one, that’s more experience-led, experience-driven, what are the stories that you find are compelling, that, that help people understand what it is that you’re trying to achieve? Rachel: Yeah, there’s a couple. So you know, telling a narrative about a person, right. Telling someone’s story, right. And bringing people in and bringing them close to the customer so they can understand. And you, you bring those insights that you glean through research to life, right? We’re very comfortable doing that. But the piece that actually connects the dots for the business is when you’re aligning on shared outcomes. So the narrative that you’re telling is aligned to the outcomes that the business is trying to achieve and not just for, you know, the bottom line, but also for our customers. So, in this case, travelers, partners, developers, et cetera. And so the way that I found it’s most successful is, instead of being in our own heads, in our own kind of black box of magic sometimes, that design can be in, where people don’t quite know what’s going on in there, you instead open up that box and you create transparency in the process. You bring people in, you make them part of that process from day one, but then when you’re telling the story of it, you’re starting off on the foot of, we’re all aligned to shared outcomes. Like, meaning, like, what are the metrics for success? How are we measuring this? If we do this or, or what’s the goal we’re trying to go after, and then working backwards from that, what has to be true leading up to that, to know that we’re on the right path. And then you have kind of, like, milestones or checkpoints of, of progression throughout that. So you’re not just at the very end talking about the success in the case study, people are feeling the progress. They’re seeing the progress over time cause they know what to look for. And so then when you get to the point of, you’re talking about the case study, you kind of wrap it up and that becomes your proof-point of, like, here’s the beacon program that we did and look at the great outcomes. Everyone was already aligned to what success looks like. And so when you then blow the doors off of whatever those metrics are, everyone is like shouting from the rooftops of how awesome that was, how they felt completely engaged. They’re excited. Why are we not doing this everywhere? You, you, you create this environment that people get excited about, versus having to try to convince them that this process—and, and I think that’s the thing, don’t, don’t harp on the process itself. Actually focus on the outcomes, and when you have shared outcomes together, you’re gonna be set up for success. So the case studies in my mind always need to talk about, like, who are we designing for? What do we know about them? What are the goals and the outcomes we’re looking for? And then you are telling the story of how you got there and that it’s, that’s, in its essence, the simplest way to do it from my perspective. Managing change Jesse: I’d like to go back a little bit and ask about this wholesale reshuffling of design away from your brands and your products and toward journeys, because when you described it to me, it sounded to me like a recipe for just an army of unhappy designers who previously had their own sandboxes and their own toys that they played with, and their own rules that they played by, and now kind of having this new structure foisted upon them that is forcing them to let go of some of the things that they held close. And for you, potentially, you’re a couple of levels removed from them in the organizations. How did you reach out to and engage that population as part of this change management process? Rachel: Yeah, it’s a great question. It’s, it wasn’t just happening to design, right? This was happening across the whole company. So if we think about how the, the organization was evolving and shifting, and we moved from a world where individual brands were siloed and kind of optimized for that system itself and vertically integrated, we moved to a world where everyone is working together and thinking more holistically about the work. And so it wasn’t something that I was off in my corner or in my function saying it’s just happening for design. This was something that was happening across. We were all going through this change together. And yeah, to your point, people can associate an identity with a brand, right? So you have that piece. But I had less of that. And more of, how do we take the goodness of what we learned working in this space for so long? And how do we translate it and cross-pollinate it across the whole company to, like, raise the waterline for other parts of the organization. So it was less about like, worried about, like, well, this is who I used to be and, and, and how we used to function, and I don’t really know what this looks like. It was more of a, how do, in this new environment, how do I become successful, and how can I con- contribute so that all of the work gets better? So I didn’t find that that we had people that were unhappy in that way. In in fact, they were more galvanized to our vision of where we’re trying to head to become an experience-led company. And so that, that becomes that ignition of, of awesomeness, right. But, but I did, but there was, as part of that change management, there is an evolution that had to happen with designers, right, in, in the, every day of like, well, how does that change? How you think, like, how does it change when you move from designing for one feature on a specific brand, to having to have a more platform mindset, right? That’s a complete shift for a designer on a, on a daily basis. So not just myself, you know, my entire leadership team, their, their directs. We were all having those type of conversations. I even set up some, you know, round tables. I tried to keep, we have every quarter, we have like a more formal town hall, but then monthly, we do what’s called, like, a monthly meetup. And it’s almost, like, a very, like, lowkey Q and A, where we talk about, like, what’s going on? What questions do they have? I have some updates and things like that. And so that time, that type of format or forum, I find works really well to get people to talk. You know, what’s on their mind, what are they thinking about? And you’re very accessible. You’re very approachable. So I did everything from, like, skip levels to, you know, having, like, you know, mini, like, fireside chats to, you know, roundtable discussions, any kind of forum to make people understand that we’re all in it together and we’re all creating this thing. And I, you know Doug says this all the time. Doug Powell, as, well, like, it’s a prototype, right? We’re creating a prototype together and we’re gonna iterate on it. We’re gonna make it better. And so, so yeah, I didn’t find, I didn’t find that people were just, like, not into that evolution. It was more of, like, trying to understand their place in what that evolution looks like. Jesse: Mm-hmm. What role does brand play now in your design organization? Rachel: Oh, a huge, a huge portion, because even though we’re thinking holistically about the experience, there are, we still have brands, right. And so we’re still thinking about those branded moments across those experiences, high brand and low brand moments. And so we have a very strong partnership with brand because we wanna translate the essence of the brand into the product experience. Right? Jesse: Mm-hmm Rachel: So that’s an, that’s an everyday conversation. So, earlier, when I mentioned that it’s not just three in a box, it’s like four and five in a box, it’s ’cause brand’s at the table, too. And so we never, we never lost that thread. Peter: Are the brand designers in your org or are they in a separate organization? Rachel: They’re in the brand organization, but we do have some designers in our world that are part of the design systems team that are thinking about what is that brand expression in the product experience. So there’s a really nice symbiotic relationship between myself and the brand organiza– or our organization and the brand organization to be able to create that cohesion across all of those different touchpoints. So we didn’t forget about the brand. Not at all. We just work, we work at it from a different angle in order to be able to have more– to make, to make the work extensible, right. To build once and then be able to use it across. Jesse: Yeah. Peter: Following up on Jesse’s last question, and you mentioned these town halls and kind of a, almost like an Ask Me Anything. I’m curious, what are some of the, the themes that emerged through those conversations over the last year and a half or so, coming from the design organization? What’s working, what’s not, and I’m also curious, what’s surprised you coming out of those conversations. Were there things that you didn’t foresee or didn’t realize that started to emerge that you needed to address? Rachel: Yeah, ironically one of the biggest themes that always comes out of these conversations or, or that I’ve noticed a pattern is that we’re talking about operating models. And so one of the things I noticed was when we would talk about like, well, how do we work in this new way? How do you know, how are we evolving and what do you need? What do we need to unblock? A lot of times it was because parts of the organization, as we’re all transforming together, We’re still, maybe, operating in silos, right. And you have to break down those silos to be able to orchestrate an experience end-to-end. And so when other people are still getting their mindset around, or their head– headspace around what that means, usually the things that you have to enable for the groups are new operating models. And, you know that became a theme that came up pretty early because you’re operating across, like, what used to be eight teams to be able to get one experience done. And this is in any, you know, any complex organization, any matrixed organization, you have to work across multiple teams, there’s interdependencies. But to the customer, it’s all one experience. And so you have to break down those, those barriers or those walls for the designers, for the researchers, for the content designers, so that they can do the best work that they can, right? And so in those town halls, one of the things that came up was like, how do we evolve our operating model? How do we, you know, evolve our practice, or our process for a world where we want to increase quality, increase velocity, and be experience-led. And so those, those are some of, like, the deep conversations we had. Some of the other conversations are just about change management, right. You know, people handle change or evolution much differently. Like, you know, you have some people that are, like, this feels awesome. I love it. You have other people, you know, they think– those are the people that say, like, change is the only thing that’s constant, right. And then you have other people that are like, wait, hold on, you moved my cheese, what happened here? Like, you know, I was used to a certain way of working or evolving. What does that look like? How do I show up? And that goes back to my earlier comment. Helping people manage through that. The other thing that came up, which was surprising, to answer that question, is that– and, and I thought it was a actually awesome, a lot of our principals felt like they were becoming unleashed by operating in a strategic design environment, right? So they were used to focusing on one feature or one domain or one area, but by, by being able to look crosscutting and looking more end-to-end, more holistically, they could actually have much more impact. And so that’s, that was a, an upside benefit of this new way of working, was to be able to leverage their talents and their skillset, a lot of our ICs across the board in new ways. And so they didn’t feel necessarily, like, you know, sometimes people talk about being, like, I’m in a box, I’m in a category. I only can do this thing. It actually unleashed people to be able to say, you know, to really stretch themselves and to unleash their talents. So it, it fostered, I think a lot more of an education and mentorship across the organization as well. Going deep with everybody. Playing nice between strategic design and product management Peter: However much, we want to think a rising tide lifts all boats, the reality of humans is that there’s, there can be a perception of zero sum. Your benefit is my deficit, and I’ve noticed this in between, as design teams get more strategic, product managers start getting nervous. They start getting anxious ’cause they’re like, wait, that was my job. I used to be responsible for product strategy. I was responsible for that vision. Now, now, you, a designer who doesn’t have an MBA and who draws pictures all day, are trying, you know, is coming into my realm. I’m, I’m being hyperbolic here but I’m wondering how, as your organization has gotten more strategic, how you’ve handled that relationship with product, because that’s usually like that’s, that’s where magic happens or where like implosion happens, is, is at that, yeah, is at that relationship, and I’m so I’m wondering kind of how, how that’s and, and as these product folks who maybe in the past were in charge, ’cause a lot of organizations, product kind of had that authority. It sounds like you’re shifting to a model, this operating model where there’s probably more there’s meant to be more partnership. And so how, how is that playing out? Rachel: Yeah, that’s all– that’s always the thing, right? Because it’s a change in power dynamics essentially, when you’re going through this type of process and, and some are more open to it than others, I think. I think we use the term running buddies, which I think is a very good term to use, to have the right mindset of like what we’re trying to achieve together. To your point though, I, I think that it, it requires relationships and trust, and in order to be successful, to have true partnership, right. You have to trust each other and respect each other’s expertise. I definitely follow suit with the, the, the way that Apple is set up, where experts are leading experts, and they hold decision rights for their specific function, right. And so if you were in a world where in past lives, or in an environment where design didn’t actually hold the decision, right, on design, it’s, it’s a different type of world when you’re trying to then change those dynamics to then have an even playing field where product, engineering, design are showing up together as, as partners. And so, that requires time, and, and going, you know, going deep on what that means, figuring it out together. And also building strong relationships and earning that trust because otherwise, if people do not look at it as assuming positive intent, to your point, they look at it as, like you’re coming in on my territory versus instead, wow, all of us are coming from different perspectives and bringing different expertise and together we’re actually awesome together, right. Versus looking at it as like, oh, you leaning in on that thing takes away some something from me. Instead it’s more of like a 10x, right. You’re more amplifying each other. And so it’s all about, from my perspective, it’s all about the, the way you show up. The, the relationships that you have with others, the way you build those partnerships and the way that you earn and keep that trust with each other. I think that that is the biggest thing. Like, the most pro– the most problems that I see happen with teams or individuals is, is usually due to two things, communication and trust. And when you don’t have those two things, you’re not gonna get very far. So, so what I– I really take the time to communicate. I take the time to stay, like, to get in sync with people and then sit, like, stay in sync. And then I also take the time to build those relationships. And I encourage all of my leaders, not even just people at my table, like throughout the whole organization. I talk about, you are your actions, how you show up every single day sets the environment. It sets the culture. It, it determines how people treat you, and how they interact with you. You, every single moment you have, whether it’s in a conversation, a meeting, a presentation, you have an opportunity to change that environment. And so by being that way, then when you show up with, you know, whether it’s engineering, product, brand, et cetera, if they understand why you’re there and what you’re trying to achieve, and you’re aligned on shared outcomes, they’re going to be much more receptive and open to a new way of working versus you just come in and say, everything you’re doing is wrong, and this is how we’re gonna do it, right? Like that’s, that’s not gonna get you very far. And I think, I think sometimes leaders, they kind of come in with that kind of bravado and you’re not gonna get what you, you’re not gonna get the results you’re looking for if you’re coming to the table with that, with that perspective. Relationship dynamics with peers and executives Jesse: It seems to me, there’s an element in that of, trying to influence the culture of your partner organization from the outside. So that, you know, all of your product partners throughout the organization are engaging with design in similar ways. And to my mind that comes back to the relationship that you have with your peer on the product side. And, and I’m curious about the negotiation that is involved when you are elevating design to, that executive level where, you know, now there’s a new seat at the table and you’re in it. And, and they’re trying to figure out how to engage you in the conversations that they’re used to having. What did you do to establish those relationships and establish those dynamics? Rachel: Yeah, I kind of love where this conversation is going and how deep we’re getting in this area. I think it’s so important. ‘Cause I don’t think a lot of people talk about this stuff. So in, in that regard it, I, I take, you know, I take my own advice, right. You know, I, I lead by example. So the same thing I just mentioned about, like, what are the expectations I would have of anyone at my table or leadership in my organization about, you know, earning trust, building relationships, having, you know, clear communication. I’m very direct. I’m a very direct leader, like, as far as, far as communication goes. I, I don’t, I don’t waste words in that way. By the same token, you know, every moment in every interaction is a moment that you could have of influence, right. And it– but you have to have a foundation. And so it, it was very important for me to build relationships with the other functions and the other leaders across the company. And then we’re talking, you know, not just in one part of the organization, we’re talking about leaders across the organization. And, and I look at that as– there’s a term teaming, right? You’re not just, it’s not just your first team, that’s in your direct vicinity, but it’s also, how are you teaming across the company to get to specific outcomes, right? You have different teams that you have to interact with and work with. And so for me, it wasn’t just the relationship of the people in my immediate vicinity, but it was also those relationships and how I’m building team, like actually teaming with others or becoming a running buddy with others across the organization. So those, those relationships are critical, because that’s where it starts. So if you’re not aligned, so let’s just give an example. If product and, and design together, as leaders, are not aligned, that dysfunction flows throughout the entire organization because that, because the product organization is hearing one message and the design organization is hearing another, but if you’re spending the time to get in, like joined at the hip and you’re getting, you know, getting together and having alignment in what you’re trying to achieve, how you’re gonna get there, then the communication that happens throughout the organization is, is aligned. And so you can go deeper in the organization. You can ask that same question and they’re going to pretty much respond very similar, whether they’re in design or product. So, and that’s not easy, that takes time. Because again, you have to earn the trust. You have to build the relationship and you also have to influence others to a new way of working together which does take, you know, effort. And, and it is kind of an evolution that happens over time that doesn’t happen overnight. And then from that base, that solid base and foundation, you can then push that communication. And that, that, this is how we show up. This is how you should show up. And kind of people are seeing that from their leaders, they’re gonna start to emulate that. That’s, that’s how I’ve approached it. So I, I definitely am one of those people. I’m like, you know, I wouldn’t say I don’t tell my team to do something that I wouldn’t do. And so when I’m talking about the importance of the relationships, it’s where I spend a lot of my time. So I spend a lot of my time, you know, working across and working up across the, the whole company to make sure that there’s clear communication, there’s trust and, and we’re building relationships so that people understand what we’re doing. You cannot explain to people enough what you’re doing and why you’re doing it. Peter: When I teach design leadership, one of the things that’s both true, but in some ways, unsatisfying, is, what I say over and over again is: it’s about relationships. And I just find different ways of saying it’s about relationships for four hours. But that’s the reality. You use the term running buddies. I tend to think of it as, I get more mammalian, and I think of it as like primates picking nits and grooming, right. There’s just something very primal. Well, there’s something, there’s something very primal about the, the nature of, of how we relate and, and that affects our work. And we, we, we lose sight of that, especially I think working in, I wouldn’t even just say design, but like product development, ’cause I’m sure this happens in engineering too, where for so long, your value was in your ability to craft and make, and then at some point, as you become a leader, your taste, your discernment is important, but what becomes more important is now this ability to engage and relate with others towards some, some common goal. You, you mentioned directness and I’m wondering, you know, I, too am a direct communicator and that has not served me well inside organizations. Rachel: You don’t say, Peter. How to communicate directly without upsetting or pissing people off Peter: And, and, and so it’s not simple enough to be direct, right. And so how have you learned, how have you developed a communication style that allows your directness, but that doesn’t come across as, I don’t wanna say attacking, but like too assertive or aggressive, right. ‘Cause that’s been criticism I’ve received, is that when I’m direct in feedback or engaging with someone, it can feel like, oh, like overwhelming and, was that a challenge that you had in your directness and what have you learned in terms of how to communicate, so you can maintain, be authentic in, in your direct style, but not deflate people with what might be seen as criticism or something. Rachel: Yeah, Jesse, we’re going a little deep on Peter today. Maybe he should tell us how he really feels. So yeah, so for me it there’s a couple pieces there just because I’m direct does not mean I’m directive. So I can be very forthright. I can be very transparent, but it doesn’t mean that I have to come in with a hammer, Jesse: Mm, Rachel: or be prescriptive, right. And so my approach has always been explaining the why behind something. If people have the why behind something, they don’t feel like it’s happening to them. Number one, they don’t feel like it’s being prescribed. They don’t feel like you’re just telling them what to do, instead you are giving them transparency. And I think that they appreciate that. I’ve been told throughout my career, how, how much people appreciate my transparency and my directness in that way, maybe I can help you, Peter. Maybe we should talk offline. But, but, but and that’s because of the delivery, right? You can say the same thing, like the same sentence you can see on paper and how you say it, how you deliver it, or the nuance of it can be received completely different and you can be direct in your communication and people can walk away smiling, or they can walk away pissed, right. So, so I think for, you know, my, my perspective is that it’s, it’s definitely about being transparent and it’s definitely about making it so that people have the information. They need to be able to make informed decisions, because I, you know, I don’t wanna be the person that’s making decisions for them. I want them to come to those conclusions on their own, but I wanna inform, like, I wanna give them the context that I may have or the why behind something and why it’s happening so that then they understand it before they then go and, and, and go off and do something about it. So that’s how I’ve approached it. I think it is, I think it’s empathetic. It’s a directness that’s sympathetic is, is kind of how I, how I approach it. Instead of one, that’s more like, more of like a top down mentality of like the hammer, the golden hammer approach or a prescriptive mentality. So it’s a little bit different. The qualities of a good design leader Jesse: You’ve talked a bit about the mindset or frame for the work that you try to instill in your teams, and a big part of making that happen are the leaders within your teams and your, the philosophy of leadership that you establish for your organization. What are your thoughts on what makes a good design leader at every level? Rachel: Oh, this is… how much time do we have? Peter: Yeah. Rachel: This is, this is a meaty one. So it starts with, for me, they need to be able to have vision. They need to be able to understand what operational leadership is, meaning ’cause they have to work through others to get things accomplished. They’re not gonna be able to do it all on their own and they need to be able to show up in a way that carries the torch for the culture. And I know that sounds a little cheesy, but that’s, that’s definitely something that I look for. Meaning someone that’s going to be in a room with other people. Are they carrying the torch for our craft for our culture? Are they, are they helping others see the, why are they helping others see the strategy? Are they helping them understand what great looks like and how to get there? What is their definition of success? So for leaders to be successful or my, my perspective is it’s three things. You’re, you’re managing people, you’re managing process, but you’re also, you’re you’re also managing operations, operational leadership in order to galvanize things and bring them together, to be able to get to specific outcomes. And I think that where, where leaders can fail is if they over index in one area and ignore others. And so an example of that is someone who has high craft, but does not like building relationships and, and actually working across the organization to get things done. They’re not gonna be successful in an executive role or in a senior leadership role. They’re only gonna get to a certain point because they’re kind of antisocial. That, that, definitely is a, is a blocker or a derailer for people, right? So I, I look for leaders that have all three that they can manage the people, they can manage the, the process and the craft and, and the quality of the thing. And they can also galvanize the support and, and kind of rally the resources to get things done, because you’re not like, like it’s not the Superman complex of like, you just do everything on your own. You have, you, you have to work through others to get the outcomes you want. So that’s, those are the three areas I look for. Jesse: So you talked a bit about stepping to this role at this level in the organization, this centralizing force that didn’t exist before and the need to build out a different layer of support functions to enable that organization to gel. I’m curious though, about the support functions that you found yourself needing in order to support yourself as a design executive and like, do you have an executive branch sort of underneath you or what have you created around yourself to support yourself and your success? Rachel: Well first off, I have my partner in crime, Kristin, who the listeners will know as Kristen Skinner. You mentioned her earlier, Peter. All right. So let’s see, if we imagine the org chart, the, the left hand side of the org chart would be practices and horizontals, things that work across the entire organization and in the right hand side would be customer types. The ones I mentioned before, where it’s like traveler partner, agent, et cetera, employee. And on the left hand side you have things like design, operations, practice management. You have, you know, research and exploration. You have our experience platform and, and mainly the design operations function, the practice management function, and my phenomenal executive assistant slash strategic program manager, become the support structure for the organization. There are other pieces when you talk about embedded capabilities, things like experience architects that become ,you know, I think Peter has written an article about the secret strategy team Peter: strategy team. Rachel: Shadow. Yeah. Uh-huh that also becomes a support function. But for myself you know, I, in order for me to scale, the design operations team, practice management and my EA are, are my lifeblood because they, they can be– talk about proxies. They, they can be in all, all of the conversations. You know, our design program managers are in every single meeting, every single presentation, every single crit. They know, they are the eyes and ears and they know what’s happening throughout the entire organization. And they can bring all of that to me. Right. Not just updates on how programs are going, but like hotspots, things that are, you know, happening, you asked earlier, like things you’re hearing in the organization, things we need to go after and fix. Those parts of the organization really help me. I don’t have like some special office of the, you know, chief executive. Like, no, I don’t have, I don’t have that, but I have an implied version of that. That’s kind of embedded throughout the organization and, and I’ve been lucky, you know, I would say blessed with the, the leadership team that I have and how they show up and how they they are also my support structure. So they look at themselves as a first team and they, they make it so that I don’t have to be everywhere at once. And so that allows me to be in more of the higher level conversations about, you know, what’s the trajectory of where this thing needs to go versus having to be in the weeds on every single conversation. The thing I would mention though, and, and I don’t know what you’ve experienced with some of the other people you’ve been talking with. You know, you have to move from macro to micro though, right? And for me, there’s certain, when I mentioned like beacon programs or beacon projects, there’s some programs I stay very close to extremely close to where I’m actually in those reviews, I’m in those crits for some of that work and I’m looking at it and I’m helping and it’s not to, it’s not to have, oh, Rachel’s in this meeting. It’s not that, it’s more of a, how can I champion the work for the organization? Well, the way that I can do that is intimately knowing it and, and helping in some ways connect the dots between the conversations in the boardroom and the strategy of the company to how it needs to manifest in our experiences and creating that direct connection for the team, so they can get that context. They can get the why, they understand the expectations and they, they actually could be more successful by doing that. So there are certain programs. I, I went a little bit deeper. But there are certain programs I stay very close to. Even though you’re getting in the weeds, because I know the importance of that program and the high, the visibility of it, the transparency that’s needed there and the level of quality that’s needed there. And so so I think that, that, that is something, when I talked about transforming, you know, the experiences transforming the function, transforming the company, transforming the company is really transforming the culture. Transforming the function is creating the space and the actual capabilities for strategic design, but transforming the experiences, you can’t lose sight of that. Right? Sometimes, you know, leaders, they are charting the vision for tomorrow without delivering for today. And so I have to, I have to move, you know, in that context to be able to go deep, to be able to make sure that we’re building for today. There’s my soapbox. I gave you a little soapbox. Incubating new design practices Peter: It’s a good soapbox. You mentioned this phrase, practice management, and I would appreciate a definition. I think I know what it means, but it’s not a common term. And so how do you define practice management within your organization? Rachel: Right. It’s not, it’s not the version we’re familiar with in the medical industry. But, but yeah, so take the perspective of a helix management model, right? And so when I talked about Apple and their innovation model of, like, experts leading experts. One of the ways that you can nurture and grow new practices or new embedded capabilities is by centralizing them first, before you federate. Right? So we’re a centralized partnership. But by that same token, we have some new practices that are getting off the ground. Right. So we have things like design and research, and we have content design as well, which are more robust and more, I would say more on that maturity model. But then we have new ones, like I mentioned, service design, right. You know, we have communication design, we have experience architecture. We have other disciplines that are really at their very beginning. You’re planting the seeds for those things. And so the practice management team does a couple things. They are the champions and stewards of what we call traveler-centered design, which is our flavor of human-centered design. And so they codify the practice and the methodology. They are the ones that are teaching across the organization, not just to XD, which is the experience design organization, but across the company, right. And educating and bringing everybody along. So we’re all having that, those mindsets and behaviors. That what also lives there are things like these, embedded capabilities or these disciplines underneath one leader, so that they’re all in a, they have a sense of community. They have almost like a COE for those practices. So that’s what practice management is. It’s a way of, you know, it’s, it’s the practice of design. It’s the methodology that we use. It’s also the different disciplines and practices within it. Peter: Excellent. And that was something I’d noticed when I was just looking at your profile on LinkedIn was the degree to which your team goes beyond product design, UX research, and content design to embrace, as you said, experience architecture, exploration, service design, and these other areas. And so it sounds like practice management is the space by which you can develop these newer disciplines within design. How were these new practices identified? There’s, like, edges, I guess, of design practice that you’re trying to push at. And how are you finding those edges and how are you putting shape to those edges and figuring out, oh, experience architecture’s a thing ,we should hire some people to do that. Wait, what is it again? Like, I’m just, you know, there’s like, how are you even understanding what these edges. Rachel: Yeah. Couple different… I like to triangulate data. And so, you know, some of it is understanding what’s happening across industries and what the needs are. And there’s other… example of, I’ll give you an example of this, in other parts of the world, there’s more advanced practice. In things like service design, let’s, let’s say it that way, where they’re at a higher level of maturity than we are here in the United States. And it’s used, it’s utilized in a different way. And so I’ve learned from best practices and, and other, other environments, other companies around the world of like, what did it take to transform that company? What were the different disciplines or different capabilities that were needed in order to infuse that, that thinking and that, I would say, mindset behaviors throughout that company and to get to better outcomes. And so you can go down the list of case studies of like how they got there and you start to pull apart what were the different things that were needed to be able, like to make that true. And, and what I found was things like service design were one of the key, like linchpins in order to get to that level of success in those companies. And it was because people needed to look at things more holistically and see the interdependency of things in the cause and effect of their actions. Meaning if you’re just working in product design, you can think you’re creating the best product ever. And you release it to the world and all of a sudden call volume goes up. But if you’re only the product design team that doesn’t pay attention or care about the end-to-end experience or what that’s full service is, you’re like, not my problem. You’re like, you’re not even looking at that, right? And so I, I was looking at ways to have a more interconnected view on what it takes to make impact for the business and to transform the business. And so you need to have kind of, those threads pulled together. You need to be the dot connector essentially, and identify what capabilities are needed for the future. And service design was definitely one of them. Experience architecture is another because what, what I find there, and that’s, that’s a more, that’s definitely a newer discipline, but you have fragments of it in what we used to call information architecture. You have fragments of it in what we, you know, what we have as like an architect in development or in, in the engineering function. And what this role can do is it can bridge all of those gaps, the things that fall between the cracks, the things that no one really feels like that’s kind of their job. And this role can actually bring all those things together in a way that they connect all of those different pieces to show what is the architecture of the experience system and how does it actually need to manifest and how do we actually make it happen? Understanding the technical constraints, right, and things like that. And so those are, I can nerd out on that one for a little while, I saw you smile. So, but like, those are the types of disciplines that are, that are new. They may be nascent for some people. But that I saw as like, where you, when you think about where the puck is going, that are needed to be able to make the whole company or the whole group successful. And so I started to invest in those and not, not largely, like, not like, okay, all of a sudden we have a team of 50. It’s bringing in some key, like, planting the seeds of that discipline by bringing in some key individuals that have done this in other environments and then building around them. Focusing your time and energy Peter: You know, it’s clear, you’re looking at the future and, and where all of this could be headed. And, and as I imagine myself in your shoes, I get very tired, because I am, I’m imagining that, like, it’s just, there’s a lot of work. There’s a lot to be done. How do you figure out how to focus your time and energy, given all the things that you could be engaging with? All of which sounds super compelling. Like everything you’re talking about, I would, if I were in your shoes, I’d want to do it all. And I know I can’t, or I wouldn’t be able to. So how are you, figuring out where to spend that time and energy for yourself. Rachel: Yeah. I mean, you, you pick up a rock, you find an opportunity, right. And so you kind of, you, you have to put the blinders on. I use what is called a, a framework it’s, it’s called Ruthless Priorities. And I literally have a, you know, and I, I didn’t make this up. There there’s an awesome executive coach Patty Azzarello who has a book called Rise and she talks about this. But, ruthless priorities are like, these are the things that have to happen, right? And I am going to focus on these things. And when I accomplish these things, then I will move on to other things. I don’t put everything on my plate at the same time. So I literally have a list that’s, these are the things I’m focused on, these are the things you think I’m focused on that I’m not, and these are the things I’m not doing. And I, and I have that list and I, I, I curate it like a constant gardener, so that I’m always focused on the three most important things right now. And, and I get those things accomplished before I move on. So the reason I say this is you can’t do everything. You have to be focused. And if you’re not focused as a leader, your organization will not be focused as well. So what I do is I work very diligently to make sure that I’m aligned with the focus of the company, and what are the, gonna be the most important things that can create impact for where we’re trying to head as a company. And then I translate those into the things that I’m going after and that I’m focused on. And to your point of like, you know, you get overwhelmed, ’cause there’s so much opportunity. There is, there are so many awesome things you can do, but you can’t do all of them and you b- you would burn out, like if you tried to do everything, you wouldn’t do it well and you would burn yourself out. And so I find that being very very intentional about what I’m gonna focus on and what I’m not gonna focus on, gives me the space to be able to be successful. And I do that even with my, my calendar. If I have my top three things that I’m focused on for the quarter or for this half of the year, I analyze and do an audit of my entire calendar. And I wanna make sure that every single meeting, every single work session, every, every single thing I’m involved in is moving the, that agenda forward is moving those, those goals and those outcomes forward. And if it’s not, I will decline meetings. Like it’s my… literally we’ll be like, I’m, I’m not gonna go to that meeting. It’s probably not the best use of my time. Let me send somebody else. Or is there something we could do offline? I’d love to work async, right. But that’s, that’s how I save myself from like, imploding essentially, or like a supernova. I wanna make sure that I’m keeping my resilience and my stamina up and my energy up and I’m focused on the right thing so that I can then be there as, like, a servant leader for the rest of the organization. And if I’m, if I’m kind of like scatterbrained and running after, like, what’s the next shiny object, I’m not doing any service to the, to the rest of the organization. So that’s how I handle it. Jesse: Rachel, this has been wonderful. Thank you so much. Rachel: Thanks for having me, Jesse and Peter. Peter: How can folks keep up with you, connect with you? Well, one of the things I’ve seen is you’ve been doing a lot of writing and tweeting and stuff. How would you appreciate folks engage with, with the thinking you’re putting out there? Rachel: Oh let’s see. So on Twitter @kobewan, so that’s the easiest way to find me. And yeah, I’ve been trying to build a writing practice. So let me know like what topics you wanna hear more of. So I’m trying to do it daily. I’m trying to ship daily. We’ll see. Yeah, I know. But that’s like the main way to get in touch. And then I also have a, a newsletter that I, that I push out intermittently on some of that thinking as well. And that’s on substack, same name, kobewan. Peter: Excellent. Well, thank you. Rachel: Thanks again. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s peterme and I’m JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter:  I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show veteran design executive Greg Petroff, formerly of GE, and now head of design for Cisco Security, joins us to talk about how to be the first design executive in an organization, the role of design in defining products and transforming organizations, and some reasons for hope in the evolving relationship between design and engineering. Peter: So we have with us today Greg Petroff and Greg, the reason we wanted to have you join us is Jesse and I are pursuing a topic in particular around what does it mean to be a design executive, like a true design executive, not a make-believe design executive that I think a lot of folks are, but like real deal, very senior, in board meetings, access-to-C-suites kind of design executive. And when we were thinking about who to have on to address this type of topic we thought of you. You’ve done this role in a few different firms. You and I, when we’ve…. just over lunches and, and whatnot, I found you to be very reflective in thinking about what it means to be a design executive. So that’s why we wanted you on, so thank you for joining us. Greg: Thanks for inviting me. I’m happy to be here. Peter: It’s an interesting time for you, ’cause you’re about to start a new design executive role and I’m wondering, and, and you’ve had a moment or an opportunity to reflect, I think on just what it means to be a chief design officer, an SVP of design. I don’t know if you have a favorite title, even we can get into that, but like what is, what, what was that journey of considering a new role? Like and how did it inform kind of your definition of what it is that you do. Greg: Yeah. I mean, it’s interesting. I had an opportunity this summer to take some time off and spend a little bit more time entertaining offers than I, I probably normally have in my career. That I think helped me get the right kind of perspective about what would be the right next role for me. And, you know, if you remember Peter, you and I actually met in, in Berkeley and talked a little bit about this a couple months ago, you know, in that early part of that thinking. And I think it comes to a couple things. One, there’s sort of what I’d like to do, but there’s also what I’m good at. And, you know, you kind of have to recognize the two and you know, there’s one thing that, you know, I’ve done successfully over the last few years is create balance teams that perform well. And, you know, I sort of see my role as being someone whose design problem is the practice of design in the organization I’m in. And and as much as I love being in the details of the individual design decisions, which I like doing, you know, my, my strength is more in empowering other people to, to be successful. And of the opportunities that were sitting in front of me there were, there were sort of small, medium and large. And you know, I was really intrigued with the role that I am taking, which is I’m gonna be the Chief Design Officer for Cisco Secure, which is the secure business at Cisco. Very large organization, actually fairly mature with a lot of strong design leaders already in place. But also some challenges from a transformation perspective, you know, Cisco went through a whole bunch of acquisitions over the last five years. They’re, they’re, they’re struggling with coherency. Some parts of the business are, are really effectively managed really well from what I can tell, and other areas, you know, need some TLC and, and some nurturing to help them get better. And at this point in my career, you know, I feel like that’s a good spot for me, like an environment where I can be an advocate for the other design leaders in the organization and, and hopefully set them up for success. Defining the role of Chief Design Officer Peter: Well, what does it mean to be a chief design officer? Was that something that they said they were looking for? Was that how you kind of shaped the role? What, what, what is that? Greg: Wow. I, I think we’re early in trying to figure that out. They defined the role as chief design officer, so that was interesting to me because they, they had thought through a, a certain, you know, executive leadership level. The CDO has sort of three interfaces, you know, they have the interface up, which means that they’re spend time in relationship with senior leadership and an organization all the way up to the CEO and board and are advocating for design to, you know, people in the organization who may not actually understand the value of design as much as they could. And, and if they understood it better, you know, the organization probably would be more successful. And then there’s a second interface level, which is, you know, you’re sort of leadership peers. So you know, your head of product, head of engineering, research, the, the marketing team, but people who are, you know, the SVP and VP level in the organization, and working with them to, to recognize how to successfully, you know, implement and empower their design team so that they’re getting real value and impact out of them. And then the last interface is really about creating the conditions for the design team to be successful. And, you know, and that’s really connected to making sure that, you know, people’s incentives are aligned, right, that you’re, you know, growing your people and your talent, that you’re empowering them, that you’re finding ways to give them agency and, and you’re kind of building a growth mindset culture. And I, I think a big part of a CDO’s role is to be actively engaged with the whole product life cycle. So not just design’s role in the product life cycle, but, you know, co-creating that with your product and engineering peers, so that there’s a shared understanding of everybody’s role in creating great product and, and, and really trying to, not build a us versus them culture, but you know, a product culture that really wants to drive impact. And, you know, CDO’s job, I think, is really to kind of wear that hat as a, you know, a partner in the organization towards, you know, really try to make impact. Being an organization’s first true design executive Jesse: I have the impression from the work that you’ve done, that you’ve often been the first person in these organizations with that level of executive responsibility over design. Is that accurate? Greg: Yeah, that has actually sort of been my M.O. You know, when I joined GE which was 11 years ago, which is amazing, you know, I became a chief experience officer at GE Digital and, and there definitely was a vacuum in terms of the understanding of design and, and it was the first time for that role. You know, I think along the path, it’s similarly, you know, ServiceNow, my time period there was a new role. They consolidated a couple of different design groups under one leader. I was the global head of design for that team and, and started build a, you know, a singular culture for the design organization. Compass, where I was most recently had a leader before I arrived, but not an executive level support leader. So it was sort of, again, a new role. And at the, in Cisco again, yeah, this is the first time that they’ve actually are building a CDO into the role. So who knows. We’ll see what happens. Jesse: What are some of the challenges for being the first one to step into that executive level leadership of design? Greg: I, I, yeah. Wow. I, I’ve certainly made lots of mistakes. Yeah. So, I think you need to build trust with the team, right? So the folks that are working for you, have to feel that. The things that they’ve brought to date are, are valid, that you know, that you’re not gonna rock the boat too much. You may shift things or change focus on areas, but you know, you need to gain trust of your design colleagues and the design organization as a whole. So that’s kind of a first step. I think selling the story of design, the narrative, and getting that story, you know, so that people understand the value is something that every senior leader has to take great care at, and it’s a balance because design— the impact of design can take time. Yet senior executive attention span can be quite short. And so you have to find ways to show demonstrable quick wins and benefit, while leaving room for the things that, you know, that are actually more substantive and impact-driven, that are gonna take more time. And, and in a way, like you have to move chess pieces before you can actually get to the, you know, the outcome that you’re looking at. And the, one of the things I’ve learned is that you have to make sure everyone understands each time you move a chess piece on the board. And you can’t just do that in a vacuum. I, I made that mistake where I’m like, you know, I’m responsible for the outcome. They got me here. I don’t have to tell ’em everything we’re doing as long as I deliver. And the reality is no, you really do need to spend time and say, “Hey, we’re gonna do this. And here’s why we’re going to do it.” Peter: Who, who do you need to spend that time with? Are you, is that your leadership? Is that your team… Greg: That’s with leader. That’s that’s with leadership. Yeah. Specifically, you know, I think it’s, it’s, multi-level. One, it’s with the, your direct. So, the person that you, you know, report to you know, and in, in every instance I’ve always been reporting to a chief product, you know, officer in, in the relationships I’ve been in. So, making sure that the relationship between you and that person is airtight, that you are communicating regularly, that you’re aligned, that you understand their objectives very clearly. And that the things that you’re going to do are going to connect to their objectives. And at the same time, you have the, hopefully, the transparency and trust with that individual to bend those objectives if you feel that it would benefit the outcome that they’re looking for, like to, to sort of say, I understand what you’re trying to accomplish, and to get there, maybe we take this path because, you know, my experience says that this might get us there in a more fast or, or effective way. So that’s, that’s, it’s really important to be crystal clear at that level. And then at some point early in your tenure, you have to sort of set a vision for your team. Because design teams in general have to feel like they’re connected to something. They have to have a sense of purpose. And, and that adds clarity, actually gives them autonomy because they can see how they might contribute to that broader perspective. And so it, you know, at some point in, you know, as I’m imagining myself going into to my new role, which starts next week, you know, I don’t know, will, it’ll be six months or nine months, but some point in we’ll come out with a picture of what the future might look like. And we’ll, co-create that. It’s not gonna just be, it’s not coming from me. I’m gonna actually have the team help us build it. But then we be very transparent about that so that people can identify with it and align themselves towards it and say, okay, here’s how I can contribute towards that. Setting a Vision for your team Peter: And when you say vision is this, like a literal envisionment, some future state experience, or is it more a direction we’re heading in and desired outcomes and impact, something kind of a little more, maybe a little less specific, a little more vague, but that allows folks to fill in the picture. Greg: It’s a little bit of both. You know, I’m a big fan of north stars. I don’t think you actually execute on a north star. You use north star to drive the art of the possible and to, and to scratch the itch on like, tough questions. And you know, words are valuable, but artifacts are more tangible and easier for people to, especially our community who are visually oriented to, you know, identify with. But you have to do them, you know, in a way where people have permission to break them and, and change them and, you know, and, and, and, and challenge them and say, you know, we’re gonna come up with something different based on, you know, the results that we have. And then I think there’s a fair amount of of brand work. I think, you know, working with the marketing team is actually really important to sort of understand how they want to sell the product, how they want to pitch products. What’s the, what’s the, what’s the onboarding process for customers? I mean, it’s not enough anymore just to design great product. You have to actually understand how people learn about the product, how the product is sold to them. What’s their first set of experiences using it? What happens, you know, after they’ve used it for a period of time? And a lot of that connects to the overall narrative, the story you’re telling as a company, not just from the, you know, the UX perspective, but the brand perspective and a big part of what I will work with you know, with my marketing colleagues is understanding how they’re positioning, you know, the security business at Cisco and, and making sure that the work that we’re doing aligns with that as part of that strategy. And, and so we’ll probably have a, a, you know, a couple of documents, one that sort of like a brand house with very descriptive kind of levels to it that, that describe the kind of experience and the principles around that experience that we’re trying to deliver that’s connected to how we’re gonna tell the story and the narrative, and then we’ll have some future looking artifacts that tell a story about what it could be. And then, you know, we’ll look at the period in between that and start working towards it. Peter: At GE, Beth Comstock– it was, my understanding was Beth was a, a main advocate for building out this design and UX center of excellence. And I also believe she was a chief marketing officer. Were you, what was that? Were you in her org? Were you reporting up to her? Greg: Yes. When I joined GE, I reported to Linda Boff who worked for Beth. And I had a very direct relationship with Beth. She was one of the great mentors in my career. She, there’s a really funny thing. My very first day at GE, I met her in, you know, GE’s corporate offices in, at the time were in Connecticut in this just sort of, you know, massive complex. And she had one of those offices that, you know, was just enormous. And, I walked in, I had the temerity to ask her this, uh question. I said you know, “on a scale of playing it safe or getting fired, you know, like where do you want me playing in this role?” And she said, “as close to getting fired as possible. And I will give you a couple of get out of jail cards.” Um, and uh, it was awesome. It was like a really, you know, empowering thing for a leader to say. And, you know, we, we, we did some things in the first two years when I was there that were difficult to do and, you know, were sort of courageous acts, but were the right things and, and it was really great having a leader who really supported you in terms of doing that. Peter: You mentioned you’ve been, I guess, more recently reporting up through a chief product officer, but there you were in marketing. And I think that’s a different experience than a lot of design leaders have. The ones at least that we engage with, right, ’cause we tend— typically are talking with UX and product designers who are, are reporting up through product. What, what, what, what was that experience like? I know that’s a weird question, but, to report up through marketing, but, you were also responsible for creating product and doing user experience work. Was that a, a happy and healthy relationship? Was it weird and, and kind of fractious, because there were different masters that you were trying to serve or how did that all shake out? Greg: Yeah, well, it did shake out. And you know, the history of GE was kind of interesting when they did made the decision to, know, become a software company, which they already were. You know, when I joined in 2011, they were like the 14th largest software company in the world and didn’t know it, because they had so many conglomerates in different divisions, but if you looked at just the headcount of engineering it was enormous. And so they, they recognized that they had to build in a more platform approach and and the way they started it is they built a, a software center of excellence and a user experience center of excellence. And the software center of excellence reported to GE Research and the UX center of excellence reported to global marketing. And we were supposed to work together, hand in hand and, and we did but we had some independence at that level that you know, was one of the first early friction points, but I think ended up being a good thing for everybody. In that what we ended up doing at that point was there was, it was a really interesting role building the role at GE. Building design systems before they were cool Greg: There was no way for us to hire enough designers to do all the work. And so the position that we took was, all right, we are going to make the engineering teams have a toolkit that allows them to at least do reasonably good design. And so we built, you know, a design system. This is early days in design systems. You know, now design systems, everybody builds one, but in 2011 there were, you know, maybe a few out there and you really didn’t see internal houses having their own. And we we built a design system, but we didn’t build it for designers. We built it for engineering and we built a site for engineering that was really kind of snarky and inside baseball and very GE and, and we, we built full reference design. So it wasn’t just components, but all the way to like, Hey, you’re building an analytics application, you can download this entire kit of software and just connect your APIs to it and build a key software. And, and then we launched it in a very open source model inside of GE. So there was no perm— you know, that you didn’t have to check in if you used it. There was no review process. It was just intended to like, you know, use it, if you want to, you know, don’t, if you don’t. And early friction point for us was the software center of excellence was trying to build a platform and they were trying to get the rest of GE to use the platform. And they wanted us to only allow people to use the design system with the new platform, which I thought was a silly idea because GE had many platforms in all of its different businesses and it would benefit from having more cohesive user experience across all of its applications, and then they could fix the platform later. And so that was a little bit of early conflict. We actually resolved it. The, the head of product who later became my boss, ’cause of consolidation of the two centers of excellence into GE Digital recognized that it was actually a good strategy for the company and it was really successful and like it grew like fire in the company. And you know, we had all kinds of really interesting metrics. We saved the company a ton of money just in speed of development and the quality of the experience that GE customers were getting improved, you know, remarkably. Even without designers being involved. And then one benefit out of it was that teams started to recognize that, Hey, if we have this system, it would be good to have some additional designers on board. So the organization started hiring more and more UX people because of the work that we did. Changing the organization itself Jesse: I’m noticing with that story, the way in which vision that you were pursuing for a particular product offering or thing that you guys are putting out in the world led to a shift in the organization itself into how it organized itself and approached its work. Greg: Yeah. Jesse: How much of that do you feel is necessary in order for design to be successful in organizations in terms of… Greg: Oh, I, I, I think it’s critical. Yeah. I think you know, one of the things I think’s really interesting right now is the tools have changed so much in the last five years that the roles in software are all open for some degree of redefinition. And, and so that conversation, you know, for instance, for me, I only wanna work in organizations where leadership is willing to, to not stand on its laurels, but really is willing to look at how it works and is continuously sort searching for how it can be better. And and that goes for how product managers work. It’s how engineering works, how design works and that they’re in constant conversation with each other. Defining that relationship and are willing to explore the boundaries where they overlap a bit and define what makes most sense for them in terms of who owns what, and, you know, one of the things I think we’re seeing more and more of is the framing of the actual outcome or the project that we’re, you– you’re trying to solve. Design is showing up more and more in that inception moment, whereas they didn’t used to, there used to be, you know, product managers would kind of go out, canvass the market, figure out a, a product outcome, figure out like the business model for it, might even do some early kind of thinking about what it might be, and then they bring their design partners in and ask them to kind of start working on it. And you know, what we’re seeing now is that you know, the design teams don’t have all the answers, but we have a set of tools in our toolkit that are really good at framing outcomes. And. If we’re involved early, then we can co-create, you know, together more effectively. And so I think a big part of any of these kinds of things is transformation. It’s about helping organizations grow. It’s about changing hearts and minds, ’cause sometimes you have people who have been really successful and, and there’s, and, and, and there’s nothing wrong with that. And yet the knowledge that they have may not be what they need to move forward in an organization. And, and so you have to be open to both listening, to like, how our profession should change. But also promoting how, what we do could help others be more successful in, in their roles. And, and that’s that’s not an easy task. Sometimes you have to be a little on the, down low to do that. And sometimes you have to be very open and public about it, but you know, it depends on the culture of the organization and, and it’s maturity and, and sometimes it’s not, sometimes parts of the organization are great and others aren’t, right? You know, and like, you know, in GE one of the things we did at the beginning was we only worked with two kinds of, of teams in GE. It would change later, but at the very beginning was either they totally got us and they totally understood design, and they were all in, or they had tried everything and were failing and the business was about to die. And, and, and, and those are the two teams we work with, right. And if you’re in the middle, we didn’t have the time for you. We were sorry. We, you know, we were growing the team. We only could work on certain sets of things, but our reasoning behind that was if we could take a, a business that was, like, struggling and make it successful, that had currency in that culture. Like, people would go, oh, I want that too, you know? Wow, can you replicate that? And so and, and we did that a couple of times. And so, and then, because we had success, we promoted the heck out of it, and that gave us currency inside the organization. And then the net promoters, the people from the beginning, they were our friends, they were the ones who like, you know, if things were kind of tough, they could kind of support us in a moment. So we were always, you know, willing to help them be successful. And, and there were a couple of really great people early on you know, specifically a guy named Tom Gentile who I think no longer is at GE, but he was a very senior executive in the company and had no design background, but went to school to learn it and then was all in with us. And so, you know, like that was fantastic to have, you know, like a, a customer inside of that organization that you could have a trusting relationship with. Building trust as an executive Jesse: Trusting relationships I feel are such a critical part of what you do at the executive level more than anything else. Just working and maintaining those relationships and that foundation of trust. Especially early on when a design leader steps into an organization for the first time, it can be slow going to build that level of trust, to be able to do some of the things that you want to do. How do you approach that stepping into an organization for the first time building trust with your peers and with the senior executives? Greg: Well, some of it’s just breaking bread, right. You know, like, Hey, let’s go have a beer or, you know, a meal and learn about, you know, what’s important to each other. Sometimes it’s listening to what challenges they have and offering help, even if it’s not in your alley. And, and, and, you know, supporting it. And then, you know, obviously trust is earned. So, you know, you’ve gotta do some work and your early work has to be, you know, you know, clear and smart and you know, people have to attribute impact to it. Right? So, you know, it’s a combination of things. I think, you know, you always wanna make sure that the, your partner is the one who gets the attention, right. So, you know, at GE, one of the things we did very early on is, you know, we, we celebrated the wins, but the win was not us. The win was the business unit. Um, And the team that made the decision to work with the UX COE. When I was at ServiceNow, you know, I built a, a, a shadow comms team inside my org. I, I hired a young woman straight out of college with an English degree into our content design practice. But really what she did in the beginning was she wrote a monthly newsletter about all the things that we were doing. And it was always a story about, you know, someone else in the organization that we promoted, you know, SVP of product does this, you know, and, and, and here’s the decisions that they made that were great around design work, because you want to celebrate them, too. They want to feel like they’re getting value, but they also want to feel like you’re supporting their career objectives. And so, you do it in a sincere way, an authentic way. It’s not, you know, you’re not trying to pump up somebody who doesn’t deserve it. You’re really just trying to recognize that, you know, the good decisions are happening at every level and not just within the design team that impact how the design team can work. And if you have good partnerships, you wanna celebrate that in some way. Peter: So earlier today, I gave an internal design leadership workshop for one of my clients and one of the activities I encourage of design leaders is evangelism, is, is celebrating your team’s success. And what you said is not that, right, you’re saying we wanna celebrate our partner’s success. And so I guess my question is, When is it appropriate to crow about yourself, to shine the light on yourself? ‘Cause if no one else is doing it, the, the risk in only celebrating partner success is people don’t realize the role that your team in, in making that successful and, and it might get lost in the organization. So how do you make sure that your team’s work is recognized and celebrated it? How Design’s ‘voice’ can best be heard Greg: Yeah, absolutely. And, and by the way, I mean, the answer to Jesse’s first question was how I communicate. What I try to do with my organization is the organization communicates its role authentically at every level. Right. And so you know, one of the things I always encourage, you know, an IC 2 designer is take your engineering and product partners out to lunch, like get to know ’em well, you know we should have a really strong design culture, but it shouldn’t be so strong that it alienates the rest of the organization. We really should have a really strong product culture of which design is a member of. And that’s what I’m really interested in, is building really great, you know, cross-functional relationships and make sure those are solid at every level. Like that’s it from a career perspective inside the team, you know constantly be celebrating the work. So, you know, you have an all-hands meeting. It’s not about me getting in front of talking about people. Take a, a team and have ’em show their work to the rest of the organization as a whole. If there’s a product meeting where you’re showing the product to product, engineering, and design, make sure that the cross functional team is represented when they present that work, so every member of that team has a moment in front of everyone to describe what it is that they’re doing. And you celebrate that as a, you know, a, a, a group of equals or, you know, a triad that’s solving a problem for a customer together. And you know, I made the mistake earlier in my career of, of over amplifying the design culture and alienating some of my cross-functional peers. Like you guys are so strong, but you, you know, you don’t let us into your house. Right. And, and so, you know, for me I want to be able to build a design culture that is… people feel a part of, they feel purpose connected to it. They feel like their careers are growing in it. They feel like they’re doing great work and everyone else is invited to the party too. And, and we’re members of a bigger party, which is the product culture that celebrates engineering success and product success and design success. Because if you start building you know, silos in the, in the roles, you know, when you have adversity or challenges or things that happen, people fall back into that versus coming together and solving the problem together. So you know, I think for me, I’m really a, a big fan of, of, you know product as the category. And then we each have a role in it. That’s really important towards a successful outcome and, and we should celebrate everybody’s contribution. Creating culture for your teams Jesse: I think for a lot of leaders, especially when they get to that senior executive level, it can feel challenging to influence culture when you’re not sort of in the weeds with people. And it can feel like you’re kind of trying to send culture down from on high, you know? And I wonder, how has that gone for you? What has been effective for you in feeling like you actually are connected to creating culture for your teams? Greg: Yeah. That’s a great question. ‘Cause it can be very lonely sometimes in leadership roles. I, I think there, I think you have to give autonomy to your team to do grassroots thinking. Right. And and then you can build opportunities for you to have connection with your team. So, you know, as an example, and I may do this in my new role, I don’t know, but in my previous role at Compass, I used to do a couple of things. I had this thing called Leadership Club and it was IC-4 and above and all managers except my direct reports, and we would meet once a month and they could ask me anything and they would set the agenda and we might read a book or we might, or we might invite an outside speaker and ask them questions. But it was an opportunity for people to just sort of have a question about, you know, what does influence mean? Because you don’t have to be a manager to be an influencer. And in fact, for me, the definition of like uh IC-5 or IC-6 designer, someone is not managing people, but is very senior in their role, is that they are a massive influencer in the organization, that they have, you know, networks of people and impact. And so that’s one vehicle that I’ve done before. You know, I’ve always supported, you know, culture initiatives where, you know, we give a budget and a team and we ask the team to, to come up with ideas. I certainly have some, but at this point I try to stay out of that and and just be a catalyst when they come up with something that sounds like a good idea. And, and, and we can do that. You know, other things, when I was at ServiceNow, we, brought in an outside group to bring a lecture series in for us and workshops. So we had Josh Seiden and Jeff Gothelf you know put together, you know, kind of a 10, eight or 10 episode, you know, thing, which was open to design and product and engineering, by the way, right. So we had topics that were about, you know, about design mostly, but they were set in a way that we could include, you know, others into it. And I’ve done other things. I– one year at GE I took our education budget and I spent it on the product managers. So I told the design team that we weren’t gonna go to conferences and we weren’t gonna do training. But it was gonna benefit them if we sent our product managers to design thinking bootcamp and they would actually understand us better and therefore ask for more of us or, or ask better questions of us or work better with us and… Peter: How did that… what were the results of that initiative? Greg: Totally worked. It was awesome. Yeah. It, it, you know, and it wasn’t that expensive. We did a couple of different workshops. There were half day or one day events and, and I’m sort of joking. We didn’t, I mean, I still had some money for education for my team, but I took a, a big chunk of our education budget and spent it on the PM community. ‘Cause they wouldn’t, it was ridiculous, but they wouldn’t. But we convinced them to come. And then after that, had sort of, you know, these A-ha! moments where they were oh, that’s why you do research, right? Like, you know, like, oh, okay. There’s an insight there. And, and, you know, that was the biggest thing we were trying to get into GE’s culture was, we had a lot of experts, and they had a lot of expertise, but they might miss a key insight if they hadn’t actually talked to their users. And we wanted their product partners to be curious about, you know, that aspect of their world. And we wanted them to do that kind of work, but they also wanted, we also wanted them to recognize that there were people, you know UX designers and professional researchers on our team that could help them do it even better. And, and my hypothesis was at the time that if we sort of democratize some of that process, internally inside the company, it would actually drive the need for more expertise, because as people would recognize the value of it, they would say, oh, I’m okay at this. But you know, I actually want someone who’s really good at it to do this work. Let’s hire somebody. So, and I’ve kind of used that a version of that trick ever since, you know, at some level is to try to, you know, bring people cross functionally into these kind of a-ha moments that allow them to recognize, you know, the value of, of, of certain things. Defining outcomes with cross-functional peers Greg: Like right now, I’m, I’m all about co-defining outcomes. I think that’s like a missing gap in software development. And I think a lot of product teams start without actually having a lot of clarity about what they’re trying to accomplish and they feel like the agile process will help them get there and it’s just nuts. And so you know, I am, I’m all about working with product teams early on to do things like, Lean UX canvas work, or, or trying to understand, like, what are the things we know and what are the things we don’t know and what are we gonna do about learning the things we don’t know, so we can know better so that we can make better decisions. Because if you do that then your design team’s gonna be much more successful. You know, designers need a box, they need clarity. You know, it’s, it’s funny. Like, I used to, used to say, I love ambiguity. I can surf with ambiguity. It’s no problem. But, and ambiguity sometimes can be your friend, but if you design the box, then the designer can design outside of the box or inside the box. But that frame allows them to use their time productively and really solve a problem, versus sort of meandering around lots of different solutions and wasting time. And it’s the product and design team’s responsibility, and engineering at some level, too, because engineering may have an impact on that to have as much clarity at the beginning of a project as you can possibly get because then you’ll move faster and, and the outcome will be better and it’s something you can test for. And, you know, there’s all these things that kind of benefits from doing that. So right now, I think if I was thinking about my soapbox, it’s really about properly defined product outcomes before you, you know, invest too much time and then they, this can always change as you learn. But that’s the one thing I think that helps teams be more successful. Peter: I hear this from the design leaders I work with, they would love to be co-defining outcomes, but they’re quote, not invited to the meeting. Things are happening before they even realize what’s going on. And by the time it gets to them, some definition has happened. It’s often not super rigorous, but, but some, some work has been done. And I’m, I’m wondering you, you mentioned earlier, you used the word transformation. I’m assuming you’ve had similar experiences where your teams weren’t necessarily at the outset of your time there in those upfront meetings. Greg: Yeah. Peter: And so what, what strategies did you use to help encourage your team to, to get involved earlier that worked, and maybe what didn’t, like, did you try stuff that you thought would work and it didn’t work at all, primarily what are those things that actually get your team in the room when they should? Greg: That’s a Peter, that’s a really hard question to answer. Peter: I– I always default to like, complain to your boss, right? Because like elevate it, right? Because your boss, theoretically, the bosses are bought into three in a box and all this, but that always feels like running to your parents or something. Right. It’s not, it’s not a satisfying solution. Greg: No, I think, I think this is why I think I’m… defining the PLC, the product life cycle, is super, super important for a senior design leader to be actively involved with their partners on planning, on looking at the ratios in an organization of the different roles very carefully, defining budgets together instead of in silos, right? Instead of saying, Hey, engineering gets this budget and design gets this budget and, you know product gets this budget. What you really should say is, this outcome gets this budget and design, product, and engineering get together and figure out how you wanna spend your budget towards that outcome, ’cause you’re co-responsible for delivering that outcome. So the first thing I’m always trying to do is get triad leadership in an organization aligned, meaning that there are three co-owners of the outcome and they have equal voting rights. It’s not easy. It’s a big cultural change. We did this at Compass. It was really difficult. But I think it made a lot of sense. And, and, and it wasn’t like a two against one, like all three leaders have to agree and if they couldn’t agree, then they could escalate it up to the next level of a triad. And usually the next level would just push it right back down and say, well… Peter: figure it out. Greg: figure it out, right? And, and then, and then when you’re looking at your budget and staffing, you’d be like, okay, seems like you don’t have enough design to do this, or you don’t have enough product to do this, or you don’t have enough engineering to do this. So, you know, like what are you gonna do with the resources that you have and how are you gonna allocate against it? And you know, that’s why I talk about like whole product teams is really important for that kind of conversation. And, yes, it’s new for design to be in that conversation. But it’s also, I, I feel like there’s a generation of product and engineering people, now, who are, they wanted to work that way because they’re tired of the, the handoffs that don’t work or you know, the finger pointing that can happen in an organization if something doesn’t happen, like design isn’t delivering on time, or engineering’s taking too long, or product doesn’t know what they’re doing, you know, and those are kind of common memes that happen in large organizations. And, and, and then what invariably happens when you don’t have that co -ownership model, if a problem does arise, the reporting goes back up the food chain in the individual roles. And so all of a sudden you get an, you know, an email or a phone call from, you know, the CTO, this isn’t going right? What’s going on? You know, we need to make dramatic action, right, or something. And it gets escalated and then the partners lose trust with each other because they ask their dad to get involved or their mom to get involved versus working it out together in the triad model. You’re co-owners like, you’re responsible for an outcome and if you don’t do it, you know… So that’s a big part. So a big part for me is like making sure the incentives are aligned. And it’s really hard because each of our roles has different incentive structures. Developing common objectives across functions Greg: You know, designers are incented by doing great work. Product is incented usually by scope. Meaning that the more scope you have, the more seniority you have in an organization. So that can be very challenging because people from a career perspective could be just acquiring scope to grow their influence when maybe some of that scope is irrelevant or not necessary for an outcome that you’re trying to drive. And then engineering gets measured on all kinds of metrics of like, you know, how many lines of code are written and, you know, quality defects and you know, a bunch of other things, right? And so when the, if the three sides are measured by different outcomes, then you’re gonna have challenges. And so the conversation that I’m always trying to have in an organization is, how can we move towards a common set of objectives for every product that we’re working on? And can we organize our teams around an outcome, not a feature and not cross functional features, where I have to depend on two, three different teams to, to kind of pull things together so I can be successful. I own everything I need and we’re all on the hook. And if we deliver it great, if we don’t, we’re, you know, we’re accountable. And it’s, it’s uh… it’s not easy. And, you know, we’ll see. I mean, I think every culture’s different. And I’m super curious, you know, when I enter into my new role, what that new culture will be like. And, you know, I, I, at this point in my career, I probably won’t shut up about like getting ratios right. And, and getting teams their work the right way, because it creates the conditions for success. It really does. Like, it creates the moment where you can say, you know, and, and everybody wants it. Right. And everybody is keenly aware now, that the outcome of your, the, the, your product’s success in the market is connected to the outcome it delivers. And, and if there’s a comparable product in the market, how effectively and beautifully and delightfully it does it. And so now, not everyone knows how to get there, but if you can tell the story about, well, these are the steps we need to take as an organization, and, and these steps will give us the highest probability of landing that outcome, then let’s go do that, right. And if you have skeptics, then what you do is you say, okay, let’s take a part of the organization and try it. Jesse: mm-hmm Greg: And then if it works, you demonstrate it and then you bring it back and, you know, kind of tell a story to everybody else about like, Hey, this is cool. Jesse: it seems to me that driving the scale of impact that you’re talking about requires a great deal of oversight, much more oversight than you personally can provide to these processes that you’re orchestrating. Greg: Yeah. Building your leadership team Jesse: And this is a, this is a topic that comes up with my coaching clients, building an effective bench at that… at that next level down below you as a leader. What are some of your thoughts about getting that team together that you can trust to run the big machine that you’re orchestrating? Greg: Yeah. I think that, well, first of all, there’s a couple things. One, you still need to kind of know what’s going on. And so you know, I, I need to see work, and you know, I will try to find a way in this new role to continue to see work. I used to spend all day Tuesdays looking at work and it wasn’t a design review by the way, it was just so I could see everything, so if someone asked me a question, I could, I could make connections between things, but also if I saw two teams doing something similar, I might say, Hey, team A talk to team B. Jesse: Mm-hmm Greg: And in that role I never critiqued the work. If there was something I saw I might talk to the design leader, you know, in the background, after a meeting. And it was always about supporting the ICs, asking what was fun about what they were working on, what was exciting, pumping them up, being really celebratory in that conversation. But, you know, the meeting was really, for me, it was for me to have kind of a picture at the leadership level. I think there’s a couple things. One you want to give your leaders as much autonomy as possible and ownership of the area that they have. And you wanna hire people who are smarter than you. You know, you know, a couple of people that I hired at GE all, you know, my first two hires could have easily had the job that I had you know, that Andrew Crow and then Dave Cronin ,you know, Dave later took over the team and Andrew later kept, stayed in marketing at GE for a period of time and took on brand for GE, which was an awesome opportunity for him. The team I had at Compass was one of the best teams I’ve ever built. It was just phenomenal group of people. And we just look for really smart, you know, folks. I am now and, you know, kind of at this point in my career, trying to find people who don’t think like I do. And so I have some diversity of opinion and also some people who can kind of push back and, and challenge. And so that’s one. And then I think the role that you have as a senior leader to those leaders, is mostly as a coach. And what you’re trying to do is unblock them. If they have any blocks, walk them through, you know, their strategy hold them accountable for delivering, you know, what they say they’re gonna deliver. And as I said earlier, you know, give them as much autonomy to do whatever they need to do, including getting in a little bit of trouble, like, you know, that’s okay. Right. You know ’cause you don’t learn otherwise, you know how to do that. How to move things forward. Peter: Kind of related to Jesse’s question, something I noticed, or reflected on, as I was thinking about the roles you’ve had over the years, is that there’s an intent in how you compose teams and I, I find you are also building particular, like, within the realm of design or user experience, cross- functional teams. So… Greg: mm-hmm The composition of design orgs, and when to roll out what functions Peter: Not just design, but research, content teams, you’ve led content teams, not every design team has content teams, but you seem to have made that part. You mentioned design systems earlier, maybe design operations. I’m kind of, I’m wondering how you think about the functions within the, this organization that you’re building and what— what’s important to you to, to establish. As you look out, what, what are new roles or new functions that we should be considering, or just kind of curious how you, how you think about the intentionality of those practices within your org. Greg: Yeah, some of it has to do with the size of the organization, too, right? So if, you know, you know, you’re zero to 50, it’s pretty hard to make an argument for a content practice. You can have a content designer designer on your team, but you know, it may not be a practice. If you’re a hundred then, yeah, absolutely. Have a content design team, you know, hire uh… first leader and maybe one or two people who can do that. It also depends on the content, you know? So, you know, like if you think about Compass you know, it was a real estate technology platform that had a very specific audience and a very specific way, way of talking and a very strong brand yet the brand’s voice wasn’t in the product. So the argument for content design was incredibly important. And so, you know, we hired Morgan Quinn out of ServiceNow. Someone I had worked with before, who helped build a content design practice and, and she did an amazing job and, you know, Morgan’s now at Google and you know, thankfully she was with us for, you know, the time I was at Compass and did a amazing job, you know, building that practice. I think you have to be careful, you know, I think you need to look at the culture of the organization, like roles, like the design ops role. You know, there are other roles in organizations like technical product manager, TPMs, PMMs, et cetera. And you wanna make sure that you’re not overlapping in responsibilities and you don’t wanna make, you wanna make sure you’re not having, like, design needs an interface to work with engineering’s interface. It has to have an interface that works with product’s interface, like that’s… that, that, that becomes a little nuts. Right? So what you want is, you wanna look at your organization, look at the needs, look at your leaders and say, what are the set of tools that we need in place that will allow us to use our resources most effectively, right? So I’m a big fan of design ops, but I think it needs to be about resource allocation, about visibility, and how fast the team’s working. So that when an executive comes with a, “and I need you to do this,” you have the ability to say, well, then what would you like us to stop doing? Because we’re at capacity, right? And historically designers get screwed because they don’t have that information. So they end up saying yes, and then they try to do everything. And you know, you have to actually have the discipline to be able to say, what should we take off the board? If there’s a new thing we need to drive into because there’s a customer issue or, or, or a new marketing thing that, or, or new business outcome that you need to get to market quickly, for whatever reason you know, you gotta have that ability. So it’s a little bit dependent. Some of it depends on, you know, are your other cross-functional partners, is the brand and marketing team really strong. If so, then, you know, you don’t have to lean in there. If they’re not so strong, you might have to build, you know, a little bit of a practice inside of your own practice that works with them to help their message show up in product. So and then, you know, certainly in design systems, you know, I’ve managed design systems teams where I’ve had the engineering on my team and it’s been in the engineering organization. I think that there’s models that work in both. But you know, getting, getting that right, you have the right, have, you have to have the right kinds of people to do DS work, right? You have to have designers who understand tech, and engineering who understand design and, and they have to be, they have to love working together. And, you know, the reporting doesn’t really matter as much as long as you figure that part out. Lessons learned on the path to design executive Jesse: So you’ve been working at this executive level for a long time now across a number of different organizations. So this question might be, might be a little hard for you to reach back and remember what it was. Before you took on these kinds of roles… Greg: hmm. Jesse: What did you get totally wrong about what this job actually is and what it entails? Greg: Okay. So I, I think there’s a couple things that happen. I, I think as you grow in design leadership from a manager to a senior manager, to a director, to senior director, there’s this feeling that you get to direct the outcome and the design work and, and that you’re dictating to your design team, like, how to do the work. And there’s some truth to that. Like, you know, if you’re in the earlier parts of your, you know, your more a player/coach, you’re in the work, you’re doing the work. And then you hold onto that for a really long time. And that can be unnerving to your own leadership. Meaning like you’re, you’re in their work, when they own it, you know, or you want them to own it, but you’re in their work. So that’s a mistake I’ve made, which is not given my, my, you know, they might do it differently than the way I would do something, but that doesn’t mean it’s wrong. It just means it’s different. And, and it still might satisfy the outcome that we’re trying to address. So learning to have that ability to detach from the work is really, it’s, it’s hard because, you know, I, I, I like designing work. I like designing things. I have lots of ideas. I have, you know, plenty of things to do, but I don’t have enough bandwidth to see most of that through so I can nudge, I can course correct, I can encourage, I can offer things to look at. But you know, you don’t want me in your Figma files. Right. So , so that’s, that’s something I’ve had to learn. And I think one of the things I learned in my last role was to really get out of my director’s way and let them have ownership and, and, and, and let them have those relationships and let them be the person who presents that to senior leadership and and talk less. You know, and, and that’s hard, hard, hard to do. So that’s one thing. The other thing that I’m trying, and I don’t know if I’ll be successful at this, I have, you know, I’m very stubborn about sometimes with the way I think things should go and and I hold onto it. And and you know, you have to recognize that you have product and engineering leadership that you have to work with that may not always align with that. I think at this point, my career’s super important for me to have like a really tight relationship with the person I report to, his peers and my peers at the leadership level, and to be really aligned with them about what they’re trying to accomplish, even if that’s challenging for the rest of my team. Because if you’re not aligned there, I can’t help my team. And and so and, and I think that’s a hard thing because, you know, sometimes, if you’re only talking about design in those leadership meetings, you know, what you really want to have happen is you want your peer to talk about design and you want me to talk about a product outcome or an engineering issue, and you want engineering to talk about design, right? You want to have that kind of relationship where, you know, together, you’re kind of sorting things out. And you know, and, and, and that’s hard because you know, there’s so much work to be done to, to empower designers that you feel like any opportunity in any moment that you can tell the story you should. But if you overtell that story, then you just become kind of like a, a, a parrot, right? Like people think you’re just, you know, they, they, they tune out. And so that’s something I’m… I had to learn the hard way, you know, at some point I, I actually remember being in a meeting where someone, just out in front of me and the leadership, said, you only talk about design, you know, stop. Balancing cross-functional peer and team needs Peter: Stop it. But you mentioned something as part of that, you said it’s important for you develop those relationships with your peers, your boss, their peers, even when it could be challenging for your team. How would it be challenging? Greg: Well, I mean, one of the challenges in leadership is you can’t always tell people everything that’s going on, right. You know, organizations make decisions that take time to mature. Leadership is fallible. It makes mistakes and course corrects and, and sometimes those things have to be orchestrated carefully to you know, protect the business and to support the objectives. And sometimes those narratives don’t feel like, to everybody, like you’re really pushing the design, you know, like we’re gonna do A+ design all the time, right. And, you know, and you know, one of the conversations I’ve, you know, I have with people, which is, is, is a really hard one, but it’s like, it’s in the knowing of the project that you’re working on. Like, are we, are we trying to hit, like, this is a bad baseball analogy, but are we hitting singles? Are we trying to get a home run? Right. Jesse: Mm-hmm Greg: This is a project where we’re hitting singles and it’s gonna take us two to three years to, to score a bunch of points. And that can be, for early career designer, like, horrible, right, because they’re just like, you know, I know this sucks and we’re making it incrementally better when we could really make it really better if we really, really tore it apart and, and built it the right way and did a home run. But the organization may not have the resources or the institution to, to execute on that, right. And so it’s in the knowing. Right. And, and so you have to be able to sometimes present information in the organization to say, here’s where we’re putting a lot of attention and here’s where we’re placing good intention and good attention, but it’s, you know, we know it’s incremental in nature and, and that that’s okay too, you know, I mean, engineering makes compromises, product makes compromises, design has to make compromises sometimes. And you know, the important part about doing that is that that’s not a consistent part of your culture and that you’re transparent about that decision making with your people, to the extent that you can be. So I don’t know. It sounds sounds that sounds completely underwhelming at the moment. Cause I’m always trying to push for us to do amazing work. Peter: That’s kind of the challenge between idealism and pragmatism, right? I tend to be a very pragmatic leader. And so when I’ve been in situations, like what you’ve talked about, I’ve pissed off my design team because what engineering built was better than what was currently out there, but didn’t meet the specs of whatever was on the design files that, that we had created. And I’m like, well, it would be irresponsible for us not to ship something that is better than what’s out there, even if it hasn’t hit this ideal. And so, but yeah, you also want a culture of greatness and so, so trying to figure out how do you navigate pragmatism and idealism… Greg: Yeah. And you know, and the, but there are some weird things happening right now. I mean I don’t think people have quite figured out the impact that Figma is making in our community, but engineering gets incredibly perfect specifications for pixel accurate location of every aspect of their build from their Figma files. So it’s almost impossible for them to come back and say, I did it a different way. Jesse: Mm. Greg: You know, if they did, you kinda go, dude, check this out, it’s right here. It tells you, you know, two point, you know, two pixels here, bup bup bup bup bup, you know and it’s even got code enabling built in it, if you built it the right way, right? Like, there’s like a one to one to your design system, like, boom. And so some of the, the quality outcome issues that, you know, you experience with engineering teams are starting to disappear because the tooling is getting better. And then there’s another aspect, which is we all experience great software every day. All of us do, regardless of role. And so, you know, I, I personally find engineering teams want to deliver really awesome stuff. And so, you know, like in my mind, you know, the partnership that you… that’s super important is, you know, it all three are really important, but have a great relationship with your engineering team. Like make sure that you know them, you understand what pressure they’re under and how they work. And you know, they’re just trying to do great stuff and you know, if you make their life easier, they’ll love you for it. To your point though, sometimes there are compromises along the way and you know, that’s and you know, and those compromises invariably happen when you have legacy platforms that you have to munge together to deliver a new outcome and refactoring and rebuilding. Some of that technology is just too hard, or there’s not an economic viability to do that. And so you put together the best possible solution you can, and it’s useful for customers, but it may not be as delightful as you would like it to be. But you do your best. An optimistic view of where things are heading Jesse: I’ve noticed a couple of times through this conversation that, unlike a lot of folks in the design industry, the ways in which things are changing are giving you reason to hope and reason for optimism. I wonder, what’s got you feeling the most optimistic about the future of this work. Greg: Wow. That’s a great question. Well, I’m always half-full person. Glass is half full. And I think you have to come to the table that way with your partners. Personally, I think some of the stuff I’m a big fan of Jeff and, and, and Josh you know, the Lean UX canvas, because I think it’s a really great model for very early on at the inception of a project of defining everybody’s insights and understanding of the program and what you’re trying to accomplish and what you don’t know and what, how you might go about learning what you need to know. And I just find that if we do more of that, then everybody’s job is more fun. Product’s job is more fun. Engineering’s job is more fun, design’s job is more fun. And so you know, I spent a lot of my attention on trying to teach that practice, whether I bring those two guys in to do workshops, or I teach them in times of organizations. But I think that that sets the foundation for curiosity amongst the team and and builds trust. And so if you can do that, then you have a chance of doing great product and, you know, we all wanna work someplace where we have good working relationships with the people that we’re working with and that we’re proud of the work that we’re doing. And the other thing that that activity does is it, if you define your work the right way, it also creates boundaries. Like it, it… the more clarity you can drive into a project means that you can actually deliver on timelines, right? And the more ambiguity you have, the more likely that you’re gonna be spending weekends working on stuff, because you still have, you know, an executive has publicly said, this is gonna be delivered on, you know, June 1st. And you know, we’re ready and, you know, teams burn midnight oil trying to, to get it done. And, and you know, sometimes you have to do that, but, but you don’t wanna do that all the time. Right. You know? And, and so I that’s, what I’m optimistic about is I think the tooling is helping. And I think that, the conversation around how we work together is changing. I do think, you know, and this may sound a little controversial, but I think that Product’s role is changing. Jesse: Mm, Greg: A lot of product people like to figure out how a product worked. Jesse: mm. Greg: I think personally Product should let Design figure out how a product should work and Product should figure out the business and the outcome and the, the value that it creates for their customer. And then orchestrate and understand what are the minimal set of things that you need to deliver that outcome, you know? And, and that’s their role and and they should do it together. And, the, the, the Product people who understand that are a delight to work with and the people, Product people, who, uh, struggle with that are harder to work with. Balancing clarity and partnership Peter: Earlier, you talked about co-defining outcomes and the importance of that kind of co-ownership, that kind of three in the box ownership of product, design, and engineering, Greg: Yeah. Peter: and, just now you kind of distinguish between what, at least product and design, we could talk about engineering, if you wanted to add, each of them owns, because you also talked about clarity… Greg: yeah. Peter: … clarity of like role, clarity of function. But I find that in organizations, when you’re building something, there’s a desire for a single owner, right? ‘Cause that’s clarity, right? The one throat to choke, which is a terrible metaphor, but often spoken. But you see it in other contexts, filmmaking, there’s a director, there’s not multiple directors, there’s a director. You are trained as an architect, there’s an architect. They, they decide ultimately what it is. How, how do you achieve clarity when you have multiple owners who might not necessarily agree? Do you actually need, is one of them the real, even if they’re a shadow, leader, is one of them the shadow…? Greg: Lead? I, I, I don’t know how to answer that question, Peter. I think it’s cultural, you know I understand the need for SPOA right. You know, that’s, single person of AOR accountability. Um, you know, uh, I think that’s the, the acronym. Yeah, right. Yeah, that’s right. There’s and I understand that. And, and certainly historically product has been the, the, the, the owner of that. So I, I think the way I think about it is, I think probably it’s still Product, but the best Product leaders share it, right. And, and they say, Hey, we’re a triad, and we’re gonna work this out together, and, and you have an equal voice. One of the challenges you have is that, you know, historically we haven’t been in that conversation. And so learning how to be in that conversation for designers is hard. And, and including the compromise, right? It’s easy, if someone else says we’re not gonna do something, but if you say I agree to not do something, and then you gotta go back to your team and say, you know, you can’t blame anyone else but yourself in front of your team, whereas in the past you say, oh, Product, they made this really bad decision, right? But we’ll get through it. Right. No, you have to say, collectively we came to this conclusion and here’s how we’re gonna deal it. And we’re gonna roll up our sleeves and figure out how to work with it. And you know, some of it’s hierarchical, right? So I think one of the challenges in our industry is that we are under-leveled across our, against our peers. So, you know, a director in design is usually working with a senior director in product or a VP in product, right? And, um, Peter: and you, you are reporting up through product, Greg: I am I report to the CPO… Peter: That shows, right. Product is… the, the head of design is reporting to the head of product. Greg: Yeah, that’s right. But I, I, I personally, I think that you can create the conditions for that. And then, you know, if there needs to be a, a, a, a decider I guess that’s okay. Peter: When, when will design be ready to report to the CEO? I mean, you’ve had a lot of opportunities probably, or, I mean, you’ve been at that, that near that level for a decade now, right? Since you started at GE, you’ve been really damn close, keeps not quite happening. How do you think about that? Greg: I, I don’t know the answers. I think it has to do the size of the organization. You know organization like Cisco, which is a hundred thousand people with, you know, sales organization and a marketing function and accounting and you know, all the other different functions that happen. There’s a part of the organization that builds product, right. And then, and so the, the, in my mental model, it’s sort of like, you know, I report to the CEO of product and, and, you know, and, and so in a very large organization, I think the CPO is probably the right leader. I think, there, I do think there will be CPOs that were CDOs, right? So chief design officers who become chief product officers, right. That they become, they own, they own the whole thing. I think there’s evidence of that. I mean, you look at Airbnb, you know, that pro– that’s a company that was created by a designer, right? So I do think that you’ll start to see product, the ownership of product be there, but ultimately product has to have a leader for it. And whether that’s the product or the designer, you know, I think it’s situational as a whole. It could be in some future incarnation that there’s a role for a CDO who is kind of, you know, looking at next level down CDOs that are working in different business units. And that person reports to a CEO. I haven’t seen that model yet. Maybe that’ll happen. I, I don’t know. I don’t know. I’m not, I’m not that worried about that kind of stuff. Like, you know, I think my biggest thing is just make sure you make great product and the way you do that is, you know, work as hard as you can to influence the organization to practice good practices. Jesse: Greg, thank you so much for being with us. This has been fantastic. Greg: Hey, I appreciate it. I was really fun. I I was like thinking like, what would I talk about? And you guys asked a lot of great questions, so you got me yaking away, I’m sure. You know, all the people in my new organization are gonna be listening to this to try to figure out, figure me out. Don’t worry, guys. I don’t bite. Um, And um, uh, thanks again for hosting me today. Peter: Thanks for joining us. Do you keep a public presence? Is there a way that people can engage with you out there in the world, on the internets, et Greg: well, on Twitter, I’m at @gpetroff, and I’m on LinkedIn. And so those are my two kind of spots that you can kind of see me. Sometimes I’m active, sometimes I’m not. But you know, I’m out there. If you want to get ahold of me, you can just, ping me in one of those two platforms. Peter: Excellent. Well, thank you so much. Greg: Thank you. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s peterme and I’m JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show Kaaren Hanson, chief design officer for Chase offers her perspective on what she had to learn and unlearn on the way to the C-suite, how the leadership challenge changes as you move up, and creating design teams that leave a lasting impact on their organizations. Peter: Hi, Kaaren, thanks for joining us. I’ve been working with you now for couple of years, almost a few years in a couple of different contexts, and I’ve seen how you are leading these sizable teams, particularly inside a couple of banks, and Jesse and I are pursuing a thread right now, which is What does it mean to be a true design executive? There’s a lot of people with design leadership roles and titles, but there’s not a lot of people who are operating at an altitude that I would consider errr… Being a real executive. And, and you’re definitely one, given the size and scope and scale of, of the operations that you’re responsible for. You’re currently the chief design officer at Chase. Is that right? Am I getting that right? Kaaren: Yep. Defining the role of Chief Design Officer Peter: Okay. So what, what is that role? What does it even mean to be a chief design officer at Chase? What do you, what, what are the responsibilities? What do you do? How are you held accountable? Kaaren: Yeah, those are good questions. So, you know, it’s interesting ’cause I think about this as the role evolves over time. So right now, what I’ve really been focused on is: first, how do we create a truly strong and robust design team? One that has strong leadership, one that has strong craft. One that is appropriately resourced. And one that is integrated into the business yet is also able to go up an altitude, so they– we can look at the end-to-end experience. So that’s been a big push of mine for probably the last year and a quarter or so. And I’ve been there for about a year and a quarter. And just in that time, for example, we’ve grown from about 300 people on our team to about 800 today will be about 850 by the end of the year. And by the end of the next year, we’re gonna be about a thousand. Which is a lot of growth. Um, so you can imagine I was spending a ton of my time hiring, but also a ton of my time working with leaders across the business, including, like, the CEO of consumer bank or the CEO of connected commerce or the CEO of wealth management, to ensure that design is sitting at their table, and that the operating mechanisms are supportive of us being customer- focused, customer- first and really starting to hold a bar. The other area that I’ve been focused on is metrics. So any executive knows like metrics fricking matter, right? You manage what you can measure and we can measure customer experience. We’ve all been doing this for years. Sometimes just more systematically than others. So one of the first things that I did when I joined was to connect with our data science team and to really work with them, they are very excited about customer experience metrics, and they were thrilled that someone else was excited about them and championing them. And so as you just need two different voices in the org to really make something happen more quickly. And so we aligned on three key metrics that we’re using for our customer experience. And then it was all about how do we make sure every single team has customer experience metrics that ladder to the bigger OKRs of the company. So for example, one of the OKRs that we have is Net Promoter Score of at least 70, right, which is a, a reasonably high bar. And then we can look at well, what impacts that net promoter score and some very basic areas. Customer success rates, right? If you’re not successful, you’re unlikely to be very happy, right? It seems super obvious. We can easily empower teams to go after that success rate. We’re using something called a customer experience gap. This is something the research team started before I joined. And essentially what it does is the lead researcher, lead designer, lead product manager, do a heuristic evaluation of the five most common tasks. And they note all of the gaps that are present. And then we figure out, What severity are they, one to five. Five actually prevents you from accomplishing your task in some cases. And one is more like, you know, padding this size, that size. And so once we’ve got those in board, then it’s about how do we start to change the way that the company views our products? So now I’ve been working with the people who operate the bank to make sure these customer experience metrics are part of the business reviews. They’re part of the quarterly business reviews. The CEO is asking about them. They’re part of monthly updates. And this helps the teams to focus on them. While at the same time, we’re really building this muscle of strong design-research-content, et cetera, that is able to help the teams on the ground become much more customer focused and rigorous in that way. And then at the same time, what I’ve started to do in the last three to six months is focus on how our design, product, engineering, and data working together. And toward that end, we’ve been bringing in Silicon Valley Product Group. They do a really good job really helping teams to understand that together, they are collectively there to understand the customer problem, to solve, to figure out how the heck they’re gonna measure if they made any difference, and to just go fast. So I’m looking at it as you know, there’s this system that’s in place at Chase. And my job is to figure out how to use whatever judo moves I can to make it a system, you know, that supports the customer and creates conditions in which our teams can do the best work of their lives. And when I think about our teams, our teams are not our design team. Our teams are our product managers, engineers, data, and design. Peter: So you’re, you’ve clearly thought about this, ’cause ’cause you had these four bullet points ready to go: team building relationships, metrics, product management. You’ve been a reflective leader. I’m wondering when you stepped into the role, did you know that’s what the job was? Is there a, are you working from a playbook or had you so, so, so you, so you’re, you’re shaking your head uh, which the, audience wouldn’t be able to see. So how did you, what, what– did you have a playbook coming in? What did that look like? And then how did you unpack that these were the four kind of initiatives to engage in? And it sounds like in roughly this order, like how did that come about? Kaaren: I mean, well, like, you know, anytime you start a new job, your first thing to do is to just listen and learn, right? And to figure out what’s going really well. What are the points that you can really shine and amplify, right? Like those CX gaps, huge point of light, all you have to do is help amplify it, right? And then also what’s not working as well. And what doesn’t make sense. And then, you know, I took a lot of notes and I thought about, wait, what’s going on? Where’s this? And I thought, okay, which of these could I make progress on quickly versus more slowly? I have tried a lot of different things, some of which were taken up like this, and some of which were not. So those customer experience metrics, that was a huge surprise to me how quickly it happened. I thought it would take two to three years. So I got started and I was like, all right, we’re gonna go, we’re gonna try this. And literally, yeah, within six months it was present in 70% of the dashboards that teams were working towards, like blew my mind. I couldn’t believe how quickly this company moved. If I had my plan, I would’ve said I was gonna do that for the next three years. So that was a nice surprise. There’s some other things though, that we’re still working on, like the ratios, the ratios of designers to product managers, to engineers. They’re not where we should be. And I’m trying to hire as fast I can, right. While still holding a high bar for talent. And I am not making enough of a dent on these ratios. Right. And so that is something maybe I thought would happen more quickly and it’s happening more slowly because we continue to hire all over the place. And so, you know, so I, I think a part of it is also just seeing, well, where is the organization? What is going to get traction, right? There are probably 10 levers to pull that will make a difference. Let’s try one. If the org is ready to go with it, awesome. If they’re not ready yet, that’s okay. We got nine others. And so I’m very, yeah, I don’t necessarily have a playbook, but I do feel very strongly, the first job as a design leader coming in is to create a strong, robust team. Because if your team isn’t robust, there’s no way you can push for change. Jesse: Mm-hmm , I’m curious about where they were when you started, what was their approach or attitude toward design when you came to be the face of design to the leadership there? Kaaren: Yeah, I think it’s hard when you have organizations of this size, because it’s so, it’s so variable depending upon where you are, and depending upon the people. I will say what really impresses me at this company is the people are incredibly smart, but they’re also so darn open. And in fact, when I first joined, I was like, really? Are people really this nice? Like, hmm, is this just an act? You know, like when am I gonna learn that it’s not true. And I still haven’t learned that it’s not true, right? Which is astonishing. So really smart people open to trying new things. Maybe they just under didn’t understand the rationale for why this mattered. So a lot of what I’m trying to do is articulate the rationale for why I’m doing something and why the team is doing something. And one of the trainings we’ve brought in, we’ve brought in two really important trainings for the design team, meaning design, research, content strategy, et cetera. But one of them is Articulating Design Rationale with Tom Greever, right? And what that’s all about is, how do we help our team to better articulate why they’re doing something and why they think it’s important? Because usually if people have the same information, they come to the same conclusion, right? It just helps the overall broader team operate more seamlessly. And the second one is Facilitative Leadership. A woman named Wendy Castleman has been helping us with that. And it’s really about how do we help everybody on the team drive alignment if there isn’t alignment and particularly that alignment on the customer, right? And again, like we’re getting better in pockets, you know, it’s faster in pockets, but overall it’s just a foundational skills we expect everybody to have. And sometimes I’ll talk to people and they’ll say, wait, I thought that was product management’s job. And I’m like, yeah, it is. And if the team you’re on, isn’t aligned, well, you go fix it, right? And it is so important. That’s why everybody needs to do it. The need for prioritization Peter: You mentioned going your team growing from 300 to 800. Was that real– was that a realization that had occurred before you joined and, and they wanted to bring you in as part of this expansion, or was that part of your listening tour? Where, in looking around and reflecting, you’re like, wait a moment, I see one of– a way forward is we need to grow the team in order to address the challenges that I’m hearing about. Kaaren: I would say it’s yes, and. So I think when I joined my charge was to grow us from like 300 to 500. Right. Which was sizeable. And then it became clear that, you know, that wasn’t nearly enough. And now, by the way, I’m the one that’s saying we’re not growing to more… by more than a thousand. Like we’re not, and I’m getting all of this pressure, yeah, but we want 60 more people and I’m like, get in line. Because everybody wants 60 more people and, and no! Right? So, but then that forces the question of, well, then what’s the prioritization? And I will say I have, I’ve had two amazing bosses since I’ve been there. One hired me and she’s such a high flyer that after five months she became the CEO of Card and also the CEO of Connected Commerce. So, the biggest business and the most strategic business, which just gives you a sense for how freaking smart she is. So she’s lovely. And then my second boss used to be the chief technology officer, and now he’s in charge of product, design, data, et cetera. And and he has been fabulous because I said to him, look, one of the issues we’re running into is what is the prioritization? What is the prioritization across these lines of business? Because everybody thinks their stuff is most important. So he has been driving some really tough conversations about what actually is most important. Because we don’t have unlimited resources. Even if we have money, it doesn’t mean we have unlimited resources. And so again, like he’s been hugely helpful. And the amount– the amount of impact that had on me and the team was tremendous. And we also, you know, he’s also been incredibly helpful just to make sure that we are having every design leader that sits within a line of business sits at that CEO table, right? One design leader per, which is critical. And, though, I’ll tell you this, just ’cause you get a design leader up there, then they have to figure out how to act when they’re there. So there is someone I was hiring and you know, we were doing some feedback. I give everybody feedback after 90 days or. And some of the feedback was, Hey, you need to step up more and have a louder voice. And this person said, “Okay. Yeah. I mean, like I’ve always been fighting. We need to get at the table, but I’ve never actually been at the table. So like, so, so now that I’m there, I kinda don’t know what I’m doing.” And I’m like, that’s okay, well, figure it out together. Stop fighting, start partnering Peter: So many design leaders, and you’ve probably had this experience as well, you know, your posture is one of fighting, it’s fighting for your team. It’s fighting to be understood. It’s fighting for resources. It’s, there’s, there’s a kind of struggle that happens. And, but, when you get to be at this, what I think of as true executive level, if you come across as a fighter, you’re… That, that becomes a problem. Yeah. Kaaren: You are junior. If you come across as a fighter, if you’re not looking at the bigger team, if you’re not looking at the bigger business and if you’re not respecting, like, you know what? You are the best player in that role. So, you know, just let me know what you come to. I’m gonna run with it. I trust you. Peter: So, how do you, what is that coaching that you’re providing to help people kind of flip from that fighter mindset into… So I have the Patrick Lencioni book behind me and he talks about “the first team,” right? And, and to reflect like, as a design executive, your first team, isn’t your design org, it’s these other executives that you’re now partnered with. What have you done to help people kind of shift that thinking? Kaaren: Well, you know, it’s funny ’cause one of the things that I do deliberately is I’ll ask people, you know, who is it that you’re …whatever, whatever tool you use, right? So in our case we use Symphony, but great. Who are you Symphony-ing with the most, right? And if it’s not your product, eng, and data partner, then what are you doing? Right? Then you’re spending the wrong amount of time with them. And so I think that there are some little ways that you can reflect on how are you spending your time. I think the other bit is to figure out… what I realized is I often ask the exact same types of questions in every room that I’m in, and I’m asking those questions because usually other people are not, and they’re very important, right, to me. And I believe they’re important to the success of us as a bigger company. And so what I’ll often do is I’ll coach the people that report to me, I’ll be like, okay, so let’s go through this business. Let’s talk about this business. What comes to mind? What questions do you have? What do you think might be important? What might not be being talked about? Let’s get your point of view on that. Let me help you to strengthen your point of view on that. You can bounce it off of me and then you’re ready to go, right? So it’s almost like you do the practice before you get in the room, because sometimes people feel like they’re a little bit caught flatfooted as like, well, Is this really important? Should I really say this? Is it really my place to say this? You know, what is my role? And the other thing I would say also that I got, which was great coaching from an executive coach many, many years ago, is that you don’t know where the edges are until you run into ’em. Jesse: Mm. Kaaren: Right? So have a point of view on things that maybe you are like, well, that’s not really about design stuff, yeah. But you better have a point of view and someone will give you feedback if they’re like, can you stop talking about security? ‘Cause you know nothing about security. Like, okay, fair. Jesse: Mm-hmm. Kaaren: But I think a lot of it is just, is just prepping and then being kind to yourself and realizing that, you know, it’s an experiment. How to successfully make change Jesse: I think a lot of leaders get caught up in that fighting mindset in part because they see it as necessary to what they see as their role in the organization, which is as change maker, driving the organization toward some different kind of culture and more innovative culture, more human-centered culture, more design-led culture. What do you see as, as the role of design in making organizational change, and how do you navigate that… between making change in gentle ways that can be more successful versus digging in and fighting? Kaaren: Yeah. So I think about it as, you know, I’m also, when I join a company, I look for points of light, right. Or goodness to highlight. And so you know, I’m always looking for a, wait, so who are the product managers that are really killing it? You know, that you guys are working with? Who are the engineers that are really killing it, which data people are really involved in the customer problem? And then I make sure to highlight them and to bring them into, you know, broader presentations to the org or to leadership. So we’re really highlighting those points of light because a) it reinforces what they’re doing as well, and then b) it’s a model for other people. And that way you’re not always telling people don’t do this, right? ‘Cause if you just say to somebody don’t do this, they don’t know what to do. That’s not helpful. It’s more helpful if you help me figure out what to do. And then the other thing that I’m working on is, how do we pair people? So you’ve got a product manager with a designer that they’re working together so closely with that they really start to trust each other, right? And then it’s easier to move people along. Now, the downside to this is it’s not a fast change, right. It takes time. On the other hand, it’s more likely to last, right? And I think if anybody tells you they’re gonna change in org like a year, they’re just absolute liars. Unless the org is like three people, you know, it’s just not gonna happen, right? ‘Cause we have such habits, and organizations have habits and then they all reinforce each other. And those operating mechanisms usually reinforce the old habits. And especially if you’re at a successful company, and Chase has been unbelievably successful for like over a hundred years, right? And so yeah, we can get better, but we’re gonna do it by, by having people see that it’s more fun and more impactful as opposed to feeling like what they’re doing now doesn’t work. The other thing is, I am not a fan of perfection. Like I don’t seek perfection. I know things aren’t gonna work. I know teams aren’t gonna move as fast as we’d like, you know, and that’s okay. But what I don’t have a lot of patience for is you know, when people are rude about it or disrespectful. So there have been instances when I have heard about someone being disrespectful, and we’ve gone after that right away, ’cause it’s not okay. And part of it is going after and making sure that person gets clear feedback and that person’s not rewarded for it. But part of it is also helping our team to say, okay, I’m gonna have this hard conversation. It’s not okay for you to treat me like that, which can also be really scary for designers to do. Jesse: Mm. Kaaren: We actually just piloted a class on that Peter yesterday in Ohio. Peter: A class on… Kaaren: On hard Peter: …respectful hard conversations. Kaaren: Yeah. How to have a hard, how to say it to somebody, you know what, when you did this, it’s demotivating and it feels bad… Jesse: mm-hmm Kaaren: and I I’m sure your goal is not to have me be demotivated and feel bad. Yeah. So let’s talk about what’s going on. Peter: Chase, you know, in some ways is a Wall Street banking firm. Not known for being a touchy-feely enterprise though, as you said, you’ve experienced a lot of niceness and… Kaaren: Oh. So much kind people. Peter: And kindness. And I do wonder how this language of, de-motivation, you know, like you could, you could imagine maybe in another company with a more, “suck it up, buttercup” mindset. Like, this is work, we’re all here to, to succeed and you know, I don’t have time to coddle you and your concerns. ‘Cause this is a, a newer way of approaching these types of interpersonal dynamics within a business to, to be a little vulnerable, to, to, to acknowledge feelings. I mean, business is a place where we’re often taught, historically, legacy, not to acknowledge emotions and feelings to focus on “it’s just business,” to focus on the problem at hand. And so maybe, maybe that I, this is a long way into the question, but maybe the question is around, how do we acknowledge and accept these are humans with feelings and emotions and motivations in this context in a way that doesn’t turn into one giant like therapy session, right? You also don’t want it to just kind of bog everything down. Kaaren: Mm-hmm Peter: But you don’t wanna ignore it. How, how have you managed that? Kaaren: Well, and what I would say is, again, like it has to do with what is the culture that you’re joining and Chase has that good culture where people are valued, right? And so by and large, this is very much a part of how people operate. And what I’ve found is I dug into some of these issues sometimes it’s that the designer maybe approached it more as a fight, right? And then there was a fight back, that everybody felt bad and it was all a mess. And so again, it’s part of how do we both change how we’re operating, right? And how do we have these conversations, but also recognize how might we approach it differently. But one of the things I find really helpful is there’s a woman named, uh, Teresa Amabile. She wrote a book about like I think it’s called the power of purpose and this was probably back about 10 years ago or so, but she was at Harvard and she did a whole bunch of research on organizations and people and what makes them effective. And essentially there are three things that matter. It matters, do you have people that you feel good around that you trust. Right. Do you have a clear purpose that you care about? And then do you have evidence you’re making progress? And if you have those three things and you have to have all three of them, you’re gonna be pretty darn happy and pretty darn productive at work. And so, you know, I think that people part is a big part of it. Are you being treated respectfully and whatnot, and then the purpose, it goes back to what is your company’s purpose and how are you living it? And so I work really hard to tie everything we do to our purpose, which is help people make the most of their money so they can make the most of their lives, right? Like I am happy to get up every day and go after that. And then the progress again goes back to those CX metrics. So I also think a lot of framing about this is why we’re doing what we’re doing, but I will say that at Chase, you know, it is very much expected. There’s a high bar for people interacting with others. Well, and really operating in accordance to the values of the company as they get more senior. And in fact, they won’t get more senior if they’re not operating according to those values. Now of course, anytime, a very big company or there’s some people that sneak through, of course, but not, not very often in my experience, in fact, almost never. Jesse: I’m curious about some of your previous roles in design leadership before taking on this challenge at Chase and how they prepared you for this and maybe how they didn’t. Kaaren: Hm. Good question. So what I would say is, you know, when I was at Intuit for the longest, I was there for almost 12 years and I worked very closely with Scott Cook, who was one of the founders. And I also worked with Brad Smith, who at the time was the CEO and, and a bunch of other people, and yeah, we went after design for delight and we went after upping the craft and we went after upping design leadership, right. And changing the ladder, so they went all the way to VP and I spent a lot of time on compensation and all that good stuff. And you know, there were, there were cadre of us who got the crap beat out of us again and again and again and again, well, we tried things that failed and tried other things that failed and tried other things that failed, but eventually it succeeded. And I feel like what I learned there was a lot about how do you stop talking and get people to do, right. So how do you make it easy for them to take action? And so that’s been a big part of how I look at the world. Then I went to a startup and that was just a ton of fun. And there were like four designers and me and I got to do hands-on design, which I hadn’t done long time and it was exhilarating. It was great. And it was also chaotic ’cause startups are. And then, so I think from there, I just, I laughed the most I’ve ever laughed in my entire life. Like literally every day would just be busting out laughing. It was amazing. And then I went to Facebook and what I learned at Facebook was really this relentless focus on a metric. And how, if you get teams that are super driven, focus on a metric, they will run fast. Now obviously there are downsides if all you’re doing is running fast towards a metric. And we can see those downsides all over the place. Right. But it really did teach me the power of metric. And I was astonished by how much time was spent, figuring out really what is the right metric that we’re going after. So that was really interesting. And then when I went to Wells Fargo, you know, they’re under consent order and they were super candid with me that they were under a consent order when I went, I didn’t actually know what that meant. You know, it just like, you know, I, who knows? What it actually means is that there’s a whole bunch of scrutiny from regulatory perspective, which means that the amount of fun, impact you can have is very little, because almost all your resources are going to, you know, help with regulatory issues that need to be solved. Right. But I would say that at Wells Fargo, I learned more about the banking business. Right. And so I learned more what the lingo was and how that worked, which I think made it easier for me to go to Chase and step in quickly because I already understood the words people used. And then it was more about what are the patterns that I’m seeing. Jesse: Mm-hmm hm mm. Kaaren: But I mean, honestly, like, I feel like throughout my career, I’ve been so lucky because I’ve worked with so many smart people that have taught me so much. And that really is, I think how you learn the most is just on the job. Jesse: Yeah. The leadership skills needed to develop Peter: Reflecting on that and what you’ve learned and you, you just shared some, kind of bullet points or not bullet points, but, but experiences you’ve had that have kind of stepped you up, but I’m wondering, you know, what are things that you, in order to become an effective leader, what are the things you needed to work on? What are the things that, that, that, that folks pointed out to you as like, Hey, this isn’t going so well, you might need to try a little bit less of this, a little bit more of that, whatever that was. And so, yeah. What are the things you needed to work on? And then what were those skills that you had to, to develop, to become an effective leader? Kaaren: So, so I remember three things pretty clearly. So one is being transparent, right? So if you’re not transparent about what you’re doing and why you’re doing it, it’s easy for people to read all kinds of other things into what you’re doing. And they may assume you have nefarious intent. And so like having to be super transparent about what I’m doing and why it didn’t come naturally to me, because it’s so obvious to me what I’m doing and why, right? And, or maybe I’ll have said it once. And I just think, of course, everybody remembers, right? And they don’t. And so now I’ll often use words, I’ll be like, okay, right, “just to be transparent about what I’m doing,” right. I literally say that. And then I’ll unpack why I’m doing what I’m doing. And that has been incredibly helpful. I think another item that I had to work on was judgment. So judgment is toxic. Like being judgmental is toxic. On the other hand, as someone who’s been in this field, we are incredibly critical of things. We are like, nobody is more critical. That’s our job is to be critical, right? Jesse: Right. Kaaren: But that’s not helpful when you’re working with other people, and you’re trying to drive change in an organization, because if you’re judgemental, it’s almost like you’re adding toxicity to relationship. So I’ve had to rein that way back. And I, I worked on that, I think for like five years before I felt like I had actually made enough difference, but now I’m, I feel like I’m pretty good at that. But it was a lot of hard work. And then the third one was, you know, I still remember the first time I went into the CEO staff meeting and this was at Intuit. And this is way back when, when we, you know, Intuit was seen as really intuitive and such a good experience. And it turns out we weren’t and we had done some benchmarking. And if you looked at the success rates of people using TurboTax versus using our competitors, or, you know, QuickBooks versus our competitors, or Quicken, whatever, we were basically maybe a little bit better, maybe a little bit worse, or maybe the same. And so I got to bring this data to the CEO staff meeting and, you know, my boss was there with me and he was like, okay, you know, here’s how it’s kind of gonna go. And I was like, okay, okay. Okay. I was so focused on sharing the information that I wasn’t reading the signals around the room, because I think my brain was so overwhelmed that I couldn’t do both. And so it was interesting that when we then walked away, he was like, okay, well, the feedback for you is you talked a little bit too much. You didn’t listen quite enough to this person or this person. ‘Cause I thought my job was to share the information and yes, my job was to share the information, but I would’ve been even more effective if I had been listening in and navigating to where the conversation wanted to go. And that’s not to say I did it terribly, like it was totally fine, but that’s where I could have been better. And so there’s always like what’s actually happening in the room versus what are you sharing, right? There’s just those different altitudes to be aware of in the context. And so that’s also something that I’ve, I’ve gotten much better at, and now it’s natural for me, but the first few times you’re in that situation, it’s not, ’cause you’re like, oh my God, what’s going on, I’m so nervous, you know? And, and then I also remember just to make it better. So when I shared the data, they were like, that’s not right. We’re Intuit. And I was like, no, the data’s right. Peter: The data’s the data. Yeah. Kaaren: Right. Like, this is, this is real. Like, we’re not. So that was also this like awkward conversation. But it did prompt us to start to look at things more deeply, right. Which was great. And the other learning there is, you know, eventually when our CEO put together a tiger team for what’s beyond ease, right, I was a part of that tiger team, as were a couple of other people in the, in a couple general managers, the chief strategy officer. He did that in part, because he knew it had to come from everybody involved, which again goes back to, if you want everybody to solve the problem together, they’d all better understand the customer and the problem together all the way through solutions, right? So again, like, you know, he was teaching me so darned much, he wasn’t necessarily being explicit that he was teaching me, but I just learned a ton. Coaching your leaders Jesse: Yeah. Speaking of teaching, I wonder what role that plays in your sense of your relationship to the leaders underneath you in the organization, as well as, you know, the whole downstream design organization. Kaaren: So one of the things I do spend time focusing on is I will help our designers think about how they’re gonna share their information. Right. And so I will spend time saying, okay, you’re gonna share this. And I think this is gonna be a story that we’re gonna wanna share. It has to be really good. So I’ll be like, great, why don’t you share it with me? Okay. Here’s some feedback. This seems most important. This, you know, this is one of your most salient points. How do you make it more clear? And we’ll kind of go through stuff, do it again, come back tomorrow. Right. And so I’m very positive, but I want them to walk through it because once they learn how to do this, well, they’ll do it well again and again, or at least better again and again. And they’ll have those short stories and snippets that they can share with their executives in the elevator. Jesse: Mm-hmm Kaaren: Right. And so I feel like that’s something really important and useful. And then I make sure the organization is sharing across the board. So we’ve been doing some teardowns, you know, of various experiences. And we’ve been sharing those with the broader team, not the 800-person team, but like the, you know, 80-person leaders, so that everybody starts to have the same expectations for what they’re going to teach with their teams. Right. And then the work that Peter’s been helping us with on career pathways has been incredibly important because this, again, helps you to understand here’s what I need to go from here to here, right. But it really is all about how are we all upleveling our game together and doing it in a way that’s transparent enough that the rest of the org will, you know, kind of pull us in as opposed to trying to push us away, okay. Jesse: One of the things that I hear about from people who are in executive leadership roles is that there’s a qualitative difference in the job when the people that you are managing are also themselves managers, when you have people who have pretty large chunks of their own responsibility and their own needs for autonomy associated with that. And you know, the potential for competition and you know, friction across the various teams. And I’m curious about what you see as the as the difference between managing leaders versus managing individual contributors or design talent. Kaaren: Yeah. It’s interesting. So, I mean, I guess I think about it in some ways it’s sort of the same. It’s just that they’re gonna play different roles. I’ve hired, like, a number of very, very, very senior people who have run large orgs already themselves. And that’s great because I can plug ’em in with a CEO and they’re gonna figure out what the hell is going on. And they’re gonna say, here’s what we need and we’re just gonna make it happen. Right. And so they have enough space that they can do that, but they’re also aligned to the broader goals of the organization. So we can do it across, right, more synchronously, which is going to be more helpful for the overall org. Jesse: How do you drive that alignment? Kaaren: How do I drive that alignment? Well, it’s, we bring it back to, we’re creating one experience, Jesse: Mmm… Kaaren: Like there’s, whatever, 800 people, it’s one freaking experience. And so we start to look at, you know, what are, what is the experience as you go across these 25 products in one journey. Jesse: Mm-hmm Kaaren: And yes, it might touch Michelle’s team and it might touch Ryan’s team and it might touch Will’s team. So let’s look at it all together. And the good news is I’ve hired people that are senior enough that they they don’t have a big ego in that. Right. They’re like, great, let’s figure out how to make this happen. And there’s enough work to do that. You know, you can take that on. Oh, thank God, because I’ve got these 20 fires over here. Jesse: Mm-hmm Kaaren: And I do think that’s a difference is that when there’s a lot of meaty work, people get less territorial. It’s when there’s only one bit of interesting work or like a handful of interesting work that everybody’s trying to get into the interesting work. Jesse: Mmmm. Kaaren: Right. And that’s when you have usually not good behaviors. And to be honest, I also hire for people that are focused on the bigger team. Jesse: Mm-hmm Kaaren: Yeah. But with individual contributors, I think it’s the same. You have to give them a meaty role that they’re likely to be successful at. You have to coach them to make sure that they are successful. You have to make sure they’ve got the connection to the other people that they’re, you know, dependent upon. Right. Or they’re going to benefit from. And you also have to assume that these are smart people and they’re gonna figure out how to work together well, and if they’re not, well, then you deal with it. Right. And like, that’s cool. The “Vision” Thing Peter: You, you mentioned one experience, and it made me wonder, when it comes to design leadership, the word vision is a common word in that context and… but vision means different things at different altitudes of, of an organization. And so what does it mean for you? To have, to hold, to communicate a vision. What’s your responsibility around that idea of a vision? I’ll leave it at that. Kaaren: Yeah. So I would say that it is my responsibility to drive a shared vision around the experiences that we want our customers to have. That doesn’t mean it’s like a picture of a thing that we’re gonna build, ’cause that thing may shift over time, but it’s much more around, you know, it should be concrete, it should be measurable. It should be aspirational. Right. And so what is that vision? That vision is that our customers are, you know, I mean, I just adopt and go, “making the most of their money so they can make the most of their lives.” Okay. What does that mean? What does that look like? So that means like we have a Net Promoter Score of 70 plus, that means that we have measurable benefits that we know customers are getting more benefit from us than they are from others. So how are we gonna make that true? Right. And then what does it mean when we’re starting to operate more by journeys as opposed to by products? Right. So if you look at a customer journey, you often would cross many quote unquote products, which sometimes are maybe features. And so that is what we need to start to look at. I feel like a lot of the work though has been done and sometimes I think leaders make mistakes by thinking I have to make this all my own. I have to do it all my own. And it’s like, no, no, no. What’s good you can just run with, and go do that. Jesse: Mm-hmm. Peter: It sounds like you entered into an environment that was a little more mature. I think a lot of design leaders find themselves in a less mature environment where they’re– what’s expected of them is to be a visionary… Kaaren: mm-hmm Peter: which the people around them don’t even know exactly what they mean by that, but they, they have some vision of Jony Ive and, and brilliance. Kaaren: Yes, but they would kick Jony Ive out, if you were in that, in the organization they’re in, right? Peter: Right. But they don’t know that. Right. And so kind of navigating that, but, but to the, kind of, to this vision point, you mentioned the NPS of 70, you mentioned earlier that change doesn’t happen in a year, right. That, that you recognize that there’s, there’s a longevity to this. Managing and Leading when Things Keep Changing Peter: How does that square? So one of the things I’ve been poking at, I actually wrote a blog post about recently, what I called the management carousel. Right. Because people come in and out of organizations every two or three years, it’s pretty typical. I did a poll of designers and found out on average designers have a manager for about a year. Some, they might have two or three managers in a year, some maybe longer, you know, when you were at Intuit, you mentioned 12 years. And you mentioned that like, there was a relentlessness you needed to bring in order to see some of these ideas through. And because you were there so long, you could kind of do that. What does it mean to make change in a context, in a reality where things are shifting so much? Kaaren: Well, and that’s where those operating mechanisms count so damn much. Right. ‘Cause it doesn’t matter, who’s in position. If you’re having to report out on your CX metrics and the CEO is gonna read it, even if the CEO changes that helps to hold it all together. Right. So I feel like that’s Peter: Incept these… variables, these… Kaaren: Yes! That is like, that is like this secret judo move, right? You can build the best damn design team in the world. If you’re not changing the operating mechanisms, it doesn’t matter. And it’s not gonna last long. And the worst thing that happens if you’re a design leader is you do something, you walk away, in six months, it’s gone. Jesse: Right. Kaaren: Because that meant you didn’t build it for durability, but to build it for durability, you have to get into the operations of the company and companies have like a, heartbeat… Jesse: Right. Kaaren: … which goes back to, what are the expectations for designers? What are the expectations for product managers? How are we bonusing people on this stuff? Like, those are all the operating mechanisms you have to, you have to infiltrate. And at, Intuit, we, we did it. I didn’t have the idea to do it, but fortunately someone was like, oh, you need to bring this into blah, blah, blah, and so we did, you know, but it was like our fast path program, our rising star program. Right. All of a sudden we indoctrinated them with design thinking and that became, here’s how successful people operate here, which again, helped, you know, change the culture and make it last. And I actually saw Scott Cook at someone’s retirement party, not that long ago. And he was, I’ve been out of Intuit since ah, seven years or so. And he was like, we’re still doing design for delight. We’re still training every new hire on it. Do you wanna come? And you know, it was really sweet and thoughtful. Right. And I was like, oh, maybe but you know, it was great ’cause it had lasted that long because it was, it was in the DNA of the company. Jesse: Mm-hmm. Kaaren: And that’s what takes a while. And that’s where you’re persistent. And you say, well, can it work in here? Can I get in here? Can I get in here? Okay. These doors all shut, but this one’s open. I’m going in here. And then another couple, you know, months, I’m gonna go back to these three, ’cause by the way, the characters might have changed in there. Or I might have new information that might make me more, you know, compelling. Your job is to make your partners successful Jesse: So you’re describing this kind of constant cycle of relationship building and almost like relationship renewal as you’re re-engaging with people with a new perspective, as the context has shifted around around you. What advice would you have for people who are getting into that partnership-building routine for the first time? Kaaren: I think part of it is also that…. I mean, you guys know this too, ’cause once you’ve been around long enough, when, early on you think, oh, that person just doesn’t like me or oh, that person just doesn’t get it, and later on, you know, you’re like, you know what, maybe their kid is in the hospital. Maybe their dog vomited on their shoe this morning. Maybe they’re late to a flight. But maybe this just isn’t the right time. And that’s cool. Right. And so it doesn’t matter if I go back in three months, not at all. Right. And how can I help them in the meantime? And again, you take the assumption that you assume positive intent is so important. They’re trying to do the best they can. Right. They’re working with what they got. If you’re asking them to take a risk and operate in a new way, but they’re under the same damn deadline, it’s not a good time for them. Jesse: Mm mm-hmm. Kaaren: If it is, you’re there to make them so darn successful. And that’s something, actually, Joe O’Sullivan was really good at when we were at Intuit. He and I have worked together a few places now. And you know, When we started the innovation catalyst, the role of the innovation catalyst was to make whatever team they joined incredibly successful. It was not about let’s get them to do X practice or Y practice, but it was like, we are gonna make them more successful than they ever would’ve been without us. And as part of that, we’re gonna use some different tools because it’s gonna make them more successful. Right. But it was all about making them successful. And so if we go into it from that mentality, my job is to make you more successful. And I may not even say that explicitly, but that is absolutely how I operate. So you say, oh, thank God. Kaaren came by. That’s the win. Right. And then if I start to ask you like, oh, Hey, what would you think about tracking these metrics? You’ll probably be like, yeah, okay, fine. Yeah. I’ll give it a try for her, ’cause she helped me do this thing really quick and fast. How to hit the ground running Kaaren: The other thing that I’ll say that was interesting for me, that I suspect people may run into when they join a new company is…. This happened when I was, when I joined Chase, is we were launching something, something was coming out and it wasn’t good. And I had been there like six weeks and my boss said to me, what do you think of this? And I was like, eh, yeah. It’s, it’s not very good. Right. Something hard to say that when you’ve been there six weeks, but I was like, yeah, you know, it could be better. And she’s like, yeah. So fix it. And I was like, oh fuck. And so, sorry, language. Peter: It’s all good. Kaaren: And so, and so I was like, okay, what am I gonna do? And I thought I’m gonna do my best facilitative leadership. And so I found all the characters that were involved. Right. And I made sure that we all were saying the same stuff. Right. And like, well, what’s the value and how are proud of this? Are we? And what about this? And you know, then I pushed on some of the assumptions, one of the assumptions is that it had to go out in June because, you know, name drop person wanted it. And then we came up, people got comfortable with the idea of, well, no, we’ll do it in August because it’s better ship something good in August instead to ship something not so great in June. And the conversation was had with that senior leader and the senior leader said, great. So there had been all of this concern that this particular woman wanted something by a certain date. She didn’t care. And if you ask an executive, would you rather ship something kind of not, not that good or two months later, would you rather ship something pretty damn good. It, 90% of the time, they’re gonna say pretty damn good. Jesse: Yeah. Kaaren: Right. You just have to figure out how to share that in a way that people understand, but there’s a lot of that type of navigation, right? Of how do you align people? How do you help them see what you are seeing? Sometimes they have information that you don’t know, Jesse: Mm. Kaaren: and which case do you, you change your mind, too? It’s really fun though. It’s so fun. Peter: You mentioned facilitative leadership as, as kind of the, the means by which you helped realize this change. And led me to wonder, is facilitative leadership kind of distinct to design, because of the posture that design has in organizations. Often a synthetic function bringing kind of all kinds of different things together and trying to make sense of it. Like, I’m looking to unpack this idea of design and facilitation, ’cause you see it over and over again, not just facilitative leadership, you mentioned design thinking and I’m assuming kind of back at Intuit, the D the design for delight program, there was a lot of facilitation going on. Is that something specific to design? Should other functions be also facilitating or is it not authentic to their postures? And it is authentic to ours. I’m I’m curious if you’ve, your, just your thoughts on, on facilitation as a thing designers do, but not others. Kaaren: I mean, I think there are certain practices, like being transparent, focus on outcomes, facilitation. Those are just good practices as a person. Right. And I think about this, like I use those on my kids all the time. Right? So like one of my, one of my sons, he was you know, he was not spending much time doing his homework, just put it that way. And I was like, you know, that’s it, I’m like, you don’t get more A’s than B’s, you’re not mountain biking. And he was like, what? He’s like, you’re terrible. You’re one of those moms that only cares about achievement and, you know, blah, blah, blah, blah, blah, blah, blah. And I was like, well, you know, if you were working three hours a day, and you were not doing well fine, but you’re not at that point. So we’ll talk about it later. But it was just really interesting that I, you know, he had this conversation, I was like, I’m managing you to outcomes, not activities. Right. And he was like, oh my God. Right. And then, you know, at other times I have been like, okay, so what do you think is the right path? Here’s what I see, what do you see? Right. And so then we’ll kind of come together. And I find it incredibly helpful. So when I think about us teaching these skills to people, it shouldn’t just be design, but we’re not teaching them for people to be successful at work only. Right. It’s just to be successful in life. And I just, it made me super happy later on like two years later, my son was like, I was so mad at you, but you know, he’s like, that was actually probably the right call. I was like, wow. I’m like writing that on a piece of paper. You are signing it. It’s like. Okay. It’s going in a vault. Peter: Yeah. Kaaren: The one time. Jesse: Entered into the record. Kaaren: But I, but I do think design has a special ability to do that because we are customer-focused, because we are human-focused and a lot of that facilitation is being attuned to your partners and really figuring out, well, wait, what do you know? What do you think? What if we did this? How might we align? And that becomes almost like a, it was like a game to play, right? Like, oh, did that work? Oh, that didn’t work. Okay. Let’s try this play. Jesse: Yeah, well that gets me wondering, what are the design skills that you feel you are still using in your role these days? Kaaren: Wow. Gosh. It’s hard to know. What’s a design skill and what’s not a design skill, right? Jesse: Yeah, your call. Kaaren: Mean, holy cow Peter, I’m looking at you with our career pathways. What’s a design skill versus not? I mean, I think about it more as I’m trying to design the organization, I’m trying to design the system. Right? So trying to design the design organization for sure. Trying to design the broader organization and how we interact, and then trying to design the system and the mechanisms that they support doing great customer centered work. So I feel like that’s what I’m designing now. Jesse: Hmm. Kaaren: And then I am a, I’m a social psychologist by training. And so there are also some, you know, I was telling Peter this, there are some, you know, techniques in social psychology, you learn. So for example, basics, and I tell these to people all the time. If you send an email to 40 people, you’re gonna get very little response. If you send 40 individual emails to people with their name on it, you are gonna get a much higher response. And so when I need feedback on someone for midyear reviews, I write individual emails to everybody. Right. Because I know I’m gonna get greater response. So, you know, am, am I using that training? Yeah, I am. Jesse: Mm-hmm. Peter: So one of the things I’ve learned when it comes to organization design, at least the way I approach it, is that I tap into my background as an information architect to think about the design of these systems and structures. And I’m wondering if, like, just curious kind of whether it’s the social psychology or, as you started in user experience, what are those design habits or patterns that you practiced many years ago, I won’t say how many, um, that, that you are now, that you are now reapplying, as you’re thinking about organizations, right? Because it’s different to draw a set of wire, you know, draw, draw a flow diagram and a set of wire frames for a software interaction than it is to be thinking about org charts and business models and connecting people to strategy or whatever. Kaaren: Yeah. Bringing your design practice to your leadership practice Peter: But there might be some, some things that you’re bringing forward, just in terms of your practice, if you even think of it as a practice, Kaaren: it’s interesting, I think a lot about what is most prominent, what is most important, what is second most important and how are we making what’s most important, most prominent and how are we getting rid of the noise? Right. That would just be distracting. So I do think a lot… Peter: almost like a visual hierarchy or something.. Kaaren: It’s a visual hierarchy. It’s kind of in my head, but yeah. It’s like, okay, wait, what really matters here? What doesn’t —get fricking rid of it. Right. And then I also think about, okay, well, if we’re gonna do, you know over time, we’re going to unveil more, right? What is most important to unveil now? then do progressive disclosure, right. And at what point do we do progressively disclose versus not? Right. So I do think a lot about that. But I also think it’s interesting ’cause you guys know this. I mean, when you’ve been in the design world for 20 some years, it’s just how you see the world, too. Right. So I, I don’t know how I would operate if I didn’t see the world this way. Peter: In terms of how you see the world, I wonder… you’re working now with peers who probably see the world differently… Kaaren: Oh yeah. Peter: And how cognizant are you of your different way of seeing the world from them? How cognizant do you find them to be? How reflective of their own like, like when you get, you know, this is kind of, I, and I’m, I’m thinking about this, especially as you are in the position you’re in, right? You’re the lead designer, the people around you are not designers. How are you, how are you understanding them and their perspectives? How are they understanding you and your perspective and how are you making sure that you’re working well together instead of talking past each other or somehow at odds. Kaaren: Well, you know, one of the things I, I think about when I’m meeting people and I’m working with them, I’m like, wait, what’s most important to them, right? Like I’m literally noting that and I’ll be like, oh, this language has come up twice. Now this is clearly an important construct through which they’re viewing the world. Right. And so I’ll note that, so that I understand where they’re coming from. And then it also helps me better understand where I’m coming from, which again goes back to, I ask a lot of the same fricking questions, right? Like, oh, what’s the impact to the customer? How are we gonna know what the impact of the customer is. Right. You know, what is success gonna look like? You know, like, so it’s basic questions that we ask again and again and again, and when I ask those questions, it also gives clues to everybody as to where I’m coming from. And then they start to expect me to ask it, right. Or if someone else asks it, I let ’em, I’ll be like, I love that you ask that about the customer. Right. And I’m always, not always, I try to, to give praise to things that I see that I really like again, ’cause then people tend to do them more. Jesse: So you are part of a r ising wave of design leaders who have been elevated to this executive level to engage, in these conversations, bringing that design lens or mindset… Kaaren: Yeah. Jesse: …that you’ve developed over the course of your career to these conversations. And there are other people just like you… Kaaren: Mm-hmm… Jesse: …who have similarly been elevated all over the world. Now, what do you think that represents in terms of the opportunity for design as a whole? Now that we have design leaders engaging at this strategic level. Kaaren: I mean, I think it’s never been a better time to be in this field. Like I can’t, I mean, I cannot believe how lucky we are to be in here. I have no qualms at all, when I talk to people about being, oh, you should totally go into this field, blah, blah, blah, blah, blah, blah, blah. It’s fun. You know, it’s impactful, you have great purpose. And the growth is tremendous, right? And so lucky for us. But I also feel like now we have a real responsibility to actually make these experiences much better and much better for all people. Right. And so, you know, I, I feel like we’re very lucky, but frankly, there’s also a tremendous responsibility for those of us who are in these positions, because if we don’t do a good job, that can harm people that come behind us for years. Jesse: Hmm. Kaaren: Right. And you’ve seen that, you’ve seen companies where someone’s come in and they’ve burned out and they’ve, you know, burned some bridges and all of a sudden design is nothing. Jesse: Yeah. Well, I am seeing a lot of leaders these days who are the ones who came in after all of that went down and they are having to repair those relationships and rebuild the credibility of design inside these organizations in some cases. Kaaren: Yeah. Yeah. Which is why, I think, a lot of our job because we’re not as understood as engineering is, is about helping to teach people and understand what we do and what we’re about. And frankly, that we’re on the same team, right. Because I think sometimes when people don’t succeed it’s because it is more of an us-them mentality. Right. Where it’s like, no, no, it’s just us. Jesse: Hmm. Making a space for design in a business+tech context Peter: So for design, design, as a practice, right, is, is different than engineering and different than businessing, right? Design is generative and creative and can be even playful. Whereas, you know, stereotypically at least, you know, a bank is going to be risk-averse and quantitative and metrics-driven and analytical, and those can be seen to be at odds. And I’m wondering what you’ve done inside organizations to allow that space for that generativity and the uncertainty that you need for design to actually have its full impact, but that kind of runs contrary to maybe the existing business culture of certainty and, and kind of analytical rigor or whatever. That, like, how do, how do we hold these two things in one space and allow both to thrive? Kaaren: Well, and I think that’s a really good question. And so I have, I have two parts to that. One is that I think of it as a portfolio approach. So if you come in and you say, we’re just gonna do everything big, wide open space, and we’re gonna slow everything down, you are gonna fail. Right. But you can look at your portfolio and be like, okay, when we look at this portfolio of initiatives, these we’re just gonna put points on the board, move ’em out. These two seem ripe for really having a bigger impact by being much more focused on discovery and definition and whatnot. And so we’re gonna put our points here. Hope like hell at least one of them works, right. And if it doesn’t whatever, but like at least one of the two, and then that’s a story we can share. So I think about it as a portfolio approach across the board and that way you’re hedging your bets. The other thing that I found really helpful, and even in terms of with our data partners, is talking a lot about how there’s inspiration and there’s rigor, and inspiration can come from anywhere, right? It can come from your own experience. It can come from, you know, looking out at the universe. It can come from big data sets, right? Big data sets can give you ideas for inspiration. It literally comes from anywhere. And so part of this is, as we’re doing these broader explorations, we’re looking for inspiration and then you go into the phase where, okay, now let’s be a rigorous. Now let’s test the hell out of it. This is a hypothesis. Is it true? I don’t know. Let’s find out. Right. And so that also, I think gives people comfort because I think when there is discomfort, it’s like, oh my God, these designers, they just want nine months, they’re gonna go do this stuff, they’re gonna make a bunch of slides, it’s not gonna ever work. And then we’re gonna waste some more time. You know, we did that five years ago. Right? So you run into those stories. And this way it’s much more balanced and the notion of like, yeah, and then we’re gonna test the hell out of those ideas and see which ones have legs just gives people comfort. And again, you’re doing it on a few as opposed to on everything. And then over time you start to do it more, which goes back again to this is a long-term play building. An effective design org is not gonna happen in a year, but every year we’re gonna get more and more and more and more effective. And the way I measure my success is do I have a happy and engaged team, are Net Promoter Scores getting up to the seventies, you know, are the leaders being credible and are they respected? Right. And then are the processes changing in a way that they will durably reinforce these conditions that are needed to create great experiences. And like, those are the only four types of metrics that matter. And every day that’s what I’m thinking about. And that’s what I hold my leaders accountable. I’m like here, what, how are you doing on people? How are you doing on partners? How are you doing a process? And how are you doing on products and experiences? It makes it simple. And then it’s just hard to actually do it. Peter: Easy to say. Kaaren: Yeah, but it also makes it easy to be transparent. Right. So when I hire in a new leader to sit at CEO table, have a conversation with CEO and I’ll be like, great. Let’s talk about your expectations for this person coming in. Here are my expectations. This is generally what I would expect of them in the first 60 days. Here’s what I’d expect them to be within six months. What do you think? And they’ll be like, oh, okay. And they’ll read through. And they’ll be like, yeah, that makes sense. I’ll be like, okay, so here’s how we’re gonna measure their success. And that way we’re aligned from the beginning. Right. Because the worst thing I could do to this person that I hire is to stick ’em on a CEO table, have the CEO think they’re gonna do something other than what they’re actually gonna do. Right. ‘Cause that’s just gonna create awkward conversations and unhappiness. Yeah. So a lot of it is just thinking about how do we set up the leaders’ experiences so that they’re set up for success. And that’s my job. My job is to set up people on my team for success. Navigating idealism and pragmatism Peter: A theme that I think might be emerging for me in design leadership. Jesse and I, we have themes that emerge from conversations that we have. And one that’s emerging for me in the last few months is, the balance of, or navigating, idealism and pragmatism. I think a lot of designers get into this work because there’s an idealistic sense of making the world a better place through understanding our users and delivering them amazing experiences. And then as they become leaders, inevitably they get, they hit some walls and then they have to figure out a pragmatic… how to be a pragmatist towards that goal. And some fail somehow, or that might be strong, but have real struggles figuring out how to be both at the same time. Yeah. I’m wondering what has your experience been trying to navigate idealism and pragmatism? Kaaren: Again, I think it depends upon the context in which you’re in. Like there was a leader, Ginny Lee, who’s lovely. She was at Intuit, and then she went to the Khan Academy and now she’s retired. But she was all on board with saying, look, if it doesn’t make people proud, we’re not shipping it. Right. And so she would ask the team, are you proud of what we would release to customers? And if people on the team were like, well, no, just wait until you’re proud. So there are gonna be some leaders that are more willing to try that out. And then our job is to make d arn sure that those teams are incredibly successful. Right. So I feel like I’m always looking for opportunities and then you go, and again, we’re working with a lot of different people in a lot of different areas. So if we’re idealistic on everything, we’re gonna get nowhere. But if we find a few choice areas, yeah. Then we can do it. And if we find out our results are not very good as a result of being idealistic, well, we better be ready to say, yeah, and that didn’t work. Jesse: Mm-hmm. Kaaren: That’s cool. You know, not everything works, but you have to be confident enough to say that. Right. And sometimes I think that designers get stuck in feeling like they have to say it’s working, even if it’s not, because so much effort was put towards it, or they start to blame, oh, well, this would’ve been great, except the engineering team, blah, blah, blah, blah, blah. And it’s like, you’re all one team. Didn’t work. Move on. If you’re going into design leadership, like, you know, your, your ass is gonna get kicked periodically, you’re just gonna dust yourself off. You’re just gonna keep going. Right. I mean, like that is reality. So if you feel like you’re alone, if you feel like you screwed up yeah. You probably did. Yeah. You probably are. You know, like, and, and that’s okay. Right. You just, you just get up and you just dust yourself off and you just keep trying and you try something else ’cause whatever you did, didn’t work. Right. And that’s okay. Managing the loneliness of leadership Kaaren: I had a, a CEO one point and he was great. And he talked about how, you know, it was kind of lonesome to be him, right. Because he’s a CEO and who the heck does he talk to? And if you’re the design leader, well, it’s kind of lonesome for you too, because who do you talk to? I, I don’t know. I talked to my cats sometimes. Right. I don’t know. Um, And uh, I shouldn’t say that. I mean, I actually talked to a bunch of people that are lovely. People like Daniela Jorge. I’m not sure if you’ve spoken with her, but I stay touch with Daniela and Sara Khoury, and a whole bunch of others. But it is interesting that, you know, he would say that he’d get the crap beat out of him by the board. And then, you know, his staff would be angry with him and that managers would be yet mad at him for whatever reason. And he had all these problems and legal’d be on him. And, you know, he’d wake up in the morning and he’d, he’d look in the mirror and he’d comb his hair and he’d say, hello, handsome. And then he’d go to work. ‘Cause someone had to give him positive feedback and so. Peter: We all need the attaboy. Kaaren: We do. And so, you know, there are gonna be times that it’s like the best job in the world and there are gonna be times that it’s so damn hard. And then I just remember that story and I’m like, yeah, guess what? It’s part of the job. And it’s also part of how we get smarter and better and, and frankly have more empathy. Peter: You referred to a network of people outside of the organization that you’re connected with. And I’m wondering how, how you think about how as that leader, where you are lonely, yes, you need to kind of psych yourself up or, or, or get yourself into a good spot, but almost practically, what are the means by which, what, what, what have you put around yourself to kind of help you maintain your positivity, maintain your energy, maintain that, that engagement and passion that can very easily be leeched away if you’re feeling stuck and alone on an island where nobody understands you. Kaaren: Okay. I’d say first. So like just myself, I’m relentlessly optimistic, right? Like probably like more optimistic than I should be. So that’s like not a… Peter: Just like a personality trait? Kaaren: Exactly. Just a personality trait, like whatever. But I think also, you know, I mean, I do reach out, you know, I was just, I literally was just saying Daniela, ’cause I text with her, you know, a couple times a month you know, just about, oh, do you have five minutes? Yeah, I’ve got five minutes. What about this? Right. And I’ve got a, you know, a small group of other, probably four other people that I do that with as well. And it’s just helpful to have somebody else who is in the exact same damn position, you know, is either dealing with it today or dealt with it three months ago or is gonna deal with it three months from now. And it’s so darn useful. Right. And again, that makes you feel like, well, actually you’re not alone. We’re all just doing the same thing, in different companies, but we’re really doing by and large the same thing. We’re just doing it with different players in different contexts and we have different leverage to pull. Jesse: Kaaren. Thank you so much. This has been great. Kaaren: Oh, it was so much fun. Thank you for having me. And Peter, I finally got to meet Jesse and hang out with him almost as much as I hung out with you, today. Peter: How public are you on the internets and interwebs? How can people follow you, engage with you? Are you, do you, are you writing or like what’s how, how would you like people to… Kaaren: oh, that’s good Peter: think about connecting with you in a professional fashion? Kaaren: Well, they should connect with me on LinkedIn, and they should just ping me questions anytime they have them. And I love that, you know, I think that I’ve just been trying to get my head around, what is this organization? Right. And I’ve been trying to ground myself and I’ve been feeling like yeah, I purposely stopped speaking because I just had to get my act together. And now that I feel like we’re getting stronger and more robust and I’m gonna be able to have more time to spend writing and being out there which I’m really looking forward to. Peter: Excellent. Kaaren: Yeah. But ping me on LinkedIn. That’s probably the easiest. Yes. I might get back to you quickly. It might be a little while. Peter: Well, thank you so much for, for sharing your, your experiences with us. Kaaren: A pleasure. All right. Take care. Bye bye. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Katrina Alcorn, GM IBM Design, discusses the challenges of being a design executive, including time allocation, setting boundaries, and shifting priorities. They also talk about maintaining team engagement during the pandemic and the importance of showing compassion for yourself.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Peter and I take a break from interviewing guests to ask each other some questions and answer a few of yours as well. Along the way we get into topics like organizational maturity, career trajectories, the role of diplomacy and leadership and connecting leaders to their true sense of purpose. That’s right. It’s time for the mailbag. Peter: Hey, Jesse. So today I thought we do something a little different. Instead of a conversation with a friend of ours, have you and I converse. I think it’s, you know, it’s been a little while since you and I have had an opportunity just to chat. We didn’t want to do this in a, as… a navel-gazing fashion. So we’ve, we’ve elicited questions from the community through various channels: LinkedIn, Twitter, and email. And we have some questions that we’ll get to, but I, taking my co-host prerogative, do want to ask the first question and it’s a question of you. And it’s… I realized, I don’t know, kind of where… what your perspective is right now on matters of design and design leadership. Like what, what your point of view is. And I’m curious what patterns have emerged in the conversations you’re having with design leaders in your coaching practice. Improving UX maturity in an organization Jesse: So for those of you who don’t know I’ve been away from my leadership coaching practice for a bit as I’ve been dealing with some health issues. Last year I was in treatment for cancer all year long, but I’m happy to say that I’m feeling much better and I’m back at it now. And so I’ve been back into the swing of coaching for the last few months, and it’s been interesting to return to it with this perspective, having taken a year off and noticing the conversations that I’m having with folks now. And you know, one of the interesting themes over and over again, that’s coming up in my coaching conversations, revolves around something that you I’m sure have a strong perspective on, Peter, which is organizational maturity. What I’m finding is that a lot of these leaders, the biggest struggles that they have are the fact that they are embedded within organizations that are not as mature in their UX practices, as these leaders feel they need to be in order for them in their teams to be successful. So over and over again, what I’m seeing is the main question that these leaders are dealing with is the question of, do I stick it out here and try to push this organization toward a level of maturity where it can deliver on the promise and potential of design? Or do I cut my losses, get out, and go find another organization that’s already operating at that level of maturity? And it’s a difficult thing for individuals to find their way through because that task of pushing the maturity of the organization forwar,. It asks something very different of you than simply jumping in and operating in a, in an… in a situation where you were already sort of set up for success. Peter: A clarifying question: when you’re talking about maturity, are you talking about maturity of the UX organization, the UX team, or are you talking about maturity of the broader organization to embrace user experience or…? Jesse: It’s the well, it’s mostly the the maturity of the broader organization. Although I will note that along the lines of our conversation with Tim Kieschnick, the maturity of the larger organization ends up strongly influencing how mature your UX team can. Peter: Right, right. And so. That’s interesting. I mean, this… I’m reminded of when I joined Groupon 10 years ago and there was a lot of interest in being design-driven. And so if we use the leadership ceiling kind of framing, there was actually a pretty high purpose ceiling in, in that regard. And, but when I, so I inherited a team and what I saw was that, that it was the team that was immature much more than the broader organization. Not that the broader organization was all that mature, but it didn’t matter how mature or immature the broader organization was because the team was evidently immature. And that’s actually what led to writing the book, was this realization that we need to first mature our design organizations before we can then start trying to mature design within the broader organization. And I’m wondering if you’re, if, if that is a pattern you’re seeing. Whether or not these design leaders, you don’t, I, you know, I, I guess, I guess it might be hard for you to diagnose just how mature somebody’s design organization is. But let me, let me just say that I’ve seen too often design leaders, rail…they get frustrated by what they feel is the immaturity and the constraints the broader organization is putting on them, but they don’t accept responsibility for the fact that their organization isn’t, isn’t even measuring up to the ceiling that that broader organization is, is affording. That they’re not doing that initial work… Jesse: right. Peter: …to mature their teams. Jesse: Right, right, right. Well, and. It becomes a question of what kind of maturity you’re talking about because there is a level of maturity of team structure, of process, of governance that are the kinds of things that I think you’re exactly right, that if a UX team isn’t, it doesn’t have that stuff in place, there’s no point in asking for a broader mandate because you haven’t demonstrated that you can deliver value at that scale yet. But the, I think the, the kind of maturity that these leaders are running up against that I’m hearing about has to do with a maturity of understanding of expectations, of design, of appreciation of the value of design that they’re seeing doesn’t really exist in these organizations around them, or doesn’t exist at the level that allows them to really do what they feel like they’re there to do. Peter: And that pain is real and I see it all the time. And, and Yeah, so then it becomes this question of, it’s funny, a lot of this is going back to our conversation with Tim, you know, you’re, you’re, you’re going to operate below the organization’s maturity ceiling. And so as he pointed out, you have kind of two options. You can bide your time or you can bail. And that’s, that’s individual to the person in terms of what, what, what path they choose based on what else is happening in their relationship to that organization? I say, I think primarily around their commitment to the mission or purpose of that organization. And if it’s an organization that they feel strongly committed to and they want it to succeed, then I would say, and then it’s your job to, then, as Tim pointed out with the letter C, change the ceiling and that’s, as he said, it’s not for the faint of heart, but this is the real work of design leadership. And I think one of those things, that when people ask why, how, is being a VP of design different than being a VP of marketing, it’s– it’s this immaturity question, companies are mature much more mature in thinking about marketing, thinking about engineering, thinking about sales. And so your VP doesn’t need to keep evangelizing and educating everybody as to what it means to do it, right? Companies are immature about thinking about design. So part of the job of that design leader is education and evangelism. That’s just… that’s… that, you can’t get away from that. I mean, the last thing I’ll say is, on at least in this front, is I have been surprised… so I’m, I’m currently supporting an organization where this type of maturity, in- increasing the maturity is, is, is a goal that the design team has. And so they’re having to communicate how design works to a broader, primarily product, organization. And this is a big company. These are, you know, billions of dollars; very senior leaders. And what surprises me is how rudimentary the conversation is that the design leaders are having with the broader organization to educate them. I mean, I’m working with design leaders with 25 years experience who are rolling out the double diamond at its most basic to communicate, This is what design is, and who are leaning on the DMI index of how design-centered companies do better in the stock market, like reports from 5, 10, 15 years ago. Jesse: These are old tools that have been used for a long time to evangelize design. Peter: And they’re still working and they’re still working. And so I think one of the things that we have to recognize as design leaders, who, because we’re experts in it and might think that this stuff is not all that valuable, they’re not all that useful or, or too basic. What’s basic to us is mind- expanding to others and, and to not shy away from, from returning to those rudiments in, in starting that process of maturing the organization. Because if you’re trying to meet them at your level of maturity, they’re not going to get there. They’re not going to get there. The delta is too big. So you have to kind of get to where they are at their level of maturity and then grow them. The reality of conflict fatigue Jesse: I wonder about the psychological toll on leaders of taking on this role that you described, where you are inevitably, constantly putting yourself in situations where you have to su—… you have to have arguments with, you know, you, ….changing people’s minds means getting them to let go of their old ideas. And that is hard work. It’s difficult work. It is also, it means plunging yourself into conflict over and over and over again. And it’s this conflict fatigue that I see setting in with design leaders that they’re just like, it sounds like the way that you’re describing it, taking this job means signing up to be sort of a crusading holy warrior. And not everybody who wants to run a design team wants that mantle put upon themselves, you know? Peter: I think so. So yes. And a couple of thoughts in this design team I’m supporting, they’re hiring amazing design leaders from other organizations. Design leaders… so, so this, this team has 500 some designers on the way to 700, by the end of the year. It’s just, I’m saying that to reflect on scale. And they’re bringing in design leaders who are leading teams at other companies of say 500. And…but bringing them in to lead a team of 50, a 100, 150. And it’s because those leaders are done fighting that holy war. And they want to be part of an organization where someone else is above them. Who’s waging… waging those battles as it were and they get to focus on the work. And so that’s a decision for design leaders is do… I’ve… I’ve had in my conversations with, with the leaders I work with, there’s another one in particular, he was a head of design for one company, 40-ish person team, moved, became a head of design at another company, 50ish person team. Both of them, there was this jockeying and evangelizing, educating. He was actually really good at education. He was really strong at connecting business value with UX metrics. And so his leadership tend to really like him, but the, the, the, the, the more recent company he had been working for, they had their fortunes turn a bit and the job changed. And he’s like this isn’t the job that I signed up for. And he realized, “You know what? I don’t want to be the guy. I don’t want to be the guy. I want to be a guy.” And so he found a job at a ginormous tech company to run a team that’s the same size, maybe even larger than what he ran before, but in such a bigger context that he’s, he doesn’t have to wage those battles and fight those fights. Playing politics instead of fighting battles Peter: ‘Cause he just doesn’t have the energy for it. So that’s one thought. The second thought is there’s probably, there’s more than one way to skin a cat. And I think leaders, and I’m wondering, kind of, in the conversations you have, the strategies you’re developing for these leaders in terms of figuring out how to address that, does it have to be waging a holy war or can it be more political? Is there a Realpolitik approach to this? And I think about this in light of, one of the things I did in this past year was watched The Wire. I’d never watched The Wire before. And the first season of The Wire is filled wiith grist for leadership conversations. In particular, Lieutenant Daniels ,I’m spacing on the actor’s name, Lance Reddick, Lance Reddick, the bald one who’s kind of running the group. And there’s an amazing scene, I forget which episode, where he’s, he’s got his kind of gang of misfits that are, they’re trying to, he’s trying to stand up this group to do this investigation and he needs something from somebody and it shows him very slowly and purposefully escalating his ladder, to his leader, talking to his leader’s leader, all the kind of background stuff that needs to happen in order for him to secure the resources that his team needs in order to succeed, that his team doesn’t realize he’s doing, right? This is that thankless work that design– that leaders do ,not just design leaders. But he’s not fighting. It’s not conflict. It’s politics. It’s, it’s diplomacy. It’s, What do you want that I can provide in exchange for what you have that I want? And it’s, and it’s, and it’s working a system. Now, that’s also tiring, but it doesn’t have to be as conflict-driven as perhaps more just like, more, you know, in the context of designing leaders, it’s like, okay, I don’t want to fight about it. I don’t want to argue about it. I just, I want the thing I want. So what do you need from me, so that you’ll give me the thing I want and just trust me that the thing I want is right for all of us? And I’m wondering if there’s a strategy there that design leaders could be employing more. I think we seek education and evangelism as the one tool we have to influence an organization, and don’t recognize there’s other means of influencing the organization. And then when we get what we want, by whatever means, and our team does great work, then we can evangelize and educate. I think we try to do too much ahead of the output, and instead don’t rely, don’t, don’t use the good work that the team is doing to then get what we kind of want further down the chain. Why does design leadership always feel like a fight? Jesse: I like the metaphor of diplomacy. I like the idea of engaging in this conversation from a place of, we’re going to sit down at a table as equals and talk about how we work together toward the common good. You know, one of the questions that we got in the mailbag was this question from Dimitris Niavis on LinkedIn. “If you had magic and a time machine, what would you do differently as a design leader?” And honestly, this thing for me, as I reflect on my career, I think that this framing of our work as a fight is something that I have indulged in much too much over the years that I, as a consultant, engaged with our clients with an eye toward who’s on your side in the organization, who’s not on your side in the organization. What are the, what are our tactics for you know, winning those battles. And I don’t think I encourage my clients to take enough of a diplomatic approach to these things. I did see it as a battle to be won, and I don’t think that that served the work. And I think that a lot of people throughout the industry have taken on that framing. And I don’t think it’s serving them as creative professionals either to be constantly on the lookout for enemies and not to engage people from a position of mutual trust and good will. Peter: And, and, kind of, common, common goals. And I I’ve been guilty of similar stuff and I, and, and I still am, I suppose, in that I teach, when I teach my design leadership workshop, I use this framing of the four archetypes, the coach managing down, the diplomat managing across and the champion managing up . And the champion, is, I’m drawing upon kind of medieval, if not earlier, right, kind of models of the champion, that person who is fighting in your stead, who is representing you and fighting in your stead. And, and I use the champion framing when talking about managing up and out primarily, which is this mode, right? How do we, how do we engage stakeholders and executives? And I actually say “fight for your function.” Jesse: Yeah. Peter: And I, and I’ve, and I’ve been wondering about that language and I haven’t dropped it because there’s still, I guess it’s not as an aggressive fight, right? I’m not saying like, it’s our job to, like, land grab and claim somebody else’s territory. But there, there is a shielding that often– that design leaders I think need to employ, to protect, for lack of a better phrase, their team from the slings and arrows of executives and stakeholders who are doing everything they can to kind of get to your team, for their, whatever they perceive as their specific needs. And there’s a role that the design leader plays, too, to shield their team from that kind of randomization in terms of how they spend their time and their effort, to shield their team from the executive swoop and poop, right? When, when someone shows up at a meeting well along in the process and craps all over the work. And, you know, ‘ cause what I’ve seen is a design leader who doesn’t shield the team from that unhelpful commentary by an executive, if they back off and just let the poop land on the team, then the team is like, okay, so you don’t have my back. Like, you’re not there to help me. And they feel exposed and at risk. And so, you know, maybe fighting isn’t quite right. “Protector” sounds a little, um, paternalistic or, or like, oh, my team can’t handle it themselves. So I have to protect.. Jesse: Like they’re Peter: …them. I like champion and there was a certain advocacy and agency to it. So, so I guess my point there is, like, there’s still some of that aspect to the role that we do need to have a little bit of fight, but we probably, it’s probably not a helpful place to start from. And, and I guess the, the, the other thing would be for these design leaders to really be thinking about, kind of, what does success look like? What is, what is their goal? Because I sometimes think we fight for fight’s sake, or mature for maturing sake, as opposed to, like, are you trying to just ship some better software? Let’s focus on that. What is it going to take for your team to ship some better software? Let’s focus our leadership efforts on that. And then you might realize, oh, there’s a diplomacy aspect. I don’t need to fight. I need to coordinate. I need to cajole. I need to… one for you, one for me, whatever it is, the politicking that enables that, instead of just this kind of diffusely expressed energy around design needs to be given more, more better, more access, seat at the table, et cetera, et cetera, oriented on, on something more specific. A mature product management practice Jesse: Well, it’s interesting, too, because I feel like in some of these questions, you’re starting to stray into product management territory. Like I wonder how much of the executive swoop and poop is mitigated by having a mature product management practice, right? Shouldn’t those, shouldn’t that be your buffer with the executive suite? Am I wrong? You’re laughing, but what am I missing? Peter: I’m laughing, as you said, ’cause you said the phrase “mature product management practice”, which is kind of an oxymoron, at least in any in any context I’ve ever been in. And I’m sure there are mature product management practices out there. But the companies that bring me in are often the companies that don’t have those and they’re trying to stand up a mature UX practice. And one of the challenges they face is figuring out how to also mature product management. There’s probably something to be said for an immature design org is more likely to be found in the same context as an immature product org. There’s probably a a shared… Jesse: There’s a correlation there, Peter: Whatever’s led to that immaturity is a root cause that has led both of these organizations to be immature. And so, no, you can’t Jesse: Which yeah, Peter: You can’t hope that that product management practice is going to, to drive the maturity you’re seeking. Jesse: Yeah, yeah, yeah. Cause it comes back around to the maturity wall that I’m hearing about from leaders, which is not a maturity of you know, organizational understanding of how to deliver design, it is a lack of maturity in the organization’s overall mindset and culture of what constitutes quality delivery, period. And that is not just, it doesn’t just affect design. It, it, it affects all of their practices. You know, I’m really struck by, along these lines, one thing that Tim said when we were talking with him, which, he said, you know, the world needs more design than we are ever going to have trained designers. And I’ve really been sitting with that because, to my mind, the implication of that is that most of the organizations, statistically, that employ designers are going to be immature in the ways that we’re describing, because they’re not ready for professional designers, because there aren’t enough professional designers to go around. And so everybody’s improvising, then you bring professional designers into an environment like that and ask them to professionalize it. And that is… The potential of design thinking and design sprints Peter: Yeah. Yeah, though, that speaks to another lever of trying to mature an organization, is through the use of what have now been oft-ridiculed, within the design community, approaches like design thinking or design sprints, and these, these ways of enabling teaching, enabling non-designers to embrace some design in their practice, much like designers, you know, have to embrace some non-design in their practice, right? And instead of resisting that, like, that is a lever and I, and I, I don’t have enough. I wish I had more amazing stories. And maybe people listening to this can tell us of amazing stories of how, when they worked on bringing, like, using design thinking and other design facilitation, and bringing that to non-designers in an organization, how that helped mature the organization’s view of design in such a way that primed those professional designers to do even better work, ’cause the rest of the organization was ready to receive it. I have a few stories and they’re not all mine to tell. Jesse: Right. But far and away, the, the more common story that you hear is we taught the executive team design. The executive team decided great, we know everything we now need to know about design. So we’ll take it from here. Thanks design team. And the design team doesn’t see an increase in their mandate. They don’t see an expansion or a deepening of their scope. They don’t see a broadening of their influence. They they get a pat on the head and then sent out of the boardroom. Peter: Well, and I think that’s interesting because I suspect the leverage point is not the executive team when it comes to this, but the teams doing the work and finding a way to weave design thinking and, and sprints and that kind of practice into almost like a learning and development curriculum at the point where people are, are actually doing the work. Because executives don’t do anything. So, so teaching them design thinking, isn’t going to get you very far. But well, in the executive thing, sorry, I’m, I’m now free associating a bit, but part of this conversation, I was reminded of a, a interview I witnessed Marty Cagan taking part in, talking about product transformations, and this ties back to what we were saying earlier about the issue isn’t just design immaturity, it’s kind of product development immaturity, right? Product management practices are immature and possibly our engineering practices are, are immature though, those, I think it becomes so standardized that you can have a mature engineering practice within an immature product development practice. And, and so you can decouple it. Whereas I don’t think you can have mature design and immature product management. One is immature and one is mature, like they’re like they can only be as so mature as the least mature partner. Jesse: It’s a ceiling of sorts. Peter: Yeah. it is. It’s a bit of a Jesse: LIke a partnership ceiling. Yeah. The secret to successful product transformations Peter: Yeah. And so what Marty pointed out in this conversation with respect to this, and this gets back to the executive thing as well. He had an insight that I really liked. He’s like, you know what? We know, we know how to structure high-performing product teams and product development organizations, and, however hard that is, that’s not the hardest part of this because we can get our product people and our designers and our engineers working better together, doing discovery, doing delivery the right. way. But the issue is he has never seen a product transformation succeed that didn’t have CEO involvement. Not because the CEO needed to understand how product transformation worked, but because the CEO needed to make connections or clear obstacles with the teams outside of product development that ended up being this constraint on the ability of product development to transform in the ways that it needs to. And this interview was in the context of banking. You understand this inform your time at Capital One. Funding models are a huge force within how product gets developed. I have a bag of money. I give this bag of money to people in exchange for some output and CFOs love those funding models. CFOs love this idea of this org spent $10 million on product development and should receive $10 million in value for it. And what Marty points out is that the CEO needs to work with the CFO to change how they think about funding, that they can’t fund based on projects, that they have to start funding products or programs, things that are ongoing, and that it’s not this transactional relationship anymore, $10 million for a project to ship a thing that realizes some gain, and instead it’s more of this long-term commitment of just continuing to fund some group on, in an ongoing fashion to continually deliver value. And, and what he sees is the issue is, is if you don’t have the CEO involvement, you can transform product development, they’ll start to operate in these new ways, but then these other forces like funding don’t change. And so the product transformation stalls, because it now has to respond to the… Jesse: right, right. Peter: immaturity, Jesse: right, right.. Peter: …to use that word, of the rest of the organization and how it thinks about product development. And so you need the CEO to tell the finance folks to change how they’re operating, to tell HR to change how they’re operating, how they recruit and hire people, how they level folks, how they bring them up in the organization, potentially to change sales and marketing in terms of how they relate to product development. And, and because if you just do it within product development, your ability to transform is constrained. And so I’m saying this from a maturity standpoint to suggest like all the different levels that you’re Jesse: yeah. Right. Peter: And that, and that need to get aligned in order for design to be mature. And this is part of the reason why I advocate, like, your head of design can’t be more than two levels from the CEO. Because your head of design needs to be able to talk to all the people that report to the CEO. Jesse: right, right, Peter: And so if, if, if you report to somebody who reports to the CEO, not only can you talk to your boss, your boss can now connect you with all those other functions that report to the CEO. But if you’re lower than that, there’s no way you’re going to talk to anyone in HR at a high enough level. There’s no way you’re going to talk to anyone in finance at a high enough level. And you, as the head of design, need to have access to the CFO and the head of HR and the head of marketing for, for these exact reasons. So who does the Head of Design report to? Jesse: So again, like, how would you fit a head of product into a structure like you’re describing? Because again, in a lot of organizations, for anything to do with product development, maturity, a CEO is going to have a head of product increasingly who would be tasked with that stuff. How does that fit into the mix of you know, the executive product and design? Peter: Yeah. I mean, I don’t know, in my experience, it fits pretty easily in that I’ve reported up through a head of product who reported to the CEO. And so through my product leader, I had access to the… Jesse: So as long as you can be, you know, it’s okay to be two levels away from the CEO. As long as the level between you is a head of product. Peter: It doesn’t have to be ahead of product. I don’t think necessar ily. It often is. Jesse: What you were saying. Yeah, go ahead… Peter: Yeah, it often is. And we’re starting to see design leaders advocate for being direct, direct lined to the CEO so that they’re, they are seen as true peers to product and engineering. There’s any number of reasons why that’s not happening. The two primary ones are scale, design teams are just smaller, usually, and maturity of our industry in that there’s not that many design leaders who could really deliver value to contribute at a true reporting-into-the-CEO kind of executive level. They just don’t know what that job is. More and more will over time, but we’re still not there yet. Jesse: So your sense is that we don’t yet have enough design leaders operating at the level of maturity to qualify for that seat at the right hand of the executives. Peter: No, we haven’t, and, that’s changing, but it takes time. I mean, we’re, that’s the other thing to always remember about this stuff is that we’re still, that design is still a much more nascent function in most of these companies compared to any of the other ones. So it’s going to take us time to build our bench, build our leadership profiles. I mean, this comes back to the conversation we had with Gordon around chief design officers. right? ‘Cause there’s that point at which, and this is where the fighting becomes an issue. I was talking with the CEO who wanted to hire a head of design and the biggest issue he had with the candidates who were coming through is that they saw themselves as design leaders first and executives second, like, stewards of the business second. And he’s like, that’s exactly backwards. If you’re going to report to me, and I’m the CEO, I need you to be as an executive first, your first team is the executive team, your peers and product and engineering and marketing, et cetera. Yes, you have a design background. That’s great. You’re bringing that perspective to this conversation, but I need you to not be fighting for design. I need you to be fighting for the company, fighting for the organization, fighting for our successes as a, as a business. And secondarily to be the function lead for that thing that you’re responsible for. But if you approach it with, I’m fighting for design, you’re never going to cross that chasm, that Rubicon into being seen as a true organizational leader. Jesse: That’s such an interesting thing too, because of, again, that evangelism role that people often have to take on in order to become design leaders, they have to demonstrate that they’re good at beating the drum and arguing for the value and, and pushing the notion of design forward. That’s often how you end up getting that job, and then to have gotten to that point and then have to let go of that evangelist identity that got you there, I think it’s very challenging. It it’s actually… Peter: I mean, it reminds me… Jesse: yeah, Peter: Oh, I was just going to say, it reminds me of the same challenge that you have when you go from being a designer to a design leader and you have to let go of your identity as a maker. Now you’re a leader right now. We’re saying, as you go from being the design leader to an executive, you have to let go of your identity as a design leader, to being a business leader. Do you think Brian Chesky, the CEO of Airbnb thinks of himself as a design leader? Jesse: Yeah. Peter: At some point you just let go of that stuff. You know, he’s got a design degree, but that’s not his job. The legitimacy of imposter syndrome Jesse: Right, right. Well, and this is connected actually to another question that we got this question from Matt Bouchard by email about imposter syndrome among design leaders because, you know, every time you go through one of these transitions of identity, right, from designer to design leader, and then from design leader to design executive there is a certain amount of letting go of the old identity and welcoming in the new identity and the new identity may not fit at first. So there’s inevitably going to be a little bit somewhere in there of imposter syndrome, if you’re actually taking on something that is genuinely new for you, the challenge is that imposter syndrome frequently, kind of, the way that it manifests in people’s minds is in these, the sense of the expectations that are being put upon you in the new role and the, and the, the question of, well, do I, am I going to be able to measure up to these expectations? Am I qualified to do these things that are being asked of me? And in a lot of cases, I feel like design leaders sense of themselves as imposters is entirely legitimate for exactly the reasons that you’re describing. They, they are imposters because they are being asked to do things that they actually are not qualified for, that they have not been trained to do, that they don’t know how to do, that they’ve never done. So it’s very, very natural to feel like you’re an imposter in that situation. The question is, can you trust yourself enough to improvise and navigate your way through a situation that you’ve never faced before? And that again, requires letting go of a lot of your sense of identity that is tied to your expertise and your experience stepping into something new. Peter: I well, yes. So I suppose, Hm, imposter syndrome is real, but it also kind of doesn’t matter. Or it matters only, it matters only to the degree to which it is in your mind and it’s holding you back. Jesse: Yeah. Peter: And, and I think, I’m trying to think, like, you know, just suck it up. Like unfortunately, any thoughts I have about it are you kind of don’t feel all that helpful. Just like, stop letting it hold you back. Jesse: Well, I will say that there is an element of this that it’s very easy for us to say as… Peter: as middle-aged white men? Jesse: …precisely, I mean, imposter syndrome, and I see this with my clients, it takes on a whole different dimension when you are the first or only woman leader in your organization, when you are the first or only person of color in a leadership role in your organization, those kinds of things. And even if you’re not, you’re still going to be carrying over the experiences that you’ve had throughout your entire life of being told that you’re not right for this, you’re not right for that. You’re not enough. And so there are layers and layers to that that are not adequately addressed by simply sucking it up. Peter: Yeah. Yeah. I mean, I guess… trying to think how many of the leaders I’m working with demonstrate some form of imposter syndrome. It doesn’t come up in the conversations that I have with my thought partners as much. I think there’s something to be said with, yes, you are an imposter, but kind of assume that almost everyone around you is as well. Like no one has it figured out, we’re all making it up as we go. Jesse: That part is very important that I think a lot of people, especially younger designers tend to, you know, receive all the, all the wisdom of method and process and deliverable and assume that this stuff has all been buttoned up in advance for them. And it’s not the case at all. Peter: And I think kind of related to that, you know, it’s still burgeoning, but there is a growing corpus of material around design leaders and, and, and becoming a design leader, and what that path was like. I’m thinking back to the Leading Design conference I was at a month and a half ago in New York, and people telling their stories of becoming design leaders and you realizing like, oh, they were, all of the people that you hold up as, as models were imposters once. You know, kind of recognizing, the distinct value you have in terms of your perspective, right? You are in that position because you bring something that no one else in that organization does and, and really drawing from that value that distinct value that you have. Jesse: Yeah. Yeah. I mean, The power of self-reflection Peter: If I’m reflecting on this, I don’t think we do enough to prepare, literally prepare, people to assume these leadership roles. And that’s true across, across the organization and not just in design, but for designers, the responsibility then is when you are in a leadership role to like to do your homework. You know, I follow Abi Jones on Twitter and she is a very reflective leader. She reads books. She, she tweets about her experiences, reading these books. She thinks about how those experiences she’s reading in the books aligns with the experiences that she’s had as a leader. And, and I don’t think enough leaders are doing that. Doing the homework. To take it from a totally different space, Steve Kerr, coach of the Golden State Warriors. You know, you might not have known, but now, you know, you see that I’m going to bring a basketball analogy. And before he was coach of the Golden State Warriors, he was never a head coach. And in his rookie season as a head coach, he wins a championship. Now he probably felt some degree of imposter syndrome stepping into that role. The, the prior coach had been successful taking them to the playoff two years. Who’s this guy, who’s never had this coaching job before, think he is that he can somehow do it better and he’s never done it before? Now. He had some success, he worked for two amazing head coaches as a player :Gregg Popovich and Phil Jackson. So he saw what good coaching looked like. But he didn’t just see it. He was reflective on it. He took, like, took it and like broke down those principles of what he saw and built them back up into his own philosophy of coaching. So he was very explicit and intentional about how he was going to coach. And then part of the reason he got the job is he had a binder, you know, an inch and a half thick of what he would do if he were to coach the Warriors, how he would change things, the plays he would run, like he had gone through that process of really being, of being thoughtful about what it would mean to be a coach. And, you know, that’s a different kind of job than what we’re talking about. The money is different. The opportunities are different. I’m not saying you know, before you become a head of design, you need to have a binder an inch and a half thick about what you would do, but you need to think a little bit, right. Like, like, and I wonder how many leaders are doing that work to take time out and reflect on what it means for them to be a leader and how they will perform in that role as opposed to, they’re promoted or they’re hired, and they show up one day and maybe they’ve read The First 90 Days. And that’s the extent of, of, of their thinking about management. Jesse: Yeah, yeah. Yeah. So, I mean, I definitely hear the need for leaders to continue to invest in their own growth as leaders and not just be crank turners, doing the job, because if you are, if you don’t have a point of view, about the work, if you don’t have a philosophy about the work, what that means is that other people’s philosophies can run roughshod over everything that you’re doing. So I think that leaders do need to have a point of view. I will say that I can definitely hear, as you’re talking about taking the time to read the books and listen to the podcasts and, and do the the reflection and research. I can hear the voices of those leaders saying, Hey man, I’m already putting in 50 to 60 hours a week just trying to hold this thing together. The last thing I need is homework right now. And that part of it is real too. So yes… Peter: Can I push back on that a little? Jesse: Well, sure. Yeah, go ahead. Peter: I’m thinking measure twice, cut once. I suspect, if you do some of that homework, some of that 50 to 60 hours a week might reduce, ’cause you’ll learn where to focus your energies, right, Those 50, 60 hours a week, who’s saying you need to do all that work? And, and what, what are you doing as a, as a, as a leader to be responsible for your own time? And, and, and when I hear 50, 60 hours a week, that’s me hearing leaders who don’t have a philosophy and don’t have a perspective letting others drive their labor, their, their, their activity, instead of being self-determined. Jesse: Yeah, yeah. So it sounds like the, the way that you break this chicken and egg cycle to your mind is for the leader to invest some extra time in themselves and their growth in order to be able to show up differently in the organization and reduce their workload. Peter: I mean, it’s, it’s, you know, the Steve Kerr story, or or, we’re thinking about actors and rehearsal, right? You go through a lot of work and you do a lot of rehearsing and, and you might do research if you’re a method actor, this, that the other thing, so that when you show up, you’re prepared. It’s still going to change. There’s going to be circumstances that you didn’t account for that you’re going to need to adjust for. But I, I, and I hadn’t quite had this thought before. I’m actually enjoying this part of the conversation because it’s kind of a new notion for me that like… Part of our, there’s a role that senior-most leaders have, with the leaders in their orgs that they’re trying to bring up, in making sure they’re prepared. There’s a role that people like you and I, and others who are kind of operating in this independent consultant coaching ecosystem have in helping prepare leaders for the work that they’re doing. But I don’t hear a lot about preparation about, about the work before the work… Jesse: yeah. Peter: …that you do in order so that when you show up, you are ready to do that work. And I think we too often are just thrown into or throw others into a situation without any preparation and context. And then no one benefits, no one gains. And so making, making this idea of preparation, a real practice that, that we encourage that we ,yeah, we encourage the people who are listening to us to, to be part of whether it’s for themselves or for the people they are responsible for within their organizations. Your practice and purpose as a leader Jesse: Yeah. You use the word practice, and I think that’s a really important one. It’s definitely a big theme in my work with my coaching clients. Because my sense is that because of the, the nature of the role, the nature of the work being something that requires a lot of adaptation, you know, you talked about Steve Kerr and his binder full of plans, and I don’t think this is a role where you can show up with a binder full of plans and be successful, actually, because you probably have made a bunch of assumptions about the situation that you’re stepping into that are not going to hold true, because this is, to your point, a less mature practice than coaching a basketball team. So you’re going to have to adapt more and again, I feel that once you’ve got the job, you know, your experience and your expertise may have gotten you the job, but they’re not going to be what makes you successful at the job. What makes you successful at the job is going to be your ability to adapt and roll with things and surf the situation. And it’s your practices, your day to day, week to week ways that you keep yourself sharp as an individual, as a leader, that are going to make the difference more than your knowledge or your expertise. Peter: I would say your practices and I would include, and I don’t quite know the right word for this, but, but whatever your true north is. Jesse: Oh Peter: Right, So, so I agree, right, You’re going to, you’re going to need to adapt. You’re gonna need to ride the wave, but if you don’t have a compass bearing on what, what is true to you and in how you operate, you’re going to get buffeted by those waves and thrown around. But if you have a true north, you’ll always kind of tack back toward it and you’ll be able to make decisions based on it. And, and folks will, we’ll have a sense of who you are. Jesse: RIght. right. Peter: We’ve talked about trust in the past. You’ll, you’ll show up in a consistent fashion so that folks know what to expect from you. So, so even if you’re not doing preparation in. A binder full of design process that you want to Institute within this organization, and if they just follow these processes, they’ll put out better design, you can do preparation in terms of taking that time to identify your, your principles and your purpose and, and your, your, your values as a leader. But much as we talked about a couple of years ago on, on for a design team, you know, the, the, the, the the importance and the utility of, of a clear purpose, clear values, clear norms, how you, how you behave, those are true for you in your leadership. And shouldn’t take days, you should be able to do that and hours if not hour. And with that, just making that explicit, I would think would help guide you through the uncertainty that is definitely going to be par for the course in whatever you’re doing. Jesse: Yes. Yes. Well, I will say that with my coaching clients it takes more than an hour to articulate somebody’s philosophy of design and, Peter: Did you, is that a, is that a practice you work with them on? Do you, do you have kind of tools for helping them get at purpose and vision and values for themselves? Jesse: It is central, to your point, it is central to what I do. Because a leader who is not engaged with their own authentic sense of purpose of what they’re doing in the world again, their decision-making is going to be more easily influenced by the, by the factors around them. They also are not going to be showing up with that level of passion for the work that is often necessary to drive through those difficult situations and get through to the other side. So yeah, every single client that I work with, we have extended ongoing conversations about their values, about their purpose, what they want to create in the world. Because if they’re not connected to that, they’re going to be miserable no matter what their role is. Peter: Uh, do you see how that clarity of purpose and personal mission helps them act? And I don’t know if you’re, if there’s anything you can share in that regard. Jesse: it’s more about practices than it is about, like, I’m going to write up a self manifesto and create a deliverable, that’s going to encapsulate my philosophy for the world. That’s… Peter: oh, that’s just what I do. Jesse: As well. I mean, it’s, it’s fine. If that’s, if articulating it to yourself at that level of detail is what is what you need, but people often get lost in the weeds of trying to pin down exactly the thing that they can sign their name to and say, I’m going to live by these values all the time. It’s more of how are you incorporating that inquiry into your practices on an ongoing basis. And how are you continuing to ask yourself how your approach needs to evolve based on your evolving understanding of what you’re doing and the best way to accomplish what you want to accomplish in the world. Peter: I think that reminder for folks to, to, to kind of engage in that reflection and inquiry and making that part of a personal practice this, this is as good a place for us to end this conversation… Jesse: terrific. Peter: …as any. Well, thank you, Jesse, for taking time with me to grapple with some stuff that allowed me to have some realizations that hadn’t at least been as clear for me. Jesse: This has been fun. Peter: I appreciate the time and the engagement. Jesse: Apologies to everybody whose questions we didn’t get to. We ended up running off on some of our own tangents says we like to do, but… Peter: …that’s how it goes. Well, take care and be well. Jesse: Thanks. Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @jjg. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com. You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript [This transcript lacks the polish of some of our others. Please forgive!] Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Adaptive Path co-founder and author of the forthcoming book, Time to Listen, Indi Young joins us. She’ll share some of what she’s learned from her career, giving organizations tools for empathy with their users and individuals, the skills to listen deeply to each other. Origins of Indi’s methods Peter: Hi, and welcome to the podcast. So I, we’re just going to dive right in. We’ve known you, we’ve known each other for well, over 20 years. We started Adaptive Path together. I knew you, I think, through the Miller Freeman web conferences even before then. And I’d love…. So we, when we were working together at Adaptive Path early on, you introduced me to your pro… process, in particular the mental model process, and then you ended up writing a book on mental models, and then you’ve written a book on practical empathy. And now you’ve about to, and you can tell us kind of the details, release a book called Time to Listen. And this is a big question and take as much time as you want answering it. But I’m curious about this trajectory that you were on and how you’ve seen kind of your progress or your evolution from when we first started working together, building mental model diagrams, to kind of your, where, where your head is today in, in, in how you approach your work. Indi: I could take like the whole hour answering that one question, Peter: Well, Indi: you guys will, but, but in with other clarifications yeah, the and yeah, I, I was trying to think back, like how, how did we meet? And I only remember meeting Mike from Adaptive Path on the ski lift at Sugar Bowl. So I can’t remember all the other origins story, but anyway trajectory, I started off, trying to embrace and adapt the the business, or rather the engineering approach of writing functional specs. This was long, long, long ago, Jesse had written, he, he wrote that book. Uh, What was the one? I can’t remember the title of it. It has Jesse: My book, you’re talking about my book. Yeah. Indi: yeah. Your book. Yeah. And that that’s it. Yes, the layers one. Peter: right. Indi: But that came out like after I had given up on the func spec and it reminded me a lot of the func spec, the functional spec is just kind of like writing out everything that the thing has to do. And that is very much about understanding how a process works, how a standard operating procedure works. And, and in coding it and how do we encode it? And then, you know, w- how do we make an interface on it? And so that was very much about processes, methods, procedures, all of these things have different contexts, where there are edge cases where like, okay, in this context, the method doesn’t work quite this way. This is how it is done, or how other people have done workarounds. And so we need to encode those work arounds or those other contexts, and those are called edge cases. And what was happening when we started Adaptive Path was that we were no longer focusing only on engineering and science as things to encode or business processes to encode. Right. We, we were starting to encode things that had more of more of a service aspect to it. We, what did we do? The NPR site or something, right. Peter: NPR, PeopleSoft. Yeah. Indi: Yeah. W- it was not a process. I mean, sure. Sell PeopleSoft. We were working with a sales group and sales could sort of be said to have a process, but it’s the closest thing to listening deeply, actually. So So we were w- w- that shift had happened. And along with it, we pull a little bit of the functional spec with us. And we also pulled that word edge case. And the edge case was now a word that was applied to people. And this is where I started going, like, okay, there’s friction there. That’s not right. So that was my personal response. And because you don’t call a person an edge case, no person is an edge case. No human mind is an edge case. There are communities and groups and ways of thinking. Yes, but nobody’s an edge case. The edge case belongs to the process. Anyway that was my personal sort of issue with it. And the rest, the rest of the evolution is really all about me learning from the people who are working with me, or me learning from the people who are learning from me about how. How to, how to make a clear guide, a clear method you might say for working at understanding people’s minds so that we can create support for different thinking styles for different approaches to the same purpose. Evolving mental models Peter: How so, you know, in 2001, we worked together building mental models, right? You’re, you, you talk to folks, you listen deeply, you take a lot of notes and then you kind of decompose and recompose what you heard to create these structures that help you better understand how folks think about how they solve problems and then also go about solving those problems. Right? There’s almost that it’s almost kind of two layers to it and you call it that mental model diagrams, a book about that. I’m curious because that’s where you and I kind of diverge is, is you, you know, you left Adaptive Path and continued to develop your practice. And you’re mentioning how you developed it in response to collaborating with I’m guessing people within various organizations. I’m wondering if you’ve had kind of, if you have a stories to tell of kind of a clear aha moment where you thought things should be one way or behaved one way or where you used to practice one way, and then based on an experience you had in collaborating with someone you’re like, oh, wait a moment. This is, I have a better idea of a better way of approaching it, given this kind of experience I’m having. How, how has, what were some of those steps… step changes been. Indi: The there, yeah, there were a lot of step changes. Probably too many for us to cover or from even to remember what his step changes was that aspect of taking notes, lots of notes. I, when I started trying to teach her, I think our team members at adaptive path, right, how to do this, it’s like, Ooh, paying attention to what a person is saying and, and writing things down about what they were saying. I’m a light, just let it be a transcript. It has to be a transcript cause otherwise you’re going to be doing too much thinking and not hearing. And, and and this happened even after I, I left Adaptive Path as that people would want to write notes and they would say writing notes is how I make sense of the state is writing notes is helping me analyze this data so I can come away with insights. And that was a huge aha moment for me because, and of course this is layered. First of all, I don’t want the insights to happen while you’re listening to someone. When you’re listening to someone, you have to pay rapt attention and that’s it. You’re going to follow that person. And that’s it. You’re not going to bring up topics. You’re only going to follow their topics. The thing that you do as sort of a background process in your own mind is making sure that they are getting to their interior cognition and helping them there, or helping them clarify points that their interior cognition for each topic. So there’s a lot to unpack here. So the first aha moment was okay, no notes. This is at the time you know, we, we would sometimes be bringing recording devices in. We would sometimes be doing this by conference call and sometimes just doing video recordings or whatever. Right. But we’re recording, so we’re not taking notes. And that was a huge, aha. I think that really helped people understand that in a listening session, it’s not, it’s not where you’re trying to forge insights. You not trying to do your work there. Your work happens later. What you’re trying to do in a listening session is understand another person’s perspective, another person’s approach to the purpose, another person’s, you know, if you’re not spending that time, understanding them, you’re not going to get their perspective. What insights you’re going to pull out of this are going to be your own insights. Not understanding someone else’s way of thinking. And this is why we continue to have software and services that, that don’t support anyone. That’s very different thinker than the team themselves, because we automatically, we feel like if we’re going into a listening session, we have to work. We have to do some thinking and come out of it with insights. And in, in, if we’re going to understand somebody else’s way of approaching this purpose, what we have to do is let go of… we are not an employee at that point. And so this was an early on thing I would say, you’re not an employee, you’re just a person you’re just listening. And then later on, I ki– you know, and no notes, right? You can, if you think they’re bringing up a topic that they may want to unpack later, and you both may forget about it, you can jot down that topic, but that’s all, you’re not going to write notes. And then later what happened was this idea that the rapt attention and the following and the topics really help people or give them sort of a guideline for paying attention to the other person. Being able to recognize that you’re not allowed to bring up a topic. You’re not going to bring a question into this that you invented outside of that. You’re only going to be asking people about their interior cognition, their inner thinking which includes, you know, all sorts of inner thinking, their emotional reactions and their guiding principles, which are kind of the rules that they use to make decisions or how to act or react. Types of empathy Indi: So so those are the interior cognition things and that’s so I was sitting at breakfast with Lou Rosenfeld. I really wanted to write this next book. We were, it was like a perfect day and we were at this restaurant that was on the water and there were sailboats going by and we’re both like, oh my gosh, this is like, how did we end up here? It was beautiful. And so I’m trying to explain to him what this is. And he finally goes, he says, well, so what you’re talking about is kind of a practical empathy, right. And um, Okay, that works. And that’s when and so, and then he finally agreed to let me write the book. And and that’s when I started researching, well, what is it the mean anyway? Cause like the way people use it as varied and it turns out that there’s so many different types of empathy in the psychology world and they’re all totally valid. And there are books written by particular professors of Yale um, who um, who take one definition of empathy, which is the def– the type of empathy called emotional contagion. And then they’re all like I’m against empathy. And and the kind of empathy. I meant that when I’m paying rapt attention, what I’m trying to do is get my head inside their mind and understand their perspective and see their perspective. And that kind of empathy is called cognitive empathy. It’s just a different kind of empathy. There’s a third kind of type of empathy that this very popular, Dr. Brene Brown speaks about it. And that is what the psychologists call empathic listening. So it’s an in the moment, empathy, cognitive empathy is building an understanding of somebody. It can, it can happen over time trying to get their way of thinking their interior cognition and empathic listening is noticing something’s going on for some. And it’s normally introduced as an emotion going on for someone normally a negative emotion going on, but it can be anything, it could be interior cognition, which includes inner thinking. It can includes like a, a pause, like so normally my guiding principles to do this. And normally I would decide that, and you know, you’re not thinking that consciously, but you’re pausing. And if you notice somebody pausing or you notice somebody having something going on, then what you can do is offered, listen, and that’s called empathic listening. And so in the moment, what happens is that the end of it, the other person feels heard and maybe their pause or the something going on is a little easier for them to deal with. But that’s a, in the moment thing, whereas cognitive empathy is long-term thing. It, it gathers information for us to be able to understand what those groups and communities of thinking are so that we can start writing support. services for those different communities of thinking. And those are what I call thinking styles. So there’s another, there’s another a day. But I tell you about when Christina was talking to me about thinking styles, but um, Peter: Christina Wodtke Indi: yeah. Do you want to insert anything first? Peter: uh, Jesse, Jesse looks like he’s got a Jesse: I, I am going to change direction here a tiny bit. Seeking the intangibles Jesse: I curious about this turn that you described in your thinking and not just in your thinking, but I think in the thinking of a lot of people at that same time, from a process oriented approach, to thinking about how we structure the requirements that will ultimately drive design decisions toward an approach that looks at more of the intangibles, right? Less of the things that you can measure with a stopwatch in the old fashioned industrial style And ended up curious about what you went through in bringing organizations around to this kind of thinking as someone who was working most of the time as an independent consultant, just one person coming into an organization as you have over and over again, over the years, and helping people see a different way of doing things. And and I wonder what you learned about about helping to create that shift of mindset inside organizations over the years. Indi: THat’s a really good question. That’s the thing that I have had the hardest time with because I’m I’m naturally an introvert, so I’m like, I don’t want to get in other people’s business, you know, they can do things the way they do, but I was so on fire about this and I actually caught fire. Stronger after we have sort of this populist political scenario happening in the mid 2010s. So the, the fire pushed me past being an introvert. Um, And I utterly did, I, I’m not naturally gonna go there, but, but this had to be done because, and I did not do it well, I didn’t know how to do it. I still am struggling to do it, but I’m getting a lot better at it, which is taking this idea. So I’ll, I’ll, I’ll sort of lay it out as a, before and after, before what would happen is that the. Methodological-ness of it. The, the way that a an opportunity map, which is another change that we did looks, it’s a mental model diagram on top with the capabilities aligned beneath, it looks like a city skyline in that that sort of like solidity attracted people to to this approach because you’re right. We’re trying to, we’re trying to understand the intangibles and having a tangible method for doing that was really reassuring, Jesse: so you think it was the visualization itself that helped make it feel real? Indi: yes. I think it was. And then my confidence in being able to build that visualization based on cognitive empathy. So to, to make that intangible, tangible, I think is what made people reach out in the beginning. And so for many, many years, that’s all I was doing was I was relying on an individual to get interested in the way of looking at it, that city skyline kind of thing, and interested in how it is built and then to hire me to build it. And I would do that. And then I would work with them with the, with what we’ve got, okay, what are we going to do with this? How are we going to approach it? How are we going to find you know, a solution? And in the beginning I knew these things would last for decades and it wasn’t about a solution. It was about many solutions, but it was very hard to convince people of that now Now I speak about it in an entirely different way that that bring that starts there. This is a, this is a way for us to go forward over the next 50 or a hundred years. We’re going to find little areas that we’re interested in right now as an organization or as a team. And we’re going to dive into that. What I call it is we’re, we’re looking at gaps between how we support some thinking in the mental model, part of the opportunity map and how we support the thinking styles there. what we can also do is, well, we’ll find a gap that we’re really interested in right now. Let’s say, Hey, we’re not supporting people who are hard of hearing or are deaf. And in this one particular area, now that is not a thinking style. That is a demographic lens on a thinking style. So what we get to do is we get to look at thinking styles who are both deaf and not, they have the same thinking style, but what extra things do we need to add in with this extra lens? So we’ve got a tiny sandbox and we’ve got this information in the sandbox, but we can also put other information in the sandbox, pull other toys into the sandbox, other data from secondary research, other data from institutions, other you know, quant data that we’ve collected ourselves. Survey data. What have you, right? We can put all that information into the sandbox work on that one small thing at once and create something that is different, something that is specific or, or in a way bespoke for that community of that. With that demographic lens and be more intentional about it rather than say, oh, you know, we can just, you know hire or use AI or something to make the captions and it’ll be done. And that does not work very well for someone who is deaf. And so we’re paying more intentional attention in this way. And this, now I want to go back to this idea of measuring the intangibles. Is it in the first few? Probably the first decade, maybe that I was doing this half the time we would get this information, we would set out to do something. And then, and then somebody, that person who was leading the team would either leave that company or would get changed positions or get vetoed or something by someone higher up. And so we didn’t get a lot of traction. We didn’t get the things we did every once in a while, like PeopleSoft was a good example. Or we got something out of it and it kept that project kept going. And indeed, that’s actually a good example because the person who hired us, they’re moved to a different company and hired us again. Right. So that’s how it was like sort of the, the Tinker’s cart, like clanking along, down the road the beginning. Jesse: Yeah. Indi: Yeah. Problem space and strategy space Indi: But, but now it’s much more the idea that I speak about, Hey, we need to create support more equitably, and we all agree on this. And yet we’re spinning so fast through our processes of development that we need to understand that there is a different space, a strategy space. There’s a problem space to. Where we understand a person’s approach to the purpose. And there’s a strategy space where we’re collecting. I mean, we’ve already the strategy space exists right now, but it isn’t, it isn’t cohesive. It’s just kind of like held by a couple of leaders and the leaders aren’t all that intentional necessarily about it. At least in my experience. But if we have an intentional space that we call the strategy space and in that we have all this knowledge that we’re building and all this knowledge from past places that we built knowledge, all this knowledge from that is coming out of the services that we’re providing right now. And if we can then look at those with relationship to where we want to S you know, exit a gap or move, I’ve got these help and harm graphs now that you can actually do with numbers, where you can measure this benchmark is. And then see yourself getting better over time moving the, moving the marker up. So so that’s now I think that’s a whole different way. That’s a much less tinkers cart kind of approach, and I’m still, I’m still trying to get better at it, but yeah. Long-term thinking Jesse: Yeah. I’m interested in what you said about the idea that this kind of work can guide an organization strategy over the span of decades, 50 years, a hundred years. What is it about this? Because you don’t often hear people talk about deliverables that have that kind of staying power. What is it about this work that enables it in your opinion, to be the foundation for that kind of longterm thinking and longterm strategy on the part of an organization? Indi: THis opens up a whole other book, which is to say there is a lot when Silicon Valley started developing, it was, it was making Silicon chips, right as a totally different game. And then the game changed and a lot of money could be made at places like Google and Facebook and Google and Facebook are not necessarily for the long-term they’re in it for the money, right? They’re not in it to be a business that is going to sustain its employees for a hundred years or a business that’s going to sustain its employees and the people that is trying to support because it does such a good job supporting those people that is going to be around in a hundred years. So many businesses right now are like, oh, I’m going to like spin something up and then get bought by Google or whatever. And that’s a totally different mindset. Now you can still use deep listening and mental model diagrams and opportunity maps and gap analysis and the help and the harm diagrams to help you get bought by Google. But so like venture capital is about return. It’s not about sustainability necessarily. At least at its outset, I think there are VC firms that are about sustainability and there are lots of people across the entire world who are in it to be sustainable, who are spinning up their own businesses without venture capital, because they’re running a small business. So in a way, that’s, that’s the difference between like a startup and a small business is that VC is involved in the former and not the latter in a way. And I think that this small business mindset, this idea that I’m going to run something that not only supports me in my employees, but also really does an amazing thing in the world for people, not for me, not getting me famous and rich, but for people then that. So that’s, that’s kind of that whole water that we’re swimming in. Jesse: yeah. Indi: So the the idea of being able to… to have a way to think longterm to think, and especially for culture here in, in the us, we tend to think short-term, I don’t think all of us think short term, I think all of us at least think individually within with respect to the next generation, but not a couple of generations. Right. At least in terms of popular culture. And there are certainly a lot of cultures and communities in the United States who do think farther, but this is a way of, of giving you permission to bring that kind of thinking into your organization. Long-term thing. It gives you a way to use it in the near term. And also it is usable in the long-term. Finding users’ purpose Indi: So one of the, one of the things I say is like, we are listening to people about a purpose that they have, and purpose can be defined in any way you want a goal. I think that you need done now, or thing that you’re doing over the course of 10 years. It can be anything. And if we frame each study by a purpose or a sub purpose or something uh, it can be it, you know, many levels of granularity, but we frame it by that purpose. And people talk to us about their interior cognition as they address that purpose in the past, then we can see patterns. And the neat thing is, is that that purpose is not the solution. That we create the service that we create. The neat thing is, is that that purpose is something that they’re trying to get done no matter which tools they’re using. And I remember in the early days, Peter, I would call it like agnostic of your of your solution. And Peter used to give me a little bad time about agnostic of the solution. Cause, cause this is, this is what we’re trying to do is like, let’s say the solution is insurance and insurance. Wasn’t a solution a hundred years ago, but you could get in a time machine and go back in time and talk to people about certain purposes that you could talk to people today about like how did you recover from this injury where, you know, you were, you know, you couldn’t work for a year, right? You couldn’t earn anything for your family for a year. How did you deal with. The the time that your husband who was a minor died in an accident, and now you have, you know, your six kids and you have to leave that town. Right. Nowadays we might have a tool called insurance to help with that. They didn’t then, but it’s the same purpose. And so if we did get into a time machine and go back and collect that information about what went through people’s minds, it would still be useful today. Peter: um, Indi: The, yeah, go ahead. Peter: Oh, so I am wanting to unpack the word purpose. It’s, it’s one of those words that I think can have a lot of, not just definitions, but valences, and it’s also very bound in perspective. So I think about purpose typically in my work with the design teams that I’m supporting and what is the purpose of that design team? Cause I see purpose as essential for any team to have a thing to rally around. And what I say in my workshops as a team, without a purpose is just a group of individuals. um, so. Indi: a mission Peter: Yeah. So you have, you have teams having purpose, you have businesses having purpose or purposes. Indi: and those, Peter: I think, let me just finish this thought though. You’re not talking,I think more on the side of the person. The customer or user of whatever the business is providing and you’re using purpose in a singular way, but I don’t think you mean it that way. Cause cause you might talk to 20 different people and around what you think is the same purpose. But, but you know, you were talking about healthcare, right? So I want to, I want to be, you know, I have, you might have some higher order purpose of, of feeling confident in your long-term health, but as you talk to 20 different people that might be interpreted, maybe not in 20 different ways, maybe through your analysis, you realize four or five different purposes that have emerged. And I’m, I’m just wondering kind of how, like how you unpack purpose cause so that it becomes something you can really work with. Indi: So the, I told you that it was at any level of granularity and what you’ve been talking about is the super broad umbrella level. I have be healthy. Right. I did do very early on a study where it was like, how do I cope with my health? And it was too broad, no patterns come from it because everybody has different approach to different aspect of it. So a study where we looked at people who have three chronic issues, medical issues at a time, and how do you cope with those three chronic medical conditions that kind of narrowed it down a little bit. So it’s like, you know, you can, you can narrow it down further and I prefer narrow or purposes. It because of the patterns, you’re not going to get patterns enough patterns or, or you would have to do listening sessions to get patterns with like, 55 times as many people. And I tend to make very small studies. So the purpose is very compact. You can think of it like the Goldilocks, right, kind of thing. It’s like a small purpose, very small. It’s just an aspect of, of this taking care of my three chronic conditions. And it’s only the aspect of say changing doctors. Okay. You could take that with the insurance thing and only talk about the aspect of when you are when your co family income earner dies and you have to go on and you have dependents, right? So you. Think of it in this very small, very well-defined way. And still the beauty is, is that people think about it differently. And we can then find patterns with a smaller set of people. We can do listening sessions with say 15, 25, people instead of 50 or 75 people. So the idea of purpose can be quite grand, but it is granular. I used to call it intent. And something that Jared Spool said made me dissuaded me from using intent. Purpose is not the greatest word to use, but it gives me it’s like language is going to evolve. And so at some point that word is going to change swell. It gives me a place though, to actually react and say, Hey, this. Can be a very small thing. It can be a very large thing. It can be a thing that you do in a couple of hours. It can be a thing that you do over the course of years. But if you’re going to do a study with the big thing, like it could be a very small thing that you do over the course of years. And that could be a very well-defined purpose, which could be something like develop a way to not get so stressed. When I am in front of a person who behaves in a certain way, and it could be a certain person, it could be any type of that representative of that person. But it’s like over time, I’m developing a way to handle that situation for myself better. So I don’t get stressed. and that’s over time. Right. But it’s still a very small purpose. So the idea that. Purpose can be any level of granularity. It can be a goal, it can be anything. From insights to solutions Peter: It feels like, Indi: the thing, the thing that it is not is the use of the service or the Peter: is the solution, right? That’s that’s what I think I’m kind of getting, getting to here is that you’re you’re you’re you were being. If, if if there’s any rigidity in kind of how you’re approaching this or thinking it’s to distinguish between an insight and the solution, and I’m sure we’ve all seen this where especially working in software folks want to get to solutions very quickly there. We want to solve problems and they don’t spend the time, provide the focus or attention to really understand the insights, the, what you’re calling purposes, all the they’re… they don’t sit with that long enough to then better understand what solutions are best given this whole range of purposes and insights and stuff that, that that’s in front of them. They instead to quickly jump on a solution and kind of drive to that. And so you’re really trying to distinguish between purpose and solution. How much in your work then though, do you stop at the identification of purposes? You know, or are you working with the, your who, your collaborators to turn that corner and identify solutions? Where, how, how directed do you end up getting there? Indi: it depends on the teams that I’m working with. So a team that I just worked with is extremely experienced, but also stretched extremely thin. They wanted me and my team to help them. Develop thinking styles in, for employees who have the purpose of getting through a very particular intensity or a couple of months of intensity or a year of intensity in their work. We called it a challenge. And sometimes that challenge was this manager and I do not get along. Sometimes that challenge was I’m not getting the attention or the, the, the what’s the word, the promotion that I want. Sometimes the intensity was, oh my God. There’s layoffs. Okay. And so the purpose was to get through whatever that thing was for employees and that team knew what they were doing. They just didn’t have the time to do it. And, and that’s very typical. So you’re right. Everybody. So much weighted. I like go off camera entirely because there were weighted way over there on the solution land. And we don’t spend enough time over here. And this is, this is the way it doesn’t give you permission to spend some time over here. Cause it’s actually very very well laid out. There’s a very strong framework, a trustable framework. But the, so we stick around with some teams like that team to help them get that first sandbox designed like which out of all. So the insights don’t happen with the listening sessions. The insights happen all the way down after we’ve got the opportunity to map and we see the gaps, the gaps or the insights, and there’s going to be a plenty of them. There’s going to be like 50 to 199 sandboxes that we could play in with various you know, Layers to them. So like maybe this sandbox, but that thinking style or the sandbar, same sandbox with the other thinking style or with that demographic lens on it. Okay. So, so we help them figure out what set first sandbox that we’re going to play in. We can help them with playing in it, finding other toys to bring into it. Other knowledge that got built as what I call toys to put in the sandbox so that we have more toys to play with. We have more understanding as we’re developing some solutions out of that sandbox. Aligning team culture to user purpose Jesse: It seems to me that part of what that requires is a culture of a cultivation of these insights and of this knowledge and a, and a culture of knowledge stewardship in the organization that looks beyond the immediate project. Because most of the time, what you see is insights that are generated for the context of a specific product problem that’s been defined. And then they work backward from the context of the proposed product to to populate the insights. And then as a result, those don’t get used in any other context. And I’m curious about what you’ve seen in terms of organizations that do that ongoing cultivation of their insights really well and, and separating them from solutions the way you’re doing. Indi: Yeah, exactly. There are a few and they’re they’re growing. So I mentioned insurance because oddly enough, several insurance companies are very good at this. Eh, they, I think most of them have a central kind of team that works with different divisions, right? In terms of, Hey, we’ve got this knowledge, we’re building this knowledge. What knowledge do you need? What are we missing here? Maybe we don’t need to do a study because we’ve got all the, all the knowledge we need in this sandbox. Maybe we need to extend our. Mental model diagram. One of the things I did with the airline project was we worked on it. We did eight studies one after the other and just kept extending it so that we had some sort of framework for people to work with in the future. It, isn’t going to be complete in the future. You may need to add a little study here and there to build knowledge. That’s very specific to the thing that you’re trying to solve for, for the gap that you’re trying to solve for. But but the idea, so, and a certain financial companies are doing it as well. There’s one, I’m not sure if I’m allowed to mention company Jesse: I don’t need names. I was really, it was really just more curious about methods and approaches. Indi: yeah, yeah. They’re the one that’s doing it without a centralized office actually has. Baked into its very founding day, the idea that we’re supporting a person trying to accomplish a purpose. So they’re very much focused on the people’s purpose. And that makes it a lot easier for them to be, to not have like a centralized team that is helping other teams build knowledge or use the knowledge Jesse: interesting. So there’s already a larger culture in place. That’s keeping them all aligned toward common purpose. So you don’t need these mechanisms to do. Indi: It may not work a hundred percent in every case. They do try to share knowledge with each other quite a bit. There’s a lot of work done internally. So it’s not. If nothing is perfect yet we have not made the perfect shift, but there are companies and you’re right. It is definitely a culture. And I like this idea of cultivating to the whole idea of growing something new part of, part of what attracted people to the tinkers cart in the beginning was it, it felt so right. And I think most practitioners out there who aren’t like already drunk on the Kool-Aid of going fast, this feels so right to have to have. And this is how it works mostly is it? You’ve got your solution space and that’s where everything’s spinning really quickly. And that’s fine. Keep it spinning quickly. I’m not asking you to slow that down, but you’re adding the strategy space and to fill that strategy space. The things we need to make better decisions to support more people, to be more equitable. We need to understand people’s thinking, and that’s the problem space. That’s where we go and understand different purposes. People have. We try to s– skill, scope them down so that we can get patterns. But there’s other data too, from different sources, not just listening sessions that go into the strategy space. And I think that that just feels amazing. It’s like, yes, that’s, what’s missing. I get that phrase all the time that this is what’s missing. You have a way of thinking about it. That’s very clear and feels trustable. And what happens normally is that teams will will do work in the solution space in the strategy space. with their work in the solution space. Okay. It doesn’t, it isn’t a vacation from the solution space. There are some companies where they can take a vacation from the solution space and go and do this. The airline for one, it was merging, there was this space where all of a sudden we had time because during the merging of the two airlines, there was that space. And so they paid, they put their team a hundred percent into the problem space. But most of the time there isn’t that vacation space. And so it’s done interleaved like when you do a listening session, you only do one a day and you may only do two a week. Or with respect to the one that we just finished with the employees, looking at the employees handling that intense period. I don’t think they did more than they had different team members. Maybe one team member was doing one a week. It took us probably 26 weeks to finish that. There was another startup. I was doing this with and we, we reached 38 weeks. Before we came up with our final gap analysis. Just because it’s interleaved, that’s how it works. It’s okay. Because we’re not in a hurry. It’s okay. Because we want to spend time with our data. One of the things is that when you’re paying rapt attention in a listening session, it’s only that one person and it’s only that one person for the day. And when you’re done with the listening session, you still pay rapt attention to that person. You still let it dwell within you. You may jot down a couple of concept types that they said little concept summaries. Just to help you meditate on that person. And, and it’s not a race to like do six or eight interviews in one day. It’s a totally different animal. Peter: now like how we used to do it. Indi: I never did listening sessions that way. Peter: Well, and I mean, I, I guess it speaks to one of the probably a difference between being a con consulting firm, doing this stuff where you don’t usually have 38 weeks to ease into it, versus it sounds like you’re operating in almost more of a coaching and then somewhat embedded realm with an, with a, with an established team so that you can ha you can operate with this. Interleaving, as you’re talking about it, it’s not chunk projects that are chunked up with clear, like um, Gantt charts and, deliverables. Indi: well, sometimes there are Gantt charts, but they always get blown out of the water. Peter: Yeah. Um, Indi: To be, to be honest, though, there are teams that do want to do this and we try to get it done in 14 weeks or 16 weeks or something. And they have a little bit more time, but yeah. Designing for inclusion Peter: So I’m looking at the cover of your new book and I’m thinking about the conversation we had around making time and space for the insights, understanding the problems and purposes distinct from trying to solve them and the cover of your book, time to listen. And it seems to have, I guess it’s the subtitle though. It’s above the title on the on the image of the book I have, how giving peoples, how giving people space to speak. Invention and inclusion and the, the word inclusion is what I’m picking up on, because the last few months, like many of us, I mean, probably for the last couple of years, like many of us, but in the last few months in particular, I found myself taking part a bit more actively in some of the conversations around inclusion and true well and, and issues of equity and kind of thinking more and harder about how we do our work and also paying more attention to the work of folks in diversity and equity and inclusion kind of practices. And one of the things I’ve learned that runs contrary to my own behaviors is… my behavior is… diversity, equity inclusion is a problem. Let’s solve it. Let’s, let’s, let’s fix it. If it’s a problem, we should be fixing it. And what I hear from people who know better than I, who operate in this space is, is, is to not rush to solutions, to actually there is value in sitting with the discomfort, sitting with the… sitting in that problem space and not, not, not, not to get comfortable with it, but I guess to better understand it. And, and I’m wondering how, if I, you know, given, given the new book, given, given your continued evolution as a listener, given the, the use of the word inclusion and giving people space, it feels like you’re also embracing, this mindset around in, in your practice. And I’m, I’m wondering kind of just, yeah. What your thoughts are as in your continued evolution in your work and how it aligns with what we’re hearing about being truly human centered and about kind of how we adjust our practices to be much more equitable and inclusive than, than they have been. Indi: this is what drives me. This is, this is the singular thing that drives me. Inclusion. We have been running roughshod over, I’d say 95% of the people that we’re developing for. This is why I use this, the listening is the basis of it. So when you talk, I’ve talked to a lot of people who run diversity and inclusion to one extent or another, and whole point is to listen. The whole point is to give a person a chance to on the one side, feel heard. And on the other side, start to explore what their inner cognition is. What is their inner thinking? What was their emotional reaction? Why was that their emotional reaction? Where did it come from? What were the roots? Right. So the, the idea of taking time is so, so, so important. The idea of letting us. ‘ cause I mean, Jesse said measure the intangibles, right? What, what intangibles did he mean? He meant our interior worlds. Our reactions to things are, are our guiding principles for how to handle situations and how those shift and change over time and how they maybe get crusted up with worse and worse reactions because of the situations that we’re in. And we can’t find our way through the crust, right? So if we, if we are developing support for people and again, developing support for people is not necessarily something. Every business is about. A lot of them are only about making money for themselves, but if you’re developing support for. You have to understand that those people have different approaches than you. I think that, I think that we, we can, we can speak to this. Yeah. Okay. They have different approaches. Okay. So now let’s go off into the solution land, got to solve it without understanding what those differences are and without truly dwelling in it’s doing in it, I used to call it, simmering yourself in it. So to understand it, somebody at the Lousanne conference years back made a little badge that had a pot that was simmering. And this is like our, our brains, our teams, if we truly want to support people and you might not be working in an org where that’s the goal, and it’s important to recognize the difference. Okay. But if you are in the team who desire to support people, spending that time is so important. You’re, you’re not gonna understand it in one year. You’re not gonna understand it in two years, you’re going to keep understanding it and it is going to be your practice, right? It is an ongoing thing of trying to, to help another person’s perspective, be discovered and supported. And we do this for communities of thinking for thinking styles. I’ve been calling them. Other people have called them mindsets or mind states. There’s, there’s a variety of ways of thinking about this. We’re still building it, but there’s very much a desire, a yearning. This is what, what is missing amongst leaders and practitioners. The value of slowing down Jesse: I noticed very much throughout what you were saying here. A theme of making the argument for slowness in the face of a culture of speed. And I wonder what advice you might have for folks out there who are trying to make that argument inside their own cultures of speed to get the people around them, to slow down, take a breath connect, take the time. Listen. Indi: Our world is full of other examples of other fields that have slowed down to great benefit. One obvious example is slow food, food. Has you, you take your time to prepare it. Sure. But it’s been grown locally and not covered with chemicals not being fed chemicals, if it’s an animal to make it grow big, faster, To take a natural approach. We’re doing this with respect to unfortunately being very slow with respect to our transition to green energy. But green energy is another way of like let’s, let’s produce energy in a slower way. There’s authors who write about the idea of bringing back sailing ships and bringing back dirigibles as a way of traveling where you’re slowing down, you’re getting your, your movement of your body and your mind from one place to another. And during that transition, you’re able to think more clearly. And you’re able to produce and be more creative. And so there’s a lot of other fields that are using this idea of slowness that you can point to, but you’re not going to be able to persuade anybody. So one of the things is and I talked to Erica Hall about this, cause she’s on fire about you can’t persuade people. In fact, I think she referred, she talked to you in one of your podcasts earlier about this idea. But you can’t persuade people. There are people who once they latch on to the way things work in the solution space and that’s speedy methodology, those cycles spinning they feel like it has to be a way that applies to everything. And yet they have their own life and they in their own life probably has have something that they practice that takes. Anyway, you don’t persuade people. But what you do is you listen to them and if you listened to them, you can find out where that came from, find out why they’re thinking this, what were those experiences? How did that opinion or preference form, where does it come from? What are their guiding principles and help them as you are listening, explain what their guiding principles are, help them get familiar with their own guiding principles. We are not therapists though, just, just to have that communication is so missing. One of the things that I’ve been doing lately is offering a workshop to people who are having trouble with a different team, for example, maybe writers versus product owners. And they just can’t see. Communicate. And so what I do is I ask them to bring a, a typical conversation. And I break down that conversation into the parts, because there are parts when that’s what the whole book is about is it’s going to teach you what the parts are. And I break it down. I’m like, look, you are lobbing commands at each other. You’re loving opinions at each other. And you’re not talking about your interior cognition with one another at all. And so no wonder you can’t communicate, no wonder, nothing works, no wonder there’s distressed. And so as soon as they see it, every time this happens, like, there’s this like hush. And then like, that’s what that, I see what, cause I teach them how to recognize it and they see it. And then there’s like this huge round of applause. It’s like, oh my God. So that’s not the solution, but it’s the aware. And the solution is to start listening and start that practice of getting to the interior cognition. Where did it come from? What were the roots? How do you think? And maybe, maybe, and here’s the, maybe, maybe that person will do the same for you Wrap up Jesse: That’s fantastic. Indi, thank you so much. Where can people find you on the internet?. Indi: Indiyoung.com is the website. And I’m Indi Young on LinkedIn and Twitter and on Medium, I am the, in Indi Young Inclusive Software Design. So those are places I am right now. I think that’s going to shift a little bit and expand but who knows? Launching this new book as a self-published book. So that should be its own interesting journey. That book should be out. Like we have it, we’re figuring out the table of contents, it’s that close. Uh, Peter: Written the manuscript Indi: Oh God. Yes. That was done in January. And it’s been all. So one of the other things is that this has taken a long time because I met a person who’s really intentional about things and she’s doing the layout and she’s fantastic. And the life happens, you know, there were, there were a lot of things that happened where she had to take a week out or two weeks out or this or that. Right. And that’s what I accessed. I am not in a race to get this book published because it’s becoming a better book because of the time we’re spending and the time we’re able to breathe around it and let it sort of trickle into our bones. They’re like, oh, you know what? Not only is there like more typos than you could ever imagine coming out of the woodwork, but there, but there’s like, wait a minute. What if we use this word instead of that word? And now the sentence is way more clear kind of thing. So that book should be out by the end of April. I am counting on it Jesse: very Indi: we are at the point where we’re just tweaking the last bits. Yeah. It was super exciting. Jesse: Well, congratulations. And thank you again. Indi: Yeah. Thank you. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Tim: So the first piece is to align around the shared purpose and you cannot have any successful change of any kind if you don’t have something about shared purpose. Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, Together: And we’re finding our way… Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, recently retired design leader Tim Kieschnick offers insights from his 30 year career in design and innovation at the health care giant Kaiser Permanente. He also shares with us his insights into the ways leaders hold back their teams through a model he calls The Leadership Ceiling, and what to do about it. Introduction to Tim Kieschnick Peter: So hi Tim, hi Jesse. Tim Kieschnick is someone I worked with for about a year, when I was supporting Kaiser Permanente a few years ago and he brought me into his team. And what I, I, I learned a lot from just that year that I spent working with Tim, Tim had worked at Kaiser for 30 years, he can correct me with anything that I’m wrong with in, in what I’m about to say, he worked at Kaiser for 30 years, helped establish their website, kp.org, their UX practice 25 years ago. And then when I was working with him was focused on this kind of combination of service design work to help the business think about omni-channel, cross-channel more strategic design challenges, as well as a human-centered design kind of workshop, facilitation, think Google Design sprint-type style work with different parts of the business. And so, he and I, over lunches and coffees had a lot of conversations about design, design practice, leadership. And so I wanted to have him on the show and in particular, and we’ll, we’ll dive into this soon, he has this concept that he calls The Leadership Ceiling, and it’s a framework and I love frameworks. And so we’re, we’re going to have him unpack his framework for thinking about how leadership works. So thank you, Tim, for joining us. Anything I miss, any, any high points about your time at Kaiser or outside Kaiser as a designer and design leader that we should know about? Tim: Oh, no, that that’s pretty good in terms of the, the Kaiser years. I’ve– I would just augment it to say that, to me, design, human-centered design, et cetera, all of these methodologies for getting good things done quickly and well, and at scale, really go beyond any particular job or contexts. So I feel like I was doing design work before I knew it was design work. And I feel like, you know, now that I’m retired, you know, banging around my house with hammer and screwdriver, I feel like I’m doing a, I’m doing design, I’m doing human-centered design. I’m doing agile. I’m doing all of that in my everyday life too. So I’m very much a design-your-life kind of person and approach everything as a design problem because you’re, you’re more likely to come out with a decent outcome faster. “Everyone is a Designer” Peter: I actually want to dig into that a little bit. One of the controversies within the UX design field is this phrase, “everyone is a designer.” A lot of people with the title Designer feel that commoditizes or minimizes their work and impact. If anyone can do it, why do you need to hire people with degrees in it and all that kind of stuff? And I just wonder, again, given your, the arc of your career at Kaiser, you probably saw a lot of different shades of this, and your take on this controversy such as it is, is everyone a designer? Are some designers designer-er than others? Like how, how should, how, how did you end up thinking about it? Tim: Oh gosh, everyone is not a designer. Unfortunately. The first thing is that if design is limited to the people who graduated from RISD with a degree in design, then we’re going to have a whole bunch of unsolved design problems. There aren’t enough professional designers to address the number of design problems that we have. You just, we have to have people using the principles and some of the methods of design all over the place up, you know, just up and down the board. So there’s absolutely a place for the pros and the people who have formal training and the people who have experience and the people who geek out about this over several shots of espresso. There’s absolutely a place for that. But as soon as we start to confine it to them, we’ve just really, really limited the ability of the world to solve the problems that we need. So I feel really strongly about that. It’s, it’s, you know what, let’s use those professional designers very strategically when really when we need them, but let’s get as many other people familiar with the, the mindsets and the methods of design as possible. You know, for one thing, it’s, it’s a lot easier to work if I’m a professional designer, which I’m not, it’s going to be a lot easier for me to work with, with people who are not professional designers, if they have some sense of the mindset and some sense of the methods. Okay. So that’s the first thing it’s good for, for people to have, you know, have the, some of the mindset and methodologies, but then the other piece is just, I want everybody approaching problem solving in, in creative and methodical ways that, that explore the possibilities and that pay attention to the, the really the underlying needs and all that kind of stuff. And it… I’ve, I’ve, I’ve, I’ve got a real chip on my shoulder for a prima donna designers who don’t want other people to talk about design, don’t want other people to try to do it, because really this is me, you know, it’s like I’m saying, you know, really, you know, professional musicians are the ones who know what they’re doing. You know, we don’t want, we don’t want these amateurs around here, you know, strumming their guitar and singing “Blowing with the Wind.” And I think we really, really want as many amateur musicians as possible, you know? I’m… we were talking just before we started recording about how I retired a year and a half ago, and I haven’t been in the business world except in my interactions with bureaucracies in Vermont, which… bureaucracies in Vermont is a really new thing for me. It’s great by the way, the bureaucracies in Vermont all have people attached to them. It’s just amazing. They’ve got these really nice people who pick up the phone and know my name after I’ve called them once before. It’s, it’s, it’s a really amazing thing. They don’t have any computers. But they have telephones, and they have people, but anyway, so I’m banging around…. Yes. So I’m banging around my house and banging around the yard and, you know, I’m, I’m planting stuff in, in, in my yard. I am not a professional landscape designer. I’m not a professional gardener. I’m really glad there are people who can do that. But if we have to leave that stuff to the professional landscapers and professional gardens, we’re going to have most of the, most of the, you know, yards and gardens in the world are going to be crap. And that’s kind of the way we are with experiences that, that companies, that software development, you know, the, that we provide, is most of them are crap because there aren’t enough designers to come in and the people who are there just don’t have enough clues. So I, I, I’ve got a real chip on my shoulder about that. And I think as many people as possible who have some sense of this, the better. Jesse: I’m curious about your experiences over the course of 30 years with the same organization, having these kinds of conversations with people about design, about its impact, about its influence, about how you bring people into those processes and how those conversations changed for you over the course of those 30 years? How was it different by the time you got out than it was when you started having these conversations about design and what it can do for organizations? Tim: Oh, that’s– it’s a lot in there. One of the pieces is that some important changes happen really fast and a lot of important changes take a long, long time. And the ones that happen really fast, sometimes it didn’t happen as fast as it seemed like they did. We just don’t, we don’t hear about them until, boom, this thing gets implemented and you don’t see all of the slow stuff that built up to that. And so I’ve, I found it really, I don’t know if rewarding is quite the- quite the word, but meaningful to stick with something for a long, long, long time. And I know it’s, it’s, you know, it’s out of fashion, I’m a dinosaur, there’ll be nobody who works for the same company for 30 years ever, again, much less, 50 years. And we don’t even use gold watches anymore. But there’s something about having a long-term intent and sticking with it throughout. And then the, the key to sticking it with throughout is, as you’re saying, Jesse is, is to be able to morph as I go so that I’m not in, you know, 2022, fighting the 1992 battles. And that’s really, that’s really interesting, but I really– it’s interesting, very interesting to, and, and rewarding to see, to take the long view and to see where we are now, relative to where we were, whether it’s with, you know, a corporation or whether it’s with you know, the you know, w- w- with the country or anything that has, you know, that has the stamina, the staying power to last long. And one of the big things about that is this, this interplay between culture and leadership. So you see, and, you know, culture of course is more permanent than leadership and harder to change, but they’re, they’re very, very interrelated. And some of that led to, you know, my, my thinking about the leadership ceiling, which we’ll talk, talk about, I’m sure. As you see the leaders, not just the, the, the people in positions of leadership changing, but as you also see the individuals changing and morphing over time, to be able to adapt to that, to be able to fight, to be able to be very intentional about choosing, Which battle am I working on right now? You know, which, which aspect of the culture am I working on and who am I working that with? So when just before, Peter, you joined us, we had made a very– my small team had made, made a very intentional choice about which part of the organization to focus on. And it was interesting because, you know, we were trying to change the culture, to move the culture, to be more human-centric and more innovative and more designing and et cetera, et cetera. And we didn’t go to the most high profile or the mo- the biggest bang for the buck. We went to the place that we thought would give us the best shot at creating the germ that would grow into the, into the large crop. And, and so it’s always again picking, you know, which, which piece are we going after at any time and being really intentional about that? The other thing I want to say about that though, is, is in, in terms of the culture and there’s this theme at Kaiser Permanente around organizational structure, that is always the thing that is the best and the worst. The best and the worst of Kaiser Permanente all come from its organizational structure. And so whether you are inheriting an organizational structure or you’re creating an organizational structure, it’s critical that you understand what is embodied in that structure. So Kaiser, Kaiser has th- this you know, really interesting organizational structure that most people don’t know about and that they shouldn’t have to know about. But you have the physician, and the physicians, you’ve got primary care and you’ve got specialty care and then they’re all, you’ve got inpatient and outpatient physicians there. They’re all in, you know, like in a single physician group more or less. And then you’ve got the hospitals and then you’ve got the health plan, you know, sort of the the insurance side of the business and all of those three things come together and they include the pharmacies and they include the labs and they include the hospitals and they include the radiology of all of these different pieces that all have the potential to be integrated. And because of that, you can do things you can’t do other places because of that integration. And because of that, the incentives of the organization are fundamentally aligned with the incentives of the patient. So it’s fundamentally for, for decades, it’s been in the Kaiser’s best interest as an organization to do what’s best for the patient. Because of the organizational structure. And there are other places where the organizational structure is clearly set up, that what’s best for the organization is not necessarily best for the customer. And so how do you, how do you, you know, bake intentionality into the org structure. And Peter and I have talked about that a lot is, you know, how, how do you know it? You know, part of it is the hierarchies and part of it is, you know, anything from the metrics to the physical plant, to whatever it is, but how do you, how do you systematize intentions? it’s just a fabulously interesting area. The Leadership Ceiling Peter: Well, we’ll see how, how, how we impact that. We’ve been alluding to the leadership ceiling and I feel that we should unpack that now. So the leadership ceiling, Tim, I’ll let you define it, but just kind of i- it’s, it’s a tool. Here’s, here’s my little tease. It’s a tool that you’ve not really shared with the world. I’ve seen, you know, early writings about it. And I use it one-on-one with, you know, some of the design leaders I work with to help them think through their challenges. I found it remarkably valuable. So yeah. What is it, do you have a, you know, the, the elevator pitch on the leadership ceiling, and I’d also be curious, like how you arrived at it. What, what was it that got you to realize this framework? Tim: Okay. I’ll, I’ll start with the last question. So this, like many of my stories that goes back, goes back quite a while. So it, my, my son is 23 now, 23 years old. So– when he was four or five years old, my wife and I were shopping for where’s he going to go to elementary school? You know, you’re going to go to the local public school, there are a number of private schools. So we did some shopping around. We found a private school that we liked almost everything about. For one thing it was cheaper than any of the other private, private schools around. We loved the teachers. We liked that the building was great. They had a fabulous approach to an integrated curriculum, that a great afterschool program that supported people who were, you know, we had two working parents, et cetera. Just loved that,almost everything about the school, but we hated the principal. The principal was really problematic. So I called my dad because my dad was in schools and he was, he was a teacher and a principal and a school superintendent. He was, he coached principals. He was in schools his whole life, his whole career. And I said, you know, “Dad, how important really is the principal? You know, my kid may never even interact with the principal. My kid’s going to be with the teachers.” And dad, he didn’t, he didn’t skip a beat. He said a school can never rise above its principal. So we ignored his advice. He was basically saying, no, you know, if you don’t like the principal that it; we ignored him, we went to that school. And the short answer is by the time our son was in seventh grade, the school had gone bankrupt. And before that, most of the good teachers had left and the teachers that were still there were cynical and struggling, and it was a mess, the afterschool program when it was just, oh, you know, it was defaulting on the loans for the physical plant. It was just a total mess. So he was right. You know, remember note to self, you know, dad is usually right. Even when he seems wrong, even when you know better. But then what happened was I, I started looking at this in my professional life and I was seeing places where I was either really frustrated and felt like it was not getting anywhere or places where I… I had thought I was getting somewhere, but then everything back-slid, and it turns out we weren’t getting there. And I just felt like I was banging my head against the wall. And what I realized was I wasn’t banging my head against a wall. I was banging my head against a ceiling. And, and it was, and so I started calling that the leadership ceiling and basically every leader sets a ceiling above which the organization cannot rise. Now, it might be a ceiling of, of people where, How well do we treat our people? It might be a ceiling of process. How good are we at being efficient and effective? How good are our processes? And it might be a ceiling of purpose. Why are we here? What are we trying to accomplish as an organization? Any three of those, it it could be any of those three kinds of, of ceilings. Okay. Wherever the leader sets the ceiling, it doesn’t mean that the organization will go that high. It just means that the organization cannot go above it. So you can have a leader, a great leader, setting a high ceiling, and the organization below can be crap and not get anywhere. Or it can be a, a fantastic excelling organization, or it can be anywhere in between. But if that leadership ceiling is low, there’s a very small bandwidth whi– within which that organization can operate. So that’s what I mean by leadership ceiling. And then the point is, what do you do about that? So I’m mostly not thinking about, you know, you know, I’m mostly not talking to leaders. I’m talking to the people who are working below leaders, which is pretty much everybody in the world. And so for those of us who work under leaders, when that ceiling is lower than we want it to be, we have three choices. A: we can try to work on, work Above the ceilings. That’s where I spent most of my career. And that’s where I got the most bruises on the top of my head. Because it’s just, it never works. You’re never successful trying to work above it in the long-term. Okay. So, A, work– try to work above it, not going to happen. B: you can try to work Below it. Okay. So you can say, okay, that’s where the ceiling is. What am I going to do about that in terms of how I work? And it could be that your just biding your time waiting for leadership to change, waiting until your kid is out of diapers waiting until you’re out of grad school, you know, whatever it might be, or it could be that working under it, you just realize, you know, this is not the organization for me, my aspirations, what I want for myself in my job or in this organization is, is never going to happen with this set of leaders. I’m tired of biding my time. I’m going to bail. Okay. And then there’s also a possibility that we can talk about later, if you want, about kind of creating a little bubble in the leadership ceiling, where I’m going to work in this little space where we’re going to be better than the, than the rest of the organization. Just the key is just don’t think that you’re actually, that you can get too far with that. You can get a little, you can make a little bit of a bubble, but what, what, what for me, what I usually would try to do is I would make that, try to make that bubble bigger and bigger and bigger and think that I could go further than I could with it. So A, you can work above it. B, you can work below it, or a C: you can try to change the ceiling. So that’s not for the faint of heart, but that’s gets you into the space of how do you influence, how do you influence up how do you drive change? And it’s an interesting approach to change, because it’s really about how do you change a leadership ceiling in which, and, and you know, which leaders are you after, you know, what kind of ceiling we trying to raise? How will we know when it’s higher? How was that, you know, as we were talking before, how do I w– my, my strategies and my tactics to morph over time to change that ceiling to make it higher. So that’s kind of in a rather large nutshell, maybe not in an acorn, what’s a large, not maybe, maybe in a coconut shell (laughs) leadership ceiling. Peter: So you mentioned, uh, people, process, and purpose, and I think in our prior discussions about this, the leadership ceiling is only as high as the lowest of those three, right? So at Kaiser, Kaiser has a really high purpose. Right? Very patient-centered, very mission-driven. From what I saw, I wasn’t an employee, but it seems also very people-oriented, by and large good to the employees, a strong kind of ethical work environment. But process was low, right? It was big. It was bureaucratic. It was difficult to get people aligned on projects. They would operate in a waterfall way when they would try to introduce new ways of working. They would, those new ways would end up getting kind of ground down in the machine of, of kind of legacy process. And so what I, what I saw was this disconnect between the talk of purpose and potential of the people, but the reality of the process and that process ended up lowering the ceiling, such that even if you, like, you couldn’t realize the purpose that was being laid in front of you, because the process was– wasn’t being raised as well. And so I’m wondering, kind of, is that, is that how it works, where, like you can only go as high as the lowest of those three? Or do you, are those three different leverage points or like, how do you fiddle with those three Ps to try to engage? Tim: Yeah, well, I, yeah, I think you’re right, you know, for an organization to really be all it can be to it gets to have all three, and you have to raise them all. That, that said, you know, if I were in a, in an organization that, you know, had a high purpose ceiling and a low process ceiling and a medium people ceiling, it might be that the people ceiling was more important to me. And that that’s the one I really cared about. So, you know, it’s really what I’m about with the Leadership Ceiling work is, is helping people figure out, you know, what’s it gonna take for me to be happy and satisfied and fulfilled and be meaningful in, in, in, in my work or in what, even if it’s not work, you know, in my organization. And maybe I don’t want to work, you know, maybe I don’t, I’m just not a process guy. And, you know, and maybe, you know, the bad processes, you know, they bug me, but what really bugs me is when you know, somebody who’s not treated. Then I’ll go work out and I’ll try to raise that from medium to high or something like that. Or maybe I’ll just lean into, you know, the leadership. Maybe the leaders have set a really high people ceiling, but that has not permeated the organization. So I’m going to try to raise the organization up to where that ceiling is, because remember it’s just, just because the leaders are setting a high ceiling doesn’t mean that the organization is getting there. So it could be that, you know, they’ve set a high purpose ceiling and they’re saying, you know, we want to, you know, we want to change the way that people will use windows, not Microsoft Windows. They would, you know, the way that people look out their windows. We want to change that. And maybe I love that idea. I’m working for our window company and it’s not just about producing, you know, the same old windows as before we want to really revolutionize the world of windows. I may think, well, yeah, but you know what, w- w- we’re we’re really focused on just turning out the same window. So I want to help the organization rise to the level of what the leader is saying about who we are. So you really have a lot of different choices on how you go and it’s about, you know, what’s important to you at this point in your life. Jesse: I’m interested in these terms that you’re using high and low, to describe these ceilings and something in my brain just keeps asking the question: High and low. What is it? Potential? Is it performance? Is it scope of impact? What is being limited by the leadership? Tim: Hmm. Maybe that’s best done by example. So let’s take an example of equity, inclusion, and diversity. So that would be a- a people ceiling. Let’s say you have leaders who are talking the talk they’re walking the talk, they’re baking it into their systems. You have a high leadership ceiling. You can still have an organization that’s not there where there are all kinds of problems, okay. But you’ve got a high ceiling. You have high po– you might might just think of it as the potential. And what constraints is the leader putting on, on, in term, on it in terms of potential? And so what I like to do is look at this, think about well, what would it look like? If we were, if this organization were really rocking and rolling on that, what would, what, what would we be saying? What will we be doing, how it would be baked in our systems and what actual results would we be seeing, measurable and qualitative, what results would we be seeing? And that’s the good and you want, and then you want to look at, you know, how far are, how close are we to that? If we’re not there, is… and if I don’t feel like that’s happening in my space, is that because I’m limited? Is it because it’s just a really hard problem to solve? Is it because the CEO is setting a ceiling or is it, or maybe the CEO is setting a high ceiling, but you know, a vice-president someplace below them is, is, is lowering it. So it’s all about kind of analyzing, what’s keeping us from being the best we can be in all of those places. And to do about it? How will I engage or not? Jesse: Right, right. Yeah. That makes a lot of sense. And the reason I ask is because you know, you have these three Ps of people, process, and purpose, but as I think of my experiences working with leaders, or observing teams working with leaders and the ways in which leaders constrained the potential of the teams underneath them, a lot of those examples, at least off the top of my head, don’t fall into these three categories, but rather it was a shortcoming of imagination on the part of the leadership, a shortcoming of bravery on the part of the leadership, that kept the team in check. So I feel like potentially that these things that you’re describing, certainly organizationally, when you’re looking at organizational structures, people, process, purpose are great top-line things that you’ve got to hit, but I wonder about the subtler things, the ways in which from day to day, the ways that leaders show up squelch people and shut people down. And I think that I, and I wonder how much of that comes actually back to the character of the leader themselves and why they have such low expectations in some areas for themselves and for their teams, you know? Tim: Yeah, I wouldn’t get too– I’m not too hung up on the three P’s there. It’s just, so it’s a way to, to think about them and I’ve, I could probably try to shoehorn, bravery and imagination into one of those, but, but you could feel free to say this leader is setting an imagination ceiling and then you would still do the same thing: you would say, “Well, what would it look like if we had a really high imagination ceiling in this organization?” Well, it would, you know, and it would look like there were new ideas coming from all levels of the organization on at least a weekly basis. You would, you could label behaviors that would be showing up in meetings and group interactions. You would look at how metrics and project management support that. And then you’d also look at what would it look like if the leader set a higher imagination ceiling, you know, what would she be saying? What would she be doing? What would she be baking into the structure? And what results would we be seen as an organization? And, and then some, because what happens if you follow that, that pathway of, of saying, doing, baking it in and results, if you follow that pathway, you might find out that the leader is saying all the right things about imagination. What they’re saying, all the right things about imagination, then maybe this is a place where you could actually help with some change by helping them understand how their actions are, are, are blocking something that they actually want, or maybe they’re saying the right things and their actions are right, but they’re still measuring the wrong things, you know, or, you know, the, the performance reward system is still, you know, rewarding the wrong things, or maybe, you know, the core software that the company uses to run, it has lack of imagination baked into it. And so it’s, so then there were, you know, th- then you start to get that, that gives you a lot of ammunition, or not ammuniation, it, it gives you a lot of, of, of grist for figuring out How are we going to influence this? You know? Or you might look at it and you can, and you might say, you know what? I am not in a position to ever change or influence change in this organization for imagination. This… I’m just not in an imaginative organization and this organization over the next 10 years, I just can’t see it happening. Okay. Then you, then you say, okay, well, I’m a, I’m not going to try to work above the ceiling and try to be super imaginative. I’m just, that’s going to be so frustrating. I’m going to be just humiliated. I’m going to be discouraged. I’m going to turn cynical instead. I’m going to say, okay, this is reality. I am in an unimaginative organization for as long as I’m here. That means I’m going to work below that imagination ceiling. And I’m going to decide, how am I gonna approach that? You know? And as I said, you know, it might be that I’ll bail. Okay, good to know. I’m not going to try and try to be something that the organization won’t let me be here, or it might be I’m going to wait because you know what we are in the industry of windows and the whole windows industry has changed. And in another two years, it’s going to be so unavoidable that all the leaders in this company are going to realize the windows don’t mean what they used to mean. So I’m going to wait two years and I’m going to be ready so that when they say, “Hey, we need to c–, be more imaginative about windows,” I’m going to have my portfolio ready for them. The potential power of Biding your time Peter: Well, yeah. I, I’m terrible at biding my time. I’m a bailer which is why I’ve not lasted anywhere more than two years. But I think about at Kaiser, let’s take the Kaiser example, right. There were probably folks biding their time in some flavor of tele-health for decades. And then the world changed in March 2020, and they were ready to fill that void. And I, and I– you were, you were still at Kaiser when, when the pandemic happened. I don’t know how long you had, what did you see in terms of that kind of massive context shift that maybe enabled some of this change to happen that, that people like you had been stumping for for probably at least a decade, if not longer? Tim: The first telehealth projects that I was a part of were in, 1996, no, 1995. Peter: By tele, that meant telephone health. Tim: No,.. Nope, no. We’re talking ISDN video psycho, psychotherapy visits. Peter: LIke CUSeeMe or something. Tim: This was, this was, this was face-to-face with a patient and a doctor doing intake for psychotherapy as well as, as well as some similar things that we had. We had some things going on with dermatology, with some things going on with home health nurses back in the late nineties, okay. And this is one of these changes that takes a long time because so many pieces need to be in place. And what we were doing during this biding our time is we’re biding our time un- until the world was ready for it. And a critical mass of physicians was ready for it. A critical, massive patients was ready for it. And the technology, both internal to Kaiser and the tech, the consumer technology was ready for it. So biding your time, doesn’t have to mean give up and just forget about it. You know, in the early days we were flying really low under the radar and it used to be in, in those early days, like when we’re you doing this kind of stuff, when we’re doing the web stuff, our mantra was don’t do anything that will impact healthcare operations because then people will notice us, we’ll get in trouble, and the whole thing will, will be shut down. Okay. But what we could do is we could figure out, well, what does it take? You know, what does it take to make this work for the doctor and the patient? What’s the minimum amount of technology you need for it? How would this impact the scheduling systems? Because scheduling is a big deal. So the, all of these different pieces came together. So for instance, Kaiser way back when decades ago was, was really working on scheduling systems that included being able to schedule a phone, a phone visit with the doctor. Well, if you can schedule a phone visit, then you can schedule a phone visit with video in it. So all of these things were getting set up along with, you know, the policies and the legal stuff in addition to the technology. So when the pandemic hit and we needed to scale from a fairly small number of video visits to a huge number of video visits, there was some scrambling to be done, but that scrambling could be done. And it could be done, you know, you know, let’s get, you know, let’s ramp up this server base and ramp up this bandwidth and blah, blah, blah, whatever it might be. But the fundamentals were there because so many people have been biding their time waiting for this moment, but they weren’t just sitting in a corner, hoping that someday happened. They were saying, while we bide our time, we’re going to be ready because one of these days it’s going to be the time. We didn’t know it was going to be a pandemic that was going to make it happen, but we knew sooner or later this dam is going to burst, you know, in a burst in March of what was it, March of 2020, and boom, here we are. So the, the biding your time, it can, it can feel like you’re just copping out and just settling, or it can just be a really realistic way to make progress. “C”hanging the Ceiling. Jesse: If you are in the position of having to engage with a leader, whose ceiling you are trying to change, I’m curious about how you do that. Especially, as a lot of these things, I feel like, are kind of inherent sometimes personality traits of these leaders. How much is asking a leader to change their ceiling, really asking the leader to change themselves. And how do you do that? Tim: That’s what you want me to answer? How do I change human behavior in 10 seconds or less? Jesse: I mean, Peter: You have, you have at least up to a minute, Tim: So the point there is, is, as I said before, it’s not for the faint of heart. And it’s not like, oh, instead of biding my time, I’m going to change the leadership ceiling, boom, boom, boom. It’s like, if you’re going to change that ceiling, you got to commit to it. You have to say, okay, I really want to do this and I’m really going to lean into it. And then there are all kinds of things, you know, from collecting your allies, to understanding your targets, to coming up with an influence plan, to all of this kind of stuff. I’ll sort of start from, from the point of view of a leader. And then from the point of view of the person trying to change it from the point of the view of the leader, the first thing he’s got to understand, well, which leader is causing the, is creating the ceiling and what’s important to them. So it could be, I’ve been in situations where I thought my boss was setting a ceiling, but it turned out she wasn’t the one setting the ceiling, it was her boss or her boss’s boss setting the ceiling and she couldn’t move beyond. So then what happens there is my boss is– is now an ally rather than the target of my, of my, my influence plan. And, and I try to engage with her around that because she’s going to have a lot more insight and and influence in this process than I am. And if I can’t get her engaged in it, then I should probably try an entirely different route because if she’s not engaged, you know, that’s my biggest you know, that’s my biggest ally there. So first, and, you know, and I’ve also been in situations where, so that was in that situation, in that example is I thought it was my boss, but it was really like, you know, say the CEO, you could also be in a situation where you think it’s the CEO, but CEO is when you look more deeply, no, the CEO is really right up there, but it’s at a level below. I often find that, by the way, in, in large organizations, this isn’t just Kaiser, but a lot of large organizations I’ve looked at, the CEO can be setting a really high ceiling and the, you, you get like two levels below, and the two levels below, these are like, you know, division heads or department heads. Those people are a lot less focused on raising the ceiling and a lot more focused on raising the floor. So they don’t want to have the organization be all it can be. They want to make sure that the organization is not as bad as it could be. And so they want to find the, the, the outliers that aren’t as good, and let’s just, you know, raise that floor. And there are times when that’s absolutely the right thing for an organization to be doing. The problem comes when you think that’s that, that means you can’t be doing the other end too, you know? I mean, “No, we, we can’t think big until we fixed all the small things. We can’t do any major enhancements until we fixed all the bugs,” that kind of stuff. But then when you get into the, you know, so then you, you, you, you need to, you know, there are all kinds of approaches to influencing leadership. They all start with understanding the target. And then I would add if I’m going to be an agent of change in an organization, I need to, I need to be legitimate. I need to be perceived as legitimate. And Helen Bevan from, from the UK health system used to do something called healthcare school for healthcare radicals, great program on how to, how to drive radical change in healthcare. And she talked about different kinds of disruptors and, you know, the sort of the, the disruptors who are just breaking things and actually not being effective and the disruptors who are really effective. Competence, Relationships, and Initiative (another framework!) Tim: And the difference, what she would say is that one of them is really the, the loner and is driving people apart. And then the other one is collecting people around them. And so when I collect, if I’m trying to collect people around me, I like to think that there are three things that I need to do. I need to, and those three things I need to do that I need to attend to are: competence, relationships, and initiative, and I need to attend to those in that order, because if I start with my initiative to change things before I have any relationships, I’m just, you know, some guy over there who’s causing trouble. I’ve got to have the relationships. Okay. Even if this is a four person organization, I’ve got to have relationships. Okay. And then if I’m trying to make relationships, but I am not perceived at being competent in my day job, I’m going to have trouble. So I have to start by, even if I think my day job is not what I really should be doing because I am a much more aspirational and inspired and just, I’m such an amazing person in this job is I’m so much more than this job. I still have to be good at this job. Once I’m good at this job, then I can do other things, but I get good at this job that puts me in a position to get to collect relationships and to be established so that I have allies. And then that puts me in a position to take initiative. So I really believe competence, relationships, initiative in that order will get me to the place where I can understand the leaders and work with other people to drive change. Peter: And then that speaks again to one of my, one of my failings when I’m working internally, but one of the things I can help the leaders that I work with when I’m their external partner, which is taking that long view. And I think, I think a lot of design leaders struggle with understanding the role that politics play in… the role that politics plays in, in achieving that long view. And my case study is actually from Kaiser, a different group that I was working with, where they brought in a really talented design leader, human-centered design and innovations kind of guy, and placed him in an organization where they were asking him to do some of that innovation work, but also to assess emerging technologies, you know, how are we going to apply artificial intelligence and machine learning to tell– to mental health chatbots or something, you know, imagine these kinds of… there’s all these companies building all this software that they’re trying to sell into Kaiser. And someone needs to say like, yeah, this is pretty good. Or actually not, this is this isn’t good. And this leader could not get over being seen as, essentially an IT assessor, even though, that was part of the job. And if he could do that, if he could like create, a quarter of his time, a third of his time for that, he could be building… building, his case, demonstrating competence, showing that he has the interest of the organization at heart, and then slowly start making the kind of change and, and having the kind of initiative that you’re referring to. But he, it was so… he was so idealistic and I think this is true of a lot of designers. Their idealism gets in the way of their pragmatism and then they just make no change because it’s either all or nothing. And so something I work with leaders on is trying to figure out what is the “one for them, and one for me” approach that allows you to eventually get to the kind of change you want. But recognizing, especially in a company like Kaiser, I mean, what 300,000 employees, it’s been around for 80 years, like you’re not going to come in with your, you know, wearing a cape and, and, you know, whipping into shape in, in a week. So anyway… Tim: Yeah. Yeah. And, and they, it gets it’s… that actually reminds me of our conversation about, about professional designers, because there are a lot of professional designers who just want to work with the design team. And everybody in the design team is golden. Everybody outside of the design team is, is other. tThose design teams can come up with some fantastic, beautiful solutions, and, it’s really hard for them to get those solutions adopted, or adopted at scale, you know, can maybe get them adopted with the people that they used for, for co-design as they went along. But for, for them to be successful, you have to have the great dynamics within the team. You have to have great interactions between this team and all these other teams, you know, what’s in, you have to have great, great interactions between my scope and everybody else’s scope. And then you have to have great interactions with leaders, the problem is you see so many people, especially in a large organization whose primary, you see so many, uh, mid-level managers whose primary orientation is toward their leaders, so that they aren’t paying enough attention to the interactions with other teams, their interaction with their team, that it’s like, well, I don’t want to be like that where I’m just, you know, sucking up to the leaders that I’m giving, you know, I’m spending every Thursday, I’m giving them another 60 page PowerPoint, you know, status update. Okay. You also don’t want them to spend, you don’t want to just spend all your time interacting with the other team. So all you’re ever doing is project updates and having these endless meetings of everybody updating everybody else. So that’s, you know, you, you got to come up with some sort of a way, and I think this is actually an open design question. I don’t think that even the world of scaled agile has really solved this yet, that I’ve seen is, is really optimizing all three of those pieces. Working together within the team, across teams, and between teams and leadership. I think that’s was one of our big, next levels to reach just in terms of as, as, as designers, as people trying to make the world a better place. People trying to create better organizations is how do we get, you know, what are some ways to do that, to do all three of those at the same time. Peter: Yeah. You either get all or nothing. You, you…, I talked to companies that either are all independent autonomous teams, working kind of essentially in isolation from each other and maybe doing good work in very small areas, but then when you bring it together, it’s a mess. Or you get this push to a over-engineered top-down or, you know, coordination and orchestration, but then the teams don’t feel like– the teams are, are simply being told what to do. They don’t feel like they have agency and that centralized planning doesn’t actually understand what’s necessary at all the little leafs, all those little end points. Tim: Yeah. And, and it creates all these artifacts for, for the customer that the customer doesn’t understand why they’re doing such a stupid way. I’ll tell you right now, it’s because they spend all their time doing PowerPoint updates or it’s because they didn’t spend any time doing updates with the other teams. So this team didn’t know that team was doing it or it’s because the leader just kept telling them what to do. And they could just kept doing that. So you can see it in the customer experience. And it’s so frustrating. It seems like such a simple thing once it hits the customer, but it’s very complicated behind that. And I, I think it’s a very exciting place to see new models emerging. I don’t know what those models are. Peter: I haven’t seen them yet, but if anybody listening to this… Tim: I was hoping maybe they were in your book, Peter. Okay. Peter: Not yet. Not yet. Version two. Tim: Next book. Jesse: Peter, do you have something to announce today? The importance of shared purpose Peter: Sadly, no. Um,um, I want to get back to this theme of change. So, so you, you mentioned the challenges of changing the ceiling and working with those leaders and, and, and helping them figure out change. I’m wondering a little bit about organizational change and, and circling back around to the work that you’ve done, recognizing that not all …that we’ll, we will never have enough designers to do all the design work needed. How do we help in the case of a health care concern, right? How do we help, the people making policy plans or how do we help nurses and how do we help the folks doing intake? Or how do we help all those folks embrace design as, as a mindset and maybe some light set of practices in their work? And I’m wondering what, if any change you saw in that regard on, on that part of your effort at Kaiser to, to get people, get more people more comfortable with these designerly like practices, right? We’ve seen a lot of corporations, try to take on design thinking, do it at scale, it gets its flavor of the month. It, it, it works for a year and then two years later, no, one’s doing those things again. People vaguely remember that there was this thing called design thinking, and it’s just like nothing happened. And I’m wondering if you were party to anything that felt more lasting in terms of the kind of change, with, with that type of effort. Tim: I would say yes, though not yet at scale. The challenge is to get it at scale, and what it’s making me think of is what we’re talking about a little while ago about the interaction between ceilings of people, process and purpose. So if I want to work with a bunch of frontline people at the call center, or nurses, or physicians, or who, whoever, you know, or, or, you know, developers, and I’m just jumping in to say, here’s some process stuff, we’re going to use this process, especially if I’ve, you know, if they don’t know me, like why would I, why would I ever expect that to be successful? So there is something about finding a foothold and at Kaiser, the foothold was always purpose. So as I alluded to this before, because of the way Kaiser is structured, I think that that has enabled a, a lasting culture that really, really cares about Kaiser’s members. Really cares about the patients. And you’ll see this in… it doesn’t have to be in a healthcare organization, caring about its patients. You know, you’ll see this in a software company that totally cares about its users or a grocery store that really cares about the shoppers. So the first piece is to align around the shared purpose and you cannot have any successful change of any kind if you don’t have something about shared purpose Bevan was also really, really strong on that. Now it could be that you have a shared purpose, but it hasn’t been articulated well yet, okay. Kaiser Permanente, a really amazing thing happened through the marketing department several years ago when the, the, the Thrive campaign, thrive marketing and advertising came, came out, came out because what happened was people said, oh, trying to help people thrive, as opposed to trying to give people the correct surgery without errors, or trying to give them the right blood testing, or give them, you know, immunizations. They– they’ve, they suddenly coalesced around something that they already had, but didn’t have words for it. “Was off– what oft was thought, but ne’er so well expressed,’ it was, we are here to help these people thrive. And by getting that language, then now I can go to a bunch of call center agents who have difficult, grueling, low paid jobs, and I can align with them that we are all trying to do the same thing here. If I haven’t and um– and that that’s the first step to doing some design work with them. The second thing is if I’m trying to do design work with them, and they’re just coming off of a 12 hour shift where someone, where some, you know, foreman was standing over them watching to make sure they coded every interaction correctly and then, you know, corrected them, and dinged them because their calls were too long and blah blah, you know, blah, blah, blah. And I’m trying to do design work with them, not going to work. There’s a people ceiling there. So you have to get– the people have to be treated a certain way. You know, you have to get to some level of people being treated decently before they’re in shape to do design work with you. And, you know, and in many places, in my, in my world, they, they were getting to that place. They were in that place. They’re moving toward that place. And those became greater opportunities, even if it was like, you know, they’re, you know, it’s not perfect, but it’s good enough now that I can actually think about it. Or in some cases we did things where we, w- we had buy, buy in from leadership. We could pull people out of their daily grind enough, that it was actually a break from that, for them to get, for them to do some design work. But if you’re just trying to throw it on top of everything else that they’re supposed to do, and then, you know, at the end of your, at the end of every day of your five day design sprint, they have to go in and do four hours of work to catch up with the emails that they missed during the day, we’re not going to do very effective design work. So I really think all those things fit together. Start with what’s, what’s our shared purpose. You make sure they’re treated well enough to have some energy, to have skin in the game. And then, then it becomes all about process. Then, then you get into all, you know, what, for me is the fun stuff about co-design process and you know how to bring out the best in them. And how do you help them feel like,how do you help them realize just how much expertise they have and how do you not only respect their ideas, but, you know, help them grow and nurture those ideas and flesh them out. And how do you give them some confidence that something’s actually going to happen from this, so that’ll, that it’ll be implemented afterwards. And then how do you do the thing that you, Peter, and I will never do, but that fortunately there are many more people in the world who are much better than you and I, this which is stick with it and still be there two and a half years later, you know, and, and that gets to, you know, how do you get the leaders to understand not just the words that are needed, but the actions and the structures that are needed, so this thing is going to keep going, so that it’s baked– so that design thinking is baked, not just into a five day design sprint, but design thinking is baked into the structure of how we do project management and how we, you know, do performance measurement and how we do budgeting and how, you know, et cetera, et cetera. Jesse: I feel like inherent in so much of what you’re saying here is the ability to root out your natural allies in an organization and rally them to the cause and bring them in and bring them in around you. What recommendations do you have for folks to find their allies within the organization? Tim: Oh boy. Well, the first thing is to watch the YouTube video, “How to start a movement,” which is really fun TED talk. And the, the main point out of that is that the first le– the people, the first leaders of a movement tend to, just like early innovators, tend to think that more is essential than what really is. So I have this idea for a new product. I’m going to make this new kind of shoe box. It’s going to change how shoes are stored and delivered. And I, and I’m trying to get the entire world now to buy into this new shoe box. And I think that the co– you know, and it’s it, it’s blue, it’s a certain color of a certain shade of blue, you know, and it’s, and it’s, it’s, it’s measured in centimeters rather than inches, which is so important because of how shoe si–, blah, blah, blah. And I’m going to think that so many things about the shoe box that are critical. When really it’s just these two things, you know, it’s the material it’s made out of and it’s that it’s oval. Those are the only two things. Same thing with a movement. I think we need– I’m trying to do a movement now to turn this entire software development structure into agile. And I think that it means that we have to use, you know, this tool for tracking all of our–see how long I’ve been out? I can’t even remember what the tools are the– and what do they call, what are the tasks? What are the tasks called? None of this. See, I think, I, I think I’ve, I’ve, it’s, I’m trying to drive agile. We have to use this tool every, you know, every time we have a retrospective, it needs to follow this exact methodology and the, the, the what’s the agile leader person called? The… Peter: I– Scrum master. Jesse: Yeah. Tim: Let me tell you, it feels… for those of you who have not yet retired, it feels great to To have forgotten the word scrum master in just 18 months. I’d be like I’m I’m, I’m I’m really rocking retirement. No, I hadn’t thought that it was wrong last January. Peter: But you probably know you could probably distinguish between four or five different types of mulch. Tim: Yeah, absolutely. But my point here is that if I’m trying to find those allies, I don’t need to find allies who agree with me in every detail. I need…and my shared purpose needs to be pretty high level. So that’s the first step to finding an ally. So if I’m like, if I’m trying to do to drive to user centricity, I’m, like, looking for people who really care about the user experience. I’m not looking for, to, for people who call it human-centered design versus calling it innovation, innovation versus calling it CX, like whatever. I’m looking for people who really care about the customer. So go up a level to that. And then the second piece, which is just basic to any design work is, don’t get all people who are like me. And so the people who I know best will probably be the people who are closest to me, who– people who think the most like me, know the same things as me. And so I have to find people who are not like me. I just have to find people like w- whether, whether, you know, across all aspects, whether it’s, you know, work background, cultural background, gender identity, work experience, personal hobbies, approach to project management, methodologies, the, the diversity there just becomes critical. And since I’m really bad at that, because I don’t like to meet new people, it’s hard. And I’d rather stay safe with the people who are like me. That means that I need to hang out with people like Peter. I don’t know you well enough, Jesse, but you’re probably more like this, too. Peter, like people who will walk into any room and start talking to somebody they don’t know and be okay with that. So I, you know, and I’ve, I’ve, I’ve intentionally recruited people onto my teams who are just really good at, you know, I remember a woman who just, who just moved on from the team that I was part of. It was her, I, I, had this whole orientation plan for, for our first two weeks. And we got into the sec, you know, the day five, and it was time for me to start telling, okay, now I need you to really need to set up conversations. And I’ve got a list of 15 people that I want you to just reach out, to, to get to know. And went to these 15 people, 10 of them, she had already, you know, gone for a walk with them, had lunch. She had just found them on her own. So I, since I don’t do this to myself, I need people on my team who will, who will constantly be interacting with people who they aren’t working with on a project right now. Jesse: So It’s almost recruiting evangelists for the cause. Tim: Yes, it’s recruiting evangelists. And it’s importantly also recruiting listeners as those people are go– they’re going to be hearing things that I’m not hearing and it’s, it’s, it’s it’s evangelists and it’s influencers because if you’re going to make a change, especially a change that involves, changing we’re, you know, thoughts, words, actions of, of leaders, you need a whole network of influencers to come at this from a wide variety of angles. I need to find that, that link between someone I can influence and the person who I have no relationship with, I’m trying, if I’m trying to influence uh, a VP or a CEO who I don’t really know, I need to find somebody who I can ask, you know, what does Betty really care about? You know, when she wakes up in the morning morning, what is she excited about? What she worried about, what drives her nuts? I need that information. And then I need to know, and who has Betty’s ear? And it’s sometimes it’s her boss. And sometimes it’s this person that she plays tennis with and like, oh, Betty plays tennis with Rick. Oh, well, you know, Jesse knows Rick and, and I know Jesse, you know, so it’s, I mean, it’s, it’s politics. It’s absolutely politics. That is politics for a good cause. And it, you can call it politics or you can call it relationship building and networking. Yeah. But it’s gotta be Peter: We talk a lot about relationship. Tim: Yeah. Yeah. Peter: I wanted to ask you a question. Kind of rooted in the fact that you were, were at Kaiser for 30 years, which is uncommon… it’s it’s I, you know, it’s like being on a sports team, your entire career, like no one does that anymore either. Right. Everyone’s always moving around. Yeah, we’ll see with Steph, uh, and I’m wondering how intentional your career choices were, how… the degree to which you fell into them. I’m asking because you might not have listened to our prior conversation was with a friend of Jesse’s and mine, Abby Covert, who made a choice to kind of remove herself from the kind of typical employment game and is now focused– she’s independent, she’s a writer. She’s made a choice to make a lot less money, but to do what she loves. And I suspect you were given opportunities to be an executive that you might’ve turned down because that wasn’t what you wanted or something that like, how did you, you know, figure out your path forward and what was, what were the, what were the decision points and the, and the influences and just, how did you arrive kind of at, at, at where you landed and now you’re retired, which is also a choice. Um, I’m just kinda curious. Yeah. What, what w- what led to those decisions in, in your career path? Tim: Boy, I might have more perspective on that in another year and a half. Peter: Were you ever a striver? Were you ambitious or did– were you someone who just always found themselves in a situation like, I guess this is what I’m doing now? Tim: Well, it’s not, certainly not the first and not quite the second. I do want to clear up that nobody ever wanted me to be an executive. Nobody ever offered me a position as an executive. I think that they, they knew better than that. And had they offered it, I would not have taken it. It just, just too much trouble, too much of a certain kind of responsibility, too much HR bullshit, et cetera, et cetera. That said, I’ve always, just asked what’s the next step. And you know, I– I don’t know that I’ve, there may have been times when I thought about my own position more than a year out, but mostly not. Mostly, I’m like, where do I want to be a year from now? And I never interviewed for a– I’ve never taken– in the last 35 years, I never took a job that I interviewed for. So I always started, I started as a temporary secretary and turned that into being a you know, office manager turned that into being a network administrator and database manager, and then turned that into being a technology prognosticator, which then turned into e-health stuff, right. And which then turned into UX. So it was always starting by being as competent as I possibly could be at my current job, as I was saying before, really starting with that and then having relationships with interesting people and then asking myself, what’s my purpose? So it really, I mean, for me, it really resonates. I don’t know if it resonates for anybody else, but for me that has really worked. I’m going to be good at my job. I’m going to get together with people and get people to respect me and know people and enjoy working with them. And then I’m going to ask, what do I want? And I personally, I know it’s probably, you know, very, almost certainly a function of my privilege in that, you know, I always, we weren’t rich growing up, but we always had meals and we always had a roof. There was never a doubt about that. If there was, my parents didn’t let us know. So I, you know, that privilege puts me in a position where I wasn’t concerned about that. So that got me to a place where it’s like, well, what’s really important to me right now. And at one point what was really important and what I was really learning about, what I really loved, was learning DBase3. And how do you, how do you program a database so that it’ll spit out the address labels you want. At one point, that was just really, really interesting to me. It wasn’t part of my job, but that’s what I did, right. So always, you know, and another point, what was really interesting to me was um, uh, user experience and user experience methodologies and baking that into development methodologies. And so that, wasn’t my job, but that’s what I did. And then, you know, you get to a point where, you know, I frequently, I would go to my boss and say, “Hey, I don’t know if you noticed, but I’m doing a different job than you hired me to do. And by the way, this job gets… the job I’m doing now should be paid better than the job that I was doing before.” But my, my, my path has always been, do my current job well, and then start doing my next job. Jesse: So now you have moved on to your next job, the job of being retired. Tim: I have moved on to my next job. Yup. I think it’s it’s still evolving as it goes. I’ll be really curious to find out what my perspective on it is in another year and a half, because honestly I’ve been doing more about, poring into my new life in the woods in Vermont than I have been kind of poring over my, my, my work life. I will say that I feel, I feel a lot of pride in having stuck with something for so long. And the long, in the long view, you can really see progress. And in the short view, progress can be so, so frustrating. And the other piece of perspective is really using the leadership ceiling construct as an explanation. You know, we’re, all of us, I think who are… all of us who are at all introspective and reflective about our lives are trying to make sense of what happened and what didn’t happen. How come, I never got that thing going, how come that didn’t work? How come that project that I just put my entire, well, how come that fell apart two years later, how come I never got off the ground? And the leadership ceiling has really helped me understand it, not just because, and I want to make clear, not just because, oh, you know, every time I got squashed, it was because of a leader, but it’s also because looking back and saying, you know what? I approached that situation with an inadequate assessment of where the leadership ceiling was, or invalid assumptions about what was important to the leaders so that I was ineffective at influencing them. So it’s really helped me make sense of when things worked and when things didn’t work, which things did I, where did I do things that got me where I was trying to go? And where did I do things that were, that were less effective for me? Jesse: Fantastic, Tim. Thank you so much. This has been great. Peter: Yes. Thank you. Tim: My pleasure. Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @jjg. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.