37: From Design Leadership to Product Leadership (ft. Che Douglas)

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.