34: Design leadership to support organizational transformation (ft. Rachel Kobetz)

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.