Finding Our Way: A Conversation With Executive Level Design Leaders

Jesse and Peter drink a “Warp Core Breach” at the Star Trek Experience, 2007. Photo by Leisa Reichelt.

In this episode, Peter and Jesse reflect on the conversations they had with senior design leaders, the themes that emerged, the challenges facing design leaders today, and our hope for a brighter future.

Transcript

Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Together: And we’re finding our way…

Peter: …navigating the opportunities and challenges of design and design leadership.

Jesse: On today’s show, for our season finale, Peter and I take a look back at our recent conversations with design executives to explore some of the emergent themes we’ve heard, including how to make sure you’re set up for success as a leader, the personal qualities such as resilience and pragmatism that help leaders thrive under pressure, and how to succeed as a design leader by being truer to yourself.

Design leadership as change management

Peter: So probably kind of most obvious place for me to start when thinking about the conversations we had was this thing I wrote at the beginning of the year where after the first five discussions we had with design executives, I went back, I analyzed the conversations we were having, I tried to pull out themes and topics, and as I went through my process, I hit upon what struck me as an an overarching emergent theme, which was around change management, how four of the five design leaders we spoke with very intentionally approached their job as a change management initiative. and Katrina, the very first person we spoke with, said that right out of the gate, at the start of our interview with her, that design leaders have to be change agents because businesses still don’t really know what to do with this function.

Jesse: Right.

Peter: And that was an interesting start because then Greg, whether or not they said change management, Kaaren’s approach was a change management approach, Greg Petroff’s approach was a change management approach, Rachel Kobetz’ approach was a change management approach, in terms of an intentionality of taking not just their team, but the function of design wherever they found it when they got there, to some new place and a set of activities that they were going to use to get them there.

Jesse: Right, right, right. Yeah, it’s a really interesting thing, because if you think about the different kinds of change that a leader could potentially make, you could definitely see how in a more mature organizational function, something that has a more robustly defined value proposition than product design currently has, that has better entrenched practices and ways of talking and thinking about that value proposition, you can see in a lot of those kinds of functions where change management wouldn’t really be part of the job. There isn’t a lot of change to be made if you’re a CMO, for example. I’m sure there are people out there who would disagree with me.

But for design where it is in its maturity, on its trajectory, there is still a lot that is not understood or not widely understood about what the value proposition of design as a function to an organization that creates digital products actually is. And what we see across this range of leaders that we’ve spoken with are a bunch of different frames for that value proposition. But in any case, they all have bridges to cross with their partners, with the business, to help them fully appreciate that value proposition.

Because that understanding is going to be discontinuous through an organization. Not everybody’s going to get it. Because of the level of maturity of digital product design as a practice, because of the breadth of understanding of it beyond people who have engaged directly with design processes.

So there’s a lot of evangelism, education and, really, shifting people’s mindsets, that’s necessary in order for these leaders to deliver on the promise that they see as there.

Peter: Totally agreed. Even before these conversations, when people would ask me, well, how is a VP of design different than any other VP…

Jesse: mm-hmm.

Peter: … it’s because they have to spend so much time educating and evangelizing and increasing organizational maturity or awareness around the design function, which is

Jesse: Yeah,

Peter: understood for engineering, for sales, for marketing.

Jesse: Exactly. Right, right.

But I then I think that for the design leader, it’s a question of how far do they want to take that? How far do they want to go? You wanna level the product up to, you know, to be something more than it was, to take the design to someplace that it hasn’t gone before. Do you wanna level your team up in terms of expanding the capabilities of design, changing the shape of that value proposition of design as a function within the organization?

Do you wanna change the organization beyond design? Are you interested in seeding, you know, for want of a better term, design thinking beyond design functions in the organization? Like these kinds of ambitions are all part of the balance that you have to strike as an executive design leader.

The importance of clarity of vision

Peter: One of the leaders that we spoke with, Kaaren, had the most clarity in terms of, like, ultimately where she was trying to head, and she used this phrase, “one freaking experience,” right? So she’s responsible for the consumer bank for Chase, JP Morgan Chase. And she saw kind of ultimately her vision is how do we create one experience for customers across the suite of products and services that Chase offers consumers.

And when you do that, when you have that kind of clarity of vision, it ends up that gives you the almost marching orders to address the questions you were asking. Is it about the product, is it about the team? Is it about the broader organization? I mean, the short answer is, it’s all of those things, ’cause in order to deliver one freaking experience, she has to figure out how do we get these different internal lines of business aligned, the credit card business with the home mortgage business, with the basic banking business. And so that can’t be just something happening within design. You need to figure out how to weave it into the broader organization.

But…

Jesse: mm-hmm.

Peter: … something else that she talked about when we spoke with her, that I’ve used since in, conversations with other design leaders is, where to begin? And in order to deliver on that one freaking experience, she saw where she needed to begin was with her team.

She talked about the very first thing she did was establish or work to establish a world-class team, right. That that was gonna be the foundation upon which everything else rests. And as someone who’s been supporting her for the past year and a half, I’ve seen some remarkable hiring at all levels, but particularly at a design leadership level, as that initial step towards that greater vision.

Organizational maturity

Jesse: Mm-hmm. And you know, it’s interesting, too, because I think there is the question of, to what extent does design, by definition, regardless of the maturity of the organization, regardless of the maturity of the design team itself, to what extent does design necessitate organizational change if design is actually going to deliver on its value? And I think that for a lot of these leaders, they feel that if we’re just delivering better product over and over again, that’s not going far enough because we haven’t gotten into the roots of the culture of the organization. And one of the things that has come up a few times in these conversations is the notion of how much permission does the culture allow design as a function to have to push the boundaries of its value proposition to offer new ways of delivering value to the organization.

And those experiences are wildly inconsistent based on the specific cultures of those organizations that those design leaders are stepping into.

Peter: I like this frame. The companies that would hire people, like the folks that we interviewed are likely more permissive…. Have a greater maturity around these things, or they wouldn’t be hiring someone to lead a team of 400, 800 people, like, there’s some investment in it that suggests a greater permission.

But I like the permission frame because I think something that a lot of design leaders don’t do, but need to do, when they enter into that new role, is assess, measure, understand where the, where that organizational maturity is at.

Jesse: Mm-hmm. Mm-hmm.

Peter: And permission is going to be caused, by that company’s maturity around design.

Jesse: Mm-hmm.

Peter: And, and that was an insight. Another one that I’ve dined out on since we’ve spoken with him uh, came from and, wow, that was an unintentional almost pun because it’s with Jehad, who’s Chief Design Officer at Toast. You know, we had spoken with these other design leaders, and they would talk about impact and they’d talk about co-defining outcomes, and it was from a place of greater maturity.

And Jehad pointed out that, at least in his growth, he had to dial in his conversation to meet the maturity of the organization he was part of. And so it might not start with impact because your company might not be ready to hear about the impact that user experience or design has. They might not be mature enough to take advantage of that.

And so he used a frame that I’ve, again, employed often since then, around “show your worth,” because your worth might be just understood relatively in the environment you happen to be in. It might have very little to do with the impact the metrics of the products that your team is building. And it might be around, Do your peers like working with you and your team? And, and measured through some internal pulse survey or whatever.

And that in an immature organization that is actually a legitimate measurement when you don’t have anything else to go on. And, and that really got me to be thinking about how important it is for a design leader to tune their message, their engagement with where the organization currently is, not where they hope it will be.

Jesse: Right, yeah. It’s huge. It’s huge. This comes up with my coaching clients all the time. The way that I talk about this with them is that the problem space at any given moment is the intersection of the trajectory of the larger organization and its maturity as it relates to design practice, the trajectory of the design team itself and its capabilities and its maturity, and the trajectory of the leader, what their past experiences have prepared them for and what new challenges they are well-suited to take on. And when you put those three things together, then you start to be able to define the shape of what the role actually is in that context.

Peter: The maturity cube.

Jesse: Sure, sure.

Peter: Well, yeah, and I’m curious how you help your clients manage through this, ’cause one of the things that inevitably leads to is frustration, because I think the design leaders often feel like they are ready for a more mature organization. Or they’re ready for the organization to be more mature, to take advantage of what they have to offer. And so then they’re frustrated because when they try to push that, it doesn’t go anywhere. How are you helping your clients manage their own sense of… not trajectory, but, cadence and, traction to dial it in with what’s organizationally appropriate and not get defeated in that process.

Resilience

Jesse: Right, right, right, right. So part of it is about resilience, right? How do you maintain the emotional resilience day to day, week to week, to keep having the same conversation, keep fighting the same fight, keep having the same argument, right? The persistence that’s required there and the patience, and this is another thing that new leaders frequently don’t really get, is how long it takes to create cultural change.

It’s one of the slowest -changing elements of an entire organization. You can turn a team over really fast. You can turn processes over, you know, pretty quickly. Cultural change is the slow-moving deep currents of the organization. And what that takes is, it takes persistence, it takes patience.

It takes a dedication. A dedication to repetition. It requires the ability to ride it out for a while and know that you might not see any significant impact of this culture-shifting mindset, shifting work for a long time before it starts to actually pay off, because you’re laying the foundation, you’re building that foundation of credibility and trust for design as a function within the organization that’s gonna enable you to expand that value proposition.

Peter: Well, and this gets to something you’ve written about recently on a post on LinkedIn, which is the job is bigger than the person. A design executive’s job is going to be bigger than any individual.

It’s just by nature there’s more work to be done than any one person can do. And so, how then are you helping your clients navigate that, figure out, given all the things they could be working on, do I work on these long-term culture things, ’cause that’s ultimately what I want to drive. Do I work on near-term quick wins? Just to get some traction. Do I work on, building my team? Do I work on managing my relationships? Like how are you helping them navigate all that opportunity or all that potential activity so that they’re not feeling like they have to work 60 to 80 hour weeks in order to…

Jesse: Right,

Peter: …get it done.

Jesse: Right, right. Well, it’s an interesting thing because, first of all, those three trajectories are a huge influence on how I help leaders set those priorities, to be able to assess where to invest their energy. ‘Cause you’re absolutely right, the job is just too big.

So you have to choose that selective focus of your attention and how you set those priorities. A lot of leaders get into trouble by not having an agenda of their own for their priorities. They’re receiving priorities from the business, they’re receiving, you know, requests or sometimes demands from their teams and they see their role as mediator, negotiator, reconciler of everybody else’s point of view about what’s needed. And they don’t bring their own point of view.

And the irony in this is that often what’s needed in order to narrow your focus of attention is to take your focus off of everything for a minute and reset and reflect. And that’s one of the big things that I help my clients with is, you know, whether we’re doing some reflection live in session, or I’m helping them create the patterns that create that space for reflection so that they can engage more strategically, so that they can get out of these reactive loops where the first thing that they do is they open their email and they’re immediately fighting fires to start their day.

Peter: Kind of related to this, what I drew from those discussions with design executives was, in order to make sense of how to spend your time, what you’re calling reflection, to me, it feels aligned with just that recognition of having a vision, like, what is it, what ultimately is it that you’re trying to get done? And, and how can you use that as some internal orienting point, north star, that helps you make decisions about how you are spending your time?

And then how you’re spending your team’s time, ’cause you wanna focus yours and your team’s time on work that moves you toward whatever that point on the horizon is that you’ve identified.

But you need to take the time. You need to make sure you’ve given yourself some time to just figure out, What is that thing that I want?

Jesse: Right,

Peter: And you’re allowed to have, you’re allowed to have that desire.

When I did my analysis and did the change management, that was clear. That each of these folks, part of their success is they had vision for where they wanted to take things, that they weren’t reactive. None of them showed up and were just like, what do you need? They all showed up with some sense of their agenda.

Cultivating a point of view

Jesse: Right, right. So having a point of view, continuing to cultivate a point of view over time, which is where this reflection work comes in. You know, when we talk about vision, in a lot of cases that’s gonna mean different things to different people. Is it your vision for the product? Is it your vision for the team?

I do come back to, I feel like leaders are able to activate the most potential when those three trajectories intersect, when the organization is at the right stage of maturity, and the team has developed its capabilities to a point that the leader can activate all of that, is really where I think the magic happens.

And in a lot of cases what’s happened is that they’ve left that third piece out, which is their own point of view, which is their own sense of, of direction. You know, one way that I sometimes talk about this is: be your own executive stakeholder, right? If you’re the head of design, head of design is one of the major functions in this team.

If you’re not regularly having meetings with the head of design, you are missing out on something. So in other words, I’m saying have an executive stakeholder session with yourself on a regular basis.

Peter: I was very recently introduced to the song ” I Have Never Been to Me.” Are you familiar with this chestnut from the late seventies?

Jesse: I, I, I, regrettably, I am old enough to know this song. Yes.

Peter: Yeah. Yeah, yeah. Yeah. It’s about this woman who’s been to Italy or you know, all around the world…

Jesse: Good.

Drank champagne….

Peter: She’s never been to her.

Jesse: On a yacht.

Peter: Yeah. Yeah.

And, anyways sorry it’s– sidebar, but, but crucial. Find the video for it on YouTube. There’s actually two of them you can find. Both of them are worth watching. One is set at a Scottish castle. The other is from a Dutch, like Top of the Pops type show, where it’s on this, it’s in a beach, but it’s inside a studio, like, soundstage. It’s, it’s, It’s awesome. it’s beyond awesome.

Well, but, but it’s interesting as you were saying that about the trajectories, it made me think, ’cause there’s one of those trajectories you can control. You can’t really control the organizational directory. You can influence it. You have a higher degree of influence over the team trajectory, but you still can’t control it. Right? There’s gonna be things outside

of your control…

Jesse: Yeah. No, it’s not about control, it’s about responsiveness. Mm-hmm.

Peter: But you can control your trajectory, by which I mean, as you look at these three trajectories, that point of your trajectory is, is going to hopefully be farther than where those other two are meeting today. right?

But what you can do is dial in where you are today on that path, right? By having that, longer term vision, you know where you’re pulling yourself and then maybe pulling the rest of the team.

If you’re too far ahead, there’s no connection, right? You’re untethered. There’s this concept of flow from Mihaly Csikszentmihalyi, which is people work best when they are operating just beyond their level of competency and capability. That’s when you get in that flow state.

I think about this a lot, in terms of how people perform, right? If you give someone a task that is way below their ability, like, that’s too rudimentary for them, they’re not gonna perform well. If you give people a task that’s way above their ability, they’re gonna sink, right? They’re just gonna, they’re gonna drown.

And so you wanna do it right at the edge plus of that. And so, how can you, as the design leader, be at that intersection of the organization and the team? And then just a little, just a, a smidge beyond it, kind of pulling both of those where they’re at and pulling them forward from that spot as opposed to trying to be at the end goal and, dragging them to wherever you are.

Jesse: Yeah. Again, I think that it’s about breaking the cycle of reactivity, creating the space to establish for yourself your own point of view. But also, you know it is about having a growth mindset for yourself as a leader. I talk to a lot of leaders; when I talk to them about growth, they talk about developing their teams, and they talk about, you know, providing support and resources for people to build up their skills and to move in the directions that they want to move.

And then when I ask them about those same things for themselves, they draw a blank. Because honestly, when you get to this executive level, there’s nobody looking out for you anymore in this respect.

If you are a Chief Design Officer reporting to a CEO, you are not having these kinds of performance conversations. The assumption is that you have the level of self-awareness.

Peter: Even if you’re reporting to a Chief Product Officer or somewhere into the C-suite. Yeah.

Jesse: Yeah. The assumption is that once you’ve gotten to this level, you’ve developed the self-awareness to be able to choose your own development paths. And there aren’t gonna be people looking out for you in this same way. But for a lot of these leaders, they are not used to taking that on for themselves, and they haven’t really defined how they see themselves growing.

And so defining for yourself your own path forward, the continuing expansion of your own potential has to be part of the equation.

Peter: No notes.

Jesse: No notes.

Peter: I’m just like, yeah, totally. Yeah.

How much design in design leadership?

Jesse: I think that this is somewhat connected to another theme that has come up, which is the notion of how much do you stay a designer once you become a design leader, and how, and in what ways, do you carry forward the skillset of design, the methodology of design, the mindset of design into your work.

And I think that that often creates some dissonance for people because they think there are things that they need to hang onto that they actually don’t, and vice versa.

Peter: And I think it’s also very much a function of those three lines of trajectory. But, in particular, the two that are a less in your full control, where the organization is at, and where the team is at. The last conversation we had was with Tim Allen, Chief Design Officer at Instacart.

It’s not his actual title, but close enough. And he was interestingly different from literally everyone else we spoke with because he remained committed to the craft and to the details of the work, even though he’s got a team of 150 or so.

And, when we spoke with him, I was kind of continually surprised as he was talking about how he approached his role. And as I reflected on it there were probably three things that arose as what enabled him to maintain that more detailed approach to design than others would likely be able to do successfully.

One, is his own perspective and agenda. It’s his own point of view. That’s just how he rolls. He trained as an industrial designer. Loves form, loves those details, likes to get in the mix. That’s why he cares about and is passionate about design. And so he was going to do what he could to protect that and enable that.

Two, he is, at least currently at Instacart, in an organization where he doesn’t have to spend a lot of time evangelizing and educating, right? We said that, that’s one of those things that many VPs of design have to do, given the state of maturity their organization’s at. By his account, his organization is actually surprisingly mature when it comes to design. His boss and the CEO, who are two different people, want him to be doing the things he’s doing and don’t need him to sell them on the power of design, and the impact of design that is understood.

And so when you take all that time that so many leaders have to spend evangelizing and educating, when you, you have that time back, it’s like, oh, well what do I do with that?

Well, he’s, he’s able to use that time in this fashion to really drive craft excellence within the organization.

And then the third thing, and he was very explicit about this, was, he has a member of his team that he referred to as his hammer who kind of runs the org for him, makes sure that all of those organizational, administrative, operational things are handled, that many design leaders themselves usually have more responsibility towards.

He’s been able to delegate a lot of that, and we talked about that we used the analogy of a director and producer, right? He’s more of the director who’s responsible for the vision and the creative output. And then he’s got a producer who’s handling all that stuff that goes on behind the scenes that enables the people who are doing the craft to just focus on, on the craft and not on all the stuff around the craft.

And so that was how he was able to be in that place where he could focus his efforts where he wanted. If he was in a different environment, he probably wouldn’t be able to do that. Or if he tried to be the craft-focused leader inside some enterprise software company that wasn’t ready for that, it would be a struggle. He would be unhappy. They would be unhappy, and it probably wouldn’t last. But he, he was able to find a context and do a little bit of work to shape it in terms of bringing on this hammer that enabled him to really focus on what he was passionate about.

Jesse: Yeah, well, but importantly, he wasn’t just focusing on what he was passionate about. He talked about how he strategically chose where he engaged to be on the things that would be highest visibility to the business. So he is not chasing design perfection down every possible path for the business. What he’s doing is he’s choosing the things that he knows the CEO is gonna be taking a close look at.

He’s choosing the things that he knows, that he’s got partners who are really deeply invested in, and he wants to be sure that he’s conversant with all of the details of that. And the way that he does that is by engaging with the team.

Peter: Yeah. And that said, that might not be the best approach for everybody, right? I’ve never led a team that large, but when I was a design executive, I recognized my strength was organizational and operational. And I would delegate creative leadership to my design directors because I knew they could do that better than I could.

I could situate the organization really well on their behalf, right? And so, I have this presentation that I give called The Evolving Design Leader. And one of the things that I stress towards the end of it is, too often we expect our design executives to be these design saviors, right? That they’re the creative visionary and they’re really good at leading and getting people excited. And they’re good at organizational building, and they’re good at the relationships with cross-functional and you can’t do, no one person is gonna be good at all of those things even.

And so, so I talk about, I call it teamifying leadership, right? How can you reflect on what you are good at, passionate about, but then also what you lack, where your gaps are, and then put around you in your leadership team, not just, like, the people that you’re delegating to, but, create a team of folks, two or three people whom you can spread all of this leadership activity across?

Your leadership complement

Jesse: The term that I have been using for this recently is I call this finding your leadership complement.

What are the resources around you that support you in the task of leadership? And in some cases that can be just having that right hand, just having that hammer. In some cases it’s about having that team of leaders of different people that you know, that you can delegate or partner with. But having an awareness, to your point, having an awareness of where your strengths are and where it’s necessary for you to provide your individual focus and attention, and then having a strategy for that leadership complement around you that’s going to support you with the rest of what leadership actually entails.

So, speaking of that high level executive engagement I’ve heard you talk about a couple of times now the notion of social contagion in organizations and the implications of that for the design leader, and I’d love to hear you kind of unpack that idea a little bit.

Social contagion

Peter: Sure. And I can’t say I’ve thought about it in this context all that deeply, but at the beginning of the year, there was an article that got some virality, around how the layoffs that we’re seeing all these companies do is more than anything a social contagion. It’s not actually a reflection of good business practices. There is some type of research or study that had been done that showed that layoffs most of the time are actually bad for business.

Businesses don’t end up healthier, a year later or whatever, because they did layoffs, than those who didn’t. And so why are they happening if they’re not good business practice and they make everybody miserable?

And the finding in this research is that it’s a social contagion. Once some people start laying people off, other companies are looking at that and like, should we be doing that? I guess we should maybe be doing that. Is that what we’re doing now is laying off? And boards are telling people to lay people off because that’s what’s happening right now in the market.

And now the thing to recognize about that concept is that literally every human behavior is a social contagion. That is how we operate.

Jesse: Mm.

Peter: And so all the hiring that happened a year and a half ago was a social contagion, right? And now we’re just kind of seeing the flip side of that, that hiring clearly was not done with real business savvy driving it. It was, “Wait, oh, that company’s hiring. We, we gotta hire, we gotta ramp up, we gotta…”, you know, it was, it was just looking around and doing what others do.

And so I’ve been thinking about that because, even in the face of all of these layoffs, I am seeing companies, many companies, hiring, for the first time, senior design executives.

So on one hand they’re laying people off, and on the other hand, they’re hiring their first ever SVP of design or VP of Design or Chief Design Officer.

The same companies are doing this. When I saw that happening, I’m like, oh, I think design executives have hit this kind of social contagion layer, where companies are seeing, well, that company… Microsoft, for example, just hired four VPs or above, of design. John Maeda, Liz Danzico, Mike Davidson, and Justin Maguire. All within the couple months.

And so companies are seeing like, well, if Microsoft, this very big important company is doing that, should we be hiring our chief design officers and stuff?

And so I think we’re seeing that. And one of the implications of that, and this gets back to the trajectories, is that these companies that are doing it are likely immature in their awareness and understanding of design, right? They’re doing it because they’re seeing other people do it, but not because they understand necessarily what it will mean for them.

And so as design leaders, we need to be quite conscious, conscientious, aware, as we’re going into these environments, what precipitated hiring at that level? What was the, what was the realization? What was that understanding? And to just go into these situations eyes wide open.

Jesse: Yeah. Yeah, I think that’s a really huge thing. There are a lot of different models of the value proposition of design out there. And each design leader is carrying with them their own model of the value proposition of design.

When you’re stepping into a new organization and especially an organization that is creating an executive level role for the first time, you’ve got to be asking where is this coming from? What is the promise that they hope gets fulfilled, ’cause it’s a huge, it is a huge organizational commitment to create an executive level role. it Is the kind of thing that is not easily undone. It has huge, deep, broad, long-lasting organizational implications. So when an organization engages in it, it’s because they see some promise there and they want to see that promise actualized.

But if you, as the leader stepping into that, don’t have a really clear idea of what that is, you are running a high risk for a mismatch that is going to create some grief for you down the road.

Peter: Yeah. And on that note, especially in this market where I think there’s a lot of anxiety about work and getting jobs, people might lower their own barrier to entry to a new job. And if you’re looking at a, a role like this, you need to be as, if not even more, particular about the environment that you’re stepping into, that it is ready for someone like you, that it can set you up to succeed.

Too often what I see is designers are brought in to an environment like this, but they’re not set up for success. And so you need to be the one to figure out, to ask the questions.

Jesse: You can’t assume that you’re being set up for success. You can’t.

Peter: No. And not, with any ill will…

Jesse: No, no, no malicious intent there.

Peter: They’re obviously, they want this, they wouldn’t put this role together if they didn’t want it to succeed.

But, many companies just have no idea what they’re getting when they’re getting design. They still think, primarily, I’m getting someone who can help make my design engine go. And if you have designs that are more impactful, more strategic, more cultural, more organizational, and you step into an environment where the expectation is creating a wireframe engine, that mismatch is going to be difficult.

You should feel comfortable you should feel, I dunno, in the right, in asking hard questions of your perspective employer to, to make sure that you feel like they are setting you up for success. You should be able to ask for things like headcount before you get hired. Like, okay, you’re hiring me at this level. What is the team? What are the expectations? As a condition of hiring, I am gonna need five more head count, 10 more head count.

Like that kind of stuff is totally reasonable and will demonstrate their willingness to commit to you and the role in the function.

And if they’re not willing to do that, that’s a red flag. That’s a warning sign that they don’t necessarily understand what it is they’re asking for.

Jesse: Mm-hmm. Mm-hmm. And of course you have to make the case for that headcount, but…

Peter: Sure. Sure. But, and, and that might mean doing the diligence to understand enough about their organization, hopefully you’re doing that diligence as you’re considering a job like this somewhere, because you do have some responsibility to set yourself up for success.

But it reminds me a little bit of that conversation we had with Denise Jacobs around creativity. And one of the things that she’s often frustrated with, from designers, is designers don’t do the work coaching the people they’re showing their work to, for the nature of the feedback they need.

Jesse: Mm-hmm.

Peter: And it’s not up to the non-designers to know how to give you good feedback. That’s, they, they don’t know how that, that’s not their, you know, and so you as the designer have to say, “this is the kind of thing that’s gonna help me make this design better, give me this kind of feedback.” You can do that in your role as a design leader as well.

They’re not gonna know the role as well as you will.

Communication in all forms

Jesse: Mm-hmm.

Mm-hmm. You know, so much of this, I think, when designers look at design leaders and ask what those people do all day, I notice how much of it is just trying to figure out what to say to whom and in what context. You know, so much of the job is planning your communications, executing your communications, getting feedback on your communications.

Whether that is in conversation… I would say the primary medium of leadership is conversation. You’re spending way more time talking to people than you are preparing any kind of presentations or reports or deliverables or anything like that. But there are all of these other kinds of vehicles that are available to you too. We heard this from a couple of the folks that we talked with about the importance of creating communication strategies that address the needs of all of your different audiences.

How do you communicate a vision amongst your business stakeholders? How do you communicate about your value proposition and your mandate with your product and your engineering partners? You know, how do you communicate where you’re going as a team with your team in a way that they can engage with and understand? You’re spending so much of your time just thinking about your language and just finding the right, the right moment in the right vehicle to get the right message across.

Peter: Yeah, that was one of my biggest kind of surprises after the first five conversations we had, and I wrote this post around design leadership as change management, was how all of those design leaders, the degree to which they were intentional in their communication strategies. Because this was not something…

Like, I would talk about the importance of relationships, and I would work with my clients or in the classes I teach around how design leadership is more talking than doing. And I would talk about the importance of evangelizing, but what I heard from these leaders was the work they did, the effort they did around having an almost overarching intentional communication strategy, right? And so you had Greg Petroff, having a quote “shadow comms team,” you know, one or two folks, a content designer that would help him write the newsletters or whatever that would go out there to make sure that he was on message.

You would have Kaaren Hansen doing the pre-work with her leadership before they would present to others to make sure that the messaging was right, that it was focused, that it was right for that audience. Rachel Kobetz talking about how you are never not done with that communication and how she would just, every channel she had, she used.

And what I think also tied them together, because you’re right, much of this happens in conversation, and so what you need to have, this is something I’ve started to stress in my classes and with my clients, are talking points. What are 2, 3, 4 messages…

Jesse: yep.

Peter: Kinda like in politics, what are the two or three, four messages that you’re just banging away on?

Jesse: Mm-hmm.

Peter: …just banging away on them in every situation you have.

And you’re gonna get tired of hearing yourself saying these same things over and over again. but you know it’s working when you start hearing it back, and you’re gonna realize that it’s gonna take months if not years, to hear it back.

In one of the classes I taught recently I had someone who’d been at a company, a big entertainment company that you’ve heard of, but I don’t want to say too much ’cause you know, it’s that person’s story. But they’d been there three years, four years. And in every session that they would lead, they would put the double diamond in there as a way to reflect on like what, where we are in the process, and to highlight the first part of that diamond.

Like, the work we’re doing is, around discovery, is around definition. It’s around the strategy, right. To continue to orient people. And literally in every conversation for two years, she would do it and it wouldn’t get much notice. But then in the third year, she started seeing the stuff coming back to her in terms of people using that as a frame for talking about their work, right?

And she, and she realized like she had been incepting this company with this thinking and it finally had worked. And so having that, you know, I think you mentioned earlier, persistence if not, you should have. This is part of that persistence. It’s just…

Jesse: yeah.

Peter: …banging away on that message.

Jesse: And that tolerance for repeating yourself, right. To just be willing to say the same thing over and over and over and over again. It’s very, very much analogous to the way that a political campaign is run.

Peter: And, it works, right? The people that we interviewed have achieved their success because they’ve employed these strategies. Thinking of talking points in politics and something else that I’ve been talking a lot about, and I wonder how you’ve approached this in your practice. I now in my masterclass on design leadership fundamentals talk about playing politics. I just call it out. You are playing politics. In order to succeed as a design leader, you have to be willing to play politics. That means some quid pro quo, some horse trading, some diplomacy, some talking points, like whatever you think of when you think of politics, bringing those to bear because your colleagues are doing that and they are, going to succeed through the politics they play.

Playing politics

Peter: If you’re not playing politics, if you somehow think that the value of the work should be evident in its quality, and just by doing the right thing, you’re going to succeed, you will not, you will fail. You need to do the work to play politics around it.

Jesse: Yes. Yeah. There is no rising above it. There’s only going through it, you know? I really think that’s true.

Peter: I think too often design leaders have this sense of purity around the nature of the work. And because it’s backed in research and we have this evidence, and if we just do the things that are obviously the right things to do it’ll succeed.

And when you start talking about playing politics, there’s this concern that you’re gonna be disingenuous or something. And that’s not what we’re talking about at all. It’s not about somehow hiding things or being someone that you’re not. It’s about recognizing the tactics that work that enable you to advance your agenda, right? Which, when we talk about, that’s why we started with talking about vision, that vision is your agenda. The politics is what allows you to realize that agenda.

Jesse: Right, right, right. I think that for a lot of leaders, they don’t realize where their effectiveness is hampered by their own sense of what design is and what design offers.

I think too few design leaders know what’s truly worth fighting for in terms of design outcomes. And they put the emphasis in the wrong places and drive things that don’t really matter.

Peter: So as you’re saying that, I’m reminded of Erika Hall, right. Kind of yelling at designers who worry about the alignment of elements on a page when she’s trying to get them to think that the business model is the grid, right? Like, is, is that the kind of thing you’re talking about? Like design leaders should be aiming for something more fundamental within the organizations they’re operating in and their ability to affect that and not just the presentation layer?

Jesse: Well, it’s that, but also I simply think that there is a degree of pragmatism that is required at the executive level that designers haven’t necessarily cultivated within themselves until they get to that point.

Peter: Yeah. Okay. No, that’s fair. But yes, ’cause one of the reasons people get into design is, there’s an idealistic bent. You’re trying to be an idealistic design executive, like you need some of that, for the passion, for the fire, for the North Star to keep you oriented.

Well, this is a story I tell around politics. I supported an idealistic design leader who, basically, he wanted to bring human-centered design practices into this large healthcare organization. And he’d had some success doing that at another healthcare organization. And he came to this new healthcare organization and he’s like, I’m gonna bring HCD, true blue…

Jesse: mm-hmm.

Peter: … you know, human and patient-centered design practices into this organization.

Now the issue was he’d been hired by an IT function within this organization. And so there was some expectation when he joined, that the team that he was leading would continue to look at Innovation with a technological lens, or at least through some of the work that technology was part of it.

And he was such a purist. He’s like, no, technology is a means to the end. If you’re having me start with technology that’s sacrificing my dearest principles around the nature of the work I do.

And he didn’t, he barely lasted a year at this organization because he could not approach it pragmatically. He had let his idealism get in the way of his ability to have, ’cause he likely could have, ultimately had that impact he wanted.

This is the playing politics thing. By playing a little politics, given them a little bit of what they want, which wasn’t wrong, it just wasn’t what he was passionate about, but it wasn’t a bad thing. Give them a little bit of what they wanted, build that social capital internally. He could have within three years to five years been advancing a true human-centered agenda. He would’ve demonstrated his commitment to the organization, to the business and those types of things.

But he just could not get over himself…

Jesse: right.

Peter: and, he, he ended up having no impact.

Jesse: Yeah.

This is a great example of exactly what I’m talking about. There are strategic design compromises that are sometimes necessary in order to create the momentum to get where you ultimately want to go as a design leader. But if you take every step as an all-or-nothing step, you’re never gonna get there.

Peter: Right. Right.

Jesse: So as we are winding this season up and you know, we’ll be back with more sometime soon but as we are looking back, I wanna look forward a little bit too and ask you, how are you feeling about the prospects for design and design leadership these days in the spring of 2023?

Peter: I am feeling decidedly mixed, which is surprising me, ’cause usually when we have this moment of reflection and, and then looking forward, I feel like I’m pretty positive. Like, I have, I often see opportunity on the horizon. And so I want to be more hopeful and positive in my outlook, but, like, I haven’t done the work to unpack why I’m not more hopeful.

So I’m teaching these Design Leadership Masterclasses. I’m also doing a bunch of work with specific companies. And one of the areas of focus I’ve had recently is at this level, not at the executive level, but at this design director level, kind of the middle management layer of design.

The struggle of the UX Director

Peter: I jokingly put a meme a few weeks ago on LinkedIn and it was a UX director who was being drawn and quartered, like this old woodcut drawing of somebody being drawn and quartered. You know, pulled apart by four horses and the UX director was that person, because this is what I’m hearing from that population.

They’re having to cover for inadequate product partners who don’t understand their job. They’re not being given the staff they need to build out a team. So they’re having to do more of the hands-on work. Many of them are the senior-most designer in their organization. I, I do work with heads of design who are director level, who are not executive level, and so they have to show up with executives many layers in the hierarchy above them. But they have to be able to play in that realm. And they’re getting pulled in all these directions and it’s causing frustration, anxiety, burnout, and many of these folks are, are leaving the field.

They’re just saying, you know what, I guess this isn’t where I want to be.

Jesse: Well, who’s holding the ropes on this poor soul being drawn and quartered here?

Peter: That’s a good question. In the cartoon I had, you know, your product partner pulling you in one direction, your team pulling you in another direction, your engineering partner pulling you in another direction. The business is this kind of shapeless entity pulling you in another direction. Those were the four, you know, HR in the background.

And this is maybe why I’m, I’m having some trouble with hope right now. It’s a function of a lot of systemic factors. I mean, we can start with capitalism, right? But, one of the challenges, and I think Erika actually just posted something about this on LinkedIn recently, one of the issues we have is that the core values of people in UX and the core values of late-stage capitalism are at odds.

And so the companies we work for, which practice late-stage capitalism, and then the UX kind of mindset that we’re bringing to it, are at odds. And I think trying to figure out how to square that is one of those forces.

This wave of layoffs where middle management is targeted is one of these forces because the work of middle management’s not appreciated. And so these folks are getting pulled in more directions because there’s fewer people around them now. Whereas before they used to help coordinate and orchestrate the work, they’re now having to do it because they’re who’s left.

So I think there’s these systemic forces at play that are doing the pulling and why I’m trying to figure out like how do I get to a place of hope in terms of, where is evidence of realization of frankly what Katrina said and when we talked to her, right? That design, when woven into business in an appropriate level, things are better.

And there’s still so few examples of that. Even though, we have the obvious, almost textbook, examples now of Apple or whatever that like, if you embrace it the right way, you could realize a lot of success.

But companies are still so resistant, kind of deeply, fundamentally at their core, resistant to not just the value that design has to bring, the approach design brings in order to realize that value. And I don’t know where it’s getting unlocked or, where it’s being integrated more successfully.

Jesse: Yeah. Yeah. You know, this comes back to some of the stuff that we’ve been talking about really since we started this podcast. Having to do with the leader’s role in creating kind of a bubble within which the design team can thrive and reconciling the need for a distinct culture within the design team that is not the same as the larger culture that they’re a part of.

And the design leader kind of having to serve as the partition, bouncer, semi-permeable membrane that keeps the cell intact.

Peter: And I still use that metaphor, I use it all the time. And I think it’s just like, I dunno, at some point that cell wall dissolves under the onslaught of, all that effort, all that heat that gets applied to it from both sides, right? The designers who want to operate in one way, the rest of the organization trying to operate in another way. And, and this design leader just kind of like that friction that’s being created.

Jesse: Mm-hmm. Mm-hmm. Like the design leader is sort of the WD-40 that has been, squirted into the, squeaky hinge.

Peter: Right? And then it’s all used up. And that’s, I think, what’s leading to this, to, to this burnout.

I think there are, you know, the opportunities, so, when you mentioned pragmatism, right? I think pragmatism is a helpful concept to rest on.

A better recognition of one’s own power in these dynamics. I think design leaders in particular, maybe because they’re so new to it, don’t recognize that they actually do have power and they can set boundaries.

‘Cause a lot of, you know, burnout is, often a function of just an inability to set boundaries. And design leaders have trouble with that because they’re afraid if they set boundaries, if they say no, if they don’t take it all on, then they will be seen as not a team player.

Someone that’s difficult. And that might be true, but then do you really wanna work in the company that expects to just, like, wring you dry?

Like that’s not sustainable, right?

Jesse: Yeah. Well, again, if you are being forced into this continually reactive stance you are not being set up for success as a leader. You are being set up for burnout.

Peter: Right. how are you helping your charges? I guess they’re not your charges. How are you helping your clients? I’m assuming many of yours navigate some of these challenges and you talked about resilience and you talked about pragmatism. How do you guide them towards an ability to stick with the program, maintain that vision, maintain that passion, but in a way that doesn’t allow them to get taken advantage of?

The future we want for design leaders

Jesse: Yes, it’s absolutely true that a lot of design leaders need some practice in setting boundaries and in setting priorities for themselves because they’re used to other people driving their priorities because that has been their career experience. So yeah, definitely a big part of it is just helping leaders come into every situation with a little bit more intentionality, knowing what your point of view is, knowing what your desired outcome is, knowing what’s authentic for you, separate from what’s right for the organization and separate from what’s right for your team.

What I see a lot of design leaders do is they so completely over-identify with their team, that they lose a sense of who they are in the mix and what they bring and what their strengths are that will enable the organization to go farther and to expand that value proposition.

So for me, in my work with my clients, it’s always coming back to what’s really true for you and what does your insight, your acumen, your experience, your wisdom as a designer and as a design leader, where does that point you? Where does that take you? What direction does that suggest for you in bringing that into how you set your priorities, how you set your boundaries, how you focus your attention?

Peter: Yeah, I think if, more of the people I worked with had a firmer sense of that for themselves in general, like, I think that could have like a multiplier effect. It would be interesting, like, if, leaders were more actualized across all of these organizations. That, that could be like, interestingly powerful.

Jesse: You just described why I do what I do.

Peter: I want that future. Let’s get to that future.

Jesse: I agree with you.

One last thing that I wanted to throw out there. We’re gonna take a break for a little while and then we’ll be back with more episodes of Finding Our Way. We’ve had this wonderful series of conversations with executive level design leaders. We would love to have more, but we don’t know the people that we don’t know, and we don’t know what stories there are out there that might really be worth hearing.

So if you, listener to this podcast are working for a really awesome design leader that you feel like would have a lot to contribute to a conversation like these conversations you’ve been hearing on this show, we would love to talk to that person. We would love for you to nominate your design leader, to be a guest on Finding Our Way. So please go to our website at findingourway.design, hit the contact form and let us know who we should be talking to. We would love to hear from you.

Peter: Yes. Excited to see who comes in, who we’re introduced to and looking forward to having those conversations in the future.

Jesse: Peter. It’s been a pleasure as always. Thank you so much.

Peter: Oh uh, the pleasure is all mine, Jesse, thank you. And to those who have stuck with us both this long into the season and this long into this episode, thank you for your attention. You can always find us whether at findingourway.design or on LinkedIn and see you around.

Jesse: Thanks everybody. Take care.

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.