Leadership Coaching - Do I Stick It Out Here and Push It Forward?

Transcript

Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

And we’re finding our way

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

Jesse: On today’s show, Peter and I take a break from interviewing guests to ask each other some questions and answer a few of yours as well. Along the way we get into topics like organizational maturity, career trajectories, the role of diplomacy and leadership and connecting leaders to their true sense of purpose. That’s right. It’s time for the mailbag.

Peter: Hey, Jesse. So today I thought we do something a little different. Instead of a conversation with a friend of ours, have you and I converse. I think it’s, you know, it’s been a little while since you and I have had an opportunity just to chat. We didn’t want to do this in a, as… a navel-gazing fashion. So we’ve, we’ve elicited questions from the community through various channels: LinkedIn, Twitter, and email. And we have some questions that we’ll get to, but I, taking my co-host prerogative, do want to ask the first question and it’s a question of you. And it’s… I realized, I don’t know, kind of where… what your perspective is right now on matters of design and design leadership.

Like what, what your point of view is. And I’m curious what patterns have emerged in the conversations you’re having with design leaders in your coaching practice.

Improving UX maturity in an organization

Jesse: So for those of you who don’t know I’ve been away from my leadership coaching practice for a bit as I’ve been dealing with some health issues. Last year I was in treatment for cancer all year long, but I’m happy to say that I’m feeling much better and I’m back at it now. And so I’ve been back into the swing of coaching for the last few months, and it’s been interesting to return to it with this perspective, having taken a year off and noticing the conversations that I’m having with folks now.

And you know, one of the interesting themes over and over again, that’s coming up in my coaching conversations, revolves around something that you I’m sure have a strong perspective on, Peter, which is organizational maturity. What I’m finding is that a lot of these leaders, the biggest struggles that they have are the fact that they are embedded within organizations that are not as mature in their UX practices, as these leaders feel they need to be in order for them in their teams to be successful. So over and over again, what I’m seeing is the main question that these leaders are dealing with is the question of, do I stick it out here and try to push this organization toward a level of maturity where it can deliver on the promise and potential of design?

Or do I cut my losses, get out, and go find another organization that’s already operating at that level of maturity? And it’s a difficult thing for individuals to find their way through because that task of pushing the maturity of the organization forwar,. It asks something very different of you than simply jumping in and operating in a, in an… in a situation where you were already sort of set up for success.

Peter: A clarifying question: when you’re talking about maturity, are you talking about maturity of the UX organization, the UX team, or are you talking about maturity of the broader organization to embrace user experience or…?

Jesse: It’s the well, it’s mostly the the maturity of the broader organization. Although I will note that along the lines of our conversation with Tim Kieschnick, the maturity of the larger organization ends up strongly influencing how mature your UX team can.

Peter: Right, right. And so. That’s interesting. I mean, this… I’m reminded of when I joined Groupon 10 years ago and there was a lot of interest in being design-driven. And so if we use the leadership ceiling kind of framing, there was actually a pretty high purpose ceiling in, in that regard. And, but when I, so I inherited a team and what I saw was that, that it was the team that was immature much more than the broader organization.

Not that the broader organization was all that mature, but it didn’t matter how mature or immature the broader organization was because the team was evidently immature. And that’s actually what led to writing the book, was this realization that we need to first mature our design organizations before we can then start trying to mature design within the broader organization. And I’m wondering if you’re, if, if that is a pattern you’re seeing. Whether or not these design leaders, you don’t, I, you know, I, I guess, I guess it might be hard for you to diagnose just how mature somebody’s design organization is. But let me, let me just say that I’ve seen too often design leaders, rail…they get frustrated by what they feel is the immaturity and the constraints the broader organization is putting on them, but they don’t accept responsibility for the fact that their organization isn’t, isn’t even measuring up to the ceiling that that broader organization is, is affording. That they’re not doing that initial work…

Jesse: right.

Peter: …to mature their teams.

Jesse: Right, right, right. Well, and. It becomes a question of what kind of maturity you’re talking about because there is a level of maturity of team structure, of process, of governance that are the kinds of things that I think you’re exactly right, that if a UX team isn’t, it doesn’t have that stuff in place, there’s no point in asking for a broader mandate because you haven’t demonstrated that you can deliver value at that scale yet. But the, I think the, the kind of maturity that these leaders are running up against that I’m hearing about has to do with a maturity of understanding of expectations, of design, of appreciation of the value of design that they’re seeing doesn’t really exist in these organizations around them, or doesn’t exist at the level that allows them to really do what they feel like they’re there to do.

Peter: And that pain is real and I see it all the time. And, and Yeah, so then it becomes this question of, it’s funny, a lot of this is going back to our conversation with Tim, you know, you’re, you’re, you’re going to operate below the organization’s maturity ceiling. And so as he pointed out, you have kind of two options.

You can bide your time or you can bail. And that’s, that’s individual to the person in terms of what, what, what path they choose based on what else is happening in their relationship to that organization? I say, I think primarily around their commitment to the mission or purpose of that organization.

And if it’s an organization that they feel strongly committed to and they want it to succeed, then I would say, and then it’s your job to, then, as Tim pointed out with the letter C, change the ceiling and that’s, as he said, it’s not for the faint of heart, but this is the real work of design leadership.

And I think one of those things, that when people ask why, how, is being a VP of design different than being a VP of marketing, it’s– it’s this immaturity question, companies are mature much more mature in thinking about marketing, thinking about engineering, thinking about sales. And so your VP doesn’t need to keep evangelizing and educating everybody as to what it means to do it, right?

Companies are immature about thinking about design. So part of the job of that design leader is education and evangelism. That’s just… that’s… that, you can’t get away from that. I mean, the last thing I’ll say is, on at least in this front, is I have been surprised… so I’m, I’m currently supporting an organization where this type of maturity, in- increasing the maturity is, is, is a goal that the design team has. And so they’re having to communicate how design works to a broader, primarily product, organization. And this is a big company. These are, you know, billions of dollars; very senior leaders. And what surprises me is how rudimentary the conversation is that the design leaders are having with the broader organization to educate them. I mean, I’m working with design leaders with 25 years experience who are rolling out the double diamond at its most basic to communicate, This is what design is, and who are leaning on the DMI index of how design-centered companies do better in the stock market, like reports from 5, 10, 15 years ago.

Jesse: These are old tools that have been used for a long time to evangelize design.

Peter: And they’re still working and they’re still working. And so I think one of the things that we have to recognize as design leaders, who, because we’re experts in it and might think that this stuff is not all that valuable, they’re not all that useful or, or too basic. What’s basic to us is mind- expanding to others and, and to not shy away from, from returning to those rudiments in, in starting that process of maturing the organization.

Because if you’re trying to meet them at your level of maturity, they’re not going to get there. They’re not going to get there. The delta is too big. So you have to kind of get to where they are at their level of maturity and then grow them.

The reality of conflict fatigue

Jesse: I wonder about the psychological toll on leaders of taking on this role that you described, where you are inevitably, constantly putting yourself in situations where you have to su—… you have to have arguments with, you know, you, ….changing people’s minds means getting them to let go of their old ideas. And that is hard work. It’s difficult work. It is also, it means plunging yourself into conflict over and over and over again.

And it’s this conflict fatigue that I see setting in with design leaders that they’re just like, it sounds like the way that you’re describing it, taking this job means signing up to be sort of a crusading holy warrior. And not everybody who wants to run a design team wants that mantle put upon themselves, you know?

Peter: I think so. So yes. And a couple of thoughts in this design team I’m supporting, they’re hiring amazing design leaders from other organizations. Design leaders… so, so this, this team has 500 some designers on the way to 700, by the end of the year. It’s just, I’m saying that to reflect on scale. And they’re bringing in design leaders who are leading teams at other companies of say 500. And…but bringing them in to lead a team of 50, a 100, 150. And it’s because those leaders are done fighting that holy war. And they want to be part of an organization where someone else is above them. Who’s waging… waging those battles as it were and they get to focus on the work. And so that’s a decision for design leaders is do… I’ve… I’ve had in my conversations with, with the leaders I work with, there’s another one in particular, he was a head of design for one company, 40-ish person team, moved, became a head of design at another company, 50ish person team. Both of them, there was this jockeying and evangelizing, educating. He was actually really good at education.

He was really strong at connecting business value with UX metrics. And so his leadership tend to really like him, but the, the, the, the, the more recent company he had been working for, they had their fortunes turn a bit and the job changed. And he’s like this isn’t the job that I signed up for.

And he realized, “You know what? I don’t want to be the guy. I don’t want to be the guy. I want to be a guy.” And so he found a job at a ginormous tech company to run a team that’s the same size, maybe even larger than what he ran before, but in such a bigger context that he’s, he doesn’t have to wage those battles and fight those fights.

Playing politics instead of fighting battles

Peter: ‘Cause he just doesn’t have the energy for it. So that’s one thought. The second thought is there’s probably, there’s more than one way to skin a cat. And I think leaders, and I’m wondering, kind of, in the conversations you have, the strategies you’re developing for these leaders in terms of figuring out how to address that, does it have to be waging a holy war or can it be more political?

Is there a Realpolitik approach to this?

And I think about this in light of, one of the things I did in this past year was watched The Wire. I’d never watched The Wire before. And the first season of The Wire is filled wiith grist for leadership conversations. In particular, Lieutenant Daniels ,I’m spacing on the actor’s name, Lance Reddick, Lance Reddick, the bald one who’s kind of running the group. And there’s an amazing scene, I forget which episode, where he’s, he’s got his kind of gang of misfits that are, they’re trying to, he’s trying to stand up this group to do this investigation and he needs something from somebody and it shows him very slowly and purposefully escalating his ladder, to his leader, talking to his leader’s leader, all the kind of background stuff that needs to happen in order for him to secure the resources that his team needs in order to succeed, that his team doesn’t realize he’s doing, right? This is that thankless work that design– that leaders do ,not just design leaders.

But he’s not fighting. It’s not conflict. It’s politics. It’s, it’s diplomacy. It’s, What do you want that I can provide in exchange for what you have that I want? And it’s, and it’s, and it’s working a system. Now, that’s also tiring, but it doesn’t have to be as conflict-driven as perhaps more just like, more, you know, in the context of designing leaders, it’s like, okay, I don’t want to fight about it. I don’t want to argue about it. I just, I want the thing I want. So what do you need from me, so that you’ll give me the thing I want and just trust me that the thing I want is right for all of us?

And I’m wondering if there’s a strategy there that design leaders could be employing more. I think we seek education and evangelism as the one tool we have to influence an organization, and don’t recognize there’s other means of influencing the organization. And then when we get what we want, by whatever means, and our team does great work, then we can evangelize and educate. I think we try to do too much ahead of the output, and instead don’t rely, don’t, don’t use the good work that the team is doing to then get what we kind of want further down the chain.

Why does design leadership always feel like a fight?

Jesse: I like the metaphor of diplomacy. I like the idea of engaging in this conversation from a place of, we’re going to sit down at a table as equals and talk about how we work together toward the common good.

You know, one of the questions that we got in the mailbag was this question from Dimitris Niavis on LinkedIn. “If you had magic and a time machine, what would you do differently as a design leader?”

And honestly, this thing for me, as I reflect on my career, I think that this framing of our work as a fight is something that I have indulged in much too much over the years that I, as a consultant, engaged with our clients with an eye toward who’s on your side in the organization, who’s not on your side in the organization.

What are the, what are our tactics for you know, winning those battles. And I don’t think I encourage my clients to take enough of a diplomatic approach to these things. I did see it as a battle to be won, and I don’t think that that served the work. And I think that a lot of people throughout the industry have taken on that framing.

And I don’t think it’s serving them as creative professionals either to be constantly on the lookout for enemies and not to engage people from a position of mutual trust and good will.

Peter: And, and, kind of, common, common goals. And I I’ve been guilty of similar stuff and I, and, and I still am, I suppose, in that I teach, when I teach my design leadership workshop, I use this framing of the four archetypes, the coach managing down, the diplomat managing across and the champion managing up .

And the champion, is, I’m drawing upon kind of medieval, if not earlier, right, kind of models of the champion, that person who is fighting in your stead, who is representing you and fighting in your stead. And, and I use the champion framing when talking about managing up and out primarily, which is this mode, right? How do we, how do we engage stakeholders and executives?

And I actually say “fight for your function.”

Jesse: Yeah.

Peter: And I, and I’ve, and I’ve been wondering about that language and I haven’t dropped it because there’s still, I guess it’s not as an aggressive fight, right? I’m not saying like, it’s our job to, like, land grab and claim somebody else’s territory. But there, there is a shielding that often– that design leaders I think need to employ, to protect, for lack of a better phrase, their team from the slings and arrows of executives and stakeholders who are doing everything they can to kind of get to your team, for their, whatever they perceive as their specific needs.

And there’s a role that the design leader plays, too, to shield their team from that kind of randomization in terms of how they spend their time and their effort, to shield their team from the executive swoop and poop, right? When, when someone shows up at a meeting well along in the process and craps all over the work.

And, you know, ‘ cause what I’ve seen is a design leader who doesn’t shield the team from that unhelpful commentary by an executive, if they back off and just let the poop land on the team, then the team is like, okay, so you don’t have my back. Like, you’re not there to help me. And they feel exposed and at risk.

And so, you know, maybe fighting isn’t quite right. “Protector” sounds a little, um, paternalistic or, or like, oh, my team can’t handle it themselves. So I have to protect..

Jesse: Like they’re

Peter: …them. I like champion and there was a certain advocacy and agency to it. So, so I guess my point there is, like, there’s still some of that aspect to the role that we do need to have a little bit of fight, but we probably, it’s probably not a helpful place to start from. And, and I guess the, the, the other thing would be for these design leaders to really be thinking about, kind of, what does success look like? What is, what is their goal? Because I sometimes think we fight for fight’s sake, or mature for maturing sake, as opposed to, like, are you trying to just ship some better software?

Let’s focus on that. What is it going to take for your team to ship some better software? Let’s focus our leadership efforts on that. And then you might realize, oh, there’s a diplomacy aspect. I don’t need to fight. I need to coordinate. I need to cajole. I need to… one for you, one for me, whatever it is, the politicking that enables that, instead of just this kind of diffusely expressed energy around design needs to be given more, more better, more access, seat at the table, et cetera, et cetera, oriented on, on something more specific.

A mature product management practice

Jesse: Well, it’s interesting, too, because I feel like in some of these questions, you’re starting to stray into product management territory. Like I wonder how much of the executive swoop and poop is mitigated by having a mature product management practice, right? Shouldn’t those, shouldn’t that be your buffer with the executive suite?

Am I wrong? You’re laughing, but what am I missing?

Peter: I’m laughing, as you said, ’cause you said the phrase “mature product management practice”, which is kind of an oxymoron, at least in any in any context I’ve ever been in. And I’m sure there are mature product management practices out there. But the companies that bring me in are often the companies that don’t have those and they’re trying to stand up a mature UX practice.

And one of the challenges they face is figuring out how to also mature product management. There’s probably something to be said for an immature design org is more likely to be found in the same context as an immature product org. There’s probably a a shared…

Jesse: There’s a correlation there,

Peter: Whatever’s led to that immaturity is a root cause that has led both of these organizations to be immature. And so, no, you can’t

Jesse: Which yeah,

Peter: You can’t hope that that product management practice is going to, to drive the maturity you’re seeking.

Jesse: Yeah, yeah, yeah. Cause it comes back around to the maturity wall that I’m hearing about from leaders, which is not a maturity of you know, organizational understanding of how to deliver design, it is a lack of maturity in the organization’s overall mindset and culture of what constitutes quality delivery, period.

And that is not just, it doesn’t just affect design. It, it, it affects all of their practices. You know, I’m really struck by, along these lines, one thing that Tim said when we were talking with him, which, he said, you know, the world needs more design than we are ever going to have trained designers.

And I’ve really been sitting with that because, to my mind, the implication of that is that most of the organizations, statistically, that employ designers are going to be immature in the ways that we’re describing, because they’re not ready for professional designers, because there aren’t enough professional designers to go around. And so everybody’s improvising, then you bring professional designers into an environment like that and ask them to professionalize it. And that is…

The potential of design thinking and design sprints

Peter: Yeah. Yeah, though, that speaks to another lever of trying to mature an organization, is through the use of what have now been oft-ridiculed, within the design community, approaches like design thinking or design sprints, and these, these ways of enabling teaching, enabling non-designers to embrace some design in their practice, much like designers, you know, have to embrace some non-design in their practice, right? And instead of resisting that, like, that is a lever and I, and I, I don’t have enough. I wish I had more amazing stories. And maybe people listening to this can tell us of amazing stories of how, when they worked on bringing, like, using design thinking and other design facilitation, and bringing that to non-designers in an organization, how that helped mature the organization’s view of design in such a way that primed those professional designers to do even better work, ’cause the rest of the organization was ready to receive it. I have a few stories and they’re not all mine to tell.

Jesse: Right. But far and away, the, the more common story that you hear is we taught the executive team design. The executive team decided great, we know everything we now need to know about design. So we’ll take it from here. Thanks design team. And the design team doesn’t see an increase in their mandate.

They don’t see an expansion or a deepening of their scope. They don’t see a broadening of their influence. They they get a pat on the head and then sent out of the boardroom.

Peter: Well, and I think that’s interesting because I suspect the leverage point is not the executive team when it comes to this, but the teams doing the work and finding a way to weave design thinking and, and sprints and that kind of practice into almost like a learning and development curriculum at the point where people are, are actually doing the work.

Because executives don’t do anything. So, so teaching them design thinking, isn’t going to get you very far. But well, in the executive thing, sorry, I’m, I’m now free associating a bit, but part of this conversation, I was reminded of a, a interview I witnessed Marty Cagan taking part in, talking about product transformations, and this ties back to what we were saying earlier about the issue isn’t just design immaturity, it’s kind of product development immaturity, right?

Product management practices are immature and possibly our engineering practices are, are immature though, those, I think it becomes so standardized that you can have a mature engineering practice within an immature product development practice. And, and so you can decouple it. Whereas I don’t think you can have mature design and immature product management. One is immature and one is mature, like they’re like they can only be as so mature as the least mature partner.

Jesse: It’s a ceiling of sorts.

Peter: Yeah. it is. It’s a bit of a

Jesse: LIke a partnership ceiling. Yeah.

The secret to successful product transformations

Peter: Yeah.

And so what Marty pointed out in this conversation with respect to this, and this gets back to the executive thing as well. He had an insight that I really liked.

He’s like, you know what? We know, we know how to structure high-performing product teams and product development organizations, and, however hard that is, that’s not the hardest part of this because we can get our product people and our designers and our engineers working better together, doing discovery, doing delivery the right. way.

But the issue is he has never seen a product transformation succeed that didn’t have CEO involvement. Not because the CEO needed to understand how product transformation worked, but because the CEO needed to make connections or clear obstacles with the teams outside of product development that ended up being this constraint on the ability of product development to transform in the ways that it needs to.

And this interview was in the context of banking. You understand this inform your time at Capital One. Funding models are a huge force within how product gets developed. I have a bag of money. I give this bag of money to people in exchange for some output and CFOs love those funding models. CFOs love this idea of this org spent $10 million on product development and should receive $10 million in value for it.

And what Marty points out is that the CEO needs to work with the CFO to change how they think about funding, that they can’t fund based on projects, that they have to start funding products or programs, things that are ongoing, and that it’s not this transactional relationship anymore, $10 million for a project to ship a thing that realizes some gain, and instead it’s more of this long-term commitment of just continuing to fund some group on, in an ongoing fashion to continually deliver value.

And, and what he sees is the issue is, is if you don’t have the CEO involvement, you can transform product development, they’ll start to operate in these new ways, but then these other forces like funding don’t change. And so the product transformation stalls, because it now has to respond to the…

Jesse: right, right.

Peter: immaturity,

Jesse: right, right..

Peter: …to use that word, of the rest of the organization and how it thinks about product development. And so you need the CEO to tell the finance folks to change how they’re operating, to tell HR to change how they’re operating, how they recruit and hire people, how they level folks, how they bring them up in the organization, potentially to change sales and marketing in terms of how they relate to product development.

And, and because if you just do it within product development, your ability to transform is constrained. And so I’m saying this from a maturity standpoint to suggest like all the different levels that you’re

Jesse: yeah. Right.

Peter: And that, and that need to get aligned in order for design to be mature. And this is part of the reason why I advocate, like, your head of design can’t be more than two levels from the CEO. Because your head of design needs to be able to talk to all the people that report to the CEO.

Jesse: right, right,

Peter: And so if, if, if you report to somebody who reports to the CEO, not only can you talk to your boss, your boss can now connect you with all those other functions that report to the CEO. But if you’re lower than that, there’s no way you’re going to talk to anyone in HR at a high enough level. There’s no way you’re going to talk to anyone in finance at a high enough level.

And you, as the head of design, need to have access to the CFO and the head of HR and the head of marketing for, for these exact reasons.

So who does the Head of Design report to?

Jesse: So again, like, how would you fit a head of product into a structure like you’re describing? Because again, in a lot of organizations, for anything to do with product development, maturity, a CEO is going to have a head of product increasingly who would be tasked with that stuff.

How does that fit into the mix of you know, the executive product and design?

Peter: Yeah. I mean, I don’t know, in my experience, it fits pretty easily in that I’ve reported up through a head of product who reported to the CEO. And so through my product leader, I had access to the…

Jesse: So as long as you can be, you know, it’s okay to be two levels away from the CEO. As long as the level between you is a head of product.

Peter: It doesn’t have to be ahead of product. I don’t think necessar ily. It often is.

Jesse: What you were saying. Yeah, go ahead…

Peter: Yeah, it often is. And we’re starting to see design leaders advocate for being direct, direct lined to the CEO so that they’re, they are seen as true peers to product and engineering. There’s any number of reasons why that’s not happening.

The two primary ones are scale, design teams are just smaller, usually, and maturity of our industry in that there’s not that many design leaders who could really deliver value to contribute at a true reporting-into-the-CEO kind of executive level. They just don’t know what that job is. More and more will over time, but we’re still not there yet.

Jesse: So your sense is that we don’t yet have enough design leaders operating at the level of maturity to qualify for that seat at the right hand of the executives.

Peter: No, we haven’t, and, that’s changing, but it takes time. I mean, we’re, that’s the other thing to always remember about this stuff is that we’re still, that design is still a much more nascent function in most of these companies compared to any of the other ones. So it’s going to take us time to build our bench, build our leadership profiles.

I mean, this comes back to the conversation we had with Gordon around chief design officers. right? ‘Cause there’s that point at which, and this is where the fighting becomes an issue.

I was talking with the CEO who wanted to hire a head of design and the biggest issue he had with the candidates who were coming through is that they saw themselves as design leaders first and executives second, like, stewards of the business second.

And he’s like, that’s exactly backwards. If you’re going to report to me, and I’m the CEO, I need you to be as an executive first, your first team is the executive team, your peers and product and engineering and marketing, et cetera. Yes, you have a design background. That’s great. You’re bringing that perspective to this conversation, but I need you to not be fighting for design.

I need you to be fighting for the company, fighting for the organization, fighting for our successes as a, as a business. And secondarily to be the function lead for that thing that you’re responsible for. But if you approach it with, I’m fighting for design, you’re never going to cross that chasm, that Rubicon into being seen as a true organizational leader.

Jesse: That’s such an interesting thing too, because of, again, that evangelism role that people often have to take on in order to become design leaders, they have to demonstrate that they’re good at beating the drum and arguing for the value and, and pushing the notion of design forward. That’s often how you end up getting that job, and then to have gotten to that point and then have to let go of that evangelist identity that got you there, I think it’s very challenging. It it’s actually…

Peter: I mean, it reminds me…

Jesse: yeah,

Peter: Oh, I was just going to say, it reminds me of the same challenge that you have when you go from being a designer to a design leader and you have to let go of your identity as a maker. Now you’re a leader right now. We’re saying, as you go from being the design leader to an executive, you have to let go of your identity as a design leader, to being a business leader.

Do you think Brian Chesky, the CEO of Airbnb thinks of himself as a design leader?

Jesse: Yeah.

Peter: At some point you just let go of that stuff. You know, he’s got a design degree, but that’s not his job.

The legitimacy of imposter syndrome

Jesse: Right, right. Well, and this is connected actually to another question that we got this question from Matt Bouchard by email about imposter syndrome among design leaders because, you know, every time you go through one of these transitions of identity, right, from designer to design leader, and then from design leader to design executive there is a certain amount of letting go of the old identity and welcoming in the new identity and the new identity may not fit at first.

So there’s inevitably going to be a little bit somewhere in there of imposter syndrome, if you’re actually taking on something that is genuinely new for you, the challenge is that imposter syndrome frequently, kind of, the way that it manifests in people’s minds is in these, the sense of the expectations that are being put upon you in the new role and the, and the, the question of, well, do I, am I going to be able to measure up to these expectations?

Am I qualified to do these things that are being asked of me? And in a lot of cases, I feel like design leaders sense of themselves as imposters is entirely legitimate for exactly the reasons that you’re describing. They, they are imposters because they are being asked to do things that they actually are not qualified for, that they have not been trained to do, that they don’t know how to do, that they’ve never done.

So it’s very, very natural to feel like you’re an imposter in that situation. The question is, can you trust yourself enough to improvise and navigate your way through a situation that you’ve never faced before? And that again, requires letting go of a lot of your sense of identity that is tied to your expertise and your experience stepping into something new.

Peter: I well, yes. So I suppose, Hm, imposter syndrome is real, but it also kind of doesn’t matter. Or it matters only, it matters only to the degree to which it is in your mind and it’s holding you back.

Jesse: Yeah.

Peter: And, and I think, I’m trying to think, like, you know, just suck it up. Like unfortunately, any thoughts I have about it are you kind of don’t feel all that helpful.

Just like, stop letting it hold you back.

Jesse: Well, I will say that there is an element of this that it’s very easy for us to say as…

Peter: as middle-aged white men?

Jesse: …precisely, I mean, imposter syndrome, and I see this with my clients, it takes on a whole different dimension when you are the first or only woman leader in your organization, when you are the first or only person of color in a leadership role in your organization, those kinds of things.

And even if you’re not, you’re still going to be carrying over the experiences that you’ve had throughout your entire life of being told that you’re not right for this, you’re not right for that. You’re not enough. And so there are layers and layers to that that are not adequately addressed by simply sucking it up.

Peter: Yeah. Yeah. I mean, I guess… trying to think how many of the leaders I’m working with demonstrate some form of imposter syndrome. It doesn’t come up in the conversations that I have with my thought partners as much. I think there’s something to be said with, yes, you are an imposter, but kind of assume that almost everyone around you is as well.

Like no one has it figured out, we’re all making it up as we go.

Jesse: That part is very important that I think a lot of people, especially younger designers tend to, you know, receive all the, all the wisdom of method and process and deliverable and assume that this stuff has all been buttoned up in advance for them. And it’s not the case at all.

Peter: And I think kind of related to that, you know, it’s still burgeoning, but there is a growing corpus of material around design leaders and, and, and becoming a design leader, and what that path was like. I’m thinking back to the Leading Design conference I was at a month and a half ago in New York, and people telling their stories of becoming design leaders and you realizing like, oh, they were, all of the people that you hold up as, as models were imposters once.

You know, kind of recognizing, the distinct value you have in terms of your perspective, right? You are in that position because you bring something that no one else in that organization does and, and really drawing from that value that distinct value that you have.

Jesse: Yeah. Yeah. I mean,

The power of self-reflection

Peter: If I’m reflecting on this, I don’t think we do enough to prepare, literally prepare, people to assume these leadership roles.

And that’s true across, across the organization and not just in design, but for designers, the responsibility then is when you are in a leadership role to like to do your homework. You know, I follow Abi Jones on Twitter and she is a very reflective leader.

She reads books. She, she tweets about her experiences, reading these books. She thinks about how those experiences she’s reading in the books aligns with the experiences that she’s had as a leader. And, and I don’t think enough leaders are doing that. Doing the homework.

To take it from a totally different space, Steve Kerr, coach of the Golden State Warriors. You know, you might not have known, but now, you know, you see that I’m going to bring a basketball analogy. And before he was coach of the Golden State Warriors, he was never a head coach. And in his rookie season as a head coach, he wins a championship.

Now he probably felt some degree of imposter syndrome stepping into that role. The, the prior coach had been successful taking them to the playoff two years. Who’s this guy, who’s never had this coaching job before, think he is that he can somehow do it better and he’s never done it before?

Now. He had some success, he worked for two amazing head coaches as a player :Gregg Popovich and Phil Jackson. So he saw what good coaching looked like. But he didn’t just see it. He was reflective on it. He took, like, took it and like broke down those principles of what he saw and built them back up into his own philosophy of coaching.

So he was very explicit and intentional about how he was going to coach. And then part of the reason he got the job is he had a binder, you know, an inch and a half thick of what he would do if he were to coach the Warriors, how he would change things, the plays he would run, like he had gone through that process of really being, of being thoughtful about what it would mean to be a coach.

And, you know, that’s a different kind of job than what we’re talking about. The money is different. The opportunities are different. I’m not saying you know, before you become a head of design, you need to have a binder an inch and a half thick about what you would do, but you need to think a little bit, right. Like, like, and I wonder how many leaders are doing that work to take time out and reflect on what it means for them to be a leader and how they will perform in that role as opposed to, they’re promoted or they’re hired, and they show up one day and maybe they’ve read The First 90 Days. And that’s the extent of, of, of their thinking about management.

Jesse: Yeah, yeah. Yeah. So, I mean, I definitely hear the need for leaders to continue to invest in their own growth as leaders and not just be crank turners, doing the job, because if you are, if you don’t have a point of view, about the work, if you don’t have a philosophy about the work, what that means is that other people’s philosophies can run roughshod over everything that you’re doing.

So I think that leaders do need to have a point of view. I will say that I can definitely hear, as you’re talking about taking the time to read the books and listen to the podcasts and, and do the the reflection and research. I can hear the voices of those leaders saying, Hey man, I’m already putting in 50 to 60 hours a week just trying to hold this thing together.

The last thing I need is homework right now. And that part of it is real too. So yes…

Peter: Can I push back on that a little?

Jesse: Well, sure. Yeah, go ahead.

Peter: I’m thinking measure twice, cut once. I suspect, if you do some of that homework, some of that 50 to 60 hours a week might reduce, ’cause you’ll learn where to focus your energies, right, Those 50, 60 hours a week, who’s saying you need to do all that work? And, and what, what are you doing as a, as a, as a leader to be responsible for your own time?

And, and, and when I hear 50, 60 hours a week, that’s me hearing leaders who don’t have a philosophy and don’t have a perspective letting others drive their labor, their, their, their activity, instead of being self-determined.

Jesse: Yeah, yeah. So it sounds like the, the way that you break this chicken and egg cycle to your mind is for the leader to invest some extra time in themselves and their growth in order to be able to show up differently in the organization and reduce their workload.

Peter: I mean, it’s, it’s, you know, the Steve Kerr story, or or, we’re thinking about actors and rehearsal, right? You go through a lot of work and you do a lot of rehearsing and, and you might do research if you’re a method actor, this, that the other thing, so that when you show up, you’re prepared.

It’s still going to change. There’s going to be circumstances that you didn’t account for that you’re going to need to adjust for. But I, I, and I hadn’t quite had this thought before. I’m actually enjoying this part of the conversation because it’s kind of a new notion for me that like…

Part of our, there’s a role that senior-most leaders have, with the leaders in their orgs that they’re trying to bring up, in making sure they’re prepared. There’s a role that people like you and I, and others who are kind of operating in this independent consultant coaching ecosystem have in helping prepare leaders for the work that they’re doing.

But I don’t hear a lot about preparation about, about the work before the work…

Jesse: yeah.

Peter: …that you do in order so that when you show up, you are ready to do that work. And I think we too often are just thrown into or throw others into a situation without any preparation and context.

And then no one benefits, no one gains. And so making, making this idea of preparation, a real practice that, that we encourage that we ,yeah, we encourage the people who are listening to us to, to be part of whether it’s for themselves or for the people they are responsible for within their organizations.

Your practice and purpose as a leader

Jesse: Yeah. You use the word practice, and I think that’s a really important one. It’s definitely a big theme in my work with my coaching clients. Because my sense is that because of the, the nature of the role, the nature of the work being something that requires a lot of adaptation, you know, you talked about Steve Kerr and his binder full of plans, and I don’t think this is a role where you can show up with a binder full of plans and be successful, actually, because you probably have made a bunch of assumptions about the situation that you’re stepping into that are not going to hold true, because this is, to your point, a less mature practice than coaching a basketball team.

So you’re going to have to adapt more and again, I feel that once you’ve got the job, you know, your experience and your expertise may have gotten you the job, but they’re not going to be what makes you successful at the job. What makes you successful at the job is going to be your ability to adapt and roll with things and surf the situation.

And it’s your practices, your day to day, week to week ways that you keep yourself sharp as an individual, as a leader, that are going to make the difference more than your knowledge or your expertise.

Peter: I would say your practices and I would include, and I don’t quite know the right word for this, but, but whatever your true north is.

Jesse: Oh

Peter: Right, So, so I agree, right,

You’re going to, you’re going to need to adapt. You’re gonna need to ride the wave, but if you don’t have a compass bearing on what, what is true to you and in how you operate, you’re going to get buffeted by those waves and thrown around.

But if you have a true north, you’ll always kind of tack back toward it and you’ll be able to make decisions based on it. And, and folks will, we’ll have a sense of who you are.

Jesse: RIght. right.

Peter: We’ve talked about trust in the past. You’ll, you’ll show up in a consistent fashion so that folks know what to expect from you.

So, so even if you’re not doing preparation in. A binder full of design process that you want to Institute within this organization, and if they just follow these processes, they’ll put out better design, you can do preparation in terms of taking that time to identify your, your principles and your purpose and, and your, your, your values as a leader.

But much as we talked about a couple of years ago on, on for a design team, you know, the, the, the, the the importance and the utility of, of a clear purpose, clear values, clear norms, how you, how you behave, those are true for you in your leadership. And shouldn’t take days, you should be able to do that and hours if not hour.

And with that, just making that explicit, I would think would help guide you through the uncertainty that is definitely going to be par for the course in whatever you’re doing.

Jesse: Yes. Yes. Well, I will say that with my coaching clients it takes more than an hour to articulate somebody’s philosophy of design and,

Peter: Did you, is that a, is that a practice you work with them on? Do you, do you have kind of tools for helping them get at purpose and vision and values for themselves?

Jesse: It is central, to your point, it is central to what I do. Because a leader who is not engaged with their own authentic sense of purpose of what they’re doing in the world again, their decision-making is going to be more easily influenced by the, by the factors around them.

They also are not going to be showing up with that level of passion for the work that is often necessary to drive through those difficult situations and get through to the other side. So yeah, every single client that I work with, we have extended ongoing conversations about their values, about their purpose, what they want to create in the world.

Because if they’re not connected to that, they’re going to be miserable no matter what their role is.

Peter: Uh, do you see how that clarity of purpose and personal mission helps them act? And I don’t know if you’re, if there’s anything you can share in that regard.

Jesse: it’s more about practices than it is about, like, I’m going to write up a self manifesto and create a deliverable, that’s going to encapsulate my philosophy for the world. That’s…

Peter: oh, that’s just what I do.

Jesse: As well. I mean, it’s, it’s fine. If that’s, if articulating it to yourself at that level of detail is what is what you need, but people often get lost in the weeds of trying to pin down exactly the thing that they can sign their name to and say, I’m going to live by these values all the time.

It’s more of how are you incorporating that inquiry into your practices on an ongoing basis. And how are you continuing to ask yourself how your approach needs to evolve based on your evolving understanding of what you’re doing and the best way to accomplish what you want to accomplish in the world.

Peter: I think that reminder for folks to, to, to kind of engage in that reflection and inquiry and making that part of a personal practice this, this is as good a place for us to end this conversation…

Jesse: terrific.

Peter: …as any. Well, thank you, Jesse, for taking time with me to grapple with some stuff that allowed me to have some realizations that hadn’t at least been as clear for me.

Jesse: This has been fun.

Peter: I appreciate the time and the engagement.

Jesse: Apologies to everybody whose questions we didn’t get to. We ended up running off on some of our own tangents says we like to do, but…

Peter: …that’s how it goes. Well, take care and be well.

Jesse: Thanks.

Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s @peterme and I’m @jjg. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com. You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on Apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too.

As always, thanks for everything you do for all of us. And thanks so much for listening.