Navigating Leadership Challenges and Personal Reflections

In which we look at the purpose behind defining purpose, and discover some unexpectedly useful new frames along the way.

Transcript

Peter: Welcome to “Finding Our Way,” the podcast where Peter and Jesse welcome you to their journey as they navigate the opportunities and challenges of design and design leadership. I’m Peter Merholz, and with me is Jesse James. Garrett.

Jesse: Hello, Peter.

Peter: Hi, Jesse. Today we’re going to dig into how design teams define themselves within their companies and the challenges design leaders have balancing the team’s desires with the organization’s expectations.

Jesse: You know, we’ve been talking about the challenges of the new design leader and often the new design leader is the first design leader that an organization has had. And that carries with it its own challenges in really setting the tone for how the design organization is going to be received by and interact with the rest of the organization for probably a long time after you’re gone and other leaders have taken over. There is a really, I feel like there’s this strong sort of imprinting process that happens with early leadership teams where aspects of how they approach problem solving, how they frame what they do, how they, engage with each other, the tone that they set for their teams, all sort of carries forward far beyond them. And so the choices that a new design leader is making as they are leading the formation of a new design team are particularly critical, I think, because they have long term consequences that can’t always be seen upfront.

Peter: I think that’s true. I think there are a few different types of design leadership challenges when it comes to team definition. I think there’s what you addressed, which is that initial design leader, possibly, you know, first, second, third designer, maybe more senior than others.

The company they’re working for starts growing. They start recruiting and hiring and at some point, the team gets beyond what can be handled informally and they need to figure out, “How do I manage this? Now we used to all be able to sit around a table and now we’ve got 15 people in three countries. And we can’t lean on the informal practices anymore.” So that’s one model that I see. 

But there’s different challenges that you face when you’re the new design leader inheriting a team that has evolved before you showed up and what you end up doing in order to help the team grow from the point at which you’re taking it on to wherever you’re going with it. And even, in both of those contexts though, as I reflect on it, I think what ends up being valuable is the same thing, because, it’s this matter of definition. I think perhaps the second type of leader, who is assuming leadership of another team is probably more conscious of the need of this, because they’re often assuming the leadership of a team that has not been well-defined.

But it’s 10, 15, 20 folks in there and so an obvious kind of quote “leaderly thing to do” is to do some work to define it. What I think is less well appreciated is for those folks who are that first leader who’s been building something where the informal practice has worked so well for so long to then come to a realization, three years, four years into this, “Oh, this has gotten bigger than I can handle directly. What do I do?” Sometimes those folks realize, “Oh, there are practices I can engage in to help define the team.” That’s, that’s been my experience now as a consultant, where I literally have one company that I’m working with in one design leader in particular who fits this profile almost to a T. They were the first or second designer… it’s a tech company. I’m not gonna give too many specifics, but, they were the first or second designer. they were more senior, when they joined, than the other people on the team. They might’ve even led design in prior contexts, I think in an agency context. They had it built and hired a real design team. And so as design–, as this company grew and design grew, they were the ones growing it, and they’ve gone from two to now, I want to say 16 or 17 designers. This is all product designers, in three or four different locations, including overseas, including in Europe. And, at the beginning of this year, this design leader did a check in with his group to see how things were going and what emerged from those conversations was a recognition that they needed to do work to define themselves better. That it had just kind of tipped probably somewhere, in that going from 10 people to 15 people that it tipped to where their lack of clarity around who they are as a team, what value do they serve, what value do they deliver? What are their values that they uphold? How do they recruit and hire? How do they know what work to take on? All that kind of stuff that, again, they could handle informally when they were smaller fairly easily. You know, this guy now has managers who are managing people and he’s not able to engage with all those people directly and he needs to put practices in place and have a reference point to shared understanding that can represent the definition of the team when he is not there because he can’t always be. 

Jesse: Right, another case in which this chartering activity comes up is when there’s a change of executive leadership above or beyond the design group. If you have major shifts of executive leadership among your peers, whether that’s, you know, engineering or marketing or whatever the other, organizational functions are, there is potentially a need to reintroduce yourself to people and to establish a baseline for a new relationship. and if you’re not walking in the door with a clear sense of who you are, that relationship can really get screwed up right out of the gate and can take a lot of effort to untangle down the line.

Peter: I think that’s exactly right. Upon reflection, I haven’t had that experience but I know that experience is true. And I know what often happens is if your design leader has a new boss, new head of product, new head of marketing, new CEO, if they are not out in front of establishing a positive relationship with that person, what almost inevitably happens is that new boss brings in someone that they feel comfortable with from prior relationships. So there is an opportunity to. get out in front of that and establish that relationship. But, if it isn’t done with intention and explicitly, that existing design leader might find themselves–I think what happens is they’re, they’re usually not let go, they just find themselves having a new design leader brought in over them. That is this new executive’s connection that they’re, that they are bringing in. 

Jesse: That is a pattern that I’ve seen where the executive leadership knows that the design leader has the trust of the design team and has the operational capability to continue to deliver, but doesn’t trust them as a strategic partner. And so we’ll introduce a new layer into the organization, maybe something that feels sort of fabricated, really in some cases, to create a reason for there to be this interstitial layer that diminishes the design leader’s influence. And ultimately, I think, paves the way for the design leader’s exit. And bringing in somebody who is somebody that the executives can more easily relate to.

Peter: I think that’s right. I think it speaks to a challenge that many design leaders will face, particularly those early ones who grow a team, is that the folks around them continue to associate that person with who they were when they started and not who they have become.

So it’s important for that design leader to reintroduce themselves with some frequency as they evolve so that they’re not being put in boxes by other people.

Jesse: Yeah. Well, that’s a huge challenge. It’s a huge challenge because we all carry these unconscious biases and assumptions about who people are. We create shortcuts in our brain all the time, just to help us deal with the number of people we have to deal with in our daily lives, and we don’t often consciously review those shorthand ideas that we develop about people, especially those first impressions or those early impressions. 

I’m curious though, why aren’t designers naturally sort of good at this, right? We’re used to telling stories about our work. We’re used to being able to articulate rationales for things. Why does this prove challenging for so many organizations, do you think, for so many design leaders, to carry that capacity for explanation, that capacity to illuminate, into defining a sense of purpose for themselves?

Peter: One thing I would potentially push back on is that designers are at least universally good at providing a rationale…

Jesse: Yeah.

Peter: …for their work. That’s a skill that many develop. In any design leader, hopefully if they are seen as a leader, they have developed that skill where they can help others understand the rationale behind a set of design decisions.

I think, though, a couple of things get in the way here. Designers and design leaders are frustrated that what is obvious to them is not obvious to others, in terms of evident value,

Well, they get frustrated at first. They think it’s obvious that there’s this value, that this team is able to deliver certain–, is able to do good work, is able to deliver a certain impact, is valuable. Many design designers and design leaders feel that their value should be intuited, when in fact more work needs to be done to make it explicit. But because we as designers recognize the value in what it is we’re doing and we understand somewhat viscerally or at a gut level how we are contributing, at first, we think others have that same understanding and so we don’t realize when others don’t share that understanding of the value that designers are delivering in the same way. Then we get frustrated when we realize that, and we get kind of peeved that like, “Really? I have to convince you that I’m worth it? I have to convince you that design matters?” And depending on the environment, the answer often is yes, you do. So, to answer your question, the designers and design leaders recognize their own value and assume others do as well. And so they don’t get out in front of crowing about their value and evangelizing the good work that they’re doing and evangelizing the impact that they’re having, because they don’t think they need to.

When I teach workshops on design leadership, one of the things I stress is the need to evangelize and over-communicate, that the design leader’s job isn’t done until they hear back from others what they’ve been saying to them.

And it might take five, 10, 15 iterations of you saying that thing, you talking about the work that your team did on delivering some project and the impact that it had, or talking about how important it was to conduct this user research because it led to insights that led to some innovation.

You need to say that over and over again. And you know it’s working when you finally start hearing it back from others. But design leaders feel, 1) that again, the impact should be evident. “Why do I have to tell you why I’m valuable? When it’s there, it’s in the data. It’s obvious.”

So that’s one frustration. Another frustration is that a lot of design leaders feel sheepish about selling. They think it’s marketing. It’s, it’s sales-y. It’s not authentic to evangelize. You know, we roll our eyes when the sales team does their high fives and shout outs, when they ring the bell, when they make a sale, we think that’s all kind of hokey.

And so we don’t do that kind of thing ourselves because it feels inauthentic. So we get in our own way that way. Right? ‘Cause we have to keep it cool, man. Cause we’re the designers. And then designers often tend towards an introverted way of engaging with others where they don’t speak up unless directly asked. If asked, they’ll say what they’ve done and they’ll talk about the team’s good work, but if they’re not asked, they won’t put it out there. And design leaders need to get over that quietness and that willingness to just kind of hang back and let the product people, let the marketing people, let the sales people have the mic at the all-hands. The design lead has to get that mic and talk about what it is they’re doing and be explicit and intentional in that communication, because no one else is going to do it for them.

Jesse: Well, what do you think that’s about? What is it? ‘Cause it sounds like what you’re describing is something that is in the personality makeup of people who do this job. And that is you know, an interesting thing if we collectively as a group have to get some self-confidence training.

Peter: What is it about, well, that’s, there’s some deep psychology going on there, right? I think a lot of people end up in design because they like to make, and making is largely a solo endeavor, right? There’s collaboration and there’s coordination and there is working with others, but as a designer you can spend a lot of time with those headphones on, focused on a problem and just digging deep. And so it attracts a personality type who can spend literally hours on end by themselves working through these types of problems. You know, if you’re a glad-handing social person, you’re not likely to end up willing to do what it takes to be a good designer, and so you find a different direction to go in that accords with how you engage with the world. 

Now, I don’t want to oversimplify it. There are extroverted designers, there are introverted salespeople, right? These are tendencies. These are not rigid, hard and fast rules. But one thing I have noticed, ‘cause I’ve talked to a lot of designers and a lot of design leaders in a lot of different teams and a lot of different environments, is that inevitably the designers who bubble into these leadership roles and succeed are those leaders who are more comfortable in that engaged mode. I’m thinking of a few of the leaders I’m currently working with right now. They’re all very personable. They’ve got a certain charm and a charisma. I sense it in their interactions with me and I can see it in their interactions with their teams and they’re not necessarily better designers than anybody else. They’re not better creative directors than anybody else. But the reason they’ve been able to elevate into these leadership roles is because of their personability and that has what’s given them that leg up on their peers in terms of who gets promoted, who’s put in charge. You want to put someone in charge who is able to work well with others.

Jesse: So it sounds like you’re also speaking to the–, there’s a necessary degree of salesmanship that is needed, not just in the development of a charter, but it is needed on an ongoing basis in order to be a design leader. 

Peter: Yes, definitely. I mean, as we, I think, talked about a couple of episodes ago, some of the most successful design leaders we know were not designers, but were really good sales people, right, and, so, the challenge for that more modest design leader, or person who aspires to be a design leader, is to figure out– you used the word self-confidence before, and I think that’s part of it, but I don’t think that’s the only aspect of it.

I think yes, they do need to develop that self-confidence and self-esteem, but they might have that. They just need to recognize how others perceive them and how their behavior enables or inhibits their desired impact. They need that kind of self-reflexiveness.

Jesse: One thing thematically that I hear us coming back to, as this conversation continues to unfold, is that if you are a design leader who has come up out of design, there are going to be ways in which being a design leader is very much like being a designer, and they’re going to be ways in which being a design leader is nothing like being a designer. And in fact, you may need to unlearn some of the things that served you well as a designer in order to be successful as a design leader.

Peter: Totally. I don’t know how much you need to unlearn. I don’t think a designer’s education and designer’s upbringing teaches you bad habits necessarily. But, they’re insufficient for continuing to progress from a designer into a design leader.

Jesse: Yeah. I think that’s true, but I do think that there are ways in which if you keep doing the same things that you’ve always done, you’re not going to be successful anymore.

Peter: I think that’s right. Right. That’s true.

Jesse: And it sounds like one of the things that you’re calling out is the need to have an intentional approach to relationship building. Which is maybe something that people never really needed as a designer, right, as they were hunkered down over Photoshop or Sketch or InDesign or Figma or whatever the thing was, and didn’t need to invest that effort.

And so their relationship building has always been sort of unconscious as a result. And then they take those unconscious habits into design leadership where that relationship building is now really critical. You talk about taking off the headphones and getting out there and talking to people and talking up your ideas, and all of that, again, requires some intentionality for a designer to move away from the habits and patterns that have, if not served them, at least been comfortable for them in roles that they’ve had in the past. 

Peter: I think that is a key. I hadn’t quite thought about it in this way, but, that shift from being the design practitioner into the design leader, the primary change, I think can be reduced to—, that in leadership’s role the medium is relationships, right? 

Jesse: Yes.

Peter: Whereas the designer’s role, the medium is the work. 

And relationships in all manner of, of, forms. Relationships with your team, relationships with your peers, relationships with executives, relationships with customers. Leaders are constantly navigating these relationships.

And if you don’t have an explicit set of understanding rules, practices, values that guide you and your team in how they conduct those relationships, it gets chaotic. And, you can get away with not being explicit, again, when the team is small, you can talk it out and you can kind of nudge people back towards what’s appropriate when there’s four or five, six people on a team.

But when you start hitting 10, 15, 20 people on a team and you have people in other offices, you now need to make those relationship practices explicit. Everyone needs to understand what is expected of them, as they relate with others.

Jesse: Yes. Yeah, I agree with that. And I think you can get a long way without defining a sense of purpose for yourself and your team. I think that’s why these chartering exercises come up is that the team gets a sort of an initial push off of shore. It’s like canoeing on a lake, right? And that momentum carries them out a pretty good distance. But at some point you got to pick a point on the shore that you’re headed for and start heading there. And figuring out how to get there under your own momentum. And that definition of purpose is the need that these leaders then have to try to figure out how to address.

I absolutely agree with you. I, you’ve, heard me use this phrase before. I don’t think I’ve said this yet on the podcast, but when I talk about all of this stuff, what I often say is leadership is relationships. Leadership only really exists or functions within the sphere of relationships.

When you say that relationship is the medium within which design leaders work, I think that’s exactly right. There is no leadership without relationship. 

So it feels like over the course of these last few conversations, we are starting to arrive at a couple of clear things that we agree on. That design leadership is a craft. As a craft, it needs to be approached with intentionality and a sense of purpose. And the medium within which you are practicing that craft is relationship.

Peter: So I have a contention that most companies have no idea how to hire design leaders, particularly the senior most design leader. And it’s because they see the medium that a design leaderiIs operating in as one of the work, as one of output. But the work of a design leader and the medium that they’re operating in is different. And so when you hire a design leader who is simply a strong creative director and savvy about making design decisions, that is important, but insufficient for the leadership role. 

And what I’ve seen again and again, are companies that hire creative visionaries who don’t really understand the relationship aspects of the role and those design leaders kind of get rejected like an organ that doesn’t take, because they are not developing the relationships down with their team, so they’re not creating an environment that their team is enjoying, that’s really growing the team.

They’re not relating well with their team members. They’re not creating a relationship with them. Or peers, helping their peers understand what it takes to deliver good design, hearing from those peers, what they need from design, and managing practices and processes across functions. They’re not relating well with their bosses and with executives, and so eventually all the creative, visionary-ness in the world runs dry, right? That momentum, and to use your canoeing metaphor, that might br your push off, but then you’re just stuck in the middle of the lake and people are looking at you like, okay, where are we headed?

And it loses its steam and it only goes so far. And I’ve seen again and again, design leaders who don’t appreciate the organizational, operational, managerial, 

diplomatic functions of their job end up being removed and the company often doesn’t even know how to articulate these shortcomings, they just know this isn’t working and “We need something else.”

Jesse: Again, I think this comes back to the way that designers can often intuit the value that they are contributing in ways that can be invisible to other people. And if you aren’t helping surface the signals of your success, then the people who don’t have that intuitive relationship to design, that gut response that we, as designers, have to well-designed objects. We think everybody has that response, but they don’t, you know, and for other people, these are subtle things that don’t jump out at them at all. And the need to be able to build relationships that allow you to bring people along to help them develop that sense for themselves.

But again, coming back to tone-setting. If you are coming out of the gate and you are selling your skills rather than your purpose, you have just sort of instantly commoditized yourself right from the start and it’s going to be very difficult to pivot toward a purpose conversation later. Barring some kind of catastrophe that requires reevaluation of the group and its reason for being. But, if you give people the impression that you are, right from the start, Design Depot Wireframes-by-the-Pounds, that is not going to serve you in the long term, because you need to be able to articulate that sense of larger purpose, that sense of larger value that’s being delivered, in order to maintain the credibility to stay in the room for some of these conversations. 

Peter: What I ended up doing with many of these teams that I’m working with is helping them articulate a purpose that doesn’t constrain the potential of how they can deliver.  The idea behind purpose is to answer this question, “Why do you exist? Why does this team exist? Why do we have a team doing design, product design, brand design, whatever kind of design? Why?” And you could say the answer is to produce designs-by-the-pound to solve other people’s problems. Or you can articulate a purpose that is more internally directed. 

We actually wrote one for the book, and it’s not a bad place to start. Let me find it. 

Jesse: I love that you have a copy of your own book at the ready, so you can quote yourself at any time.

Peter: So here’s, here’s one that we wrote in the book as a kind of starter mission statement, purpose statement for a design team. “We’re not here just to make it pretty or easy to use. Through empathy, we ensure meaning and utility with craft. We elicit understanding and desire. We wrangled the complexity of our offering to deliver a clear, coherent and satisfying experience from start to finish.”

So, that’s an attempt for a product design team to elevate themselves from being seen as design-by-the-pound, and shift their relationship to the work and to their peers as people who are bearing the torch for this end to end experience.

And anything that might have an impact on that experience is what this team should be involved with. And when you do that, “Oh, okay. Now I’m, maybe I have a relationship with my customer care center, my customer service, customer support, member service,” right?

Because they’re delivering on the experience. And maybe I have a different experience now with my marketing folks, ‘cause they are there at the outset, connecting with potential customers. Now I have a different experience helping our salespeople think about how they’re interacting with our customers because how they interact with their customers affects the customer experience.

So I’m no longer just being given a set of briefs and told to produce a set of deliverables. I’m now saying we ought to be involved in thinking about how we solve these experience challenges every step of the way, and then what 

that ends up doing, as you frame an explicit purpose for your team that isn’t defined by, say, its current state of skills and abilities, that starts opening the opportunity to figure out how the team might grow. You might have a purpose statement like what I’ve written here and realize, “Oh, we should be doing customer journey work. We haven’t been doing customer journey work, but if we’re going to deliver on this purpose, we need to be doing customer journey work. So are those skills we need to develop? Do we have people who could do that work, but we need to grow them to be able to do it better? Are those roles that we need to open if we’re going to be delivering on this end to end experience? Do we need to open up a new role for some type of service designer to join the team?”

These statements provide opportunities for thinking about how you and your team can grow in a way that no one else is necessarily going to ask of you, but which will benefit them. If you’re a product design team growing in response to what product management and engineering is asking of you, you are going to grow by producing more design-by-more-pounds. If you’re a brand design team growing in response to what your marketing and sales folks need from you, you’re going to grow by producing more banner ads and more sell sheets because that’s what they need. But if you are able to articulate your own purpose in a way that you can deliver greater value than what these folks recogniz, you need to kind of seize those reins and define what that purpose is and then put that out there, so that you can change the conversation with your peers in these other functions, marketing, product, et cetera, so that they start going, “Oh, wait a moment. You can do that, too? It never occurred to me that we should have you involved in some of these, like, customer experience councils.” And designers are often not involved in customer experience councils. It’s where customer support is. It’s where customer success is. It’s where people in the front line, people who touch the customer are, and they don’t recognize that you and your designers and your researchers should be part of that conversation because you’re directly affecting it. But if you frame your purpose to make it clear that that is part of your charter and what you stand to deliver, you can now use that as a means to get invited to the conversations that you should be part of.

Jesse: Yeah. I agree. So I think that the big question that I would have in response to that, as a design leader, is, How do I get started? Like, What are the tactics for arriving at this thing that is obviously going to be really important to my success, as a leader, having never done this before? Where do I start?

Peter: I think it’s going to take me longer to answer that than I currently have time for. Hold that thought…

Jesse: Great. That’s great. Well, we will hold that question for next time.

Peter: I don’t have a thirty second response to…

Jesse: Yeah, I knew I was asking a bigger question than we had time for. Can you just give me an intro and an outro real quick and then we can… Oh, you did. That’s right. 

Peter: That about does it for another episode of Finding Our Way. We appreciate you taking the time to listen to us. As always, we are eager to hear from you. so please, find us on Twitter, find us on our website, send us an email, let us know what you think. Let us know what you’d like us to talk about, and, we look forward to you continuing to join us on our journey as we continue, I’m just going to keep saying continue over and over again, as we continue finding our way.

Jesse: Finding our way.

Jesse: I imagine that your son found this a, a, a, a transformative experience, like a milestone, like, just knowing what I know about him and his personality and that film, I feel like he probably was like a discovery of something that was always meant for him all of these decades. Just waiting.

Peter: Well, I think it, I think The Naked Gun is meant for every 11-year-old. I hadn’t, I mean, I saw it as an adult. I know, not as an adult, as a teenager, and I remember enjoying it, but watching it again, you realize just how it’s perfectly dialed in to that preteen-but-not-a-kid anymore. Oh, it’s, it was gold. He loved it. He, he liked it more than Airplane and Airplane is a better movie. But… 

Jesse: That’s for him to discover. Yeah.