1: The Story So Far

In which we learn a little of Peter and Jesse, their past history together, and their more recent history apart.

Keywords: Exploring in public, leading design agencies, leading design teams, organizational design, leadership coaching, Adaptive Path, meaning, purpose, creativity, resilience.

TranscripT

Peter: I’m like, wait, a moment what do we call it?

Jesse: We gotta have something to, we’ve gotta choose some theme music. We’ve got a lot still unanswered here for sure, but we can just make the first episode about: “What should we call this thing?”

Tape is rolling by the way. So literally anything that you say right now can just go into the podcast.

Peter: And so I… just kind of free associating, critic, critique, studio, charette, alignment, white space, negative space, wayfinding. And I was like, wayfinding. Wayfinding. I liked that one.

Jesse: I feel like I thought of that and looked and I found another podcast called that or something. I don’t know. Maybe.

Peter: I couldn’t find one called that.

Jesse: I don’t know why I dismissed it then.

Peter: I couldn’t find one called that. And I don’t know if it, if that in and of itself is the right title, because it sounds like, okay, we’re your, you know, environmental design podcast, or interior architecture podcast. But if you flop wayfinding to “finding our way,” that I felt speaks to a sense of a journey that you and I are on, grappling with these ideas, as we try to figure out, we grapple with, a sense that the existing conversation, that old models, prior models, whatever, are not quite right, but we don’t know what is.

Jesse: I–I–I I love this name. I think you’ve nailed it. I love the multiple meanings of it. I love how it’s like each of us individually finding our way, plus the two of us together finding our way, plus us as a community finding our way, figuring out how our way is different from the old way or old ways. And it also communicates some of that sort of no agenda-ness that I liked about some of our earlier ideas.

Peter: Right. We– we recognize we don’t have the answers. That was the challenge with the–

Jesse: It still evokes that same, that same adaptivity and improvisational quality that the original Adaptive Path name had. So it’s got resonance on a bunch of levels. I really, I dig it. Let’s do it.

[theme music]

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: Good day. So, this is our first episode of a new podcast. We probably need to explain what we’re about.

Jesse: Yes, we do.

Peter: What do you see this podcast about, Jesse?

Jesse: So to my mind, design and design leadership finds itself at a really interesting crossroads at this point in its evolution, as the challenges that we’re facing are getting more complex. You and I are part of a generation of designers who are in leadership roles now who did not necessarily come up through traditional design education, who, you know, came up through the school of hard knocks and are finding ourselves facing new challenges as our influence is growing, and as the strategic value of our work is becoming more and more apparent.

And so “Finding Our Way” is about, in part, about how all of us collectively are finding our way through this present moment as design practices are continuing to evolve as the value of design in business is continuing to be recognized, and as the potential for us to do real harm in the world is continually being recognized more and more. And I think that those kinds of things, and how our practices and how “how we do our jobs” needs to continue to evolve to meet those challenges, I feel like is a big part of what we’re about here.

Peter: That’s right. I think we’re in a moment, somewhat liminal, with how organizations are embracing design, and doing so with more alacrity than they ever have. And, I think you and I have a sense that these organizations, as they’re embracing design, don’t really know what it is they are embracing, don’t really understand the implications of what it is that they are bringing on, and I think the people who are leading the charge, specifically the design leaders, don’t quite understand their own leadership potential, don’t understand how to be the most effective leaders they can be, because that isn’t often their background, their orientation, right, they came up through craft and practice, and now they’re expected to lead.

And so you have this… collision of organizations embracing design, not quite understanding the implication of that, and design leaders leading this charge who don’t really understand the nature of their influence and opportunity within these organizations. And it’s created a bit of a, of a muddle to be honest, which has in turn led to a whole host of support structures that have emerged very organically: Conferences like Adaptive Path’s old Managing Experience and Leading Experience conference, the Leading Design conference that Clearleft puts on. I was just at a design leadership summit in Toronto. Like, every region is now launching their own design leadership event. Active community Slacks, et cetera, as there’s this community of people, this group of people who are trying to figure out what does it mean to be a good design leader right now because it’s not clear. Whereas in other functions leadership, I think, it’s probably way clearer, in this one, it definitely isn’t.

Jesse: Yeah. And I would say that it’s not at all homogenous in terms of what a design leader looks like from organization to organization. I don’t know if it’s settled out into a few broad archetypes yet, But there’s definitely a wide array of different ways of doing this job, and different organizations ask different things of design leaders. And I think, that we are just starting to, as a community, engage in the task of sort of synthesizing all of these different perspectives and all of these individual experiences into a more holistic sense of what the role actually is, what the role actually entails, and what leadership looks like even among those people who might not be formally tasked with it, which is something that I think is going to continue to be an influential factor over the development of the entire field. So, yeah, I love that. I love that you and I are finding our way and design and design leaders are finding our way together, and that spirit of exploration, and discovery, I think is what this podcast is all about.

But why should anybody care about what you and I think about these topics?

Peter: We have, for over 20 years, found our way in public. You and I started, with five others, Adaptive Path in 2001, and really gave ourselves an opportunity to not just do design work, but think hard about the context in which design work takes place, in an effort to, in our own selfish interest, of having that design work be realized and have an impact, and so we’ve spent a lot of time in the intervening 20 years thinking about how do we allow, how do we enable design to realize its potential, in a world that often feels like it’s hostile to the work of design and designers?

Jesse: You mentioned, this exploring in public thing, which has been a characteristic of both of our careers and of our work together. And that did start, back, in the context in which we first met, which was not a professional context at all, but we met as hobbyists on the internet maintaining personal websites, who happened to be on similar trajectories until we finally found our trajectories intersecting a couple of years later.

The practice of blogging at that time, which was very much something that, where everybody was sort of lashing together, their own technology, and it was all very, very primitive. And, there was a great deal of, of experimentation with what new forms were possible, in this new medium of the web, that maybe weren’t possible before. And, that exploration was what led to the evolution of blogging. And then eventually, pretty much all of social media comes out of that.

I think that it was that same sort of curious hobbyist mindset that then informed the work that we did together when we started Adaptive Path in 2001. That it was as much an experiment as any of our tinkering with web publishing in the 90s was, in that it was a vehicle for figuring out what was possible.

Peter: Right. I mean, we were very explicit as we were forming Adaptive Path that we didn’t want to be the kind of consulting company that we had worked for prior.

And that we saw as an explicit objective of Adaptive Path was, I believe the phrase was, “advance the field of user experience.” And we saw the mechanism by which we would do that to be around writing and speaking and publishing, not just through the work, because doing the work, yes, we could benefit our clients, but we couldn’t benefit the community. And the thing that brought the seven of us together was a desire to have a platform for tackling these issues at the level of community, and again, kind of connecting with what we’re continuing to do with this podcast here, be very exploratory, be experimental, put ideas out there, get feedback, refine our own thinking based on that public feedback.

Neither of us come at this as trained designers, we both have other backgrounds. My background is in anthropology, yours is in journalism, right? That we recognized that our approach to problem solving was aligned with the work of design, particularly kind of a software design and web design.

But, we don’t necessarily identify as quote unquote designers has given us this perspective around design.

Jesse: Let’s do the career recap real quick, because I do want to provide some bonafides and reassure folks that we are not just writers and speakers, but we’ve also been, you know, active working designers and design leaders for all these years as well. So, we met through our mutual interest in blogging the late nineties.

Through that, we discovered that we were interested in some similar things, from a career perspective. After that, we co-founded the company Adaptive Path in 2001 with a whole bunch of–a whole bunch, well it seemed like a whole bunch–seven co-founders, we started the first what I call the first user experience consultancy.

Obviously, there were other consultancies that were doing UX or UX-adjacent work before that, but we really sort of staked a claim to user experience as the umbrella term for the work that we were doing as opposed to web design or interaction design or software design or…

Peter: Or usability…

Jesse: Usability was, yeah, that definitely, usability was a dominant factor in the market at that time. We felt user experience really expressed what we were trying to do, and we adopted that label for our work. We were doing that work as an agency on a client basis, as well as, as Peter mentioned, we ran conferences and workshops for, for user experience designers for many years. Our flagship conference UX Week ran for 16 years. And we did a bunch of other related stuff as well. Peter is the coauthor of the books Subject to Change and Org Design for Design Orgs. I wrote a book called The Elements of User Experience.

Along the way, these are some of the tools that we’ve tried to put out there to… The way that I think of it is I’m always trying to help other people have better conversations about the work that they’re doing through this stuff. But you know, I think what might be interesting to people is that we worked together for a long time, and then we have not worked together for a long time.

It has been nearly a decade since you and I have worked together or have, really had, more than the occasional in-depth conversation about design. And so I think this is going to be interesting for us to discover how our viewpoints have evolved in the intervening years.

Peter: I’m currently doing some work with Wells Fargo, and the first project that you and I ever worked on together was for Wells Fargo.

2002-2003. Exactly. And so, I did consulting work for Wells Fargo, PeopleSoft, Ameriprise, SKT, Samsung, I know you did a bunch of work in journalism, CNN, I remember, comes to mind.

Jesse: CNN, Disney, Skype, Microsoft. yeah.

Peter: Right. And then 2011, I left Adaptive Path to go in house. I was kinda done with consulting. I wanted to be where I felt the action was and where the heat had moved and it had moved, I believe, from kind of the design consulting realm into the in house world, companies were starting to recruit and hire and build internal design teams.

And my journey, there has been a lot of companies in nine or so years, probably most notably Groupon, where I ran design. Jawbone, where I helped run design. And then most recently, my last full time job was at a company called Snagajob, where I was the VP of design. And then I had projects and clients. I worked with OpenTable and, and other companies along that way. Capital One, actually, after the Adaptive Path acquisition. And so my career has been largely one of being a design executive, being the senior most design person in an organization needing to establish, grow, and kind of up-level design and design practice within these organizations. Make it a healthier function than usually what I found when I joined. And that’s what directly inspired the book that I co-wrote with Kristin Skinner, Org Design for Design Orgs and, and kind of the current mission I’m on as I’ve gone back to being an independent consultant, I work on my own, but, where I’m now trying to help design leaders do right by the design organizations they are building. So that’s kind of been my trajectory.

When I left Adaptive Path at the end of 2011, what did you end up, you stayed there, you were there in 2012, through the acquisition by capital one in 2014 and then for five years at Capital One, yeah, since that acquisition. So what has your journey been like?

Jesse: Well, you know, as, as you mentioned around that time that you left Adaptive Path, the market was really shifting for user experience consultancies, as internal teams were getting more robust, they were getting more mature. They were just needing us less, or they were needing us for different things that we were not necessarily optimized for. And so the business was, was solid and was stable, but was also not really growing. And we kind of felt like Adaptive Path had reached a certain level of maturity, and that was right around the time that Capital One came around in 2014, to see if we were interested in an acquisition that would help them jumpstart the development of some mature design practices and a mature design culture for them as an organization.

We were, we were somewhere in the neighborhood of 35 people. I think at the time, they already had about, I want to say, about 120 people. So we were, we were not in any way, you know, the majority of the Capital One design talent, but we were a huge injection of team and culture to that organization. And when the acquisition happened, I kind of took the attitude that no matter how this went, it was going to be interesting to watch. It was going to be interesting to see, you know, how these two cultures came together and to see the nuts and bolts of how you build, an enterprise design team at scale, from, from some core ideas about how to do the work effectively. And then, over the course of that five year period, I watched the Adaptive Path team go through various evolutions as it moved toward becoming a fully integrated part of the Capital One design organization.

And I got to sort of help nudge things along in terms of establishing cultural practices that I hope were going to be, uh, really a part of how that organization does design for a long time to come. And that process of integration had kind of run its course around the middle of 2019, as everything sort of wound up.

And I realized that I had, I’d seen the movie that I’d come for at Capital One, and I’m really happy to report that the acquisition and the transition I think went very well across the board. And now in the course of that journey, I have found myself really interested in the way that the dynamics among the individuals on design teams influences the quality of the outcomes, the way in which how we work together, how we collaborate, how we interact, from day to day and moment to moment, determines whether this is a team that can deliver consistent results, iteration over iteration. It determines whether or not this is a team that can deliver new thinking. It determines whether this is a team that can survive, you know, a technical setback, those kinds of things. And so, within Capital One, I started moving into an inhouse leadership coach role where I was supporting design leaders, helping them untangle those problems of the interpersonal dynamics of teams, to help them figure out how to make those teams more resilient and more successful.

Peter: Were you working primarily with leaders or were you working with whole teams? Was it primarily at that leadership layer? What were you observing that allowed you to help those leaders maybe be better understand their role?

Jesse: Yeah. I was working with team leads. A lot of it was, really sort of being like ship’s counselor, being the person that you can come and sit down and say, “Hey, I just had a difficult conversation with somebody,” or “I’m about to have a difficult conversation with somebody, and I just need to kinda hash it all out and have somebody to do that with.”

Peter: So, so you’re a Betazed then?

Jesse: Hopefully. Yeah. That’s the, that’s the aspiration.

Peter: In terms of your work supporting leaders, was this something that you kind of fell into? Was this something that you identified as where you wanted to be? How did you arrive there as opposed to, like, when we last worked together, your focus was on creative leadership for design, right? You were the Chief Creative Officer of Adaptive Path. You are helping set creative agenda for the company. You are leading projects for clients like Disney, doing creative work. So what was your journey from creative leadership to this organizational therapy, and how intentional was it versus if you just kind of ended up there? Yeah.

Jesse: Yeah, I would say there are two parts of that. One part of it is Capital One’s organizational journey. As they were maturing as an organization, they were minting a lot of fresh design leaders and those leaders didn’t have mentors, didn’t have development support, didn’t really have anything because, you know, it was all new. And so, Somebody would say, “Hey, you know, maybe you should talk to Jesse about that kind of thing.” And then I would have these little side counseling conversations with people that then eventually got to a place where the executive leadership at Capital One looked at what I was doing and said, “Hey, why don’t we just make that your job?”

And that was my job for the last two years that I was there.

Peter: I’m still trying to better understand your passion for this subject.

Jesse: Oh, well, so, that’s the one half of it, which is the organizational half of it. The second half of it is my personal journey, which is the occasion of the acquisition. And my transition from having been in an executive leadership role in a company that I founded for 13 years to being one of a large number of leaders with voices that had to be balanced in the mix of setting strategy for Capital One.

And, realizing that I, I didn’t really understand how to work effectively in that dynamic. I knew how to work effectively in the dynamic that we’d created at AP. I realized that effective leadership in this context where you’ve got a multiplicity of peers, and a diverse and complex set of agendas to navigate required much more sophisticated relationship management skills then I had developed as a leader, and so it was my digging into what would improve my effectiveness as a leader. That led to me starting to share some of that perspective with the people around me.

Peter: Interesting. What is the influence or impact you hope to have through your work? I mean, it could be as grand as the Steve Jobs “What is the dent in the universe you want to make?” or something, you know, perhaps more quotidian and practical.

Jesse: How big do you want to go? I mean, my sense is that when creative people are connected to their personal sense of purpose and feel a sense of connection to the people that they work with on a day-to-day basis, they produce their best work and the best work of our most creative people can change the world. And so my point of view is that if I can help a leader create an environment in which the people around them feel connected to their own sense of purpose in the world and that they feel that they are working with a leader who is connected to their own sense of purpose in the world, and that connection is authentic and mutually supportive, that is a team that is going to be resilient to any number of reorgs, or shifts in product strategy.

That is a team that is going to be able to take more chances creatively, that is a team that is going to be able to advocate for itself more effectively. The strength and resilience of the team, I think, ultimately, is the biggest determining factor of the long-term quality of the outcomes.

And that ultimately comes down to the tone and the practices that the leader puts forward.

Peter: Yeah. So I think where we strongly overlap is a recognition of an untapped opportunity for organizations to draw value from the work of creative people, right? Organizations are really bad at that. They’re really good at squashing creativity. Almost kind of famously so. And really poor at enabling creativity. And I think that’s this common ground that you and I share that’s our probably our single highest degree of overlap.

I’m sensing your emphasis is on the individuals, their abilities, capabilities, relationships… Really empowering, really kind of going deep down into the human, to the humans that make up these creative organizations and helping them realize their potential.

My orientation has been more structural, systematic, and organizational. How do I get these groups of people operating with one another and with the other functions in an organization to enable that creativity to flourish. And so I think I hadn’t known that before. And I suspect that those distinct orientations will guide how we tackle this subject moving forward.

Jesse: Yeah, I think it’s true. And I think that you have to have both things, right? I mean, you know, I often draw on examples from the arts, but if you think about, let’s say a musical performance, you’ve got to have somebody who has figured out the set list, and you have to have somebody who has figured out the lighting, and somebody to run the sound board, and somebody to put all of the things in place that support the musician in that moment of performance and make all those structures fit to support that moment.

Peter: That’s called MusicOps.

Jesse: [Laughing] Exactly.

None of that has anything to do with the musician as a musician, right? It’s all the things that make the musicians successful at being a musician, but it also has nothing to do with the core sort of activity, which is the moment to moment performance, and it’s that moment to moment performance that I think is the other side of it that has to go along with the organizational structures that support creating that creative environment. It’s an imperfect metaphor.

Peter: No, it’s, well, something I’m coming back to when you talk about creativity, creativity by its nature is uncertain, is unpredictable. When enabled leads to the highest heights. But the practice of which is paralyzing and intimidating for most organizational leaders who want to better understand what they can get and when they can get it, which runs contrary to creativity and I suspect a theme that will be recurring throughout our conversations moving forward. Is this tension between, certainty, and the certainty that organizations require, feel they require in order to do their work and, and the creative condition. I mean, almost as I’m saying, and I’m almost getting to this point where it’s like, is this even possible?

Or, or, is there a necessary blunting of creativity? Maybe creativity can still have an impact, but will it always be, to some degree, contained, below it’s potential? Within these organizational contexts that we are talking about, right? It’s one thing if you’re a band, it’s, uh,one thing if you’re a theater production, I mean, there’s constraints in all these types of things, but those areas where the purpose is the creative expression, right? That’s distinct from what we’re talking about, which is trying to bring some of that energy that you see in those areas and figure out how do you shape it and activate it within these organizational contexts that aren’t really geared towards that type of output.

Jesse: Right. Right, right. Yeah. I think it is paradoxical and I think that the role of the design leader is to hold that paradox and continue to walk that line and always to be in that place of not allowing the creative concerns to override the business concerns and have, you know, the designers go become rogue divas who are in so in love with their own creative vision that they don’t understand or appreciate or take into consideration the practical constraints that influence whether or not the design can actually be delivered. You don’t want that. And then on the other hand, you don’t want the business factors driving things too much either. So, I think that it is a balance that needs to be held on an ongoing basis rather than a problem to be solved one and done.

Peter: I like the word balance there. One of the few business books that I think speaks to our industry well is called Creativity, Inc by Ed Catmull, the president of Pixar. And he uses the concept of balance as opposed to stability.

He sees stability as brittle, and that what you don’t want is stability, you want balance, where there’s an ongoing management of equilibrium and the pendulum is always going to swing. You can’t stop the swinging. And in fact, you don’t want to stop the swinging. The swinging is fine. You want to manage the swinging, but finding, striking that balance as you move forward becomes the challenge of the leader. Maybe that’s not to cut us off here, but it feels like that’s a good capstone for, as we discussed, the mission of what we’re about here is this ongoing conversation around that type of balance as you’re on these journeys as we are finding our way forward, always kind of bobbing and weaving, trying t, stay true to our objectives.

Jesse: Yeah. Yeah. Continuing to walk that tightrope. Well, thank you, Peter. This has been great.

Peter: This has been.

Jesse: What do we say at the end of our show?

Peter: [Sighs]

Jesse: Isn’t this where we came in?

Peter: So I think at the end of this, this first episode, you know, you and I have never hosted our own podcasts. I’ve been a guest on many podcasts. I’m assuming you’ve been a guest on a few yourself. But this is our first time really trying to produce and deliver in an ongoing fashion our own material. And as such, part of finding our way is going to be finding our way with this podcast and its voice and its subject matter and how we share what we’re thinking about with a broader community.

[theme music]

So I think as a way to wrap up this first episode would be, more than, than anything else Jesse and I are interested in what you’re interested in. What are the challenges that you’re facing, that you might like a perspective on? Or, experiences we’ve had, in both consulting and in corporations that maybe you’d like to hear more about, and tell us, let us know.

In our show notes, there will be ways of contacting us. You can always hit us up on Twitter. I’m @peterme, he’s @jjg. We want this to be a dialogue, so, let us know, what you’d like to hear from us, and that will help us better understand our path forward, as we figure out what it is that, well, frankly, what it is that we’re doing here.

Jesse: Join us once again as we continue finding our way.

Peter: Yeah. Great.

Jesse: Yeah. Yeah. Actually one– one name idea that I had an immediately threw out early on was Satisficing, just because I always loved that, that concept of sort of merely adequately muddling through.

Peter: Is it good enough? It’s good enough, fine.

Jesse: It’s The Good Enough Podcast.

Peter: You could listen to better podcasts, but why? This one’s good enough.

I mean, that’s how most people choose what they watch on Netflix.

Jesse: That’s right. That’s right. All right. 

Peter: Well, that feels good.

Jesse: So,with that in mind, would you like to improvise an opening?

Peter: No. Hold on, let me, let me see here. Let me get back to the, ’cause it was, it was me in the intro…

Jesse: Isn’t this where we came in?

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