Finding Our Way

In which we discuss the challenges of relationship management when leading from home, and then start a potentially promising discussion on the subject of trust. Keywords: #OaklandSlowStreets, symbolic analysts, listservs, working from home, intent, distributed teams, serendipity, thresholds, conscious incompetence, improvisation, vision, galvanizing, trust, trust, trust. 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. We’re about in our first full week of #OaklandSlowStreets, and that one act that the city has done has measurably increased my mood positively. The major street that is nearest to us, which is this pass through street for a lot of cars because of freeway access, is now a slow street. And it is, throughout the day, overtaken by bicyclists and pedestrians. And it is like a little town square and it is awesome and it just makes me very happy and I just walk up and down it. And I want this to always be there. There are things that we are learning about our neighborhoods and communities in what is otherwise a dark time. I get nervous glowing about some of these things ‘cause I know for a lot of folks that there is almost no upside but there are things we are developing in our communities that I hope we are able to learn from and maintain. Jesse: I agree with you. I think that, despite all of the darkness, despite the, really the, the scale of senseless tragedy unfolding in slow motion all around us, yeah, it is forcing all of us to take a step back from all of the routines and all of the assumptions and all of the scripts by which we have organized our lives and the systems around us. And Oakland Slow Streets is really interesting because it’s an example of the kind of thing we talk about in design all the time, which is, the emotional or psychological effects of system choices on the people who move through those systems. And, we have gotten to a certain level of baseline tolerance of a lot of systems that maybe when those systems come back online, we’re not going to be so tolerant of anymore and we’re going to start asking for different things. And that, I think, is going to potentially create a lot of exciting system-level design opportunities across a wide range of different fields and disciplines and areas of enterprise. Peter: Well, yeah, for all of us symbolic analysts who find ourselves working from home when we would otherwise be in offices, it is unclear why anyone who is a symbolic analyst would be expected to go into an office again, at least every day. The amount of money companies spend on housing people in commercial real estate, that they could probably spend half of that, and just literally hand employees money and say, kit out your house how you see fit. And people could buy nice cameras and secondary displays and standing desks with treadmills or whatever they want. And it would still be far cheaper than housing them with commercial real estate. And that’s one of those where I don’t see how we go back to those assumptions. And it’s funny because in design, so I’m on all these design leadership mailing lists, or community slacks. No one’s on a mailing list anymore. Sorry, I’m showing my age. I’m on listservs. I’m on all these leadership listservs, Jesse: ”design leadership-l” Peter: Hyphen L, of course. You know, that one. And, I’m on all these design leadership community slacks where people are still hiring and people are interviewing and one of them has a channel called a job-search-vent. And right now, the biggest job search vent is how these companies are still expecting folks to live in a particular area, to go to an office every day when we come back from this experience, even though we know folks, at least with the kind of work we’re doing, are doing actually pretty well without going to an office. Jesse: One factor behind the historical insistence on physical colocation is in part because what it would have taken to make that change would have been so disruptive to any organization that attempted it that what would happen would be it would get a bunch of people fired before it actually killed the organization. In this case, the disruption has already happened. So the question is simply, Where do we go from here? Peter: Right, right. Jesse: And I think in a lot of cases, the cultures and the processes of these organizations were so embedded in that physical context that the flexibility to evolve toward the digital and virtual wasn’t there. But having cut all of those processes off rather abruptly, there’s now the opportunity to create something new in their place. Peter: I use the phrase symbolic analysts, and I’m being both, silly, but, particular ‘cause a symbolic —  Jesse: What we used to call knowledge workers, Peter: –workers well and knowledge workers were symbolic analysts. I remember it was like the mid nineties that was the generic term for the kind of work we do. All now the people working on computers doing this type of stuff. And often before this pandemic, there were folks who still worked remotely or would promote their perspective that we should do much more to enable distributed work. And this was my experience when I was leading design at Groupon, I would drive an hour to an hour and a half to Palo Alto to not sit at a desk. I had a desk there, but I wouldn’t sit at the desk. I would go from conference room to conference room to sit on a video call with people in Chicago, Seattle, the cities that we operated, and my entire day from nine to five would be moving from conference room to conference room to be part of conversations where a significant portion of the folks we’re not in the room with me.  Jesse: Right.  Peter: And so work had already gotten to this distributed notion. People– Jesse: And I’ve seen many organizations that work exactly that same. Peter: Yeah. If you, if you look at even people at their desks, they’re often staring at a screen on a call with other people. We were operating in this distributed fashion. We just sat near one another. I’ve come to believe that the reason we were still using offices is because we’d stopped being intentional about that. That was not an intentional decision. In the same way that we work in these bureaucratic hierarchies because it’s how we always have, we worked in offices because that’s how we always have, and we do a bunch of things because it’s how it’s always been done. And now we have a break point. My concern is that too many people will try to return things to the way they were, as if that was better, or superior or natural, instead of really taking stock and taking advantage of how we can operate in new ways that are better suited to our current reality. Jesse: I completely agree with you. And, as this has gone on, I’ve heard that sentiment from more and more people that people are, in their own lives, taking stock and reassessing how they’ve structured their lives and the priorities that have been, to your point, unintentionally, or at least unconsciously, built into those choices. And I can see organizations doing the same thing for sure. Peter: I’m working for a 150 year bank right now, and they’re all having to work from home. And it has been clearly a painful transition for them from an infrastructure standpoint. But I have to imagine that they now are realizing that there are new and potentially better ways of working that they will need to adopt.  Jesse: I want to come back to the cultural issue, around presence in the office because I think this is one that has a particular meaning for leaders in organizations, in that presence in the office for leaders often is about maintaining a certain level of visibility, especially visibility among people that you don’t directly interact with. Maintaining a degree of visibility with your weak ties, with those peers whom you may not be collaborating with day in, day out, but who you see once a month, once a quarter, and who you need to maintain relationships with. Peter: The most obvious casualty of distributed work is serendipity, is the hallway conversation, is running into someone in the break room. And leaders more than other folks within an organization benefit from that, given the nature of their roles. Something we’ve talked about in earlier episodes is how the medium of leadership is relationship. Those relationships are built both through scheduled and intentional interaction, but also through passive serendipitous interaction. And we’re now carving out a significant chunk of that, when you’re looking at things in a purely distributed fashion. That said, in my experience… So my last full time role, at Snagajob, I was part of an office of 30 people in Oakland, and the other 470 people in the company worked in Virginia and South Carolina. And I still felt I had a decent leadership relationship. You know, part of that was, five days a month, I traveled to the largest office and like literally just kind of hang around, sit around, see… Jesse: That’s what I’m talking about though. Like that hanging around has value… Peter: And I made serendipity happen just through my presence. And I would let people know when I was there, “I’ve cleared my calendar, don’t need an agenda, just here to hang out.” But, being distributed doesn’t mean being physically isolated. And that’s where intent becomes important, right? There’s opportunities to pull people together. So as a leader, you can say, “Hey, let’s get everyone together in your org, to meet, and in those company-wide gatherings, you reintroduce those opportunities for serendipity and for unintended connection. Music break Peter: The companies I know that have distributed teams, offhand, the design isn’t great. What ends up happening, I think is, it is harder to build a design culture. And in those distributed workforces, the work gets highly atomized. You get a lot of little product teams doing a lot of stuff. And so the overall quality of design throughout an organization is, on average, lower than I’d like. There might be spikes where certain teams are doing it well, because there’s a good design leader, good designers in that area. But it’s not something that you can generally, across the board bring up.  Jesse: Well, the distributed context places so much emphasis on the communication skills of the team and the ability to clearly get an intent across to a collaborator and be able to receive and incorporate and integrate whatever feedback you get from that. And to be able to handle those volleys of ideas within a team more smoothly. In a physical context that often is a matter of interpersonal attunement, right? So you’ve got a group of designers around the table that are all working together on a problem and everybody is sort of tracking everybody else in these really subtle ways in terms of, “Is everybody on board with this idea? Is there somebody who’s like, maybe resisting it a bit? You get all of this stuff from body language and all of these micro cues that are more available to us in a physical environment that I think leaders are struggling with right now, especially if you’re the kind of leader who makes decisions from a place of synthesizing and integrating these signals of attunement and alignment from your team to be able to say, okay, this feels like the direction that is going to best address the problem as I understand it from the perspectives of all the people in this room right now. When they lose access to that rich real time information source about their collaborators, it becomes a lot harder, and it’s a lot harder to do that over a video conferencing app like Zoom, and it’s even harder to do that when everybody’s attention is focused on something like a virtual whiteboard, and you may only be hearing voices in your head and seeing little pointers flying around on a screen. Peter: The voices. The voices. Jesse: Yes. Peter: In my last role, there was a problem that ended up being localized to the Oakland office. and we addressed it because we were all there and I could be pulled into a conference room in a moment’s notice and say, “Hey, this and that and the other thing isn’t working. There’s some sensitivities. There’s some, personality clashes,” et cetera, et cetera. And you could do five minutes here and five minutes there and you can kind of feel your way through addressing this problem in the moment. Whereas problems that arise among a distributed team, because you need to be so much more intentional and much more explicit in your communications, well, now you need to grab time on someone’s calendar, and when you talk to them, you need to like have your case made about here’s the nature of this problem. And now as the leader, in order to resolve the problem, you can’t just pull people aside. You now have to set up a series of meetings yourself and it just turns everything that could have been handled in a humanistic rhythm…. Jesse: Yeah, and in a graceful and informal and humane way, rather than turning it all into these formalized artificial structures that feels like you’re being sort of fed into this big machine instead of just having a conversation with the person. Peter: And so my concern is that there is going to remain a set of lower-lying problems that don’t hit that threshold, that you as a leader might not even realize are happening, right? That just don’t break through the surface. And then once it does hit this threshold, it becomes this thing that now has to be projectized. Jesse: Yeah. Triggers a whole bunch of sort of formal processes around it that may be totally ill-suited to the nature of the problem at hand. I completely agree with you and I think that this environment makes it particularly important for leaders to be continually pushing down that threshold of how big a thing needs to be in order for their people to come talk to them about it, and for them to be able to feel like they can casually shoot you a DM in Slack and feel like that’s not going to spin up into something that’s completely out of scale with the scale of the problem itself. Peter: Yeah. It might not align appropriately given the nature of the challenge that you’re trying to address. Jesse: I think also for design leaders, this technology introduces new challenges, as remote facilitators of processes and as orchestrators of conversations. And running people through exercises and taking them through the process of generation and synthesis and driving decision making, doing all of those things, in the context of virtual environments is another skillset that most of us are still learning. And, as the tools evolve, we’re going to have to evolve to keep up with them. Peter: Definitely. One of the skills that help designers facilitate those types of conversations is a certain empathetic quality, but also a certain ability to improvise. And one of the challenges, is you still need to improvise. You need to be able to realize in a context of a conversation like, “Oh, we should go in this direction. And I have to put aside the plan that I had and pursue it.”  Running these types of workshops virtually, I find requires me to be way more prepared ahead of time, and understanding what the activities are going to be, how they’re going to proceed. And the challenge is you have to be both more explicit upfront in terms of how you structure the sessions, but you still, you don’t want to be rigid and you still need to have that ability to flex, and that, that’s just harder. I think it’s just harder. Jesse: Yeah, it is harder. And part of it I think, again, comes back to how closely are you able to stay in tune with the other people that you are collaborating with? And how, are you able to track their reactions moment to moment to the evolution of the ideas? And, that improvisation is such an important skill. Peter: Design leaders are kind of being thrusted back almost into conscious incompetence like they’re having to start over their practices and what works and the things that they had internalized that they could kind of rely on. They’re now having to call into question, much as we said at the very outset like how businesses are having to call into question some fundamental aspects of how they operate. And it would be interesting to consider what are those aspects of leadership practice had become unconscious or subconscious that are now needing to be made explicit again. And I think one of them is this ability to improv. It’s this ability to flow. It’s this ability to react and realize something that has bubbled up, an issue has developed or an opportunity has arisen, and now you’re going to lean forward and tackle that. Jesse: You got me thinking again about this great reset that is happening at all scales. It’s happening at the scale of the individual as individuals are reassessing how they relate to their lives and the world and purpose and meaning and all those kinds of things, that’s happening at the scale of small groups of people, whether those are families or teams or whatever and the whole reconsideration of how those interaction patterns work. And then it’s happening at the larger scale of larger organizations and eventually institutions and governments and whole societies. So, I think that what you’re talking about is one expression of a larger reconsideration of everything that is happening. I think that this may be an area where a newer leader has certain advantages in that they haven’t yet had the opportunity to build up a lot of habits and practices that are rooted in the pre-distributed context. Music break 2 Peter: So I’m thinking about this in the context of a particular initiative that I ended up being responsible for when I was at Groupon, about six months into my time there, I was told by my boss, the SVP of Product, that in six weeks time he was expecting me to present at the company all hands to all 12,000 employees a vision for the future Groupon shopping experience. It’s one of those things, it wasn’t out of the blue. It had been bubbling, but it was like, now is the time. Because he was looking at the whole calendar of 2013. We show a vision in April, and then by October of that year, five months later, we start launching the first steps towards realizing that vision. And we wanted to get those first steps out before the holiday break. as eommerce, ecommerce is very seasonally minded. And we did a code freeze, basically, right before Thanksgiving. And so, he had done a lot of work to develop a product strategy. And so it’s like, we know the product strategy. Make that go. And he was looking to me to lead that. I, in turn, thankfully had hired an extremely capable design director, who’s now the head of design at Doordash, Helena Seo, I leaned on her and I’m like, I’m still running a design organization, so I can’t spend all of my time doing it. I think I was able to devote about a quarter of my time over those six weeks to this, but I tasked her and she in turn had one or two other designers supporting her, and it was kind of their 50% plus job building this vision, and the vision was simply going to be essentially a series of comps that told a story of a future experience. Part of why we were able to succeed is after that conversation with my boss, I could go over to her desk and say, “Hey, I need to talk to you about a thing.” We could start that planning. She could go to two people who worked near her and she could say, “Hey, we’re going to be doing this together.” And the bulk of the effort took place between the four of us, co-located working every day, moving this thing forward.  Now I’m coaching, this design leader who wants to prepare a similar vision, his ability to pull together a skunkworks, a strike team to do that is just way compromised because now all of this stuff, again, has to hit that threshold of “It’s a project” and, it was a project for us, but we were still able to be kind of off the books and scrappy about it. Jesse: It’s hard to feel scrappy when you’ve got an official Jira board. Right. Peter: Yeah. And, as I’m thinking about what this leader is going to try to do, it’s just not going to be as flow-y as I had it when I was in a similar situation six or seven years ago, and I could just pull together this little strike team to make it happen. Jesse: Yeah, I agree with that. It seems like for design leaders it’s going to be really key to find ways to create those opportunities for serendipity, opportunities for serendipitous interaction, whether with their peers or amongst the members of their teams. And also to try to find ways to culturally encourage and technologically enable more kind of looser ad hoc conversations, you know? There was a time not too long ago when people would just pick up the phone and call you without having scheduled anything to have a three minute conversation about something and then hanging up the phone when they’re done. And this was a common way that a lot of human interaction happened in the 20th century in business. And we managed to have those ad hoc conversations in these relatively informal ways, still using distributed technological tools. Peter: Slack is not a means for galvanizing, I don’t think.. That, that doesn’t mean… Jesse: …Tell me what you mean by galvanizing in this way…? Peter: Galvanizing, right? How do, how do I get two, three, four people together and light a spark and make work happen and seed… Jesse: You’re talking about activating groups of people as opposed to individuals. Peter: Yeah. Slack is great once those groups have been identified and you need to give them a tool to enable their ability to work together. But to spin up, I don’t know, maybe I’m wrong, maybe people are doing this on Slack, but, to me, that feels very much like a face-to-face, that could be distributed-face-to-face, but face-to-face set of interactions or, or at least voice-to-voice interactions. Right.  Jesse: It sounds to me like what you’re yearning for is a way to gauge and help create buy-in for people that you want to get motivated, get excited, get engaged, pour their energy into what you’re putting forward. And what I hear you saying is that that’s a lot more difficult to do in a text chat environment as opposed to face to face or even a phone call. Peter: I suspect so. A few episodes ago, we talked about leadership rarely has authority. Leadership is about influence. Management is about authority. And so the manager approach to activating and galvanizing is, “John. Mary. Joseph, you are now working on this thing, go!” and they’re like, “Okay, it’s my job. This is what I do.” You’re not going to get the best work out of John, Mary and Joseph in that context. You know, we know that people work best when they feel that connection to purpose. That’s why we spent so much time talking about purpose. We know that people work best when they feel like there is a higher order mission, and opportunity that they are realizing. People work best when they feel self-directed, when it doesn’t feel like someone has told them what to do, but someone has said, “Hey, here’s this really amazing opportunity to make significant change.” And that person now is like, “I’m in because I want to be part of an amazing opportunity.” And that’s what I mean by galvanizing. That type of galvanizing is done through, I mean, you’re now starting to speak to their emotions. You’re trying to speak to their higher selves. And I think, you know, an all-caps shout out on Slack doesn’t spur that kind of followership that’s that passionate, engaged, “I’m in” quality that face-to-face does. Jesse: I think that trust is an element in this too, that the real-time, face-to-face interaction provides for the opportunity to build some trust in the relationship. That is, again, not impossible to do through other channels, but just harder because we have less access to the physiological cues of emotional states that help us stay attuned to one another from moment to moment. And in the absence of that, it can be hard for team members to really fully buy into a leader’s vision at a deep emotional level because the leader doesn’t have the ability to calibrate the communication of that vision to the emotional responses that the leader is getting to in that improvisational fashion. So the ability to have an improvisational conversation with somebody where you are responding moment to moment, to their emotional reactions, to what you’re saying, is how you build that baseline of trust that is going to allow both the team member and the leader going forward to trust in each other’s intentions. For the team member to feel like the leader has a vision that they can invest in, that they can believe in and for the leader to feel like the team members get it enough that they can turn their back and trust that that thing is going to go where they wanted it to go. Peter: All I have to say to that is, is yes to all that.  One of the things that we don’t do enough within organizations is earn our team members’ trust, earn our employees’ trust. Oftentimes we approach things from a stance of assuming trust, that if I am engaging with you, I assume you trust me. And in fact, trust has to be earned. It has to be earned over time, particularly when you’re dealing with these types of sensitive emotional aspects of meaning, of purpose, of connection, of engagement, you can’t assume trust. If you start by assuming trust, you’re not going to get anywhere almost from the outset. And it’s funny cause trust has to be two ways, right? The individual needs to trust the organization, that the organization is living up to that purpose that it is talking about. And that their effort is connected to that higher purpose. It’s one thing when a company is selling these humanistic values of community and neighborhoodliness and all that. And then you find out that they treat their workers terribly. If anyone’s trust is to be assumed, it is the employee’s trust. Whereas the company tends to think their trust is the one to be assumed and that employees… Jesse: Right…  Peter: … have to earn the company’s trust, right. Through their performance and through their effort. And I would argue it’s exactly the opposite…  Jesse: …Showing up at the office… Peter: Yeah. And I would argue it’s the opposite, that companies need to earn team members’ trust because so often team members have been taken advantage of by the companies that they work for. Organizations, companies, individuals, leaders don’t pay nearly enough attention to trust that they should. Even more than purpose and meaning, and some of these other things, trust is as, if not more, important and far less well understood. It’s almost never made explicit. It’s almost like we’re wary of bringing trust into the work environment because, my guess is, because we think we fear we will have to break it. At some point, we are going to have to make a decision that breaks that trust. And so we almost don’t want to start that conversation for fear of where it will go. But in order for us to make the…. Jesse: Wow. That’s just, well, I want to, I want to allow some space for that. Cause that’s a pretty powerful statement, what you just said. And, the notion that leaders are carrying around with them, this burden all the time of the knowledge that whatever trust they build, they might at some point have to destroy as part of doing their job it’s a challenging place to be. It’s interesting that we came to this place just because, trust actually was a big component of the work that I was doing in the last couple of years at Capital One. And, it’s an area that I’ve been digging into and trying to figure out how to bring greater understanding of to my practice with leaders. So I have a lot of things to say about it. Peter: Well, maybe that becomes the subject for our next conversation…  With this strange fractured conversation that I think reflects a certain reality of our world today. Trying to keep on top of a bunch of different threads in new ways, in new contexts. That wraps up another episode of “Finding Our Way.” We thank you for taking the time to listen to what we have to say. We look forward to your thoughts and input. We are happy to announce that as of this recording, we actually have a website, https://findingourway.design/ Probably the best way of getting a hold of us. There’s a contact form there. It’s also where you can find all past episodes and, links to podcatchers and all that kind of good stuff, how to subscribe. So, find us there, send it to your friends. And, we look forward to having you join us on our journey as we continue finding our way. Jesse: Finding our way. Thanks Peter. Peter: The sound is so much warmer now. Can’t you tell? Jesse: Yeah. It’s like you’re right inside my head. Peter: Either that or it’s because I’m using my FM DJ voice? Jesse: You seem to be in good spirits today. They are all computers now. I think, actually that’s not true. I know someone who was an FM DJ, so… Peter: But, but at this point, Alexa could basically run radio across the country and most people wouldn’t care. Jesse: No. Most people wouldn’t notice. Yeah. Peter: I guess I’m in good spirits. I find that my spirits track with the quality of sleep. I had a good sleep, so I’m in good spirits. Jesse: Mm. Excellent. Well, that’s good. Peter: Yeah. I’m pretty simple. Jesse: Yeah. Well, you know, on some level we all are. Right.  Peter: if we had known where we were going with this conversation, we could have invited that design leader focused on distributed teams and…  Jesse: if we had known where we were going for this conversation, we never would have gotten here. Peter: And maybe that’s for next time.

Explore how establishing a clear purpose shapes design teams and their mission statements. Discover the balance of leadership dynamics, fostering collaboration while embracing creative input. Learn about setting internal norms and defining success through accountability and empathy. Understand the importance of aligning values with success metrics to enhance recruitment and team commitment. Lastly, delve into the role of designers in community building and the significance of diverse backgrounds for a more impactful design influence.

In this episode, explore the challenges design leaders face while building cohesive teams. Discover the balance between personality traits and leadership effectiveness. The importance of salesmanship and communication takes center stage, as confidence and self-awareness are highlighted. Transitioning from designer to leader is examined, stressing the need for intentional relationship building. Lastly, listeners are invited to reflect on the complexities of leadership and a film that resonates with younger audiences.

In which reflections on the coronavirus pandemic spark a freeform conversation ranging from Trump to Jobs on management, leadership, power, uncertainty, and more. Transcript 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. As always, I’m Peter Merholz, and with me is Jesse James Garrett. Jesse: Hello, Peter. Peter: Hi Jesse. Good afternoon. How are you? Jesse: I’m, I’m, doing well, all things considered. Yeah– Peter: And there, there’s a lot to consider…  Jesse: There is a lot, there’s a lot of context. Just a lot. We’ve got some extra context these days for everything. Peter: It’s funny. I haven’t had enough time to go meta on the current situation, but I think there is, there’s something about this situation that is interesting and revealing. My normal mode would be to reflect on it and I just haven’t had time to do that. Have you been able to step back and think about what we might be learning through this uncommon experience? Jesse: Oh, wow. That’s a, that’s kind of a big question. I, so just as a point of reference, for our listeners’ context, it is Thursday, March the 26th, 2020. And so that’s where we are in the overall timeline of this extraordinary year, as it has just begun to unfold for us. And you know, I don’t think anybody really can get enough distance on any of this yet to extrapolate learnings from it, except for some very broad learnings about the systemic nature of cause and effect in our modern globalized world. The ways in which systemic structures and the choices that we make in our individual lives are actually intertwined in terms of the outcomes that they create. And, I think that when we look at the differences in how the Covid–19 virus has propagated across cultures and across societies, and the dramatic differences that we’ve seen across the various countries in which the pandemic has taken hold, come back to issues of culture, issues of governance. Frankly, a lot of the stuff that we’re interested in talking about here at the scale of design and design leadership, but really at the global scale. There are these factors at play that influence how an event like this unfolds, that are hard to see in advance because they are these second order, systemic kind of effects. And then it ends up expressing itself in these really unusual ways. Just before we started recording, I was watching video of, you know, in cities all over the world, there are parks and plazas and public squares that have resident populations of feral animals that rely on the presence of humans to sustain their populations. And now there are these packs of animals kind of roving the empty streets of cities around the world looking for tourists to give them bread. And there are none coming. And so it’s a schooling in unintended consequences that has really just begun. Yeah. Peter: Raccoon apocalypse. Um, one of the things that this has done is make evident different kinds of leadership, and different responses that leaders can have in situations that are kind of revealing. There’s the leadership as demonstrated by President Trump, there’s the leadership demonstrated by Governor Gavin Newsom here in California. As Covid was starting to land in the United States, Trump’s leadership mode was to tell people what he thought they wanted to hear, which sometimes can be an okay strategy depending on the seriousness of the incident, but in this case was not the right strategy because telling people what they wanted to hear did not allow them to prepare as they needed to for the reality. This was in marked contrast to here in California, governor Gavin Newsom, who came out in front of this very early on and started talking about the seriousness and how we’re going to need to start shutting things down and that this is going to take awhile and, his leadership approach was to be upfront with the citizens of California, and he told us stuff we didn’t want to hear. I don’t want to hear that I’m going to have to be in my house for weeks, if not months, on end. But it is good for me to hear that if that is the reality, if that is a reality that I need to get accustomed to and start preparing for. Right. And thinking about design leaders, I was in a session yesterday where we were talking about “radical candor.” And, there’s a book by that title by Jill Scott. And, you know, the idea behind radical candor is that you are forthright, you are frank with people, with the situation, the issues in play. You are respectful. You are not aggressive. You are not rude or mean, but you are direct, because it is through that communication of information that we are able to understand the situation and then develop strategies for getting better. Whereas a more common approach, probably the most common approach that I’ve seen in design teams and with design leaders is what she refers to as “ruinous empathy,” which is, because we want to be nice to one another—and designers, at least the ones I’ve worked with, often tend towards the nice, the polite, the pleasant—because we want to be nice to one another, we don’t tell people what they need to hear. We instead tell them what they want to hear, and they don’t realize that they might be underperforming or that this work could be done better or that somehow they are not reaching their potential. And so then these folks end up stuck at a particular level and they’re not growing because in order to get them to grow, we would have to critique them and tell them that they are not measuring up, and that would be not nice. And we kind of get in our own way in doing that, and so it was interesting to think about these leadership styles, both at the micro level of teams and at this macro level of states and societies. Jesse: You know, and I would argue that, what all of that comes back to is, how effective are the interpersonal skills of the leader. You know, obviously there’s a lot to be said for, you know, vision and operational acumen and all of those kinds of things that are, that are asked of leaders. But I think, in order to mobilize people around a common cause, people who have a diverse range of skills to bring, a diverse range of perspectives, to mobilize them around a common cause requires being able to speak to them in ways that resonate with them and bring them along. And that’s something that design leaders get used to doing in the context of defending design work as designers, and then as they are elevated to leadership, they sometimes kind of lose their way a little bit, in terms of knowing how to bring people along with ideas that aren’t design concepts. Peter: I would say there’s a difference there. I guess it’s easy to react in a situation and provide a rationale as you said, a kind of defense of something that you have created. It can be harder to proact, right, when there isn’t a thing to react to, but you have an idea of where things should be headed.  And it can be very, disconcerting for folks to make that kind of commitment. And I think particularly for design leaders who often feel disempowered, feel like they don’t have access to enough levers to ensure that they are able to see what their vision is forward. To that, I guess I would say don’t worry about that disempowerment. Our job, particularly as design leaders, is to articulate a clear vision forward, and work with our peers and in the organization to figure out how to rally towards that goal. Jesse: I’m interested in this idea of reactivity because I think that it is something that can be a challenge to navigate as one is moving into leadership for the first time or early in the journey of being a leader, of figuring out how much to react versus how much to push against the organization or against your team. Right. How much are you a first responder there to put out the fires and clear the path for design, like you’ve talked about in your work as a design leader, versus how much do you push. So you’re a leader, you have some authority. That means you have some permission, some latitude, to take steps as you see fit.  But if driving organizational change is a necessary part of driving success for your design team, then you have to be sort of working at the edges of that permission. You have to be working along the boundaries of your authority as it is currently defined in order to orchestrate the new, to draw the organization toward what it is eventually going to become. And so there’s a balance there that I see leaders having to walk between. Being what has been asked of you versus being what the organization actually ultimately needs. Peter: I think what you highlighted, which I hadn’t quite thought of in this way, is that most design managers are design managers and probably a very small subset of them are truly design leaders, because I think that leadership is about pushing against those boundaries, taking people into, if not unknown territory, less well known territory, less well understood territory, taking them to someplace uncomfortable, with the idea that that is where ultimately success will be realized.  Leadership can kind of happen almost at any level as long as that person is demonstrating these qualities of pushing, of challenging, of coercing, persuading, bringing people along towards something new that they might not be familiar with. Jesse: Yeah, I definitely agree with that. At Adaptive Path, we saw inside a lot of organizations, where the power in the room and the power on paper were two very different things. And it had to do with the level of respect and trust that people had for the viewpoints of certain people and how effectively those people use their power. And people who were able to cultivate a broad base of respect and trust and were able to use their power in responsible ways, were able to maintain that power without necessarily being in a position of authority. Power may be a different thing again, I guess that when I’m talking about power here, I’m talking about the ability to influence an outcome. Peter: Right. A manager’s impact is through their granted authority, and a leader’s impact is through the adoption of a new mindset that continues without them needing to be around. Jesse: Yeah. When we talk about, maybe not the manager versus the leader, but management versus leadership, there are management oriented responsibilities that people have. And then there are leadership, I think, opportunities. I think in a lot of cases people can be set up to fail if they are, given a management mandate for a leadership problem, it’s like having the ops team lead your strategy development. They’re great at a different thing, and this is not that thing. Peter: This actually reminds me of an experience I had last year, in support of Kaiser Permanente. One of the things I learned, and I was working with a consultant there, who had a master’s degree or a certificate in change management. And when we work in design, we often think about change management, right? As designers, one of the things we are doing is helping people imagine new futures and then figuring out how do we get to those new futures. So there’s actually a reasonable connection or overlap with the act of design. But one of the things she pointed out, is that oftentimes people apply change management practices to what is actually transformation management. And this speaks to kind of what you were saying before, where you will apply management approaches to what is actually a leadership problem. People will apply change management approaches to what’s a transformation problem. And there’s a fundamental difference between change and transformation. Change management is going from a to B, where B is known. They call it agile transformation, but it’s an agile change basically, right? We are currently working in waterfall. We’re going to work in agile. We’re going to now change to people broken up into squads of eight. They’re going to work in these two weeks sprints, et cetera, et cetera, et cetera, right? So you’re going from one known to, another known, even if you haven’t practiced it yet, you generally know where you’re headed. Transformation management is where you’re going from a current state of known to, you don’t know, it is unknown where you’re headed. And, If you apply change management practices to transformation management, what you end up doing is trying to, I think you said, kind of operate your way towards a new future and that just doesn’t work. It ends up getting rejected because you don’t know where you’re headed and you need a different set of practices to transform. But the uncertainty in transformation ends up often running contrary to an organization’s desire for certainty. So they apply the change management approach, because there’s a certainty implied in the change management approach. Transformation management, you don’t actually know where you’re going to end up. That’s kind of the point. So you get this conflict of certainty and uncertainty fighting one another. And the certainty usually wins, right? Cause the certainty is part of the dominant existing culture. And the attempts to create something new gets squashed because it requires an organization to live in the uncertain for longer than they’re comfortable. Jesse: Right. Peter: And then, it just gets rolled back and it never happens. Jesse: Yeah. Certainty wins out because certainty is comfortable and certainty makes the fear go away and executives carry a lot of fear around, all the time. It’s just sort of the nature of the job. This is interesting though, because this connects back to something that you were talking about earlier when you were talking about the design leader pushing the organization into the unknown. And what I got from what you were saying was that it is always the design leader’s role to be pushing the organization in these ways. And I wonder how true that actually is because I can see that being true in a startup environment, where the goal is to invent the product as you go and to discover your market opportunity as you go. And certainly that same pushing into the unknown was an important part of Adaptive Path’s value proposition to its clients as well as a part of our internal culture to continue to innovate our practices and keep inventing new stuff. But I find myself wondering if it’s not mostly the case for most design leaders that the job doesn’t really ask for this kind of boundary pushing stuff. It asks for them, you know, to run the team and to run the team really well. Do you think that’s true? Peter: Yes, and that’s fine, especially when you get to a larger organization in a more stable organization. It’s about keeping that organization humming and running, and so you’re tweaking and you’re fiddling and you’re trying to, you know, continue to improve effectiveness. But if we’re going to be talking about leadership as we did last time, as a practice and a craft, I think we have to recognize that leadership is distinct from management in terms of that pushing. And in my experience, and I think this is true of most of the design managers I know, while most of their job is management, for most of them, there’s at least 10%, 20% of their job that should be leadership. They might not all be embracing that opportunity, which is a separate issue, but I think that opportunity does exist. One of the things I’m starting to see a lot more is design managers, directors, senior directors, who are bringing on principal designers. So, these are kind of director-level designers, but who are not expected to manage people, but expected to be a creative leader in a realm of work. Because I think these design managers and executives even recognize that they don’t have the time, the bandwidth to do the creative leadership as well as the executive engagement and the people management and all the other things that are expected of them. Jesse: It’s interesting because there are some leaders that I think really start to run up against limitations in terms of their potential to grow and to move up in organizations because they are able to practice the relationship building and the management and the alignment and the orchestration and the leadership within the context of their own teams. But then when they have to do that outside of the context of design process and design decisions as they are representing design on a larger stage, they become uncertain about where their power is and they become uncertain about, “How do you use it effectively?”  It kind of comes back to something that we were talking about earlier about how people end up becoming design leaders in the first place, which is that the skills that got you the job aren’t necessarily the skills that are gonna let you keep the job. Peter: Right. a challenge that many design leaders have that might be somewhat unique to design compared to other functions, is that their peers and their bosses say they want new thinking, new ways of working, the creation of new value that design can bring through its practices. But then, as designers or design leaders attempt to deliver on that, it pushes the organization into this uncomfortable and uncertain realm. And there’s this snapback, where it’s like, “Wait, whoa, whoa. When I said we wanted innovation, I didn’t mean that. I meant something that I could put on a spreadsheet and better understand and you’re giving me something that is different than that.” And I think this is in part because companies are still trying to figure out what to do with this function that is design, and how to, for lack of a better phrase, capitalize on it. I think there’s this internal conflict where like they want one thing and they asked for one thing, but then when you give it to them, they pushed back and they get upset. And so you don’t do it, and then they’re mad at you because now you’re not delivering the innovation that they asked for. And, and, they don’t realize that the people outside of design don’t often realize that they’re getting in their own way when it comes to what they’re asking for. And that leaves design leaders who are often not particularly well versed in navigating these types of things, their heads are just spinning, trying to figure out what is expected of them, and then it becomes easy to retrench or retreat into that which is safe, which would be the management aspects of their role. Jesse: I feel like the things that you’re describing are almost artifacts of this stage in the development of UX as a practice, if you are a design leader in an organization that hasn’t had design before and you are trying to engage with a whole bunch of peers and stakeholders who have never had to engage with design before. You are, by definition, trying to pull the organization into a new place, which by definition is going to be uncomfortable for people and it’s going to require a great deal of diplomacy.  I wonder at what point we start to turn a corner where those fights become less and less relevant because you don’t have to do so much of that educating, bringing people along, helping them figure out how to talk to you in a way that helps them get what they want from you. Peter: I appreciate and wish for what you say to be true. I am dubious of that happening anytime soon and I’m dubious for that to be happening anytime soon because a challenge that I believe design has in these organizations is that it is a function unlike literally any other in that it is this kind of creative function, that is being granted some measure of real influence and authority. There’ve been creative people in organizations for a long time. But often, it was designers maybe in a marketing context who received a brief, executed on the brief, and weren’t really driving the business in any meaningful way. They were executing on a fairly narrow remit, in some small part of the business as needed. And now design as a function, and it’s a practice is being brought in one or two levels below the CEO with real executive authority, with large teams that cost a lot of money to hire, and with real influence over the success of a business in terms of the nature of their output driving core fundamental business value.  The issue there though is that the dominant cultures of these businesses tend to be mechanistic, analytical, reductive, business driven, numbers driven. Engineers and MBAs, frankly, share a mindset of how to approach problem framing and problem solving, which is, which is fairly analytical and rigorous and, and detail oriented and predictable and certain. It’s a lot about removing uncertainty and, and being certain, but I think there’s this feeling in many organizations, it might even be unconscious, that those approaches have reached their limits. And design seems to offer an opportunity to unlock new value. And so they’re bringing design in ‘cause they, they want that innovation. They want that magic. They want whatever design has to offer, but they don’t recognize that when they’re asking for design to enter into these contexts that they’re bringing in a fundamentally, deeply different way of looking at the world, approaching the world, framing problems and solving problems that isn’t analytical. it tends to be more, synthetic, more generative, more creative, more experimental, less certain. It’s not blasé, it’s not dismissive to business realities and a need to generate value. It’s just a different way of getting there. And it is deeply in conflict with that dominant culture. And so, I am hopeful that we can get to what you’re asking for. I think the way we get there though is when more and more people with design backgrounds are in senior enough positions of leadership and recognize, the opportunity and the potential of this, what can feel uncomfortable, approach and give it the space to deliver as it can. And until then, design is going to find itself straitjacketed. I don’t know how much education you can do of existing broader organizational leadership, versus, is this one of those things that we just need kind of a new generation of leaders… Jesse: Right. Peter: …be okay with this lack of certainty, right? I mean, we’re coming out of 120 years of Taylorism, and management science, that was all about breaking things down to their details and creating repeatable, efficient processes, and design runs highly contrary to that. And it’s going to take a while before this more creative, generative, uncertain approach to value delivery is appreciated by these organizations. Jesse: It feels like what you’re describing is, this thing of, like, caging the wild beast. Right, this natural creative force of design that we’re trying to figure out how to, like, fit it into this Taylorist mechanistic metropolis like, sorry, mega-machine, that we can take this wild organic element and kind of plug it into somehow. And I find myself wondering whether the wild beasts can ever be truly tamed, or if it is always like, “Are you the zookeeper from now on?” Basically, regardless of how the organization’s changed, and is design always going to bump up against the practical mindedness that is necessary for successful management of a business. Peter: I don’t think so because I think much of that wildness can be practiced safely; practice safe wildness.  You know, thinking about Apple, particularly under Steve Jobs, because he obviously understood design, had a passion for design, and was willing to let that uncertainty manifest as long as necessary until the uncertainty eventually turns that corner and becomes something that is now more certain and feels real. There’s a way to approach it where you do it in a safe context where you’re not, you’re not launching this stuff. You’re not shipping this stuff. but you’re trying a bunch of stuff. You’re iterating on it. You’re weeding out 99, possibly 99.9% of the ideas until you get to those germs that catch on and then you’re building on that. And, that requires a degree of patience, a degree of confidence that most leaders simply don’t have. But, if you can see it through to that point, Apple demonstrates what the potential is of allowing that unbridled energy to be realized. Jesse: You know, one of the adjectives you’ll see most frequently associated with his name is mercurial. In that, yesterday’s great work is suddenly not good enough today. and the ways in which he would let people know that, not necessarily the most constructive… Peter: No, I, and I’m not going to, I have no desire to be a hagiography of Jobs… Jesse: …and, and this is I, yeah, no, I know that that’s not–. And my point was simply that, Jobs often, famously, couldn’t tell you exactly what he wanted until he saw it. But as soon as he saw it, then he knew and was, was very decisive in that respect. But it’s almost like the vision was actually sort of a created out of the best little bits of work of many different people rather than Steve Jobs being able to picture the whole thing in his head and then just like giving direction to a team, which is how I think people thought he was working.  Peter: That’s right. One of the interesting things about Jobs is how little vision he actually had. He was not imagining… Jesse: Yeah.  Peter: …these crazy futures. He didn’t come up with the graphic user interface, but when he saw it at Xerox PARC, he realized that is where things are heading, and figured out a way to take something someone else had come up with, and he figured out how to evolve that into something that would be accessible for everybody. But you’re right. He needed other people to show him that vision. And this kind of gets back to designers, right? When they’re working best, they are creating visions, most of which are bad. Maybe not bad, but, but, but, but ineffective or infeasible or not going anywhere… Jesse: Not right. They’re just not right in one way or another. Yeah. Peter: One of the challenges that companies that want to quote “be like Apple” have, is that their leaders aren’t able to navigate all these quote, “not right” ideas, to realize what are the right ones, the pearls within there, that are worth investing in. Jesse: Yeah. Well, one of the things that comes through in the various anecdotes about Jobs is, that one of his superpowers was discernment that, in a wide range of different areas, whether that was visual design or industrial design, or the nuts and bolts of software and hardware architecture, he had the ability to wrap his head around a problem well enough to be able to tell the difference between a good solution and a bad solution in a wide range of different areas. And he was able to use that skill to orchestrate the work of all of these different people toward something that eventually added up to a compelling product. So I think that that cultivation of discernment, that development of taste on the part of the leader, is an essential part of that orchestration of vision. Peter: I would like to think that, that quality of discernment exists in the world in many people. Jobs had developed it and refined it. I’d never considered discernment, as you phrased it, as its own skill, but, it is, there’s a quality there that can be developed though some people probably have a higher amount of it or a higher degree of it than others, as an inclination and, how can an organization identify its higher discerning individuals and engage with them, grant them some degree of influence and authority to practice that discernment, in value to the business. Jesse: That is an interesting question and I think an excellent place for us to leave off and… Peter: The biggest question we’ve had so far, and we’re just…  Jesse: …something deep to think about. I’m just going to let it hang there. I’m going to sleep on it. For, for a bit. Thank you so much, Peter. This has been wonderful. I think it’s probably time for the outro. Peter: I believe it is. So, once again, Jesse and I thank you for listening to another episode of Finding Our Way. As always, we are interested in hearing from you, whether through Twitter, email, carrier pigeon, whatever means you have at your disposal, let us know what you think about the show, or let us know what you would like us to talk about. We want to be open and responsive to this community, as we feel it’s not just Jesse and I finding our way, but all of us finding our way together. Jesse: Finding our way. Thanks, Peter. Peter:   Nope. Nope. That just didn’t work. That didn’t work. Fuck, fuck, fuck. I feel like Orson Welles yelling…  Jesse: I thought you were doing, I thought it. I thought it was…  Peter: It was going for awhile and then I, I spun out and feel again, like Orson Welles… Jesse: We know a farm in the South of England. Sorry… Peter: What is this fucking drivel! Why am I reading this shit? 

In which a discussion of David Epstein’s book Range leads to a consideration of craft, practice, and the medium of leadership. Transcript Jesse: On that note, would you like to take us out? Peter: I never took us in. Jesse: I know. Well, you can do the intro first if you like. [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 am Peter, and with me is Jesse James Garrett. Jesse: Hi, Peter.  Peter: So I actually was wondering, are you on Twitter at all right now? Jesse: Am I on Twitter? Intermittently? Obviously, there’s a lot there that, at some point you have to turn it off, but yes. Peter: I’m asking cause I recently posted to Twitter, I’m reading the book Range by David Epstein. Are you familiar with this book? Jesse: No, I don’t know this book. Peter: So it’s a book that basically makes a case for generalists in a world of specialisms. and there’s a lot of different stories about a lot of different things, but the basic theme is, people should sample many different things before choosing what it is they do, work-wise. And it also talks a little bit about where I’m at, is kind of “career winding.” And anyway, the reason I bring it up, the reason I tweeted about it, is it has caused me to reflect on design and engineering programs in colleges and it kind of reaffirmed my distaste in undergraduate design and undergraduate engineering programs as they get people to focus in on something fairly narrow early on before they actually understand what is out there. I’m wondering what you think. Jesse: Oh, well, I mean, so there are several different ways that we could go with this. You know, generalism versus specialism is, I think, an interesting thing, especially as you think about how you scale design teams and different approaches that, that we’ve seen taken to, to that question of how much generalism versus specialism do you encourage or support on your teams, and how do you structure your teams to support each of those different types of designers? I have my own complaints about design education and how design education is done. And we can certainly– Peter: That’s probably a whole other episode.  Jesse: There was a, there, there was a phrase that you used in there that I’m curious about. You, you said “career winding,” is that what you said? Tell me more about that.  Peter: Well, in the context of this book, he talks about how within society, there’s this assumption that it’s better to lock into a career choice earlier on and then hammer away at that. Right? You go to school, you’re pre-med ‘cause, you know, you want to be a doctor and you just kind of stay on that path. And one of the things he points out is that that’s actually not true in terms of that being the best way. And oftentimes many of the people who are most successful are folks who did, maybe not very different things, but different things in their career before landing on whatever it was that, this idea of matching your interests and the career world. And the issue is when you specialize or determine too early before you’ve had a chance to explore, your match might be off. And so one of two things happens. You either continue persisting in a path that you just don’t like, but you end up doing it anyway, or you end up feeling, you, you at some point you just break and you move to something else and then take on a lot of guilt about that. And, I, you know, as I’m reading this book, one of the things that I find myself reflecting on occasionally is, is how, when we started Adaptive Path, none of us had formal design degrees. We all had different backgrounds. And I think that is something that has been lost in successive waves of design and designers, kind of creating designers. That as design has gotten more professionalized, as more and more universities offer design degrees, we’re missing that generalist. Liberal arts or even engineering, whatever.It was, science background that people who, when we came up, there weren’t design degrees, so we had to have one of those backgrounds anyways. But I actually think it’s a, I think there is something lost, when folks aren’t able to draw from a broader foundation before choosing to focus in design. The last thing I’ll say that’s kind of more relevant perhaps to the theme of our podcast is one of design leadership. You know, I think, as a designer grows, and this is one of the key things that Range points out, is that when you get a design degree or an engineering degree, you are immediately worth more in the market because you have a marketable skill. But over time, people with more generalist backgrounds actually catch up to and surpass folks with more specialist education. and I suspect it’s because it’s easier for them to grow in kind of management and leadership capacities because they’re able to oversee a breadth of activity. Whereas if you’ve been on this narrow. Design or engineering track from day one it’s harder for you to interact with, engage with or oversee other functions. Jesse: I can see that. I can see that. I think also, that overseeing a multiplicity of functions requires a certain flexibility and adaptability of mindset and of management style. That someone who has previously worked in a variety of different roles or functions is going to have a little bit more of that kind of facility than someone who has come up within a single function in the organization. And so who has never had to do that sort of rapid hat switching that is asked of someone in a management role where they’re overseeing a diverse range of functions? This is very interesting and it speaks to, I think, some of what you and I’ve been talking about recently about the different kinds of design leaders and how people get to be design leaders. What are the various paths to design leadership that are emerging and what those leaders end up bringing to the role and how the role ends up being shaped to reflect the strengths of those leaders as a result. You had an initial wave of generalists, moving into these leadership roles who were generalists by necessity because there was no way to specialize in digital product design, there was no way to get any kind of formal training in it. So you had to piece it together. You had to adapt. You had to find mentors or people that you could learn from and you had to sort of make your own education, and so they are going to bring a certain sort of a management style as a result of that path, which is going to be a little bit pieced together from a lot of different sources and is going to be a little bit, scrappy and a little bit DIY, let’s see what we can lash together from, what bits of things that we can find to get the job done. Because that was how they got the job done to get where they were. Another sort of pattern of the design leader that you and I have talked about is the design leader who actually doesn’t have any background in design, formal or otherwise, who finds themselves, it’s like, “Hey, congratulations. You’re running the design team now because you seem to be good at something that we, the executive leadership, considered to be vaguely adjacent to design” and people who’ve had to adapt their management skills from other areas, notably, I think from, from technology, and, to some extent from the sort of the marketing and advertising and branding worlds, had to adapt those to this skill set in between. And so how they are going to manage it, it’s going to be different again, because it’s going to be rooted in the doctrine that they came from. And somebody who spent, you know, 25 years in brand marketing before they took over a UX team, they are going to have a whole frame for that work that they’re going to bring to it. And that’s going to influence how decision making happens. And that’s going to influence how they define the roles on their teams and the processes. And all of those kinds of things are all going to be informed by this background culture that the leader has come from. Peter: And then I, I was wondering if there was another path forward. Cause I can think of one other one which is emerging, which, I don’t know enough about the implications of, but it is, you know, now that for the last 15 to 20 years, you do have people who were trained as designers in undergrad, or at least in grad school getting jobs, working as designers, becoming design managers, becoming design leaders. I haven’t read her book. I should, Julie probably will mispronounce her last name. Julie, Julie Zhuo, from Facebook. I believe Facebook was literally her first job out of grad school, as a designer and she was there for quite a while and grew to being a VP of design. She wrote this book,  The Making of a Manager, which is about her experience and her path forward. And in this regard, and now I really want to read the book as I’m thinking about, I wonder, given what you said, how her background steered her in a way that would be different from me as someone who fell into design early in my career, but don’t have a formal design background. And, and I’ve definitely kind of had a bricolage approach to how I’ve managed my career that other archetype, which, I’m assuming this is who you had in mind. Who came to mind for me in terms of the person who leads design without any real design background or having really worked in design, was Scott Zimmer at Capital One, he was the head of design who acquired Adaptive Path, and he led a design team. When he joined to lead it, there were about 40 people. His background was in brand marketing. There are about 40 people in Capital One’s design team, and when he left Capital One, they were about 400. And he had a very, I thought, interesting, approach to leading a design organization that was directly informed by being a brand guy. In particular, I remember him talking about, ‘cause he knew he needed to scale his organization. So one, he was able to sell design internally better than most design leaders because he’s a branding and marketing person. So he knew how to frame design to the other executives in a way that they realized they wanted more of it. But then he realized in order to recruit and hire, he had to be a compelling place to work. And so he was very attuned to how brand influenced people’s decisions on where they worked. Then, acquiring Adaptive Path that had a brand name in the industry. And so, because he knew he could get press basically about how this bank is hiring all these design leaders from these companies you’ve heard of, and that allowed designers to go, “Oh, that’s a place I can work and feel comfortable at, ‘cause I recognize those brands.” So that brand marketing approach was one of the most successful I’ve seen as a design leader, and from a person who has never practiced design, that’s not in his background.  Jesse: There is an interesting sort of continuum that you highlight here between the person who has no formal training in design, but a lot of experience in design, versus the person who really is coming in from a complete outside perspective. And so it feels like there’s this, like, tipping point, beyond which you can’t call yourself an outsider anymore because you’ve been doing design work in some form… Peter: For too long…right, right, right. Jesse: …And so like, somewhere along the way, Scott Zimmer became a design leader by sort of inventing… Peter: …And, and, and inventing a role is that at the time was, exceedingly uncommon. Not being ahead of design, but being a head of design for a 400 person design organization. I mean, you could probably, at the time he left Capital One, there were maybe ten companies that had a design team that large, and one of them happened to be this bank that isn’t even one of the anywhere near the largest banks in America. Jesse: So, you know, we’ve been talking about how people who find themselves in find… Peter: Sometimes it feels like it’s an– Jesse: …accident… Peter:  …accident I, I don’t, I don’t know how intentional I was in becoming a design leader, but yes. Jesse: Hmm. Well, that I, hmm. Peter: I mean, we… Jesse: That is an interesting question… Peter: Right? I mean, when we started Adaptive Path, I mean, we had the kind of experience where when we started Adaptive Path, there were seven of us. We were equal. And then over time, As we grew, okay, I guess we’re the leaders now. And I think that’s true for a lot of folks. Leadership kinda just happens as things happen around you and you have to figure out how to accommodate to that. Jesse: I think that’s true. And actually, you know, that leadership can take a lot of different forms. I think about some of our earliest clients at Adaptive Path when user experience was a very new idea and needed champions, needed advocates, needed people to take an intellectual or a strategic leadership position in the organization, regardless of their position. regardless of the authority that their position held. So you had people who were very close to UX problems by virtue of whatever role they did hold. You know, you’re a webmaster, right? And, nobody asks you to think about this stuff, but it keeps coming up. So you start researching it and you realize there’s something there, and then, congratulations, you’re now running the UX department, when you just happened to be the person who was closest to the problem at the time.   Peter: Right.  Jesse: And I think that to some extent the intent of formal design training is to give somebody that foundation so that they don’t have to piece it all together out there in the wild from, you know, whatever people they can find on the street who will strike up a conversation with them about design leadership. [music break] Peter: Something we were talking about and maybe we can get into now, is this idea of what is the craft of design leadership? Designers talk a lot about craft, possibly more than any other role. I guess engineers might talk about craft. I don’t know if that’s the language that they use to talk about the work they do, but essentially it’s a craft discipline as well. And then as designers become design leaders, there’s this question of, well, what is the craft of design leadership? What is my relationship to craft? Do I let go of my old craft? Is there a new craft to embrace?  Something kind of in parallel that I’m starting to see, is around product management. People talking about “What is the craft of product management?” ‘Cause I think there’s a recognition that there is an opportunity to make clear what that role does. Because so far, that’s a role that has been defined by doing what anyone else is not doing. That is what product managers do. And that’s not any way to, that’s not any way to define a practice or craft.  But, similarly for design leaders, maybe because we’re so wired to think about craft and think about technique and think about process as we become leaders, we kind of fall back on those models and those frameworks of how to work and it’s not clear how, how applicable they are.  I teach a workshop on how to design your design organization and I’ve taught workshops for, I dunno, shit 20 years now. And we taught a lot of them in Adaptive Path. And when we taught workshops at Adaptive Path, they were about craft design. Strategy is a craft, design research as a craft, interaction design is a craft. And you could teach methods and you could teach technique. And when you teach those workshops at the heart of the workshops are activities, right? We were always very activity-based, usually group activities. Sometimes you did them on your own, but they were ways that we could teach methods and you could teach a discrete method. Here’s how you conduct an interview. Here’s how you construct a persona. That’s very teachable. A challenge I’ve had, in teaching my new workshop on designing your design organizations is, it’s not a process, it’s not a method. It’s not really a craft. I’m not teaching them how to draw a better org chart. I’m just, like, using it as a way to get their head in this game. But the bulk of the workshop is a deep conversation. Right now, my hypothesis is that the craft of design leadership is conversation and communication. Jesse: Yeah. Well, I think there is a lot there. You know, if you went to design school, what you were taught was that what they were teaching you, What’s the source of your power? That is, that your, your strength and ability, your capability as a designer was rooted in your mastery of craft. And, for people to get so good at that, that people want to take it away from them as they ascend to a leadership level and to have management basically say, “All of that stuff that you’re so good at, we’re so impressed by, please stop doing all of it,” it can be a really jarring transition and can leave the designer feeling unmoored and adrift and without that source of power that they have, come to rely on, to drive their work and their sense of confidence in their work. I think it’s interesting that you call out conversation and communication, in part because, I feel like we have talked about that as an element of the designer’s craft for a long time from a very pragmatic standpoint that you can’t sell an idea that you can’t explain to people. And the necessity of persuasion and politicking, to some extent in order to get creative ideas realized and get them off of the mood boards and out there in the world.  And I think that’s been a theme for us because it tends to be something that is almost an invisible craft on the part of many of these designers who are good at it, that because their definition of their craft doesn’t include it, they might not even realize how critical that conversation and communication stuff is. Peter: So that skill is actually not specific to management. Definitely not specific to design. Right? Anyone benefits from better communication skills, and I think it’s a matter of figuring out how do you apply these non-design skills to what you do in your new practice as a design leader. Companies don’t pay nearly enough attention and provide nearly enough resources for new leaders, new managers, new leaders in terms of training them up on new skills that they need in order to succeed. ‘Cause as you said earlier, the skills that got you there to whatever this leadership position are no longer the skills that will carry you forward. But, you’re just kind of, most companies put you in a sink or swim mode. when it comes to figuring out how you can excel. It’s one of those fixed mindset versus growth mindset things. I think a lot of folks assume that those non-craft skills, you know, You can either lead or you can’t, and I’m here to tell you that, Nope, you can grow those skills like you grow any other, you just need to recognize that they are growable, that they are not fixed within people, but that we can all learn how to do them better. Jesse: I think that for me, regardless of how much you believe the skills are growable, you have to act as if they are or else they definitely won’t be, right. You have to approach it as if you can develop new abilities because the belief that you can’t is going to guarantee it. Peter: I think, you and I unknowingly, had a benefit in our careers in terms of becoming design leaders, which is that we worked in a consulting capacity for so long and consulting is all about communication and conversation.  There’s things that you develop as a consultant that you might not even realize that you’re developing, but consultants are constantly having to sell their work, sell their ideas every day because of your relationship with your client. There is almost a negotiation happening that is different than when you’re simply in-house. And I think some of the more successful in-house design leaders are those that have that consulting background, because they’ve learned how to communicate with non-designers, right? ‘Cause as a consultant, often your clients were not people who were designers, so you learn how not to get so caught up in your own thing and to speak other people’s languages. And you learn the presentation and storytelling aspects that allow people to be brought along. And so while I’m not going to encourage necessarily everyone to become a consultant, or to spend some time consulting, there’s something about that experience that probably needs to be brought to bear in an internal context where people think, well, I don’t have to do that because I’m internal and these are my coworkers.  But those practices and those habits of communication that you learn as a consultant become immensely valuable.  Jesse: One thing that I’m hearing that’s implicit in what I think both of us are saying about this is that design leadership needs to be approached with the same level of intentionality as a practice as design is in the same way that designers are encouraged to think about how they develop their practice, how they cultivate their practice, how they continue to keep their practice alive, you’re not leaving that behind when you become a design leader. Your practice is a new practice now. And it’s going to involve the integration and synthesis of some new skills and maybe, some reevaluation, and, reassessment of your existing skills to see how those can be applied in these new contexts. So one of those has to do with conversation and communication, some of those skills that we develop, in consulting context. But also I think that it’s about kind of looking at what all of your strengths are as a designer and figure out kind of what is the version of this that exists in this new realm of design leadership? And this, I think, is one of the key functions of the design leader, of anyone in any kind of a leadership role, which is to create shared understanding. And so the designer having this natural strength in creating shared understanding now has the opportunity to take that into this new realm where they’re creating understanding around different ideas, toward different outcomes, but they’re still using that same tool set that they’ve developed. And I think the other thing that comes up, when you are someone who’s done a fair amount of consulting work, is that you’ve had to use these tools in a range of different contexts, which is to say that you’ve had to explain a range of different kinds of problems and a range of different kinds of solutions to a range of different kinds of people. And I think that’s really key because I think it’s really easy for our communication skills to get sort of super-optimized for the people that we communicate with the most or the most regularly, which is how, when a communication style sort of becomes the dominant communication style of an organization, people can get really good at that, and be really successful in that organization. And then as soon as you take them out out of that organization, that skill set doesn’t transfer because they were too good at working within that highly specialized context, to bring it all the way back around to generalization versus specialization, and they haven’t had the opportunity to grow those communication skills in a diverse range of contexts. So for designers who want to become design leaders who want to develop those skills that they will eventually need as design leaders, I think resisting that, that natural tendency to over-specialize our communication style and to cultivate the habit of learning how to communicate in different ways according to different people’s needs, I think is a skill that you can use as a designer. That eventually as you move into design leadership is going to serve you even more. Peter: What does it mean to be a design leader? Different from a business leader, different from, a technology leader, right? There’s going to be shared leadership practices perhaps around communication, but what are the interesting things based on these different people’s different backgrounds that they can bring to that function.  It’s a distinct component of what it means to be an organizational leader, with a design background. You can bring facilitation, you can bring visualization, like what are those things that given your design background, you’re bringing to this organizational leadership conversation that maybe others aren’t.  So I’m now kind of circling back to craft, cause I still think there’s a role that design leaders play in leading design, even if they’re not hands on in the craft anymore, they’re leading a team and a design leader still has a responsibility in that context. You know, things like mentorship, teaching people how to do the craft. I think critique becomes very important in this regard. And through critique you can communicate elements of craft and practice, and help people think about how they refine how they behave Right.  Let’s say you’re a design leader. Let’s say you’re a head of design. How do you make sure that your team is delivering quality work? The quality work that your team is doing is a result of their craft. You’re no longer practicing craft. So how do you bridge that gap? And so there’s a lot of work that a design leader needs to do to establish quality. What does quality look like? What expectations do we have around quality? That’s it’s not a craft, so much for a design leader, so what might be an opportunity for them to still keep a little bit of their craft in play, right? I think for me, I discouraged design leaders from quote, practicing their craft, because it means that they’re no longer leveraged. Leadership is about leverage, and if you’re delivering assets, you’re not being leveraged anymore. But if you’re practicing your craft in a way that is, explicitly about influencing others then, yes, there is an opportunity for you to practice your craft. So anyway, thinking about leadership, it’s thinking about maintaining quality. And then how do you help your teams deliver at that level of quality?  The only model I can think of that is relevant would be the military model that kitchens use. Right, where your most senior chef is someone who has made their way, literally touching every station over the course of their career before they become that most senior chef. Now, as the most senior chef, they are responsible for the quality of everything that goes out the door. But they are not at the fish station. They’re not at the sauce station. They’re not at the grill station, right. People doing that work, but it is up to the executive chef to make sure all those folks are doing it to a level of quality and a level of craft that is appropriate. Now there are problems with applying the restaurant model to the work we do. It’s not practical to expect a design leader in the contexts that you and I operate in to be, an excellent visual designer, and excellent interaction designer, and excellent information architect, and have gone through all those stations with a level of technique such that when we are now the ultimate leader, we can teach anybody how to do any of those things. Whereas that is more achievable in a restaurant context.  Jesse: I find myself wondering how much personal responsibility for mentorship is sensible for a design leader to take on, because, assuming that they got where they are because of not just their abilities, but their taste, right? Their ability to discern a good solution from a bad one. And that’s the part of the craft that they continue to exercise in those critiques and so I guess my question is, to what extent is it appropriate that a design leader try to pass on their taste, their judgment that critical skill in some way. As opposed to simply, here’s how you, you know, get that wicked effect in Photoshop or After Effects or whatever. Peter: Well, the way I get that wicked effect is through Kai’s Power Tools. the most wicked. Speaking of taste and aesthetics, I think it’s still the responsibility of the design leader to articulate why they would make a decision and maybe they are the ones responsible for it. So why they are making a certain decision. “Of these eight solutions, this is the one we’re going with.” And then they explain their reasons, their rationale. But being explicit about it, not just saying we’re going with, we’re moving on, but providing a reason for why we’re going for direction four out of eight, so that others can start understanding that leader’s taste, because that becomes important. But another aspect of this is, How does a leader help their team members develop their own senses of taste? Right? You don’t want to dictate taste. You want folks to develop their own aesthetics and their own understanding of how to navigate these decisions, figuring out how to communicate your taste in a way that breaks it down to these components. I know when I’ve provided critique around designs, I do so by communicating, if something’s not working for me, it’s not just, “It’s not working for me.” It’s, “Oh, that’s not working for me because it feels unbalanced. There’s a weight issue on this screen where this component on the left is overwhelming the components on the right,” or whatever it is. You talk about it in a way that folks can develop a language for their own critical eye. I guess this is part of design as a reflective practice, as we design, to be able to, upon looking at something we like, why do we like it? Being able to unpack that and communicate that, that becomes part of what you are teaching your teams, is that ability to talk about their work, not just a, “I followed these procedural steps. And so my design must be fine because I did the process,” again, ‘cause you could have any number of outcomes of those processes there. There is that last stage of the process where it’s not just, did you follow the steps, but has it come together? Has it jelled? Has it cohered into something compelling, interesting, desirable? And that’s where we need this language to be able to articulate, why something is working, why it isn’t, why you think it’s working. And then that becomes this thing that you can start talking about when it’s not just like, “Because I said so, because it feels right.” But because of these reasons. I think design leaders offer mentorship and critique, at the level that they are at. So if you are a new design leader, if you’ve recently been a practitioner and now you’re a manager, you are offering the craft help that you have just come from. But as you get farther and farther away from that, as you become a manager of managers, what you are mentoring, you’re not mentoring those designers anymore, but you’re mentoring managers on how they can do their new craft better. Jesse: Yeah. I think it’s really true that you and I might have a different point of view on whether a particular design solution is, you know, visually balanced to use your example. But we can’t even have a conversation about that if we don’t have a shared understanding of the concept of visual balance itself. So, In a lot of ways, the question is, does your design process have built into it opportunities to educate designers as to the considerations that go into your critique. Educate your designers as to the considerations that went into your craft that they should be mindful of. And it’s more about enhancing their mindfulness, enhancing their awareness, making sure that they are continuing to ask themselves the right questions as they’re going, so you don’t have to ask them, ideally. So this is a way of kind of commoditizing your own expertise in a way so that you can level up and be focusing your attention on more meaningful things. Peter: I mean, that’s the heart of leverage. Leverage is commoditizing your expertise. Jesse: Mm. Yeah. A lot of good stuff there. [theme music] Peter: Well, once again, we’re wrapping up another episode of Finding Our Way. As always, Jesse and I are interested in hearing what you have to say and think about what we’ve discussed today. So, find us on Twitter. Send us an email, and tell us what you think, and if you have ideas on what you would like us to talk about, please share those with us. We are looking forward to hearing from you and reflecting on your thoughts and comments in our future episodes. So thank you for taking your time to listen to us. Jesse: Thanks everybody. Jesse: What’s it called again? What are we doing here? Our podcast is called,  “Help. We’re lost.” Peter: That’s right. We were finding our way and look what good it did. Look what good that did. Jesse: Our podcast is called “Send someone to fetch us. We’re in Saskatchewan.”

In which we learn more of Peter’s recent adventures in design leadership, and we reflect on 20 years of Jesse’s Elements of User Experience. Transcript Peter: Let me do it. Jesse: All right. You got it. [theme music] Peter: Welcome to “Finding Our Way,” the podcast where Peter and Jesse welcome you on their journey as they navigate the opportunities and challenges of design and design leadership. As always, I’m Peter Merholz and with me is Jesse James Garrett. Jesse: Hello, Peter. Peter: Hi, Jesse. On today’s show, we’re going to follow up a little bit on our first episode. Jesse realized he had some questions for me about some of my work after Adaptive Path that we didn’t get to, that he was wondering about. And then we’re going to be talking about Jesse’s “Elements of User Experience” diagram, which celebrates its 20th anniversary in March. Jesse: Hooray. So at the end of the last episode, you were talking about that word balance and the need for balance between the design perspective and the business perspective, in the work of the design leader, and that they often are called upon to wrangle these creative energies, within a larger organizational context. So I’m curious about when you left Adaptive Path at the end of 2011, what were the problems that you felt like needed solving or that were really interesting or compelling to you, out there in the world as you were figuring out what your next step was after Adaptive Path. Peter: Yeah. So I left Adaptive Path, and I left consulting because I felt that the energy for design and user experience has shifted in house. You were seeing more and more companies building in-house design teams, but also kind of, I had felt a frustration, and I think you’ve shared it, right, working in a consultant capacity where you deliver great work that never sees the light of day. And I realized I want it to be inside the organization that is responsible ultimately for delivering these experiences and to be there when those thousand little decisions are made as something is getting delivered. And it’s those thousand little decisions that slowly but inexorably blunt the quality of the work that is ultimately shipped. And I realized I would be more useful in-house protecting design, protecting the work, protecting the quality. That that would be a better location for me.  Jesse: Right, right. So you had been working as a consultant obviously for many years. You felt sort of stymied in terms of what you could deliver from outside, and do you want to be better positioned to clear a path for success for design, it sounds like. Peter: Yeah, I mean, my–. So I’ve always had a personal mission and that personal mission evolved in bits and pieces, but tends to return to making the world safe for better user experiences. And I realized that in order for me to live out that mission, I needed to go where the decisions were being made that affected those user experiences, `and that just isn’t in a consulting capacity. You can influence them in a consulting capacity. You can try to get the ball rolling, and, and get good positive energy into the process. But really when we’re talking about delivery, it’s, again, all those little decisions that are made along the way, all the compromises you make to satisfy timing requirements, to satisfy engineering limitations, to satisfy regulatory or compliance needs, whatever it is, there’s all these things that, as a consultant, you’re not aware of, you don’t have access to, you’re not around to help think through, typically. And so if I was going to uphold my personal mission of making the world safe for user experience, I needed to go in house and do them. You know, I recognized that I was sacrificing a vision, sacrificing kind of that big, bold ideas, right? ‘Cause when you’re working in-house, you tend to be more incremental. You tend to be more iterative. Whereas in a consulting capacity, you’re usually brought in to think big and bold. And I was going to be sacrificing that top end of my creative potential in the interest of making sure that the things that actually get launched don’t suck. And that was the trade off I was not only willing to make, I was eager to make. Jesse: What constituted the kind of environment that you were able to learn from most effectively? What were you going after, in terms of what was going to drive your growth? Peter: I was headhunted for a role as the VP of global design at Groupon. And Groupon was a company that had actually interested me for a while, even though at the time their media presence was really negative, right? It was when there were all these news stories about how these small local businesses were being overwhelmed by a thousand people showing up with the groupon, on the same day, and they couldn’t deliver on the demand that the Groupon had realized. And so there’s a lot of negative press around Groupon at the time. But, I have a passion for neighborhoods, local businesses, small businesses, that kind of thing. And so when I found out about that opportunity, I was intrigued. I didn’t know what I was stepping into. You never really do until you’re inside. The leadership at Groupon were a lot of people who had been at Amazon and they brought many of those Amazon ways of working to Groupon. So it was a trial by fire on that kind of two-pizza-team approach to product development ’cause that was the Amazon way that they were bringing into Groupon. I got to oversee both product and brand design, and so I was able to take on a more holistic view of design. And then me being me, I was able to kind of treat this as a bit of an experiment. It was a Petri dish that I could try things out with because at the time, there were no kind of standards and practices really. They had grown so fast that there was little rationale behind how the company was organized internally. Where I ended up developing a lot of my thinking around organization design in-house was the work I did at Groupon trying to figure out, How do I structure my teams to deliver coherent, consistent user experiences, in an environment that otherwise wasn’t really set up to do that. And what I ended up doing was bringing a lot of what we had learned at Adaptive Path in terms of What does it take to deliver quality design? And I tried to figure out how can I abstract some of those principles and approaches, and then embed them into this more, quote unquote tech company, Silicon Valley way of working. Jesse: So it’s interesting to think that, the team at Groupon had to be in a certain shape in order for you to even really be able to realize that this set of problems existed for the organization because it’s like if they had brought you in to build a team from scratch, you would have had a sense of what to do and you would have built up something new. On the other end of the spectrum, if they had had a mature design team, a mature design function in place, with a leader, with a well-defined role in place that you could just inherit and drop into, that would have shifted your focus in a different direction. Peter: That’s right. When I joined, I inherited a group of about, at least on the product design side, about 12 men in their mid-20s. And having worked at Adaptive Path and other design contexts where I’d always had a gender equity in design, I had always had a range of ages, it was very bizarre stepping into this. This is October 2012 when I joined. So, end of 2012, beginning of 2013, and that was when I was first made aware of this job title, Product Designer, and that’s how they did it at Facebook, and at Facebook, designers own the design and there’s one designer working with a product manager and some engineers, and that’s the way we should do it, is what I was hearing from some people.  And when I was looking at that, I’m like, that doesn’t make sense to me. One designer can’t do all the things that need to be done well, and I found myself just kind of, pushing back against what was becoming accepted wisdom. And so my challenge and my opportunity as we were growing the design team was, how do we allow designers to  have their emphases right? Not every designer is going to be great at everything. Some designers are going to be stronger at interaction, and some at visual design and some at IA, they can be great at one thing, and pretty good at a bunch of things, but they’re not going to be great at everything. So how do we get designers working together in teams, like we had at Adaptive Path, right? Where you’d have two, three, four designers on a team with complementary skill sets. How do we do something like that internally? Became kind of my mantra, my thinking, my approach. And so my team at Groupon was, was basically built on a series of teams, that we’re meant to have this type of spread of skills in that they were meant to work together and collaborate on the designs that they were delivering. And then the challenge there though is that product development was happening in these two-pizza teams, or think about Spotify-style squads, right? Product development is happening, with a product owner and a group of engineers on a fairly small problem or a feature. And so I didn’t want a designer embedded on those teams. I wanted a group of designers working across these features. If I’m at Groupon, I’m engaged in a shopping experience. That shopping experience is hitting a bunch of these feature teams. I want my design to make sure that that experience is coherent. And that was the fundamental difference between how I’m working at Groupon, and how, say, things worked at Facebook, right? At Facebook, there was no expectation of coherence across products, ’cause if you dipped into the newsfeed and then you dipped into messenger and then you dipped into photos, that wasn’t a flow, right? It was this portfolio of apps. At Groupon, there’s a flow, there’s a journey that you’re on and I need to make sure that journey is coherent. And so that was my operating principle. And what led me to shape the teams at Groupon the way I did, which was not typical, right? I had to kind of invent it,  drawing from my experience with Adaptive Path and how design teams work, and then figuring out how can I hook that into how a contemporary product development organization operates. Jesse: I think it must have been a real challenge for you to, confront Silicon Valley orthodoxy in that way, especially when you’re up against the culture that is, I don’t want to say eager, but definitely ready to marginalize design, and definitely feels the gravitational pull of giving all of the power back to the engineers. And so I guess I’m imagining a lot of ideological evangelism on your part, with your peers, just to create space for them to go from, you know, from the zero designers per team to something like four designers per team. Peter: Right. Right. I was fortunate that most of my interactions and relationships were with product leaders and they were just grateful that a grownup had come in who had a vision for how this could work and could see it through. And so, understanding their concerns, making sure they knew they could reach out to me directly and immediately to address those concerns if something did come up, but just saying, “Hey, this is how we’re going to do it. Trust me. Let’s try it out.” The primary pushback I got, at least initially, was from my team. Right, I mentioned I had all these kind of cowboys in their mid-20s and they loved this maverick product designer role and, and mindset that they’re the designer and that they wield this special magical power within their squads when it comes to design. And I was moving away from that. I’m like, no, you’re not going to be the person, the owner, you’re going to be part of a team that’s working together. And some of my designers really reacted negatively to that. They liked working alone. They liked being the point person for design. And what ended up happening is those folks left, and that’s pretty typical. I’ve seen over and over again when a new leader comes in, some percentage of the existing team will leave, and that makes sense. The new leader has a different way of working, and then the people who are there are going to realize, like, “Oh, that’s not how I want to work. I came because of how it was before.” And that’s changing. And especially in Silicon Valley, there’s a lot of fluidity and mobility when it comes to work. And so people who don’t want something, they, they move on. But I was, I was easily able to, replace them, and beyond, with folks who did understand this way of working. Since leaving Adaptive Path, my year and a half with Groupon was probably the most informative and the greatest learning opportunity I had as a design executive.  Jesse: When you were at AP, I feel like your focus was really on developing a robust design practice, and that was the orientation, it sounds like, you took forward into these executive leadership roles, and then through those experiences, that evolved into a more of an organizational orientation. Peter: So while I was at AP, I was more involved with practice, but, you’ll recall, a lot of work done trying to figure out the architecture of AP project teams, creative lead, program lead, what their distinct roles and responsibilities were, what it meant to be a practitioner on those teams, as you and I became executive sponsors, what our relationship to those teams was, and I kind of had led that because as we grew AP, we had more and more people who wanted to be. creative leads, and we hadn’t defined the role well, the role, up for the longest time, the role was, well, however, a founder does it, as more and more people were doing it, we needed to be very explicit about what that role entailed. And so, I had done a bunch of org design at AP. When I went in house at a place like Groupon, I was still aware of process. And one of the ways I was able to make that realized was through whom I hired, right? I made sure to hire people who had a user centered design background. All the folks who I’d inherited were these product designers who had kind of taught themselves on the job, but had been very much, for lack of a better word, and this is going to sound dismissive, kind of these Dribbble designers, right? They were really good at polished shots, but they weren’t really good at thinking about  structures and systems of interactive media. And so, there was almost no user centricity. There was a small user research team, but they had largely been doing heuristic evaluations. And so from a methodology standpoint, when I came on, I made sure to bring on people who understood human-centered practices and processes, and I kind of let them do what they needed to do in their context. As a VP, your job is organizational, especially as you’re trying to recruit and hire and scale and grow. And that was when I realized there weren’t any resources for a design leader, scaling a team. You looked out on the web, you looked out in the world, and there was nothing for me to provide me a guide for how to do this. And that was when I realized there was something here to continue to pursue. So, so while I was mindful of practice and yes, at AP I had been very, very practice and process and methodology-oriented, I also had that understanding of organization. And then in my role as the design executive, I delegated the practice leadership to the people I hired and focused on the organizational design in my role. Jesse: I think that, sometimes it’s a question of scale. Sometimes it’s a question of the level of maturity of the organization and sometimes it’s a question of the culture of leadership of an organization in terms of how close the design leader stays to the design work over time. Awesome. Thank you so much.   [theme music] Peter: March 2020 is an interesting time, a special time, because it is the 20th anniversary of your diagram of “The Elements of User Experience.” If you go to, I believe, let me see if I can do the URL off the top of my head, http://jjg.net/ia/elements.pdf, you can see, “The Elements of User Experience” PDF, and it will say on it that it was published the 30th of March, 2000. And so, we wanted to, as we’re kicking off this podcast, we wanted to recognize this milestone. It was actually, that diagram was core to how you and I went beyond just knowing one another as bloggers and started to become professional colleagues and on the path to working together. How did the Elements emerge and what were you hoping to accomplish with it? Jesse: Well, you know, it’s interesting to reflect on because the state of web design at that time, at the turn of the century was such that there was a great deal of attention paid to aesthetics and to technology, but the practices that eventually would become known as user experience, we’re just sort of starting to bubble up around the edges. And, this was just starting to become sort of a legitimate job. At this point in my career, I had been doing content work on the web, writing, editing, managing editorial teams, and had started to see where content and design issues intersect and had transitioned into what was at the time called an information architecture role. And so I was the first information architect hired into a traditional, to the extent that there were traditions in web design consulting at that time, a traditional web design consultancy, which was very, very much modeled on a graphic design consultancy. It was very much how they structured the work that they did. And so I had to explain to a lot of people who had a more sort of traditional design background, what kind of work I did and how it fit into the larger picture of what we were delivering to organizations. And I found myself having to have this conversation over and over again, really just to sort of justify my existence at the table, and found myself in need of a visual aid to help myself understand the relationship between these ideas and to help communicate that relationship, and the elements model emerged out of that over the course of a few months of sort of noodling on it in late 99 and early 2000. Peter: So your initial desire, what you were hoping to accomplish was simply to help your colleagues understand what it was you do. Jesse: Well, yeah. And hopefully to help the organization be able to communicate to clients my value so that we had a clear shared understanding of what we were trying to accomplish and how we all participated. Peter: You release it, it catches on within a web design and user experience community, it gives you an opportunity to write a book that you’ve written a couple of editions for, based on the diagram, where you can flesh out the thinking behind it in greater detail. It’s now 2020, and people still use it. It is still, you still see it, it’s used in courses, I’m wondering what has most surprised you about the longevity of that diagram? If anything? Maybe you’re like, Nope, I expected this to have a 20 year life span… Jesse: Oh no. I mean, I–But… Peter: If you didn’t, what, what, if anything, surprises you about its continued relevance? Jesse: You know, one reason that I put a date on it so prominently on the original diagram was that I expected it to change. And, I expected to want to, iterate and evolve it. But I got it out there and, you know, so what happened was, I had been using it internally, and then I sent it to you, and you were like, “Hey, this looks pretty cool. Can I share it with some friends?” And I’m like, “Sure.” And then the next week we went to the first IA Summit. And somehow everybody there had already seen it. So it had kind of already taken on a life of its own before I even really got a chance to think about like, how I might want to, you know, change it. And then once it was out, I really felt like I shouldn’t mess with it too much. What has been surprising to me, is that, with very few changes, somehow it continues to speak to how people see and understand this work, all these years later, even though the work itself is dramatically different. Peter: How does it remain relevant? So this comes out, it’s a web world. It’s still a, I think largely, CRT world, we’re not that far removed from 8-bit Netscape, color cube, dial-up web, right? And it’s not a broadband world yet by any stretch. And now we’ve got mobile, we’ve got emerging platforms, everyone has a high speed connection in their pocket. Yet somehow it remains relevant. And I’m wondering what you attribute that to, and if you’ve ever considered updating it, given all these kind of technological evolutions. Jesse: I haven’t felt a need to update it. I think, in part, it’s not in my nature to want to spend a lot of time dwelling on things that I’ve done already. My inclination would be to make something new rather than going back and trying to continue to sort of stretch and extend the old thing to fit whatever has changed. Okay. So my philosophy has always been that, Elements has a life of its own, and that life is going to have its own cycle that I can’t really do anything about. And, it’s up to other people as to whether or not Elements, you know, stays alive, as long as they continue to find it useful.  Peter: Right. What impact did you hope to have, developing this, this model, this diagram, this framework for thinking about user experience? Jesse: I wish I could say it was that strategic. I think you have to separate the diagram from the book in some ways in that they are slightly different tools. That are created to meet slightly different needs. The diagram is really something that you would sit down with somebody and use as a tool. Whereas the book exists more to, sort of empower and enlighten the designer.  And so in terms of big picture impact, it’s trying to empower as many designers as possible. But again, the thing got away from me so quickly that I don’t feel like I am really the one driving the boat here. Peter: So there was this need in the late 90s / early 2000s as more and more people are recognizing they need this type of work done. There’s folks who are like, “You don’t really understand what you’re getting into. Let me, let me make sure you understand kind of the breadth and depth of the situation here.” All right. And just simply providing that kind of map of the territory. You thought you were just living on the city block, but it turns out there’s this whole neighborhood around you that affects what you’re doing and you need to be familiar with. Jesse: You know, I think Elements was very much a product of its time for something that has turned out to be as enduring as it has. I think that it would be very difficult for something like this now to have the kind of impact that this had, at that time, there is just so much stuff now. It’s really, it’s kind of hard to imagine a diagram taking the field by storm at this point, which makes it even stranger to reflect that, that ever happened at all.  I have these experiences all the time with strangers, because of the book. I was in a parking lot here in Oakland about, mm, three, four weeks ago, loading groceries into the back of my car, and a woman, black woman probably in her mid-thirties approached me in the parking lot, and she had her like six-year-old little girl with her. And she walked up to me and she asked if I was me and I told her that I was, and she thanked me for the book and thank me for the impact that the book had on her as she was trying to find her place in the world. And something in the book spoke to her and gave her a direction. And, now she’s leading a design team, and having that experience over and over again has been an extraordinary gift. Yeah. To see the impact that it’s made on individual people in their lives as they’re finding a sense of direction and a sense of purpose through the way that I have articulated this set of problems in this set of ways of thinking about it. That’s been far and away the best part of all of it. Peter: I realized that I’ve been emphasizing using the diagram because that’s what I have a relationship with much more than the book,how evergreen has the book proven to be, and is that something that 10 years after the second edition, do you get a sense that people are still buying it? The people are still finding it relevant? Tell me a little bit about that journey with the book. Jesse:  The book is doing great. It sells a very consistent, sort of steady, number of copies every year. Entirely accidentally, it turns out that the framework of elements is a great introductory text for a UX program. So, many people find themselves reading this book in school, as they are first exploring this career path, which is how it’s been able to have that kind of impact. And then they keep it, and they take it with them and they refer back to it and they bring it to their jobs and they recommend it to their coworkers and all of this stuff. So, I can’t really speculate as to the breadth of impact of either the book or the diagram, but I will say that I feel like the book has probably had a deeper impact on people. Peter: What has been the most common legitimate criticism that you’ve received? Either of the diagram or the book that you would like to address now. Jesse: Well, you know, it, it always smarts for me when the content people look at the diagram and say, what about content? Because I’m a content guy, you know, as I said, my roots are in content, and there are many, many considerations involved in content strategy that I would not attempt to put into this diagram.  And I think they do have a legitimate complaint in that it’s not comprehensive. Peter: But, it looks,  as I’m looking at the diagram right now, there’s something almost Kubrickian about it, right? It’s symmetric. It’s evenly weighted.It feels so whole and internally consistent that it doesn’t really invite, like, “How do I engage with it?” I just receive it. Jesse: Yeah. Well, that’s true. I mean, there have been many people who have done, you know, rifts or elaborations or extensions, of the model. There are people who have, like, seven layer versions and nine layer versions and stuff…  Peter: No kidding. Jesse: Yeah, yeah. I, I don’t, I, you know, there’s, I, I have seen so much of that stuff flow by over the years, so many student projects. So many conference poster sessions many of them really smart and interesting and thoughtful, some of them a little sort of, overenthusiastic perhaps. Peter: I mentioned Kubrickian right. And now thinking about the monolith, right. It feels like just this perfect jewel that you can look at it, but don’t touch. Jesse: Yeah. Well, you know, honestly, it feels a little bit like that to me too. I mean, it does sometimes feel like Elements is kind of a thing that happened to me.  And having made this sort of perfect, hermetically sealed little structure. I don’t know that I can crack it open any easier than anybody else could, you know?  Peter: That’s fair. That’s fair. You know, I remember talking to you probably pretty early on when we were working together, and I remember you saying like, “This is just how I see things,” which is not how I work. I’m a very verbal person. I tend to process initially through writing and if I diagram, it’s not a highly visual diagram. It’s at best, maybe a two by two here or there. But I got the sense that your initial mode of analysis as you look at the world around you, there was just a kind of visual information processing that was going on there. Do you still find that, that, visualizing mode that you’ve have had, does that still come to bear? Do you still see these things in pictures? I guess that’s another way of saying, are we to expect to any thing like that anytime soon? Are you working on any models? Jesse: “When are you going to make another one?” Peter: Yeah. Not that specifically, but, ‘cause I’m guessing you’re trying to make sense of the world around you and the way you do that is through these visualizations. How is that going right now, if at all? Jesse: Yeah, I mean, I do tend to use a lot of diagrams in my work. Sometimes they are more useful to me than they are to the people around me.  I Understand the relationships between ideas geometrically. When I am working through a problem, I am often working with abstractions that had been made concrete, in a visual way in some way, and I, this is not uncommon, I mean, this is a way of working that’s familiar, I think, to a lot of people who do design work. And so it’s always naturally going to be a part of what I do. I do think that the spirit of Elements, which is, tools for conversation, tools for creating shared understanding, tools for creating a common language. I mean, we hadn’t really talked about the way in which this work at the time didn’t have an overarching label. Before Elements. A lot of these various terms were used in muddy ways. You may remember the three conflicting definitions of information design that were floating around circa 1999. At least three. There was a lot of muddiness in terms of the terminology… Peter: Well, I’m glad all that terminology stuff has been cleared up now. Jesse: [Laughing]  It gave us a place to move forward from. And I think that is a theme that continues for me is trying to find ways to crystallize and instantiate, our current understanding of things to give us something to push off of and something to move forward with as we continue finding our way. Peter: Is that your sign that you need to sign off? Jesse: Well we have about 90 seconds. Peter: Well this is great. I actually learned some stuff I didn’t know about the diagram inandyour process and experience resonates a lot with me. I think if there is a lesson to be learned and it’s one that you, and I, I think,  have preached for years, is, share, just share with the world the things that are rattling around in your head that you might think are really only relevant to you. And many of them will only be relevant to you, but occasionally something will, get out there and really catalyze and crystallize with a broad swath of people, and honestly help move things forward.  Jesse: It’s how we move forward together. Peter: Yeah, exactly, as we find our way together. So on that note, that’ll wrap up this episode of Finding Our Way. As before, we are eager to hear from you. We are easy to find. I’m @peterme on Twitter. Jesse’s @jjg on Twitter. You can go to the website. We will have an email address there. We would love to hear from you. We would love to hear what you are thinking about what we’re sharing, other stuff that you would like us to share,  especially here at the outset of what we’re doing, as we’re finding our way to finding our way. So, with that, thank you Jesse, and, goodbye. Peter: A minor, slow motion, anxiety attack. That pretty much lasted through the evening a little bit into my sleep. So I’m great. How are you? Jesse: Oh, I, I, you know, I don’t have your emotional investment in the NBA, but, I had a similar experience last night, of,  yeah, just sort of this mounting helplessness, that, I decided to burn off by going to Safeway and, finding out what kinds of things, they might have that I might want to have around. So I got myself some toilet paper and some paper towels and some acetaminophen, and I came home feeling better.

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?