Finding Our Way

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7: Leading From Home May 26, 2020

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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, tha…

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6: Defining Your Charter, Part 2: The How May 19, 2020

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In which we break down the components of a team charter, and the ways it helps design leaders, particularly with people matters of recruiting, hiring, and retention. Transcript Jesse: Previously on Finding Our Way: Peter: Today we’re going to dig into how design teams define themselves Jesse: If you keep doing the same things that you’ve always done, you’re not going to be successful anymore, and you are selling your skills rather than your purpose you have just sort of instantly commoditized yourself right from the start you can get a long way without, defining a sense of purpose for yourself. Peter: The idea behind purpose is to answer this question. Why do you exist? Why does this team exist? Why do we have a team doing design, product design, brand design, whatever kind of design? Why? Jesse: So I think that the big question that I would have in response to that as a design leader is, “How do I get started? Like what are the tactics for arriving at this thing that is obviously going to be really important to my success as a leader, having never done this before. Where do I start? Peter: I think it’s going to take me longer to answer that than I currently have time for. Hold that thought… Jesse: Great. That’s great. Well, we will hold that question for next time. And now, the conclusion. 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. In the last episode, we teed up the importance for a design leader to be explicit about defining a purpose for their team to better establish that team within the organization. In this episode, we dig into the specific steps you can take to articulate a charter. Jesse: Hello, Peter. Peter: Hi, Jesse. There are a set of steps that you can take to get there. When I’ve led this exercise, I tried to involve as much of the design team as I can. So when I joined Snagajob, at the beginning of 2017, it turned out that the entire design team was together in one spot. We usually were in multiple different offices, but there was an all-hands for the whole company, so we were able to take advantage of that. And I had 17 people participate in what I’m about to talk about. If your team is larger than that, you probably need to pick and choose, just to make it manageable. But it’s essentially either a workshop or, more recently in the era of everybody working from home, a series of work sessions, close to one another, just because it can be hard to focus on a video conference for eight hours. But it’s essentially to go through a series of exercises to define six things. The most important is being clear about your purpose. Sometimes you would call that a mission statement. And the way that you get at your purpose or mission statement is actually fairly straightforward or even simple. Conceptually, it’s hard to do. But it’s to answer the question, “Why does this team exist?” Literally, that’s it. Why do you exist? Usually, you put that question out there, [then] What I have them do is have everybody come up with three or four answers to that question, and then we do grouping exercises and discussions and all to kind of get a sense of where the patterns are. So we had all these types of topic areas and then we did some voting to identify what were the top three that we would want to move forward on and have our purpose statement rest upon. So you don’t come out of it having written the purpose statement, you come out of it with phrases and clauses and concepts to inform our purpose statement. The act of actually writing it you do separately. It’s also, I find, typically a job for one person to do a draft of. If you do have kind of content strategists or strong writers on your team, usually the executive working with a writer to craft this. Jesse: You know, this is interesting to hear you talk about this just because I think a lot of the advice, and frankly I think a lot of the instincts, especially of the new design leader who is moving into this role for the first time and taking on new responsibilities, the instinct is to step up, take charge, take ownership, take authority. And to the extent that you do end up engaging the team in a scenario like that, it’s often simply in the role of providing targeted validation of certain aspects of what you’ve developed or perhaps recruiting them to support the socialization of these ideas to the team in some way. And so it’s interesting to hear you describe a different kind of a process and approach that is more collaborative, that is more broadly inclusive than the lone genius design leader slaving away at the details of the charter by themselves in their office. But I find myself curious about that need to assert that authority and to assert that authorship and I find myself wondering whether it’s enough for the design leader, from that position of facilitator of a more collaborative team-based process, is it enough for them to be able to hold the authority and wield the authority effectively within that context? Peter: I think that is what’s enough. So, so, as a design leader, you could choose to articulate your team’s charter all by yourself. I would discourage that as I think you want the team to feel that sense of ownership. And so the design leader is in a position of unique power and authority in the group and what I’ve done as the head of design is to get out from everybody else what they’re thinking. That helps me understand where their heads are at. Oftentimes the team comes up with stuff that I hadn’t thought of. That is great. I remember at Snagajob, one of the value statements. So, that’s another exercise that you do is come up with a set of value statements. And one of the value statements that came out of that team was “fearlessness.” That’s not anything I would’ve come up with on my own. But I really liked it and it became one of the value statements that we, we, utilized moving forward. So I think there’s a role for the design leader to create the space that allows the team comfort in generating these ideas. And then the design leader becomes the editor essentially of this. They take all this input and they help nudge it and guide it towards the strongest outcome possible. Because you’re going to get more input from your team than it makes sense to put out there. You’re not going to simply reflect everything that the team has contributed. there’s two mechanisms by which you focus all that content. One is dot voting. We had all these themes for what could be in the mission statement. We had 15 different themes. We can’t have a mission statement with 15 clauses. So what are the two or three that we really want to focus on? Dot voting helps you get a pulse check in the room. But then the other mechanism for refining is that leader’s judgment. And I always allow for that executive privilege, in these contexts. Because the leader has an awareness of things that not everybody knows, right? The leader’s in certain conversations with other leaders and just has a broader view that is important and should be brought to bear. A good leader is often more pragmatic than their team members. The team members, through these exercises can be very blue sky and, “We’re going to change the world!” and, high-minded about the impact that they want the team to have, and leader can be more pragmatic, not to, you know, squash these dreams and ideals, but to recognize that there’s also a reality that this is all taking place in. That they are accountable for it as the leaders, so that they need to manage that. When I was running the design team at Snagajob and we did our value statement, we had these four values that came from the team: fearlessness, quality, evidence, and humility. Those all came from the team. And I realized there was an additional value that I wanted us to uphold and to continually be thinking about, which we called context. And did that because I was trying to get this design team to be approaching their work in much more of a service mindset as opposed to a series of screens. And at the heart of the service mindset is recognizing the context in which any interaction is taking place, or rather every interaction is taking place within a broader context and to be continually aware of that broader context as you make your decisions. And so that was the one thing that didn’t emerge. Not a lot of people voted on it, but I’m like, “This is important.” And so I’m not going to overrule on these other things, but I’m going to add my contribution that I think speaks to something that, frankly, the team wouldn’t have generated themselves. Jesse: You know, you touched on this idea of the leader having an awareness of things that not everybody knows, and I find myself wondering about the potential risk or, you know, the possibility of a pitfall there for the design leader in potentially over-exercising, not even necessarily intentionally, over-exercising that executive privilege, that ability to tip the scales in favor of one idea or another. In particular, when the leader is using their elevated awareness of what’s going on in the larger organization to influence their own mandate toward organizational norms in a way that may not actually serve the needs of the design team. In a lot of cases design teams need to be at the cultural vanguard. They need to be change makers. And that means, in some cases, they need to define the ways in which they are not in step with the larger culture of the organization. But I think that in a process like this, it can be very easy if you’re the only person in the room who sees something, and everybody else doesn’t see it or doesn’t have the same information that you have, you can develop a distorted sense of how important that information is, how important that perspective is, and especially if you are someone who has the unilateral authority to put things into the final charter, the temptation to exercise that authority, to represent those viewpoints that are not represented by everyone else in the room can become pretty strong and it can lead to, I think, a distortion of the charters. So I wonder what you think about the potential risk or concern there. Peter: I think that’s a reasonable concern and risk. The design leaders should be engaged in this process from the perspective of the design team looking out, When you’re doing your charter work, including this purpose statement, you want it to be from the inside out. What does the design team believe and know and understand about itself that it wants to project out into the world? To help others recognize how the design team wants to contribute. And so while that design leader is balancing this broader awareness of the organizational reality with the desires and aspirations of the design team, I would encourage design leaders to weigh the design team’s desires greater than that organizational reality. And to instead encourage a purpose statement and this charter work generally to push beyond what the rest of the organization outside the design team would be comfortable with. That’s okay. That’s probably a sign that you’re doing it right? If you’re a design team, and the charter plugs right into whatever this broader organizational system is, you’ve probably done too much editing ahead of time, and you’re not enabling the design team to express and realize its potential. Jesse: Well, yeah, and obviously at the same time, and this may in some way contradict what I was saying a few minutes ago, but at the same time, the design leader can’t be held in thrall to the desires of the design team. The design leader does have a role to play in this process beyond simply being the authority in that they do have to bring their own perspective to it. But that broader perspective that the leader brings to the process has to be kept in balance with the view from inside, the view that is oriented toward the team’s values and the team’s sense of its own identity. Peter: Right. And, you’re hitting on what I think is another core element for any successful design leader, which is an ability to know how to strike the appropriate balance in everything they do. We were talking about how, earlier, one of these core elements was that the medium of design leadership, and probably any leadership, that medium is relationship. So I think that’s a core element. Another core element for any successful design leader is knowing how to balance a set of, not necessarily conflicting forces, but mitigating forces in whatever decision they’re trying to make. Design leadership is decision-making. As you become a design leader, now you’re balancing being a good team player. It’s important for design, in order to have the impact it wants to have, designers must be seen as integrated into the product development and/or marketing efforts of the broader organization. And so there’s a need to be a good team player, but it’s also important for the design team not to lose its identity as it integrates with these others because there’s a particular perspective, a particular set of practices and skills, a way of working that is distinct to design and that is valuable. So you don’t want to be unicorns and rainbows on one end, and it’s all sparkle, and no practicality. But on the other end, you don’t want to be crank turning, designs by the pound, simply to help product development release the next feature on time. And so, in everything a design leader is doing, they’re making judgment calls between these different forces. And the other thing to recognize is you’re going to do it poorly at first, probably. Your judgment is something that you build over time through doing it. So it’ll take you a while to hone that judgment. For the sake of what we’re discussing here, in particularly returning it to this notion of defining a team, defining its purpose, there is going to be a push and pull between, the team’s aspirational goals for itself and the impact it can have on the world, and the organization’s kind of pragmatic expectation of what the team is delivering and how it fits within those broader organizational goals, and it’s the design leader’s role to navigate that balance. So getting back to, what are the components of a charter? How does a design leader build a charter? I went into some detail in talking about the purpose statement. The structure is basically the same. It’s just the content that’s different. So the first thing to do: Articulate your reason for being in that purpose statement. Answer the question,”Why do you exist?” The next thing to do is to articulate your team’s values. What are the principles of your team? What is it that they uphold? What do they value? What do they align behind? So at Snagajob, the, I mentioned the, the five values that we had, humility, evidence, quality, context, and fearlessness. These were the things that we were going to uphold, particularly in light of difficulties, right? Values are what you use to return to, to know where you’re not willing to bend, much less break, but what you’re going to hold fast on. So you do a similar exercise generating values. Then, it’s important to understand how you work. Values are about a mindset. So how do those values turn into a set of practices? You want to articulate a set of internal norms for how the team relates to one another, and then a set of external norms for how the team conducts its business with other groups, either within the business or possibly people outside the business. A popular understanding of internal norms these days is that of radical candor. So this is a norm that teams are developing in an effort to be able to work together directly and honestly. In design, it’s usually in contrast to what in the radical candor model is called ruinous empathy. One of the design teams I’m working with right now, in fact, s…

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5: Defining Your Charter, Part 1: The Why May 15, 2020

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In which we look at the purpose behind defining purpose, and discover some unexpectedly useful new frames along the way. Transcript Peter: Welcome to “Finding Our Way,” the podcast where Peter and Jesse welcome you to their journey as they navigate the opportunities and challenges of design and design leadership. I’m Peter Merholz, and with me is Jesse James. Garrett. Jesse: Hello, Peter. Peter: Hi, Jesse. Today we’re going to dig into how design teams define themselves within their companies and the challenges design leaders have balancing the team’s desires with the organization’s expectations. Jesse: You know, we’ve been talking about the challenges of the new design leader and often the new design leader is the first design leader that an organization has had. And that carries with it its own challenges in really setting the tone for how the design organization is going to be received by and interact with the rest of the organization for probably a long time after you’re gone and other leaders have taken over. There is a really, I feel like there’s this strong sort of imprinting process that happens with early leadership teams where aspects of how they approach problem solving, how they frame what they do, how they, engage with each other, the tone that they set for their teams, all sort of carries forward far beyond them. And so the choices that a new design leader is making as they are leading the formation of a new design team are particularly critical, I think, because they have long term consequences that can’t always be seen upfront. Peter: I think that’s true. I think there are a few different types of design leadership challenges when it comes to team definition. I think there’s what you addressed, which is that initial design leader, possibly, you know, first, second, third designer, maybe more senior than others. The company they’re working for starts growing. They start recruiting and hiring and at some point, the team gets beyond what can be handled informally and they need to figure out, “How do I manage this? Now we used to all be able to sit around a table and now we’ve got 15 people in three countries. And we can’t lean on the informal practices anymore.” So that’s one model that I see. But there’s different challenges that you face when you’re the new design leader inheriting a team that has evolved before you showed up and what you end up doing in order to help the team grow from the point at which you’re taking it on to wherever you’re going with it. And even, in both of those contexts though, as I reflect on it, I think what ends up being valuable is the same thing, because, it’s this matter of definition. I think perhaps the second type of leader, who is assuming leadership of another team is probably more conscious of the need of this, because they’re often assuming the leadership of a team that has not been well-defined. But it’s 10, 15, 20 folks in there and so an obvious kind of quote “leaderly thing to do” is to do some work to define it. What I think is less well appreciated is for those folks who are that first leader who’s been building something where the informal practice has worked so well for so long to then come to a realization, three years, four years into this, “Oh, this has gotten bigger than I can handle directly. What do I do?” Sometimes those folks realize, “Oh, there are practices I can engage in to help define the team.” That’s, that’s been my experience now as a consultant, where I literally have one company that I’m working with in one design leader in particular who fits this profile almost to a T. They were the first or second designer… it’s a tech company. I’m not gonna give too many specifics, but, they were the first or second designer. they were more senior, when they joined, than the other people on the team. They might’ve even led design in prior contexts, I think in an agency context. They had it built and hired a real design team. And so as design–, as this company grew and design grew, they were the ones growing it, and they’ve gone from two to now, I want to say 16 or 17 designers. This is all product designers, in three or four different locations, including overseas, including in Europe. And, at the beginning of this year, this design leader did a check in with his group to see how things were going and what emerged from those conversations was a recognition that they needed to do work to define themselves better. That it had just kind of tipped probably somewhere, in that going from 10 people to 15 people that it tipped to where their lack of clarity around who they are as a team, what value do they serve, what value do they deliver? What are their values that they uphold? How do they recruit and hire? How do they know what work to take on? All that kind of stuff that, again, they could handle informally when they were smaller fairly easily. You know, this guy now has managers who are managing people and he’s not able to engage with all those people directly and he needs to put practices in place and have a reference point to shared understanding that can represent the definition of the team when he is not there because he can’t always be. Jesse: Right, another case in which this chartering activity comes up is when there’s a change of executive leadership above or beyond the design group. If you have major shifts of executive leadership among your peers, whether that’s, you know, engineering or marketing or whatever the other, organizational functions are, there is potentially a need to reintroduce yourself to people and to establish a baseline for a new relationship. and if you’re not walking in the door with a clear sense of who you are, that relationship can really get screwed up right out of the gate and can take a lot of effort to untangle down the line. Peter: I think that’s exactly right. Upon reflection, I haven’t had that experience but I know that experience is true. And I know what often happens is if your design leader has a new boss, new head of product, new head of marketing, new CEO, if they are not out in front of establishing a positive relationship with that person, what almost inevitably happens is that new boss brings in someone that they feel comfortable with from prior relationships. So there is an opportunity to. get out in front of that and establish that relationship. But, if it isn’t done with intention and explicitly, that existing design leader might find themselves–I think what happens is they’re, they’re usually not let go, they just find themselves having a new design leader brought in over them. That is this new executive’s connection that they’re, that they are bringing in. Jesse: That is a pattern that I’ve seen where the executive leadership knows that the design leader has the trust of the design team and has the operational capability to continue to deliver, but doesn’t trust them as a strategic partner. And so we’ll introduce a new layer into the organization, maybe something that feels sort of fabricated, really in some cases, to create a reason for there to be this interstitial layer that diminishes the design leader’s influence. And ultimately, I think, paves the way for the design leader’s exit. And bringing in somebody who is somebody that the executives can more easily relate to. Peter: I think that’s right. I think it speaks to a challenge that many design leaders will face, particularly those early ones who grow a team, is that the folks around them continue to associate that person with who they were when they started and not who they have become. So it’s important for that design leader to reintroduce themselves with some frequency as they evolve so that they’re not being put in boxes by other people. Jesse: Yeah. Well, that’s a huge challenge. It’s a huge challenge because we all carry these unconscious biases and assumptions about who people are. We create shortcuts in our brain all the time, just to help us deal with the number of people we have to deal with in our daily lives, and we don’t often consciously review those shorthand ideas that we develop about people, especially those first impressions or those early impressions. I’m curious though, why aren’t designers naturally sort of good at this, right? We’re used to telling stories about our work. We’re used to being able to articulate rationales for things. Why does this prove challenging for so many organizations, do you think, for so many design leaders, to carry that capacity for explanation, that capacity to illuminate, into defining a sense of purpose for themselves? Peter: One thing I would potentially push back on is that designers are at least universally good at providing a rationale… Jesse: Yeah. Peter: …for their work. That’s a skill that many develop. In any design leader, hopefully if they are seen as a leader, they have developed that skill where they can help others understand the rationale behind a set of design decisions. I think, though, a couple of things get in the way here. Designers and design leaders are frustrated that what is obvious to them is not obvious to others, in terms of evident value, Well, they get frustrated at first. They think it’s obvious that there’s this value, that this team is able to deliver certain–, is able to do good work, is able to deliver a certain impact, is valuable. Many design designers and design leaders feel that their value should be intuited, when in fact more work needs to be done to make it explicit. But because we as designers recognize the value in what it is we’re doing and we understand somewhat viscerally or at a gut level how we are contributing, at first, we think others have that same understanding and so we don’t realize when others don’t share that understanding of the value that designers are delivering in the same way. Then we get frustrated when we realize that, and we get kind of peeved that like, “Really? I have to convince you that I’m worth it? I have to convince you that design matters?” And depending on the environment, the answer often is yes, you do. So, to answer your question, the designers and design leaders recognize their own value and assume others do as well. And so they don’t get out in front of crowing about their value and evangelizing the good work that they’re doing and evangelizing the impact that they’re having, because they don’t think they need to. When I teach workshops on design leadership, one of the things I stress is the need to evangelize and over-communicate, that the design leader’s job isn’t done until they hear back from others what they’ve been saying to them. And it might take five, 10, 15 iterations of you saying that thing, you talking about the work that your team did on delivering some project and the impact that it had, or talking about how important it was to conduct this user research because it led to insights that led to some innovation. You need to say that over and over again. And you know it’s working when you finally start hearing it back from others. But design leaders feel, 1) that again, the impact should be evident. “Why do I have to tell you why I’m valuable? When it’s there, it’s in the data. It’s obvious.” So that’s one frustration. Another frustration is that a lot of design leaders feel sheepish about selling. They think it’s marketing. It’s, it’s sales-y. It’s not authentic to evangelize. You know, we roll our eyes when the sales team does their high fives and shout outs, when they ring the bell, when they make a sale, we think that’s all kind of hokey. And so we don’t do that kind of thing ourselves because it feels inauthentic. So we get in our own way that way. Right? ‘Cause we have to keep it cool, man. Cause we’re the designers. And then designers often tend towards an introverted way of engaging with others where they don’t speak up unless directly asked. If asked, they’ll say what they’ve done and they’ll talk about the team’s good work, but if they’re not asked, they won’t put it out there. And design leaders need to get over that quietness and that willingness to just kind of hang back and let the product people, let the marketing people, let the sales people have the mic at the all-hands. The design lead has to get that mic and talk about what it is they’re doing and be explicit and intentional in that communication, because no one else is going to do it for them. Jesse: Well, what do you think that’s about? What is it? ‘Cause it sounds like what you’re describing is something that is in the personality makeup of people who do this job. And that is you know, an interesting thing if we collectively as a group have to get some self-confidence training. Peter: What is it about, well, that’s, there’s some deep psychology going on there, right? I think a lot of people end up in design because they like to make, and making is largely a solo endeavor, right? There’s collaboration and there’s coordination and there is working with others, but as a designer you can spend a lot of time with those headphones on, focused on a problem and just digging deep. And so it attracts a personality type who can spend literally hours on end by themselves working through these types of problems. You know, if you’re a glad-handing social person, you’re not likely to end up willing to do what it takes to be a good designer, and so you find a different direction to go in that accords with how you engage with the world. Now, I don’t want to oversimplify it. There are extroverted designers, there are introverted salespeople, right? These are tendencies. These are not rigid, hard and fast rules. But one thing I have noticed, ‘cause I’ve talked to a lot of designers and a lot of design leaders in a lot of different teams and a lot of different environments, is that inevitably the designers who bubble into these leadership roles and succeed are those leaders who are more comfortable in that engaged mode. I’m thinking of a few of the leaders I’m currently working with right now. They’re all very personable. They’ve got a certain charm and a charisma. I sense it in their interactions with me and I can see it in their interactions with their teams and they’re not necessarily better designers than anybody else. They’re not better creative directors than anybody else. But the reason they’ve been able to elevate into these leadership roles is because of their personability and that has what’s given them that leg up on their peers in terms of who gets promoted, who’s put in charge. You want to put someone in charge who is able to work well with others. Jesse: So it sounds like you’re also speaking to the–, there’s a necessary degree of salesmanship that is needed, not just in the development of a charter, but it is needed on an ongoing basis in order to be a design leader. Peter: Yes, definitely. I mean, as we, I think, talked about a couple of episodes ago, some of the most successful design leaders we know were not designers, but were really good sales people, right, and, so, the challenge for that more modest design leader, or person who aspires to be a design leader, is to figure out– you used the word self-confidence before, and I think that’s part of it, but I don’t think that’s the only aspect of it. I think yes, they do need to develop that self-confidence and self-esteem, but they might have that. They just need to recognize how others perceive them and how their behavior enables or inhibits their desired impact. They need that kind of self-reflexiveness. Jesse: One thing thematically that I hear us coming back to, as this conversation continues to unfold, is that if you are a design leader who has come up out of design, there are going to be ways in which being a design leader is very much like being a designer, and they’re going to be ways in which being a design leader is nothing like being a designer. And in fact, you may need to unlearn some of the things that served you well as a designer in order to be suc…

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4: Management Leadership Jazz May 06, 2020

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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 expec…

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3: Range and Craft Apr 29, 2020

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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 pro…

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2: Elements Turns 20 Apr 29, 2020

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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,…

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1: The Story So Far Apr 29, 2020

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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 ever…

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