Finding Our Way

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Transcript What follows is a lightly edited transcript produced by our podcast software. It may retain some textual glitchiness. Jesse: I’m Jesse James Garrett, Peter: And I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership. Jesse: On today’s show, “mission critical” takes on a whole new meaning when you’re the Chief Experience Officer for the United States Air Force. The first person to take on that role, Colt Whittall, joins us to talk about getting things done when you have more influence than authority, finding meaning and purpose in government service, and taking risks in an environment where failure is not an option. Peter: So Colt, what I’m curious about is, I think this is a new role, right? This role didn’t exist before. I don’t know if it was created for you or if someone had the idea and then found you. But why were you the right person to be the first Chief Experience Officer at the Air Force? Colt: So, great question. First of all, yes, this was a brand new role. Well, let me just tell you how it was created, and then we’ll talk about, why was I picked to do it? So it was, it was really created because the Air Force knew we had a user experience problem, primarily with IT but also with software. We had a lot of complaints. And this has been going on for years, and I think there was a general sense that maybe things were getting worse and not better. And so the CIO at the time knew he had an issue. He also had an understanding of the importance of software, which, the CIO role is a little different in DoD, their control of enterprise IT is fairly direct, but their control of applications is less direct as in a corporate environment. There’s generally control of those that’s spread out amongst a bunch of different organizations. He knew he had an issue. He had some authority over it and wanted to create this role. Then why me? I came out of about a 20, 25 year career in the digital agency space, digital consultancies. I was at Deloitte in the nineties, built one website after another and mobile app and so on from. 2000 to 2018 with a digital agency that we spun out of Deloitte and did a lot of fantastic work in a variety of industries, media, health care, wellness, travel, hospitality, financial services, and some federal government. And Bill Marion, the CIO, had been a client of mine at one point. And so I had a, probably a fairly typical background for people that listen to your podcast, right? A mix of digital strategy and user experience and customer experience. And by 2018, I was at the equity partner level, practice lead kind of level. And we sold the company and we were looking to get out. And so that’s what I did. And took a little time off. I had always had an interest in federal government and user experience and technology in the federal government. And when I was in graduate school I pursued it a couple of different ways and kind of built on that. Did internships in DC. One of them had to do with high definition television. I worked on the high definition television project for AT&T, interacted a lot with their government affairs group with Bell Labs up in Summit Hill, New Jersey. And then I did an internship with the FCC. It was set up by my thesis advisor, who’s named Dale Hatfield. And worked on the first ever narrowband PCS auctions. This whole idea of the intersection of technology and government’s always been a big passion of mine. And so after a career in the digital agency space , I happen to know some people in government. I approached Bill Marion, Bill Marion had a problem. He knew me, didn’t know a lot about me, but he, he knew enough about me. That on LinkedIn , I basically just said, “Hey, Bill, I’m thinking about going to work for the government for a while.” In my mind, I’m thinking US Digital Services or something like that, which you may have heard of. I wanted to talk to Bill because I knew him and I need a little advice. Like, how would I even go about this? , I don’t want to just go looking for, jobs on USA Jobs and just start submitting resumes. I’m like, there has to be a better way. And Bill responds on LinkedIn five minutes later, says, “meet me at the Pentagon on Tuesday.” That’s literally what he said. And I flew up and I met with Bill and we started talking about the challenge of user experience and performance across IT and the Air Force. And I think we began to formulate what this role could look like and that’s really it. Most of my background, as you just heard, is more in the software and application, and more consumer and outward facing. However, a lot of the tools we need to fix our problem internally for airmen– which is what I focus on, I barely touch the external facing web stuff at all– but a lot of the same tools apply internally for the applications and systems and IT that airman use. The Scope of the Chief Experience Officer Jesse: So I think it might be a little challenging for folks to conceptualize what those needs might be inside the Air Force. Why you would need a chief experience officer. I would love to hear a little bit about, to the extent that you can without committing treason, the communities that you serve, a little bit the broad use cases that you’ve served just to get a sense of the scope of the challenge that you’re really talking about here. Colt: Sure. The scope is huge. I mean, first of all, think about all the missions that we do, right? You know, first of all, we’re the, air force and the space force. Jesse: Right. Colt: Delta Airlines has, I want to say eight or 900 planes. We have over 6, 000. All right. So it’s huge. And we have a vastly wider range of aircraft, right? Both fixed wing, rotor, drone, all of it. Right. Plus we have the space force. We fly satellites. We work with contractors that launch us into space. We do all of that. Right. Then we have land base missiles. We have air defense type stuff and radar installations of all types. All of that it, all of those systems have an IT component to it. All of them, right? Just one, for example, we’re replacing the Minuteman missiles that sit in ground based silos. It’s a program called Sentinel. That will have big deadlines coming up over the next few years because we have certain timelines that we have to hit. But there are 10, 20, I don’t even know what the latest number is, there’s a number of systems that support all of that. Everything from the logistics to the control, to all of it, right? All of that has to be designed and built. So we have, you know, I was talking with the CTO of a major, well, I’ll just say it was Coca-Cola, several years ago, and he was telling me about the number of systems they have. First of all, they have more than I would have thought or a global organization, right? I thought there’s a lot of duplication, right? They’ve acquired a lot of companies over the years. Yada, yada, yada. We have many, many times more than that, right. Jesse: Mm Colt: It’s a big complex. Okay. Now, so you got all these we have, let’s call it 700,000 total airman contractor. That’s active duty guard, reserve, civilian, and contractors that are like on our networks in our systems. Call it 700,000 plus or minus. And they are interacting with, call it, there’s maybe 40 systems that have more than 50,000 accounts, quite a few of those over 500,000 accounts. And then there’s this long tail of systems that go all the way out to very tactical things, some of which are extremely mission important, that might only have a few dozen or a few hundred accounts, right. And they’re doing everything imaginable, right? They’re flying satellites, they’re handling logistics, all of it, right? They’re putting together schedules of flights and sorties and getting fuel on planes and recording the hours of pilots and crews and making sure it’s scheduling of all of the above. And then you’ve got really mundane things like getting people paid on time and dealing with health care and booking their flights. It’s everything that a typical large organization does, plus all of these other long tail of missions. And then on top of that, just to make it even more complicated, we are literally around the world and supporting a lot of hardware out there. Across Levels of Security Colt: And then we’re doing it at multiple different information security levels, which if you’ve never dealt with information security in this kind of an organization, it gets a little crazy, right? Because you’ve got completely public information, right? Then there’s unclassified and essentially public, like the public could have it. And then there’s controlled unclassified information, which is just things that aren’t publicly releasable, but they’re not classified. And then there’s secret, top secret, and various flavors and things above that, So, it’s a complicated environment. And these systems, think about it, some live at one level, some live at another level, some live at the other level. So it, it is a complex environment. It’s not unique to the air force and space force, right? This is across all of DoD. Developing an Agenda Peter: Given this complexity, I would imagine a big challenge in your role is maintaining focus, figuring out what, what to work on. And I’m wondering, when you joined and then maybe over your time there, something that we heard from prior heads of design was the importance of some vision. Not necessarily destination, but generally a direction they were trying to move things towards. And I’m wondering, did you have something like that when you joined? Or what did it take for you, because it sounds like this was probably a new environment, to realize this is what I’m here to do. This is my personal North Star. And then how did that help you make sense of this complexity, where it would be very easy to get overwhelmed by all the things you could do, and you needed to focus on the things that actually advanced your agenda toward that vision. Colt: So we definitely have a vision now. But it took a little while to evolve. It’s not that the vision evolved. The way that I talk about it got clearer and clearer. And it can probably be clearer still. When I took this role it was June of 2019 and like any kind of incoming executive, I kind of set the expectation there was going to be about a 90 day sort of study transition kind of plan, and then I’ll come back with an approach. And the good news is, after that meeting at the Pentagon with Bill, I had about six months while they were creating the job, and I had a pretty good idea that I was going to get the job. So I had a lot of time to prepare. And it was a little bit my sabbatical, or you know, I call it my gap year. So I had a lot of time to prep. So I came in with a lot of preparation. Then I had my 90 day transition. I booked a lot of plane tickets. I visited a lot of places. I talked to a million people. I looked at a lot of data. I’m a career professional consultant. So I came back with a nice, big, thick document. And I thought it was very well- structured and clear. And , like a good senior executive in the federal government, my boss said, “Love it. On board. This is exactly what you need to do, but it’d be better if you could put it in a placemat.” And I’m like, okay, can do. Put it in a placemat. And did a lot of talks and you can actually go out and you can go on YouTube and you can actually find videos of me presenting my placemat in public events and the placemat was helpful, but it wasn’t clear enough. Colt: And so not long after that, people were asking me, Colt, okay, love the placemat, but what’s our strategy? And we needed something that applied to both enterprise IT and software that people can understand very quickly. And so essentially the strategy is, we’re going to treat airmen like they’re customers. Which is a big shift in mentality in a government organization. So we’re gonna treat our airmen like they’re customers. As if we’re a major IT services company, like a Microsoft or Google or somebody else, right? And so we treat airmen like customers, and then we’re going to measure the experience from their perspective. And then we’re going to track that over time, figure out how to make it better and manage service levels. Fundamentally, that’s a strategy. So it’s an outside-in type of user-centric approach focused heavily on measuring experience, because that’s something that we can do at scale. I mean, think about the scale of the organization I described earlier. I can’t think of another way to do it. Well, there’s many challenges with user experience, but one of the challenges with user experience is, at the end of the day, it improves system by system, application by application, user journey by user journey. And so we needed a way to kind of say, okay, how do we go set the bar, measure the bar, figure out where the bar is, and then start trying to get the entire culture to move the bar up. We needed a clearer, more succinct strategy and that’s when I got down to, okay, here, the strategy is fairly concise: treat airmen like customers, as if we are basically a big IT services company, and measure user experience from their perspective as they’re doing the mission. There’s implications to all those things, and then track it over time and manage service levels, you know, to improve them. And that is fundamentally the strategy. People seem to be able to understand that very easily at all levels. I talked to general officers, totally get that because they apply similar techniques everywhere. You know, the organization understands all aspects of that. They understand about measuring service levels and managing service levels. Once you start putting user experience into those terms, an organization as big as with these kinds of missions can grab on to it and say, yeah, that’s a good way to do it. Jesse: This is fascinating because it feels like such a shift for you, away from consulting work, which I know that you’ve done for many years. And I’m curious because it feels like there’s an element of consulting, which is about get in, make the strategic impact, get out and move on to the next thing. And this is about, getting in and going deeper and deeper and deeper and getting sort of more into it. And I wonder, what was attractive to you about the shift to this context? And what did you discover when you actually got to the other side? Colt: You know, you’re right. Career professional consultant going from project to project. And we had a very good run. I mean, I was with essentially the same organization the entire time, right? I was with Deloitte, we spun a company out, we sold it so I was essentially with one organization the whole time. But never really got to see a lot through in the way of our client work. I even had accounts for years, one account 7, 8 years, so saw a lot of things through, but not like this. So my goal was, let’s see if we can move the needle in a massive way for an organization this big. And I was fairly convinced that we could, but that was what was really attractive to me is, let’s attempt to measure user experience in a way that’s meaningful and relevant to airmen doing the mission, and their mission. And then let’s track it over time. And then let’s figure out what levers we need to pull in order to move the metrics and deliver a better service level. And have everybody agreed that we did it. I mean, fundamentally, that was what I wanted to do. That’s what attracted me to doing this. And I went in fairly convinced that we could do it. I didn’t know exactly how we were going to do it. But I had a lot of ideas on how we could do it. But you’re going to go look for what are the biggest levers you can find to shift how airmen perceive the service level though they’re getting from IT and focus on those areas. Peter: I want to unpack a couple of terms just to make sure that we’re all using the same words to mean the same thing. I’m not used to thinking of user experience as having a service level mindset, apart from, like, my design team will have a service level commitment, maybe to some part of the business, but that’s not what you’re talking about. So what do you mean when you’re saying service levels in this context and what is UX’s responsibility, if it’s separate from the rest of it. Colt: Yeah. No, great question. Okay. So when I’m talking service levels, I’m using the term a little bit broader than you’re probably thinking about it. So it’s, performance response time and all of those kind of aspects of computing. You know, my computer not crashing, stuff like that, it’s just service levels. Peter: Kind of what we would think of as quality and quality assurance. Colt: Quality assurance. Exactly. But I’m also just thinking of making sure that the applications that you are using are easy to get to, meet your requirements, and are easy to use without having to get a lot of extra training that is specific to the application. There’s a lot of training that you need to do your job, but you shouldn’t need so much training in the tool. So I’m using service levels just in a broader sense. Peter: Almost like, yeah, how we would think of quality. Jesse: Yeah. Colt: One other thing just to clarify, because this confuses a lot of people, and don’t even think about it so much when I talk about it anymore. But keep in mind that I work for the CIO. But my job spans both enterprise IT and software and applications. So, think Google. Google could produce the most fantastic search results on the planet, but if it took 10 seconds to get the search result back, you would still think it was terrible. And we have that kind of problem, right? Trying to putting it on our terms, our search results wouldn’t be that great, and by the way, it would take 10 seconds. So we got to solve both problems. And if I’m trying to move the bar up in a significant way, that is noticeable and meaningful to airmen out doing their part of the mission, then i’m looking for the ways to figure out how to move the bar up on wherever I can get it. So in some cases that’s on the software side, in some cases that’s on hardware systems, networks, operations, wherever I can move the bar up and deliver a better service across all of it. We ask a Big Question Peter: I want to unpack that. ‘Cause something Jesse and I love to talk about is multi-channel, omnichannel, very broad user experience, right? Experience Jesse: strategy. Peter: Yeah, we all come from an environment where people thought UX was screens, very simple kind of software mindset, but we all know that an experience mindset can be brought to bear on a much broader set of challenges. What I’m wondering is, you’re talking about hardware as well as software and other systems. I’m realizing I’m curious about the makeup of your team, right? You’re the first Chief Experience Officer. Who are you assembling in your organization in order to address this variety and complexity of challenges that you’re now facing? Jesse: Well, I actually have a related question that I’d like to piggyback on this which is what did you inherit when you stepped in? Your role was brand new, but the work being done was not, and I’m curious about what you were handed, how you shaped that into something new, and what, to Peter’s point, what did you need to create along the way? Colt: We had to create a lot. Okay. So why don’t I start with that? And then let’s come back to Peter’s question. So I didn’t really inherit much. There was not an existing team. And to Peter’s question, I don’t really have a team. So I’m what’s known as an HQE appointee or highly qualified experts. It’s basically a type of senior executive service equivalent hire. It’s equivalent to a one star general or a first level senior executive service, where the government goes outside directly to commercial industry and brings somebody in with a particular set of expertise to solve a particular problem. And then by law, maybe it’s by policy, but regardless, you have to be done in five years. And one other kind of odd rule is that as an HQE you can’t really manage government people. So it’s kind of like going out and pulling a commercial person into the government for a short period of time. And so when you saw the reboot of healthcare.gov going back about a decade, I think they brought in one, two or more HQE’s. It’s not that unusual, but so I can’t go and like build a team and have a lot of people working for me. What I can do, remember, career professional consultant, is go figure out who’s allied with this cause and line everybody up and get them all working on the same thing. And so that’s what I was able to do. There are multiple organizations that have some stakeholder piece part responsibility for user experience. Most of them don’t call it that, they’re DevSecOps organizations doing software development, or they’re software factories, or they’re software acquisition teams, or they’re IT organizations that are supposed to be optimizing the performance and the security of our networks and systems and desktops and everything else. So there’s lots of organizations that do a piece part of user experience, or they own some part of it. All of them had to be lined up, put together in teams virtually to go after this. All the organizations existed, but the virtual teams going after these problems, thinking about it as UX and performance and then going after it, none of that really existed. We did have software factories. Our largest is called Kessel Run. They’re an interesting group. You may want to talk to them sometime. Over a thousand people now, and they have a pretty robust UX capability. So they existed, but there wasn’t a lot else. And then what had to be built? So the key things that had to be built were,- -keep in mind what my strategy was, let’s go treat airmen as customers, measure UX from their perspective, track service levels, manage service levels, make it better. Okay, so what do you have to do? First thing you got to do is start measuring user experience. And you got to do it across enterprise IT. And then you got to do it across software. It’s a lot easier to do it across enterprise IT. There’s a lot more tools and products, and I don’t need so much consent from individual applications. We’re in an environment with thousands, probably, of individual applications and platforms, if I had to go to each one of them and get permission to monitor their performance, and we can’t use Google Analytics inside our firewalls, but let’s say we could, we wanna attach Google Analytics and maybe do usability testing or something on a thousand applications. I gotta work with a thousand different programs. Can’t do that. So how do you do this? So on the enterprise IT side, we had a thing called the Air Force Survey Office. They use Qualtrics at scale and there’s a FedRAMP moderate version of Qualtrics so we can attach it and we can do surveys. And this is the way, like if you hear about a study in DoD of, pick a topic, whether it’s diversity, inclusion, or retention, or sexual harassment or any other topic people research, this is the platform that they do those studies on. So what I did is, I met with them and then we set up a, what’s now it’s evolved a bit, but starting in January 2020, we began doing a pulse survey of it. And then we launched digital experience monitoring, which gives us performance of all the software running on individual computers. So now we know where it takes a long time to start up in the morning. We have people complaining of 20 minute startup times, boot up times. And, and we know where it is, geographically, bases and everywhere. And then we added a network of boxes that plug into the routers that run a set of tests, looking for things that tend to disrupt performance and mess up performance of software , tests that check our PKI infrastructure, that check various changes that sometimes happen with DNS and in various other things. And so now we’ve got sort of, this is gonna get really geeky really fast, but all seven layers of the OSI stack we’re now monitoring. So we understand the whole technology stack. Really, we understand at the top level what the user is experiencing from the technology stack. That’s on the enterprise IT side. On the software side, more complicated because in order to instrument an application with just basic web analytics… Now understand, you can’t go hook up tools like Google Analytics to our systems, right? Even the unclassified systems, you can’t really do that. On the public facing site, yes, there’s actually a really good public facing version of Google Analytics that’s run by General Services Administration. It’s a great capability, but we can’t use that for our, call it… just inside the firewall stuff. So we, we stood up something called user experience management, and it has a user feedback capability, just a simple link so that users can provide feedback with a simple 3 question survey. And then it has an open source web analytics tool and we’ve gone through two years of security approvals to get it what’s known as ATO or authority to operate on our networks, so that all of our applications on the unclass side of the Air Force for now, and we’re going to try and take this to the classified side, now, all these applications can get basic web analytics and user feedback. That sounds very simple. Like, if you were to go start any business on the public internet, those are probably two of the first things you would attach to your website, right? It’s just a feedback link and web analytics, but our stuff, we can’t, we have not been able to do that. And that’s a problem in the government, by the way. When they did the analysis of what went wrong with healthcare.gov, one of the findings was that they didn’t have web analytics. And I know why they didn’t have web analytics. It’s actually kind of hard to get that in a government site. So we solved that problem. Now that’s being rolled out. There’s several other things we’re doing at the individual application level. But one of the things that I think is unique that we’re doing is we needed a way to start managing the portfolio overall. Influence Without Authority Jesse: What you’re describing sounds like a tremendous effort of orchestration cross-functionally, and I find it especially interesting that you were able to achieve this in a role that is expressly designed to limit the amount of direct control you have over what actually happens, right? You’re expected to wield a lot of influence, but you have very little, it sounds like, direct control or direct authority to actually tell people what to do. Is that true? Colt: That is, that is true. Jesse: How do you get a job this complex done when you have those constraints? Colt: So a couple of ways. I put so much of a focus on metrics measurement because once you have that, then you can provide, what we call in DoD, situational awareness up the chain of command and get buy in. So in other words, if you can show that performance and user experience is bad with certain bases, certain applications, certain missions, and the data is clear and presented clearly, then you can, get buy in, because that’s information that has to be dealt with. That’s, I think, the most powerful thing that you have. I think that’s why I’m such an advocate of a data driven approach. That’s number one. And number two is, you gotta have, you gotta have air cover, because it takes a while to put in place the tools to get that kind of data in quote unquote situational awareness. So you gotta have air cover to be able to get you through to the point where the data is out there and it’s clear and it’s compelling and actionable. And then the third thing I would say is, you have to get a little bit… lucky is not the right word, but you have to get a little bit lucky in the sense that once you start having good situational awareness across a broad portfolio of technology, where you get a lot of data and you can see what’s really going on, then what you need is you need leverage points where sort of the, the 80/20 rule comes into effect or the 90/10 rule, and you can go and say, okay, if we solve these 1, 2, 3, 4, 5 problems, even if we solve them 75%, we’re going to get a 20, 30, 40, 50 percent improvement in our metrics. And it’s identifying those points of maximum leverage across the enterprise where you get the biggest result. And if you’ve got enough data visibility, enough visibility across the whole environment, you can start to identify those points. Fundamentally, that’s it. So that’s how we’ve been able to move the needle. Peter: Much of what you’ve been explaining, feels a lot like lifting a floor, right? There was a broadly unsatisfactory level of quality across the systems and your initial orientation was to really like dig in, get that data, really understand kind of where the breaks in the chain are in order to raise the floor. And I’m wondering, because you were, you’ve been there four-ish years, was there a point at which you started to also get to look at raising the ceiling, to think about innovation, to think about net new, or has it really been this very kind of practical, tactical, we just got to get these things working, and then that in and of itself is a win. Colt: So I probably spend at least 50 percent of my time on the “get it working.” And that’s a huge win, by the way, if you look at what airmen complain about most. That’s it. At least in IT. However, to answer your question, yes. So when we conceived my role initially, one of the ideas was there are several, I call them the mega user journeys that apply to almost everybody in the Air Force and Space Force that are not very well automated. They might be partially automated, but they’re automated by multiple different systems. There’s a massive amount of paper involved. The churn involved is insane. And so there were those that I wanted to take on. Peter: You mentioned getting kind of cover from your leadership, but how are decisions made? How do you get on everybody’s backlog or whatever, across this extremely complex organization in a coordinated fashion, such that you can make the progress that you know you need to make. Like, is that just you in a lot of meetings having a lot of conversations? Is there some communication, operational kind of a set of people and practices that can weave this together? Like it just feels daunting. Colt: Well, I mean, it probably is a little bit, but I was very fortunate that I had I’ve had some good bosses and it’s important to have a good boss. I’ve had some good bosses that I was very in sync and they were very in sync with what we wanted to do and what was possible. And so I had air cover when I needed it. But a lot of this is just a tremendous amount of communication. So one of the things that I use to our advantage, when you’re in my role, you do a lot of public speaking and conferences. And so two or three times a month, I’m giving some kind of a public talk and then probably a couple times a week for the last four years, I’m giving some sort of a large group presentation inside the Air Force, going through, okay, on improving performance of enterprise IT. Here’s all the things we’re doing. Here’s the vision. Here’s strategy. Here’s the measurements. Doing demos. Whenever we stood up the tools, people have to believe this stuff is real, right? And they have to experience the benefit. And so I do a lot of demos, demos of our digital experience, monitoring demos of our survey platform, etcetera, etcetera. And then on the software side, same thing. A lot of demos. The job is fundamentally a communication job, making people aware, showing people it’s real, getting people to buy in, coaching people, teaching people, but doing it at scale. And you know, if there’s one thing the DoD does really, really well, we do a lot of things well, actually, but one of the things I do think we do well is communications at scale. We do well. Jesse: So I’ve never worked with the military. What I imagine of that environment is one in which the default answer is going to be no. Unless you can make a pretty strong case for yes, because of the need for things to absolutely work without question. Colt: You’re right. Jesse: And I imagine that that creates a certain amount of institutional risk aversion. It creates a certain amount of skepticism toward new ideas, especially… Experiments that we’ve never tried before. And you came into this role having to advocate for all of those things. And I’m curious about, aside from having really awesome metrics to back you up, how did you make that case? How did you convince people to take on the risk of changing their processes, changing their approaches, looking at things in a new way? Make Change by Connecting to their Past Colt: Great question. And metrics were a big part of that. But there’s a few tricks. You gotta be able to learn and speak the organization’s language and speak to what matters to them. That’s important. And by the way, the notion that you’re talking about, in our environment, they call it the frozen middle. Jesse: Mm. Colt: When it comes to user experience and performance, we actually have, I would say, senior leaders at the Department of the Air Force , we’re talking in the what we call the glass doors level. So I think the top six or so leaders in the Air Force, the second half, the chief, the undersecretary, the vice chief, and the chief master sergeant at that level, they actually use the term user experience which is encouraging. They know what it means and they know what it means to them. They’re not experts, obviously, but at that level they really do get it. And they support it and they want to know how to make it better. And then at the sort of the airman level, they totally get it right. Technology is like air to them. They breathe it. It’s part of their lives. we hire a tremendous number of young people and they just breathe technology. So what everybody talks about is the frozen middle. It’s all these folks that want to say no because they don’t really want to take a risk. So I use Lieutenant Colonel Fitts story a lot. I do a million conference presentations and internal, I close practically every presentation with Fitts because it shows… The point is that human-computer interaction and user experience and human factors engineering, these things are all within the DNA of the Department of the Air Force, right? And you guys know the history here. Frankly, you probably know it better than I do. But in case some of the listeners don’t, the story at a most basic level is that we were losing hundreds of B-17s in World War II in Europe. You can read Bomber Mafia by Malcolm Gladwell, good book about it. And, but a lot of these planes, in fact, really thousands we were losing, and but hundreds of these planes flew back into Britain and the pilots would just make a lot of mistakes and the Air Force and our infinite wisdom basically said, Hey, we’re getting crappy pilots. And so they decided, Hey let’s go do a study on this? Right. ‘Cause we’re the government–studies, we do that. And so they hired a, psychologist who had been Lieutenant Colonel in the Army Air Corps. Gone back, got a PhD, comes back as a psychologist and he starts digging into this problem with the intent of helping hire better pilots or choose better pilots, select better pilots. And starts looking at the records of the plane crashes and realizes that there’s patterns in the data. Same types of things were happening again and again and again, right? Pilots that would fly a mission over Europe, come back, land in Britain, and they would open the bomb bay doors instead of put down the landing gear. Things like that. And so he and a pilot and others started looking at the planes and began to realize that what we had was not crappy pilots. It was a badly designed plane. Certain controls were too close together. They looked exactly the same. They worked exactly the same. You know, if you put yourself in the position of these pilots and crews, I mean, good God, I mean, they just flown for hours over Europe. There’s probably smoke in the cockpit, maybe one of their buddies is bleeding in the back or worse, and I mean, the stress that it must be is unimaginable, and then add into that that you flip to a console and the controls are all the same, it’s a miracle anybody got back at all, and so they began redesigning the cockpit of the plane, focusing on things like shape coding of the controls, and it’s interesting, those techniques are used to this day, anytime you tell this story in our environment, there’s almost always an Air Force pilot or a former Air Force pilot on the line and they get in the chat on our team’s call. And they’re like, oh, yeah, that explains why , this control is shaped totally different than this and this one is like a gear and this one is shaped like a flap and I’m like, okay, it turns out those things are still done to this day. So, but the point of telling that story is that anybody in our environment can understand it. They all respect it because there’s a lot of respect for that kind of history in our culture. And it conveys a few things. It conveys being data driven. It conveys solving the problem. It conveys the connectedness to the mission. It conveys frankly, it just conveys that this is within the DNA of our culture and organization already. And if we can tap into it in order to solve problems like that, we can tap into it in order to make the user experience better for our weapon systems today. In World War II, they were a B-17. Well, today, they’re still weapon systems. They’re different, right? There’s a huge IT component to our weapon systems today. It’s not just all about super expensive hardware that circles the globe or whatever. There’s a lot of software. So that’s how we do it. That’s the technique to cut through. Jesse: I love that story. You know, it’s interesting because I asked you, what did you do to talk people into doing something new? And what I got from your answer was that your approach was basically to convince them that it’s not new at all, right? That it’s actually already a part of the culture that they’re a part of. And that this user-centered thinking is really just an evolution of what’s already in the organization. Colt: Totally agree. Think about it. I mean, what are the odds that me, an outsider, are going to come in and change the culture of the Department of Defense? Not going to happen. So, you got to be realistic about that and then… Use the culture for what it’s really good at. And this is something that our culture has been good at in the past and can be going forward. Bringing a Service Mindset Peter: I actually want to build on that, because you wrote a post on LinkedIn and one of the words that I noticed in your post was, “if any of my friends from the commercial world are interested in serving,” and serving is not how we typically talk about the kind of work we do. And I’m wondering, what it has meant to be in an environment where to serve and serving is the value that everybody, to the highest level, is bringing to the work and how that’s affected how you’ve approached it, or evolved and changed how you’ve approached it. Colt: First of all, this doesn’t apply just to DOD, right? I mean, what we’re talking about here really is government service. it’s service to your country or your state or your county or city, it’s government service. I think military work in particular can be a bit of a family business, right? My grandfather was in the Navy. My dad was in the Navy. I was not, but I do this. We need people who are willing to go serve and it doesn’t have to be in the military. It’s a million ways to do it. I have the highest respect for Jennifer Pahlka, who just put out a book called Recoding America and the work that people do in that on the civilian side of the government, and it’s all vital and it’s all technology that has to work, frankly, for the institutions of our country just to operate. So I think it’s a important thing, an honorable thing, and I encourage it for everybody. We have some countries like, I believe, Switzerland and Israel basically require a certain amount of military service. I don’t think it has to be military but I think it’s a good experience for everybody to do some of this, and I think it makes you more connected to , frankly, everyone in our country and around the world, I think whenever you spend some amount of time providing service. So something I feel strongly about, and I would highly encourage anyone in the commercial sector, as I was, if you’re interested in doing something like this, if you’re a UX designer, software developer, whatever, and you’re interested, reach out to me anytime. Peter: I’m wondering how your posture in leading this kind of work shifted as you approached it with this serving mindset versus a more consulting approach. Colt: Yeah, really good question. From my perspective, you have to take sort of a balance. There was a two star general that I respect tremendously, General Schmidt, who was in acquisition and in a week or two after I started in the job he kind of asked me, okay, well, how are you going to approach this? And of course, I didn’t have much of anything at that point. And the first thing out of my mouth was, well, it’s going to take a lot of humility. And I think that’s one, that’s a big part. So when you’re going to be a change agent and you’re going to try and really move the bar in an organization this big, and you gotta have a certain amount of humility because there is so much you have to learn and you have to just recognize that at the same time, you also come in with a completely different perspective and you’ve got to be confident in that. And do your homework and rely on a lot of experts. So as I was preparing to take this job. I leaned on friends that were former CIOs, current CIOs and kind of laid out the problem to them and they all kind of pointed and here’s sort of what your strategy is going to have to be. This is the only way that will work. So I would say humility plus confidence, not arrogance, but a certain amount of humility plus confidence, making sure you’ve done your homework and have in your back pocket a plan that has been proven to scale elsewhere and will apply. Jesse: I’m curious about the future for you, and where you see all of this going, and what role do you see for yourself going forward? Colt: Sure. Let me hit four things. So Air Force, DoD, federal government, and then me. So Air Force. We have a new CIO, Venus Goodwine, and she replaced our last CIO, Lauren Knausenberger, just last month. She is committed to building on and expanding what I have been doing. And I’m not going to make any announcements beyond that, but what we’re doing will go forward in the Air Force. DoD, I think you’re going to see some exciting things when it comes to UX and performance software and I T. The CIO at the Department of Defense is named John Sherman, and he’s absolutely committed to this. They have already stood up something called the Office Performance Management. And they’re going to be doing some of the similar things. And frankly, you’re also seeing the same type of playbook we’ve executed here at the Air Force. You’re now seeing the Navy pick that up and run with it. And I think you’re going to see it elsewhere in DoD and probably increasingly coordinated DoD wide by the overall CIO for the Department of Defense. So this is going to become more than just an Air Force thing. It actually already has. And then federal government. There’s a tremendous amount of activity in UX and CX across the federal government. And I’m not really qualified to talk about it at length. But I am part of those networks, at least in terms of all the email distributions and some of the conferences and things. It’s super exciting. You’ve probably heard of the 21st century IDEA Act and there’s various federal policies and policies from the White House and OMB to raise the bar for citizen experience across the federal government. They’re also creating a lot of resources for people like me and organizations like this one , tools, resources. So the survey tool that we’re using just for feedback on applications, it’s called Touchpoints. That’s a GSA tool that we can use even in our environment behind our firewall, which is very interesting. So they’re, they’re doing some amazing things. And then last, me, personally. So I have a rough plan. And part of it’s going to be advising regarding user experience within DoD. I won’t go any more to it than that. So I’m going to continue to be engaged within DoD. And then I was with a small company before and I’m probably going back to a small company. And in fact, I’ve got a idea and a little bit of a plan for a startup. So, I may be in the startup world here in the near future. Jesse: Very exciting Colt. Thank you so much. This has been great. Peter: Yes, Thank you. This has been really eye-opening. Jesse: Colt, where can people find you on the Internet if they want to follow up with you on this conversation? Colt: Honestly, best way is LinkedIn. I’m not a huge Twitter user or X user. LinkedIn’s pretty reliable. Jesse: Fantastic. Peter: Excellent. Jesse: Thank you so much. Colt: Thank you. Jesse: For more FindingOurWay, visit FindingOurWay.design for past episodes and transcripts. For more about your hosts, visit our websites, PeterMerholz.com and JesseJamesGarrett.com If you like what we do here, give us a shout out on social media, like and subscribe on your favorite podcast services, or drop us a comment at FindingOurWay.design Thanks for everything you do for others. And thanks so much for listening.

Rajat Shail, who oversees hardware, software, package, and experience design for Vivint, discusses managing design as a holistic function, using design thinking training to engage executives, and navigating a broader mandate than their boss's.

Jesse and Peter drink a “Warp Core Breach” at the Star Trek Experience, 2007. Photo by Leisa Reichelt. In this episode, Peter and Jesse reflect on the conversations they had with senior design leaders, the themes that emerged, the challenges facing design leaders today, and our hope for a brighter future. Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, Together: And we’re finding our way… Peter: …navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, for our season finale, Peter and I take a look back at our recent conversations with design executives to explore some of the emergent themes we’ve heard, including how to make sure you’re set up for success as a leader, the personal qualities such as resilience and pragmatism that help leaders thrive under pressure, and how to succeed as a design leader by being truer to yourself. Design leadership as change management Peter: So probably kind of most obvious place for me to start when thinking about the conversations we had was this thing I wrote at the beginning of the year where after the first five discussions we had with design executives, I went back, I analyzed the conversations we were having, I tried to pull out themes and topics, and as I went through my process, I hit upon what struck me as an an overarching emergent theme, which was around change management, how four of the five design leaders we spoke with very intentionally approached their job as a change management initiative. and Katrina, the very first person we spoke with, said that right out of the gate, at the start of our interview with her, that design leaders have to be change agents because businesses still don’t really know what to do with this function. Jesse: Right. Peter: And that was an interesting start because then Greg, whether or not they said change management, Kaaren’s approach was a change management approach, Greg Petroff’s approach was a change management approach, Rachel Kobetz’ approach was a change management approach, in terms of an intentionality of taking not just their team, but the function of design wherever they found it when they got there, to some new place and a set of activities that they were going to use to get them there. Jesse: Right, right, right. Yeah, it’s a really interesting thing, because if you think about the different kinds of change that a leader could potentially make, you could definitely see how in a more mature organizational function, something that has a more robustly defined value proposition than product design currently has, that has better entrenched practices and ways of talking and thinking about that value proposition, you can see in a lot of those kinds of functions where change management wouldn’t really be part of the job. There isn’t a lot of change to be made if you’re a CMO, for example. I’m sure there are people out there who would disagree with me. But for design where it is in its maturity, on its trajectory, there is still a lot that is not understood or not widely understood about what the value proposition of design as a function to an organization that creates digital products actually is. And what we see across this range of leaders that we’ve spoken with are a bunch of different frames for that value proposition. But in any case, they all have bridges to cross with their partners, with the business, to help them fully appreciate that value proposition. Because that understanding is going to be discontinuous through an organization. Not everybody’s going to get it. Because of the level of maturity of digital product design as a practice, because of the breadth of understanding of it beyond people who have engaged directly with design processes. So there’s a lot of evangelism, education and, really, shifting people’s mindsets, that’s necessary in order for these leaders to deliver on the promise that they see as there. Peter: Totally agreed. Even before these conversations, when people would ask me, well, how is a VP of design different than any other VP… Jesse: mm-hmm. Peter: … it’s because they have to spend so much time educating and evangelizing and increasing organizational maturity or awareness around the design function, which is Jesse: Yeah, Peter: understood for engineering, for sales, for marketing. Jesse: Exactly. Right, right. But I then I think that for the design leader, it’s a question of how far do they want to take that? How far do they want to go? You wanna level the product up to, you know, to be something more than it was, to take the design to someplace that it hasn’t gone before. Do you wanna level your team up in terms of expanding the capabilities of design, changing the shape of that value proposition of design as a function within the organization? Do you wanna change the organization beyond design? Are you interested in seeding, you know, for want of a better term, design thinking beyond design functions in the organization? Like these kinds of ambitions are all part of the balance that you have to strike as an executive design leader. The importance of clarity of vision Peter: One of the leaders that we spoke with, Kaaren, had the most clarity in terms of, like, ultimately where she was trying to head, and she used this phrase, “one freaking experience,” right? So she’s responsible for the consumer bank for Chase, JP Morgan Chase. And she saw kind of ultimately her vision is how do we create one experience for customers across the suite of products and services that Chase offers consumers. And when you do that, when you have that kind of clarity of vision, it ends up that gives you the almost marching orders to address the questions you were asking. Is it about the product, is it about the team? Is it about the broader organization? I mean, the short answer is, it’s all of those things, ’cause in order to deliver one freaking experience, she has to figure out how do we get these different internal lines of business aligned, the credit card business with the home mortgage business, with the basic banking business. And so that can’t be just something happening within design. You need to figure out how to weave it into the broader organization. But… Jesse: mm-hmm. Peter: … something else that she talked about when we spoke with her, that I’ve used since in, conversations with other design leaders is, where to begin? And in order to deliver on that one freaking experience, she saw where she needed to begin was with her team. She talked about the very first thing she did was establish or work to establish a world-class team, right. That that was gonna be the foundation upon which everything else rests. And as someone who’s been supporting her for the past year and a half, I’ve seen some remarkable hiring at all levels, but particularly at a design leadership level, as that initial step towards that greater vision. Organizational maturity Jesse: Mm-hmm. And you know, it’s interesting, too, because I think there is the question of, to what extent does design, by definition, regardless of the maturity of the organization, regardless of the maturity of the design team itself, to what extent does design necessitate organizational change if design is actually going to deliver on its value? And I think that for a lot of these leaders, they feel that if we’re just delivering better product over and over again, that’s not going far enough because we haven’t gotten into the roots of the culture of the organization. And one of the things that has come up a few times in these conversations is the notion of how much permission does the culture allow design as a function to have to push the boundaries of its value proposition to offer new ways of delivering value to the organization. And those experiences are wildly inconsistent based on the specific cultures of those organizations that those design leaders are stepping into. Peter: I like this frame. The companies that would hire people, like the folks that we interviewed are likely more permissive…. Have a greater maturity around these things, or they wouldn’t be hiring someone to lead a team of 400, 800 people, like, there’s some investment in it that suggests a greater permission. But I like the permission frame because I think something that a lot of design leaders don’t do, but need to do, when they enter into that new role, is assess, measure, understand where the, where that organizational maturity is at. Jesse: Mm-hmm. Mm-hmm. Peter: And permission is going to be caused, by that company’s maturity around design. Jesse: Mm-hmm. Peter: And, and that was an insight. Another one that I’ve dined out on since we’ve spoken with him uh, came from and, wow, that was an unintentional almost pun because it’s with Jehad, who’s Chief Design Officer at Toast. You know, we had spoken with these other design leaders, and they would talk about impact and they’d talk about co-defining outcomes, and it was from a place of greater maturity. And Jehad pointed out that, at least in his growth, he had to dial in his conversation to meet the maturity of the organization he was part of. And so it might not start with impact because your company might not be ready to hear about the impact that user experience or design has. They might not be mature enough to take advantage of that. And so he used a frame that I’ve, again, employed often since then, around “show your worth,” because your worth might be just understood relatively in the environment you happen to be in. It might have very little to do with the impact the metrics of the products that your team is building. And it might be around, Do your peers like working with you and your team? And, and measured through some internal pulse survey or whatever. And that in an immature organization that is actually a legitimate measurement when you don’t have anything else to go on. And, and that really got me to be thinking about how important it is for a design leader to tune their message, their engagement with where the organization currently is, not where they hope it will be. Jesse: Right, yeah. It’s huge. It’s huge. This comes up with my coaching clients all the time. The way that I talk about this with them is that the problem space at any given moment is the intersection of the trajectory of the larger organization and its maturity as it relates to design practice, the trajectory of the design team itself and its capabilities and its maturity, and the trajectory of the leader, what their past experiences have prepared them for and what new challenges they are well-suited to take on. And when you put those three things together, then you start to be able to define the shape of what the role actually is in that context. Peter: The maturity cube. Jesse: Sure, sure. Peter: Well, yeah, and I’m curious how you help your clients manage through this, ’cause one of the things that inevitably leads to is frustration, because I think the design leaders often feel like they are ready for a more mature organization. Or they’re ready for the organization to be more mature, to take advantage of what they have to offer. And so then they’re frustrated because when they try to push that, it doesn’t go anywhere. How are you helping your clients manage their own sense of… not trajectory, but, cadence and, traction to dial it in with what’s organizationally appropriate and not get defeated in that process. Resilience Jesse: Right, right, right, right. So part of it is about resilience, right? How do you maintain the emotional resilience day to day, week to week, to keep having the same conversation, keep fighting the same fight, keep having the same argument, right? The persistence that’s required there and the patience, and this is another thing that new leaders frequently don’t really get, is how long it takes to create cultural change. It’s one of the slowest -changing elements of an entire organization. You can turn a team over really fast. You can turn processes over, you know, pretty quickly. Cultural change is the slow-moving deep currents of the organization. And what that takes is, it takes persistence, it takes patience. It takes a dedication. A dedication to repetition. It requires the ability to ride it out for a while and know that you might not see any significant impact of this culture-shifting mindset, shifting work for a long time before it starts to actually pay off, because you’re laying the foundation, you’re building that foundation of credibility and trust for design as a function within the organization that’s gonna enable you to expand that value proposition. Peter: Well, and this gets to something you’ve written about recently on a post on LinkedIn, which is the job is bigger than the person. A design executive’s job is going to be bigger than any individual. It’s just by nature there’s more work to be done than any one person can do. And so, how then are you helping your clients navigate that, figure out, given all the things they could be working on, do I work on these long-term culture things, ’cause that’s ultimately what I want to drive. Do I work on near-term quick wins? Just to get some traction. Do I work on, building my team? Do I work on managing my relationships? Like how are you helping them navigate all that opportunity or all that potential activity so that they’re not feeling like they have to work 60 to 80 hour weeks in order to… Jesse: Right, Peter: …get it done. Jesse: Right, right. Well, it’s an interesting thing because, first of all, those three trajectories are a huge influence on how I help leaders set those priorities, to be able to assess where to invest their energy. ‘Cause you’re absolutely right, the job is just too big. So you have to choose that selective focus of your attention and how you set those priorities. A lot of leaders get into trouble by not having an agenda of their own for their priorities. They’re receiving priorities from the business, they’re receiving, you know, requests or sometimes demands from their teams and they see their role as mediator, negotiator, reconciler of everybody else’s point of view about what’s needed. And they don’t bring their own point of view. And the irony in this is that often what’s needed in order to narrow your focus of attention is to take your focus off of everything for a minute and reset and reflect. And that’s one of the big things that I help my clients with is, you know, whether we’re doing some reflection live in session, or I’m helping them create the patterns that create that space for reflection so that they can engage more strategically, so that they can get out of these reactive loops where the first thing that they do is they open their email and they’re immediately fighting fires to start their day. Peter: Kind of related to this, what I drew from those discussions with design executives was, in order to make sense of how to spend your time, what you’re calling reflection, to me, it feels aligned with just that recognition of having a vision, like, what is it, what ultimately is it that you’re trying to get done? And, and how can you use that as some internal orienting point, north star, that helps you make decisions about how you are spending your time? And then how you’re spending your team’s time, ’cause you wanna focus yours and your team’s time on work that moves you toward whatever that point on the horizon is that you’ve identified. But you need to take the time. You need to make sure you’ve given yourself some time to just figure out, What is that thing that I want? Jesse: Right, Peter: And you’re allowed to have, you’re allowed to have that desire. When I did my analysis and did the change management, that was clear. That each of these folks, part of their success is they had vision for where they wanted to take things, that they weren’t reactive. None of them showed up and were just like, what do you need? They all showed up with some sense of their agenda. Cultivating a point of view Jesse: Right, right. So having a point of view, continuing to cultivate a point of view over time, which is where this reflection work comes in. You know, when we talk about vision, in a lot of cases that’s gonna mean different things to different people. Is it your vision for the product? Is it your vision for the team? I do come back to, I feel like leaders are able to activate the most potential when those three trajectories intersect, when the organization is at the right stage of maturity, and the team has developed its capabilities to a point that the leader can activate all of that, is really where I think the magic happens. And in a lot of cases what’s happened is that they’ve left that third piece out, which is their own point of view, which is their own sense of, of direction. You know, one way that I sometimes talk about this is: be your own executive stakeholder, right? If you’re the head of design, head of design is one of the major functions in this team. If you’re not regularly having meetings with the head of design, you are missing out on something. So in other words, I’m saying have an executive stakeholder session with yourself on a regular basis. Peter: I was very recently introduced to the song ” I Have Never Been to Me.” Are you familiar with this chestnut from the late seventies? Jesse: I, I, I, regrettably, I am old enough to know this song. Yes. Peter: Yeah. Yeah, yeah. Yeah. It’s about this woman who’s been to Italy or you know, all around the world… Jesse: Good. Drank champagne…. Peter: She’s never been to her. Jesse: On a yacht. Peter: Yeah. Yeah. And, anyways sorry it’s– sidebar, but, but crucial. Find the video for it on YouTube. There’s actually two of them you can find. Both of them are worth watching. One is set at a Scottish castle. The other is from a Dutch, like Top of the Pops type show, where it’s on this, it’s in a beach, but it’s inside a studio, like, soundstage. It’s, it’s, It’s awesome. it’s beyond awesome. Well, but, but it’s interesting as you were saying that about the trajectories, it made me think, ’cause there’s one of those trajectories you can control. You can’t really control the organizational directory. You can influence it. You have a higher degree of influence over the team trajectory, but you still can’t control it. Right? There’s gonna be things outside of your control… Jesse: Yeah. No, it’s not about control, it’s about responsiveness. Mm-hmm. Peter: But you can control your trajectory, by which I mean, as you look at these three trajectories, that point of your trajectory is, is going to hopefully be farther than where those other two are meeting today. right? But what you can do is dial in where you are today on that path, right? By having that, longer term vision, you know where you’re pulling yourself and then maybe pulling the rest of the team. If you’re too far ahead, there’s no connection, right? You’re untethered. There’s this concept of flow from Mihaly Csikszentmihalyi, which is people work best when they are operating just beyond their level of competency and capability. That’s when you get in that flow state. I think about this a lot, in terms of how people perform, right? If you give someone a task that is way below their ability, like, that’s too rudimentary for them, they’re not gonna perform well. If you give people a task that’s way above their ability, they’re gonna sink, right? They’re just gonna, they’re gonna drown. And so you wanna do it right at the edge plus of that. And so, how can you, as the design leader, be at that intersection of the organization and the team? And then just a little, just a, a smidge beyond it, kind of pulling both of those where they’re at and pulling them forward from that spot as opposed to trying to be at the end goal and, dragging them to wherever you are. Jesse: Yeah. Again, I think that it’s about breaking the cycle of reactivity, creating the space to establish for yourself your own point of view. But also, you know it is about having a growth mindset for yourself as a leader. I talk to a lot of leaders; when I talk to them about growth, they talk about developing their teams, and they talk about, you know, providing support and resources for people to build up their skills and to move in the directions that they want to move. And then when I ask them about those same things for themselves, they draw a blank. Because honestly, when you get to this executive level, there’s nobody looking out for you anymore in this respect. If you are a Chief Design Officer reporting to a CEO, you are not having these kinds of performance conversations. The assumption is that you have the level of self-awareness. Peter: Even if you’re reporting to a Chief Product Officer or somewhere into the C-suite. Yeah. Jesse: Yeah. The assumption is that once you’ve gotten to this level, you’ve developed the self-awareness to be able to choose your own development paths. And there aren’t gonna be people looking out for you in this same way. But for a lot of these leaders, they are not used to taking that on for themselves, and they haven’t really defined how they see themselves growing. And so defining for yourself your own path forward, the continuing expansion of your own potential has to be part of the equation. Peter: No notes. Jesse: No notes. Peter: I’m just like, yeah, totally. Yeah. How much design in design leadership? Jesse: I think that this is somewhat connected to another theme that has come up, which is the notion of how much do you stay a designer once you become a design leader, and how, and in what ways, do you carry forward the skillset of design, the methodology of design, the mindset of design into your work. And I think that that often creates some dissonance for people because they think there are things that they need to hang onto that they actually don’t, and vice versa. Peter: And I think it’s also very much a function of those three lines of trajectory. But, in particular, the two that are a less in your full control, where the organization is at, and where the team is at. The last conversation we had was with Tim Allen, Chief Design Officer at Instacart. It’s not his actual title, but close enough. And he was interestingly different from literally everyone else we spoke with because he remained committed to the craft and to the details of the work, even though he’s got a team of 150 or so. And, when we spoke with him, I was kind of continually surprised as he was talking about how he approached his role. And as I reflected on it there were probably three things that arose as what enabled him to maintain that more detailed approach to design than others would likely be able to do successfully. One, is his own perspective and agenda. It’s his own point of view. That’s just how he rolls. He trained as an industrial designer. Loves form, loves those details, likes to get in the mix. That’s why he cares about and is passionate about design. And so he was going to do what he could to protect that and enable that. Two, he is, at least currently at Instacart, in an organization where he doesn’t have to spend a lot of time evangelizing and educating, right? We said that, that’s one of those things that many VPs of design have to do, given the state of maturity their organization’s at. By his account, his organization is actually surprisingly mature when it comes to design. His boss and the CEO, who are two different people, want him to be doing the things he’s doing and don’t need him to sell them on the power of design, and the impact of design that is understood. And so when you take all that time that so many leaders have to spend evangelizing and educating, when you, you have that time back, it’s like, oh, well what do I do with that? Well, he’s, he’s able to use that time in this fashion to really drive craft excellence within the organization. And then the third thing, and he was very explicit about this, was, he has a member of his team that he referred to as his hammer who kind of runs the org for him, makes sure that all of those organizational, administrative, operational things are handled, that many design leaders themselves usually have more responsibility towards. He’s been able to delegate a lot of that, and we talked about that we used the analogy of a director and producer, right? He’s more of the director who’s responsible for the vision and the creative output. And then he’s got a producer who’s handling all that stuff that goes on behind the scenes that enables the people who are doing the craft to just focus on, on the craft and not on all the stuff around the craft. And so that was how he was able to be in that place where he could focus his efforts where he wanted. If he was in a different environment, he probably wouldn’t be able to do that. Or if he tried to be the craft-focused leader inside some enterprise software company that wasn’t ready for that, it would be a struggle. He would be unhappy. They would be unhappy, and it probably wouldn’t last. But he, he was able to find a context and do a little bit of work to shape it in terms of bringing on this hammer that enabled him to really focus on what he was passionate about. Jesse: Yeah, well, but importantly, he wasn’t just focusing on what he was passionate about. He talked about how he strategically chose where he engaged to be on the things that would be highest visibility to the business. So he is not chasing design perfection down every possible path for the business. What he’s doing is he’s choosing the things that he knows the CEO is gonna be taking a close look at. He’s choosing the things that he knows, that he’s got partners who are really deeply invested in, and he wants to be sure that he’s conversant with all of the details of that. And the way that he does that is by engaging with the team. Peter: Yeah. And that said, that might not be the best approach for everybody, right? I’ve never led a team that large, but when I was a design executive, I recognized my strength was organizational and operational. And I would delegate creative leadership to my design directors because I knew they could do that better than I could. I could situate the organization really well on their behalf, right? And so, I have this presentation that I give called The Evolving Design Leader. And one of the things that I stress towards the end of it is, too often we expect our design executives to be these design saviors, right? That they’re the creative visionary and they’re really good at leading and getting people excited. And they’re good at organizational building, and they’re good at the relationships with cross-functional and you can’t do, no one person is gonna be good at all of those things even. And so, so I talk about, I call it teamifying leadership, right? How can you reflect on what you are good at, passionate about, but then also what you lack, where your gaps are, and then put around you in your leadership team, not just, like, the people that you’re delegating to, but, create a team of folks, two or three people whom you can spread all of this leadership activity across? Your leadership complement Jesse: The term that I have been using for this recently is I call this finding your leadership complement. What are the resources around you that support you in the task of leadership? And in some cases that can be just having that right hand, just having that hammer. In some cases it’s about having that team of leaders of different people that you know, that you can delegate or partner with. But having an awareness, to your point, having an awareness of where your strengths are and where it’s necessary for you to provide your individual focus and attention, and then having a strategy for that leadership complement around you that’s going to support you with the rest of what leadership actually entails. So, speaking of that high level executive engagement I’ve heard you talk about a couple of times now the notion of social contagion in organizations and the implications of that for the design leader, and I’d love to hear you kind of unpack that idea a little bit. Social contagion Peter: Sure. And I can’t say I’ve thought about it in this context all that deeply, but at the beginning of the year, there was an article that got some virality, around how the layoffs that we’re seeing all these companies do is more than anything a social contagion. It’s not actually a reflection of good business practices. There is some type of research or study that had been done that showed that layoffs most of the time are actually bad for business. Businesses don’t end up healthier, a year later or whatever, because they did layoffs, than those who didn’t. And so why are they happening if they’re not good business practice and they make everybody miserable? And the finding in this research is that it’s a social contagion. Once some people start laying people off, other companies are looking at that and like, should we be doing that? I guess we should maybe be doing that. Is that what we’re doing now is laying off? And boards are telling people to lay people off because that’s what’s happening right now in the market. And now the thing to recognize about that concept is that literally every human behavior is a social contagion. That is how we operate. Jesse: Mm. Peter: And so all the hiring that happened a year and a half ago was a social contagion, right? And now we’re just kind of seeing the flip side of that, that hiring clearly was not done with real business savvy driving it. It was, “Wait, oh, that company’s hiring. We, we gotta hire, we gotta ramp up, we gotta…”, you know, it was, it was just looking around and doing what others do. And so I’ve been thinking about that because, even in the face of all of these layoffs, I am seeing companies, many companies, hiring, for the first time, senior design executives. So on one hand they’re laying people off, and on the other hand, they’re hiring their first ever SVP of design or VP of Design or Chief Design Officer. The same companies are doing this. When I saw that happening, I’m like, oh, I think design executives have hit this kind of social contagion layer, where companies are seeing, well, that company… Microsoft, for example, just hired four VPs or above, of design. John Maeda, Liz Danzico, Mike Davidson, and Justin Maguire. All within the couple months. And so companies are seeing like, well, if Microsoft, this very big important company is doing that, should we be hiring our chief design officers and stuff? And so I think we’re seeing that. And one of the implications of that, and this gets back to the trajectories, is that these companies that are doing it are likely immature in their awareness and understanding of design, right? They’re doing it because they’re seeing other people do it, but not because they understand necessarily what it will mean for them. And so as design leaders, we need to be quite conscious, conscientious, aware, as we’re going into these environments, what precipitated hiring at that level? What was the, what was the realization? What was that understanding? And to just go into these situations eyes wide open. Jesse: Yeah. Yeah, I think that’s a really huge thing. There are a lot of different models of the value proposition of design out there. And each design leader is carrying with them their own model of the value proposition of design. When you’re stepping into a new organization and especially an organization that is creating an executive level role for the first time, you’ve got to be asking where is this coming from? What is the promise that they hope gets fulfilled, ’cause it’s a huge, it is a huge organizational commitment to create an executive level role. it Is the kind of thing that is not easily undone. It has huge, deep, broad, long-lasting organizational implications. So when an organization engages in it, it’s because they see some promise there and they want to see that promise actualized. But if you, as the leader stepping into that, don’t have a really clear idea of what that is, you are running a high risk for a mismatch that is going to create some grief for you down the road. Peter: Yeah. And on that note, especially in this market where I think there’s a lot of anxiety about work and getting jobs, people might lower their own barrier to entry to a new job. And if you’re looking at a, a role like this, you need to be as, if not even more, particular about the environment that you’re stepping into, that it is ready for someone like you, that it can set you up to succeed. Too often what I see is designers are brought in to an environment like this, but they’re not set up for success. And so you need to be the one to figure out, to ask the questions. Jesse: You can’t assume that you’re being set up for success. You can’t. Peter: No. And not, with any ill will… Jesse: No, no, no malicious intent there. Peter: They’re obviously, they want this, they wouldn’t put this role together if they didn’t want it to succeed. But, many companies just have no idea what they’re getting when they’re getting design. They still think, primarily, I’m getting someone who can help make my design engine go. And if you have designs that are more impactful, more strategic, more cultural, more organizational, and you step into an environment where the expectation is creating a wireframe engine, that mismatch is going to be difficult. You should feel comfortable you should feel, I dunno, in the right, in asking hard questions of your perspective employer to, to make sure that you feel like they are setting you up for success. You should be able to ask for things like headcount before you get hired. Like, okay, you’re hiring me at this level. What is the team? What are the expectations? As a condition of hiring, I am gonna need five more head count, 10 more head count. Like that kind of stuff is totally reasonable and will demonstrate their willingness to commit to you and the role in the function. And if they’re not willing to do that, that’s a red flag. That’s a warning sign that they don’t necessarily understand what it is they’re asking for. Jesse: Mm-hmm. Mm-hmm. And of course you have to make the case for that headcount, but… Peter: Sure. Sure. But, and, and that might mean doing the diligence to understand enough about their organization, hopefully you’re doing that diligence as you’re considering a job like this somewhere, because you do have some responsibility to set yourself up for success. But it reminds me a little bit of that conversation we had with Denise Jacobs around creativity. And one of the things that she’s often frustrated with, from designers, is designers don’t do the work coaching the people they’re showing their work to, for the nature of the feedback they need. Jesse: Mm-hmm. Peter: And it’s not up to the non-designers to know how to give you good feedback. That’s, they, they don’t know how that, that’s not their, you know, and so you as the designer have to say, “this is the kind of thing that’s gonna help me make this design better, give me this kind of feedback.” You can do that in your role as a design leader as well. They’re not gonna know the role as well as you will. Communication in all forms Jesse: Mm-hmm. Mm-hmm. You know, so much of this, I think, when designers look at design leaders and ask what those people do all day, I notice how much of it is just trying to figure out what to say to whom and in what context. You know, so much of the job is planning your communications, executing your communications, getting feedback on your communications. Whether that is in conversation… I would say the primary medium of leadership is conversation. You’re spending way more time talking to people than you are preparing any kind of presentations or reports or deliverables or anything like that. But there are all of these other kinds of vehicles that are available to you too. We heard this from a couple of the folks that we talked with about the importance of creating communication strategies that address the needs of all of your different audiences. How do you communicate a vision amongst your business stakeholders? How do you communicate about your value proposition and your mandate with your product and your engineering partners? You know, how do you communicate where you’re going as a team with your team in a way that they can engage with and understand? You’re spending so much of your time just thinking about your language and just finding the right, the right moment in the right vehicle to get the right message across. Peter: Yeah, that was one of my biggest kind of surprises after the first five conversations we had, and I wrote this post around design leadership as change management, was how all of those design leaders, the degree to which they were intentional in their communication strategies. Because this was not something… Like, I would talk about the importance of relationships, and I would work with my clients or in the classes I teach around how design leadership is more talking than doing. And I would talk about the importance of evangelizing, but what I heard from these leaders was the work they did, the effort they did around having an almost overarching intentional communication strategy, right? And so you had Greg Petroff, having a quote “shadow comms team,” you know, one or two folks, a content designer that would help him write the newsletters or whatever that would go out there to make sure that he was on message. You would have Kaaren Hansen doing the pre-work with her leadership before they would present to others to make sure that the messaging was right, that it was focused, that it was right for that audience. Rachel Kobetz talking about how you are never not done with that communication and how she would just, every channel she had, she used. And what I think also tied them together, because you’re right, much of this happens in conversation, and so what you need to have, this is something I’ve started to stress in my classes and with my clients, are talking points. What are 2, 3, 4 messages… Jesse: yep. Peter: Kinda like in politics, what are the two or three, four messages that you’re just banging away on? Jesse: Mm-hmm. Peter: …just banging away on them in every situation you have. And you’re gonna get tired of hearing yourself saying these same things over and over again. but you know it’s working when you start hearing it back, and you’re gonna realize that it’s gonna take months if not years, to hear it back. In one of the classes I taught recently I had someone who’d been at a company, a big entertainment company that you’ve heard of, but I don’t want to say too much ’cause you know, it’s that person’s story. But they’d been there three years, four years. And in every session that they would lead, they would put the double diamond in there as a way to reflect on like what, where we are in the process, and to highlight the first part of that diamond. Like, the work we’re doing is, around discovery, is around definition. It’s around the strategy, right. To continue to orient people. And literally in every conversation for two years, she would do it and it wouldn’t get much notice. But then in the third year, she started seeing the stuff coming back to her in terms of people using that as a frame for talking about their work, right? And she, and she realized like she had been incepting this company with this thinking and it finally had worked. And so having that, you know, I think you mentioned earlier, persistence if not, you should have. This is part of that persistence. It’s just… Jesse: yeah. Peter: …banging away on that message. Jesse: And that tolerance for repeating yourself, right. To just be willing to say the same thing over and over and over and over again. It’s very, very much analogous to the way that a political campaign is run. Peter: And, it works, right? The people that we interviewed have achieved their success because they’ve employed these strategies. Thinking of talking points in politics and something else that I’ve been talking a lot about, and I wonder how you’ve approached this in your practice. I now in my masterclass on design leadership fundamentals talk about playing politics. I just call it out. You are playing politics. In order to succeed as a design leader, you have to be willing to play politics. That means some quid pro quo, some horse trading, some diplomacy, some talking points, like whatever you think of when you think of politics, bringing those to bear because your colleagues are doing that and they are, going to succeed through the politics they play. Playing politics Peter: If you’re not playing politics, if you somehow think that the value of the work should be evident in its quality, and just by doing the right thing, you’re going to succeed, you will not, you will fail. You need to do the work to play politics around it. Jesse: Yes. Yeah. There is no rising above it. There’s only going through it, you know? I really think that’s true. Peter: I think too often design leaders have this sense of purity around the nature of the work. And because it’s backed in research and we have this evidence, and if we just do the things that are obviously the right things to do it’ll succeed. And when you start talking about playing politics, there’s this concern that you’re gonna be disingenuous or something. And that’s not what we’re talking about at all. It’s not about somehow hiding things or being someone that you’re not. It’s about recognizing the tactics that work that enable you to advance your agenda, right? Which, when we talk about, that’s why we started with talking about vision, that vision is your agenda. The politics is what allows you to realize that agenda. Jesse: Right, right, right. I think that for a lot of leaders, they don’t realize where their effectiveness is hampered by their own sense of what design is and what design offers. I think too few design leaders know what’s truly worth fighting for in terms of design outcomes. And they put the emphasis in the wrong places and drive things that don’t really matter. Peter: So as you’re saying that, I’m reminded of Erika Hall, right. Kind of yelling at designers who worry about the alignment of elements on a page when she’s trying to get them to think that the business model is the grid, right? Like, is, is that the kind of thing you’re talking about? Like design leaders should be aiming for something more fundamental within the organizations they’re operating in and their ability to affect that and not just the presentation layer? Jesse: Well, it’s that, but also I simply think that there is a degree of pragmatism that is required at the executive level that designers haven’t necessarily cultivated within themselves until they get to that point. Peter: Yeah. Okay. No, that’s fair. But yes, ’cause one of the reasons people get into design is, there’s an idealistic bent. You’re trying to be an idealistic design executive, like you need some of that, for the passion, for the fire, for the North Star to keep you oriented. Well, this is a story I tell around politics. I supported an idealistic design leader who, basically, he wanted to bring human-centered design practices into this large healthcare organization. And he’d had some success doing that at another healthcare organization. And he came to this new healthcare organization and he’s like, I’m gonna bring HCD, true blue… Jesse: mm-hmm. Peter: … you know, human and patient-centered design practices into this organization. Now the issue was he’d been hired by an IT function within this organization. And so there was some expectation when he joined, that the team that he was leading would continue to look at Innovation with a technological lens, or at least through some of the work that technology was part of it. And he was such a purist. He’s like, no, technology is a means to the end. If you’re having me start with technology that’s sacrificing my dearest principles around the nature of the work I do. And he didn’t, he barely lasted a year at this organization because he could not approach it pragmatically. He had let his idealism get in the way of his ability to have, ’cause he likely could have, ultimately had that impact he wanted. This is the playing politics thing. By playing a little politics, given them a little bit of what they want, which wasn’t wrong, it just wasn’t what he was passionate about, but it wasn’t a bad thing. Give them a little bit of what they wanted, build that social capital internally. He could have within three years to five years been advancing a true human-centered agenda. He would’ve demonstrated his commitment to the organization, to the business and those types of things. But he just could not get over himself… Jesse: right. Peter: and, he, he ended up having no impact. Jesse: Yeah. This is a great example of exactly what I’m talking about. There are strategic design compromises that are sometimes necessary in order to create the momentum to get where you ultimately want to go as a design leader. But if you take every step as an all-or-nothing step, you’re never gonna get there. Peter: Right. Right. Jesse: So as we are winding this season up and you know, we’ll be back with more sometime soon but as we are looking back, I wanna look forward a little bit too and ask you, how are you feeling about the prospects for design and design leadership these days in the spring of 2023? Peter: I am feeling decidedly mixed, which is surprising me, ’cause usually when we have this moment of reflection and, and then looking forward, I feel like I’m pretty positive. Like, I have, I often see opportunity on the horizon. And so I want to be more hopeful and positive in my outlook, but, like, I haven’t done the work to unpack why I’m not more hopeful. So I’m teaching these Design Leadership Masterclasses. I’m also doing a bunch of work with specific companies. And one of the areas of focus I’ve had recently is at this level, not at the executive level, but at this design director level, kind of the middle management layer of design. The struggle of the UX Director Peter: I jokingly put a meme a few weeks ago on LinkedIn and it was a UX director who was being drawn and quartered, like this old woodcut drawing of somebody being drawn and quartered. You know, pulled apart by four horses and the UX director was that person, because this is what I’m hearing from that population. They’re having to cover for inadequate product partners who don’t understand their job. They’re not being given the staff they need to build out a team. So they’re having to do more of the hands-on work. Many of them are the senior-most designer in their organization. I, I do work with heads of design who are director level, who are not executive level, and so they have to show up with executives many layers in the hierarchy above them. But they have to be able to play in that realm. And they’re getting pulled in all these directions and it’s causing frustration, anxiety, burnout, and many of these folks are, are leaving the field. They’re just saying, you know what, I guess this isn’t where I want to be. Jesse: Well, who’s holding the ropes on this poor soul being drawn and quartered here? Peter: That’s a good question. In the cartoon I had, you know, your product partner pulling you in one direction, your team pulling you in another direction, your engineering partner pulling you in another direction. The business is this kind of shapeless entity pulling you in another direction. Those were the four, you know, HR in the background. And this is maybe why I’m, I’m having some trouble with hope right now. It’s a function of a lot of systemic factors. I mean, we can start with capitalism, right? But, one of the challenges, and I think Erika actually just posted something about this on LinkedIn recently, one of the issues we have is that the core values of people in UX and the core values of late-stage capitalism are at odds. And so the companies we work for, which practice late-stage capitalism, and then the UX kind of mindset that we’re bringing to it, are at odds. And I think trying to figure out how to square that is one of those forces. This wave of layoffs where middle management is targeted is one of these forces because the work of middle management’s not appreciated. And so these folks are getting pulled in more directions because there’s fewer people around them now. Whereas before they used to help coordinate and orchestrate the work, they’re now having to do it because they’re who’s left. So I think there’s these systemic forces at play that are doing the pulling and why I’m trying to figure out like how do I get to a place of hope in terms of, where is evidence of realization of frankly what Katrina said and when we talked to her, right? That design, when woven into business in an appropriate level, things are better. And there’s still so few examples of that. Even though, we have the obvious, almost textbook, examples now of Apple or whatever that like, if you embrace it the right way, you could realize a lot of success. But companies are still so resistant, kind of deeply, fundamentally at their core, resistant to not just the value that design has to bring, the approach design brings in order to realize that value. And I don’t know where it’s getting unlocked or, where it’s being integrated more successfully. Jesse: Yeah. Yeah. You know, this comes back to some of the stuff that we’ve been talking about really since we started this podcast. Having to do with the leader’s role in creating kind of a bubble within which the design team can thrive and reconciling the need for a distinct culture within the design team that is not the same as the larger culture that they’re a part of. And the design leader kind of having to serve as the partition, bouncer, semi-permeable membrane that keeps the cell intact. Peter: And I still use that metaphor, I use it all the time. And I think it’s just like, I dunno, at some point that cell wall dissolves under the onslaught of, all that effort, all that heat that gets applied to it from both sides, right? The designers who want to operate in one way, the rest of the organization trying to operate in another way. And, and this design leader just kind of like that friction that’s being created. Jesse: Mm-hmm. Mm-hmm. Like the design leader is sort of the WD-40 that has been, squirted into the, squeaky hinge. Peter: Right? And then it’s all used up. And that’s, I think, what’s leading to this, to, to this burnout. I think there are, you know, the opportunities, so, when you mentioned pragmatism, right? I think pragmatism is a helpful concept to rest on. A better recognition of one’s own power in these dynamics. I think design leaders in particular, maybe because they’re so new to it, don’t recognize that they actually do have power and they can set boundaries. ‘Cause a lot of, you know, burnout is, often a function of just an inability to set boundaries. And design leaders have trouble with that because they’re afraid if they set boundaries, if they say no, if they don’t take it all on, then they will be seen as not a team player. Someone that’s difficult. And that might be true, but then do you really wanna work in the company that expects to just, like, wring you dry? Like that’s not sustainable, right? Jesse: Yeah. Well, again, if you are being forced into this continually reactive stance you are not being set up for success as a leader. You are being set up for burnout. Peter: Right. how are you helping your charges? I guess they’re not your charges. How are you helping your clients? I’m assuming many of yours navigate some of these challenges and you talked about resilience and you talked about pragmatism. How do you guide them towards an ability to stick with the program, maintain that vision, maintain that passion, but in a way that doesn’t allow them to get taken advantage of? The future we want for design leaders Jesse: Yes, it’s absolutely true that a lot of design leaders need some practice in setting boundaries and in setting priorities for themselves because they’re used to other people driving their priorities because that has been their career experience. So yeah, definitely a big part of it is just helping leaders come into every situation with a little bit more intentionality, knowing what your point of view is, knowing what your desired outcome is, knowing what’s authentic for you, separate from what’s right for the organization and separate from what’s right for your team. What I see a lot of design leaders do is they so completely over-identify with their team, that they lose a sense of who they are in the mix and what they bring and what their strengths are that will enable the organization to go farther and to expand that value proposition. So for me, in my work with my clients, it’s always coming back to what’s really true for you and what does your insight, your acumen, your experience, your wisdom as a designer and as a design leader, where does that point you? Where does that take you? What direction does that suggest for you in bringing that into how you set your priorities, how you set your boundaries, how you focus your attention? Peter: Yeah, I think if, more of the people I worked with had a firmer sense of that for themselves in general, like, I think that could have like a multiplier effect. It would be interesting, like, if, leaders were more actualized across all of these organizations. That, that could be like, interestingly powerful. Jesse: You just described why I do what I do. Peter: I want that future. Let’s get to that future. Jesse: I agree with you. One last thing that I wanted to throw out there. We’re gonna take a break for a little while and then we’ll be back with more episodes of Finding Our Way. We’ve had this wonderful series of conversations with executive level design leaders. We would love to have more, but we don’t know the people that we don’t know, and we don’t know what stories there are out there that might really be worth hearing. So if you, listener to this podcast are working for a really awesome design leader that you feel like would have a lot to contribute to a conversation like these conversations you’ve been hearing on this show, we would love to talk to that person. We would love for you to nominate your design leader, to be a guest on Finding Our Way. So please go to our website at findingourway.design, hit the contact form and let us know who we should be talking to. We would love to hear from you. Peter: Yes. Excited to see who comes in, who we’re introduced to and looking forward to having those conversations in the future. Jesse: Peter. It’s been a pleasure as always. Thank you so much. Peter: Oh uh, the pleasure is all mine, Jesse, thank you. And to those who have stuck with us both this long into the season and this long into this episode, thank you for your attention. You can always find us whether at findingourway.design or on LinkedIn and see you around. Jesse: Thanks everybody. Take care. Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening.

Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, we are talking with Tim Allen, Global Head of Design and Research for Instacart, about the leader’s relationship to the craft of design, the balance between creative and operational leadership, and how growing up as a Black child in rural Japan has shaped his thinking about inclusion in design. Peter: Well, Tim, we’re so excited to have you with us today to talk about all kinds of things to do with design, design leadership. I think where it’ll be great to start, though, is just to get a sense of like, who you are today. What do you do? What’s your role, what are you accountable for? Set some context for us here. Tim: I mean, well, first, thanks for having me Peter, Jesse, it’s great to be here. My name’s Tim Allen. I, I lead design and research at Instacart. And I spend my entire day looking after a community of designers, researchers, writers, operations folks, and specialists focused on providing access to food that people love, and hopefully giving them back time so that they can enjoy that food as well. Peter: You mentioned looking after a community. One of the things that we’ve been probing in these conversations with design executives, and I’m curious your take on it, is how much time is spent with your team, managing this organization of however many folks, and how much time is spent being an executive, being with the “first team”, being with the C-suite, and your cross-functional peers? How do you navigate? Figuring out where to focus time and energy Tim: Yeah, I think, well it varies according to the time, the fiscal calendar, as well as the development cycle of any one of our, like four, we’re a four-sided marketplace. You have four product ecosystems. One is, you know, our Instacart consumer app, which, you know, most people are aware of. But most, a lot of people don’t understand that there’s a whole product and service ecosystem around shoppers fulfilling these these orders as well. So there’s a ecosystem designed for them as well. Then you have our retailer segment as well, which is, you know, how do we empower retailers and provide a technology platform for them. And then we have an advertising ecosystem as well. So brands that would like to showcase, you know, what they have for, for customers as well on the platform. So yeah, so depending on where we’re at within each one of those segments, I could be spending more time at the C-suite just in terms of, like, strategic conversations, setting visions roadmapping and so forth, down into like, where I like to spend a lot of my time, which is inspiring–… You know, we mentioned the word community a bit. I try to reserve the lion’s share of my time in empowering the community, setting the conditions for the design team, especially to do the best design work they possibly can. And, you know, be a part in their development and transformation into, you know, wherever they, they want to be. Of course that involves the product as well. So, you know, my approach to the product is to be down, you know, have hands on and eyes on, like down to the pixel, down to the comma, as much as possible. So very sort of detail-oriented there without, you know, micromanaging. But I do want to understand insights that led to decisions that led to pixels moving, that led to, you know, commas being placed and so forth. Jesse: How do you walk that line with people that you want to give, you know, authority and autonomy to, to dig into those design problems, understand them deeply and make the best possible choices there, while also providing an appropriate level of oversight over those detail-level decisions from your perspective as an executive? Leading through craft Tim: Yeah, it involves, like, setting expectations of —we’re all peers before the object. And we’re all trying to make it as best as it can possibly be, and so we’re all on the same team. And sometimes that involves and necessitates a lot of autonomy, especially when, you know, there’s domain expertise involved and there’s you know, a keen understanding of the customer involved and so forth. And then at a, at a certain level, especially during reviews and crit, there’s just craft involved and typically that’s where I want to get involved the most, along with you know, sort of envisioning and setting the vision of things. So like I’ll, I’ll come in, usually it’s, you know, you have this sort of divergence and convergence across the development cycle and I set the expectation that I’ll probably be most hands-on when we’re diverging. And then sort of definitely as we start to make the final convergence towards the end. Peter: I’m curious and, and Jesse actually just wrote something about this on LinkedIn, because you’re mentioning craft and you mentioned the pixel or the comma. How selective do you have to be in terms of your attention? ‘Cause I’m assuming you can’t be at that level of detail across all four sides of the marketplace and all the experiences you’re offering each of them. And so how do you navigate that? So that you’re not, I don’t know, overwhelmed or that you’re spending all your time in these details, like there’s so much surface area… Tim: Yeah, definitely. I make those decisions based on just business priority. So, you know, in one quarter I may solely be focused on shoppers and fulfillment. And, and another quarter may be sort of like distributed across all four segments. It’s based on business priorities, what I would say. And usually that forces a level of focus. Peter: I’m looking at Jesse ’cause one of the contentions in his article, and it’s something I’m aligned with, is, as you grow in your career, right, as you develop in your career, as you become more senior, it becomes less about craft and those details, and more about setting up an organization that can execute on the details. And so, but it sounds like you consider it important to maintain a pretty tight connection with details as needed. And so how do you navigate, like building the engine, focusing on, on the mechanics that enable success versus knowing when to dive in and get to those specific points. Tim: Yeah, well, one, and you know, there’s a light and a shadow to this. One, I can’t help myself. I love design and I love the craft of design. And so early on in my career traditionally you have this paradigm where the higher you go, the farther you get from the craft. And I never enjoyed that so much so that I almost wanted to stunt my own sort of career growth. And RGA was one place where the closer you got to the craft and the client and the work and the better that work became, and, and, and the more you use that work to influence the team and so forth, to empower them, like through the work, the, the more you are rewarded and the business thrives and so forth. So I really, really clung to that. And what was the icing on the cake? Just most recently was, you know, and at Airbnb where, you know, the CEO is a designer as well, and he is directly related to, you know, the pixels and, and the commas at the highest level of, of the company. That where I was like, oh, okay, this is, it’s rare, definitely, but this is the type of leadership that I want to emulate. I’m not saying that one way is better than the other. I think there’s pros and cons each way, but I, I can’t help myself from doing that. And I was just like, is that okay to do? And like, how can I mitigate the issues and concerns that that does raise? Jesse: Yeah. I think that question of is it okay to do is an important one because I think a lot of it, you mentioned RGA, you mentioned Airbnb. These are companies that have very design-centric cultures historically. And… there is a question of, like, how much cultural permission you get to go deep on craft. And I wonder about how you manage the expectations of your cross-functional peers when you decide to go deep on design. Do they feel… are they okay with that? Do you have to negotiate something to create that space, to get that permission to go deep? Tim: Well, at some point it just all comes down to, like, output. I’ve been in situations, I, I maybe even dare to say recently where, you know, that approach wasn’t expected. And people like you could see the, like, why, why are you doing this? Like, you were very close. And, and as the output evolves you know, the design community in, in addition to cross-functional partners, start to understand, oh, this is a different way of approaching it, but like, I see the value. Where it’s not based on like control or power or anything like that. It’s truly based on like contribution to making… Jesse: mm. Tim: … better products and just different levels of, of contribution. Learning through making mistakes Peter: When you were mentioning your, your leadership approach, you used the word “mitigate” to suggest that in order for you to have this detail orientation, at least at times you recognize that there needs to be something to kind of balance that out. And I’m, I’m curious, over your career, what have those mitigations been? How, what have you done as you’ve established your leadership practices and as you’ve built teams, what have you found you’ve needed to do, organizationally, to support your desire to get into those details? Tim: Yeah. Yes. Mainly just made a lot of mistakes, Peter: That’s how we learn! Tim: And learn… exactly, and learn from them, which is, you know, leaning in too hard. You know, I’ve leaned in too hard at some times and I’ve also pulled back too far at times. And so I’ve had to understand, like, as I’m giving direction, how can I give it in a way that allows people the flexibility to interpret it and also bring their own creative spirit to it and, and make that direction better. You know, I, early on, I must say I was probably spoiled by so much talent at like, places like RGA where just a little bit of direction comes back with a ton of improvement. And, you know, as I got into other spaces where that wasn’t necessarily the case, it was really about refining that approach. Refining, like, reviews and crits and like, I feel like, you know, workshops or crits of work are where the magic kind of really happens, I think. And, and really setting those up so people feel accountable for one, but then also like fearless and creative too. Jesse: How do you avoid being a bottleneck as you are engaging in these processes? Are people automatically expecting you to be engaged, or are you negotiating a different scale of engagement with that process of critique? Tim: Yeah. I think it’s easy to become a bottleneck. Yeah. And that’s, and that’s also one of the mistakes that I’ve made in the past as well at least for priority projects. And, you know I think the team’s only as fast as, like, their leader. So that is very front of mind, we talked about mitigation, but concern, I’m, I’m always having, like, am I responding quick enough so that I am not a bottleneck? I do in high priority business programs want to be a part of decisions and understanding like what insights are coming in, how are we interpreting data, how is that translating into design decisions, and so forth. And so I, what I’m trying to do is like limit, you know, speaking, speaking tactically, limit the amount of preparation needed for my involvement, too. So, you know, in some cases what I’ve learned in the past through my own, again, mistakes is not understanding that some people can interpret presenting to people at my level as like, “Hey, we gotta circle the wagons and, and put as much thought into this presentation as we did into the work.” And then sometimes more. And so that’s completely not the case. So I’m, I’m, I’m setting the expectation of, yes, we’re talking about sausage-making. So show the appropriate level of fidelity for the moment in time we are in the development cycle. The importance of safety in creative work Jesse: So it seems like a lot of this is about the expectations that you’re setting and the relationship that you’re creating with your team to get them to trust you, that it’s okay to be messy, and for the work to be a little unrefined and a little unpolished. What are some of the ways in which you create permission within your team for people to be messy when they know that you’re gonna be looking at their work? Tim: Well, I think that’s where the safety comes in, I, I relate safety to like, fearlessness. You know, I think, like, we do best work when we’re not afraid. And, and that’s just hopefully establishing that, like, great ideas are just great ideas no matter what the fidelity is. Jesse: Hmm. Tim: So what’s the least amount of fidelity you can give to an idea that allows people to understand that it’s a great idea, you know? And, and in some cases it’s gonna be a functional prototype, so you’re gonna have to spend a lot of time on it because like, you can talk about, I don’t know, like swipe gestures and so forth and, you know, 10 different people will interpret that 10 different ways. Or it could be like a whiteboard sketch or, you know or maybe even a document. So I think the expression of ideas is what I try to encourage the, the team to understand. Like, the tool set is very varied that you can use to express in an idea, and it’s up to you on, on how to do it. Peter: How do you set expectations for quality? How do folks understand what you’re expecting of them in terms of what the quality bar is? What have you done to define that? Tim: Principally, in terms of, like, principles, like we need you to do the best work of your life, like just straight up. So, but that can be interpreted a couple different ways, but that’s the, in, in terms of principles, that’s, like, what we’re trying to do, and it’s on us or, myself as a leader, to set those conditions so that that can happen. But the expectation is for you to be doing the best work of your career. And so, so what does that actually mean? I think it means just being world class at solving customers problems, and that that means falling in love with the customers and their goals and their needs, you know, thinking deeply about them. And, you know, I interpret falling in love with problems as also thinking orthogonally about the solutions as well, right? So, you know, going down blind alleys which, you know, sometimes can be dangerous. Again, connecting disparate thoughts. And also because you’ve fallen in love with so many different people, with different contexts and so forth, you can start connecting them in different ways as well. I had the privilege of working with Jonny Ive at Airbnb and I, there’s many things fascinating about that individual, but one of the things I was completely blown away with was, like, the connections he was making, just like organically between, cultures and ways of seeing the world and perspectives, because he’s fallen in love, literally, with so many different types of people and contexts and so forth. And so he has this like library he’s drawing on to make these connections. Just really truly stepping outside of yourself into other contexts. Making space for a design Peter: Airbnb and Apple are often held up as paragons of good design, but they’re also really weird companies, in part because of this. Because of this willingness to embrace design in, in such a elevated, robust, exploratory fashion. You’ve operated in environments, you’re possibly in one now, where design wasn’t that highest order bit the way it was at a place like Apple and Airbnb. And I’m wondering what you’ve had to do to make space, say at a place like Instacart, for your team to take this really rich approach to practicing design in a context that maybe before you were there, didn’t necessarily enable it, right? I look at the people I work with in other types of product-led, maybe even engineering-led organizations, sometimes design is a battle. Even when it’s not, and it’s seen as a partner, it’s still work on the part of the design leader to make space for design to really demonstrate that richness. But it feels like that’s crucial in your world. And so what have you done to help your partners understand, in an environment where design isn’t the highest order bit, what have you done to help your partners understand just what it takes to deliver on truly great design? Tim: Wow. I could talk about this for a while because I’ve not, I’ve, I’ve made some huge errors here. And then I think with Instacart I found a path that is, is proving to be successful. So if you, if you look at my career, it’s sort of like RGA, a couple of like huge legacy companies that like aren’t sort of like design-driven and then Airbnb. I sort of call that my Goldilocks era of like, hey, I reached a level, almost terminal level at RGA. Like, what’s the next challenge? Right? And I would say there’s a mixture of like hubris mix in there along with curiosity of like, hmm, Microsoft needs a new design system. It would be great at that scale to kind of, like, be a part of transforming a company through design and,like, thinking, sure. I’m up with that challenge. That does take a, a bit of hubris. And I would say, like, I mistakenly, I think, used a bit of brute force in that, just ’cause it’s, like, early on in my career I’m, like, I don’t really understand all of the layers of legacy and culture and so forth that turned out to make that very, very difficult task to do. But, you know, sort of through that same, you know, I, I won’t speak in specifics with Amazon as well, but like, same thing sort of there, it’s like, yeah, like, why not? Let’s give this a try. Like, how can you take the utility of an Amazon and, like, the sheer, like, usefulness of it, but then also make it, like, lovable. In my opinion, the Achilles heel with some of these, like, utility-based behemoths are, like, the moment there’s another utility that comes along that is, like, people slightly love a little bit more, or maybe it’s not quite as useful, but people love a lot more, you’re yesterday’s news, right? So in my mind, I think design plays a big role in that. So, my whole thing was, like, how do you take visceral emotion and, and love for a brand and a product and an experience mixed that with utility and then just have, like, make it, you know, obviously almost unstoppable. And that’s what Fluent design was designed for. That’s what, like, the Alexa platform and some of the work I, I was doing with Amazon was about, but getting back to your question in, you know, non-design led companies, how do you bring design to the table? I learned from those companies that it’s not through brute force. It’s not through how much you know about design. There’s a quote that, you know, people will never care how much you know until they know how much you care. And so what I did with Airbnb and what I’m doing with Instacart is allowing people to understand that I care deeply about the mission and our shared belief in this mission. That’s, like, the most, I think, critical common ground across functions we can ever have. And let me show you how the design community and the design function can bring that to life in addition to, like, the trust and respect we have for your function as well. And, like, showing how that happens leads to, I think, inspiration. And where I’ve seen the lights turn on, like, almost physically in, in rooms at Instacart is when they see that connection and they see what they believe in being upleveled and, and inspired through design. Developing a culture of curiosity Jesse: I love the way that you described, the way that you went after these challenges as a mix of hubris and curiosity. And curiosity, well, cause I think that’s essential for a leader to continue to grow. They have to continue to believe that there are new challenges out there that are, you know, worthy of what they have to offer. Right? But curiosity especially is something that I tend to think of as being one of the kind of the core values of design as a practice. And you know, when I think about hubris and curiosity in organizations that are not design-led or do not have a strong design culture, what I think of is a whole lot of hubris and maybe not so much curiosity. And I wonder what your experiences have been in trying to drive a culture of curiosity in organizations that may not be all that interested in it to start. Tim: Yeah. I’ve got war stories there, but I can’t say like, I’ve cracked that at all. \ What I was looking for and found at Instacart was a CEO that understood the power of design and wanted to be inspired by design and understood the gaps in the business as it related to design very, very well. And so it was the fertile soil. The, the gap was there. But it could be cultivated into something great. So that’s when, like, you have curiosity, no longer hubris, right? ‘Cause it’s, like, no, you know you know, we did Nike, you know, we did blah, blah, blah. So, like it, Microsoft, whatever, right? It’s more, like, courage, I’m curious about this. I know there’s a gap. It seems like there’s a way to fill the gap and, like, like, let’s approach this with courage. That’s the difference at Instacart. Peter: You mentioned the CEO, are you reporting to the CEO or through? Through what teams do you report up to? The C-suite. Tim: Yeah. So I report to the Chief Operating Officer Asha, who reports to the CEO. Peter: That’s interesting. How is operations defined then at Instacart? You know, cause usually operations, you know, you don’t think of design reporting up through operations. It might report it through product or marketing. So what’s the… Tim: well, yeah. Well. Peter: …logic behind operations? Tim: Well, it’s probably a different approach in terms of operations, but the Chief Product Officer reports to Asha, the COO, the, the Chief Marketing Officer the CMO, reports also through operations. And yeah, like me sort of standing in as Chief Design Officer as well. That kind of makes sense. Peter: And to what is she holding you accountable for, right? You’re, you’re peers now with the head of product, a Chief Product Officer, Chief Marketing Officer, they probably have very clear accountabilities, very clear numbers and metrics that they’re expected to deliver. Do you have something similar that she’s looking for you to bring or how, how is that accountability handled? Tim: Yeah. It’s couple different ways. Attract higher, retain, best design talent possible and uplevel talent and craft across the board. Bring a level of strategic insight that’s design- and research-based into strategic conversations and help us deliver against our mission. Bring our mission, which is like human-centered. It’s like one of the most human-centered missions you can have. It’s food, right? Like, access to food front and center, and inspire us with that. You know and then help us grow awareness and love for the brand and, and product. Peter: Are those measured or are those just understood? Tim: Well, I think we are in the process of understanding how to measure those to be, to be honest. But they’re, yeah, they’re, they’re definitely understood. And that was like the, the, the process of me being recruited and, and, and vetted for the role was, like, okay, like, do you understand the challenges? And all four of those things. I think there’s four, four things I mentioned. Have like great challenges, and then also, like, and some of them are easily measured. A lot of them definitely aren’t, and I, I actually really like that. Maintaining visibility to keep others informed Jesse: It seems to me that the challenge with some of these things that are potentially quite subjective is ensuring that what you’re doing is visible to people in a way that they can see the value that you’re providing, even if it is in a subjective way. How do you keep people in the loop with what’s going on for you and your team? How do you maintain the level of visibility for your work necessary for people to reach that subjective consensus that you’re doing a good job? Tim: That’s, a good question. It’s mainly through interrogating the work. So I think there’s a couple things that happens weekly. So just tactically speaking, weekly, we have, yeah, basically design and research workshops on Thursdays where all of the highest priority work for… the entire day is dedicated to reviewing work in, like, 45 minute to 90 minute sessions. And so all of the highest priority work across all those segments is getting reviewed. I host that, sort of, I, I’m, I’m the main contributor, but it’s cross-functional. So depending on what phase of the cycle the project is in, you know, you could have like the full cross-functional team across, like, data science, engineering, product management, business, so forth, even business development in, in those reviews or workshops. Or you would just have, like, the design team, sometimes even just, like, special, like, motion team, maybe even. And so I think that allows people to, like, see work, for one, see how work transforms as well, contribute to that transformation, you know, and then, you know… I don’t send out a weekly newsletter. We’re thinking about doing… I’ve done that in the past. I do send out a weekly note to the team, just like top of mind things. It’s not really, like, status or anything, it’s just, like, literally it’s meant to be inspirational. I think that helps my… and I copy my leadership team on that. Peter: Your approach to leading a team at this size is different than the other people we’ve talked to and, and often the people I work with. You place a lot of value and importance on craft and practice, right? Whereas I think a lot of the leaders that I’ve worked with delegate that to their directors or even their managers because they have other things they need to be concerned with. A long time ago, I thought there was a model, and I’m sounding this out with you, for design leadership, that was kind of like filmmaking, where you have director and a producer, right? You don’t get Ron Howard if you don’t have Brian Glazer, right? And, and I’m wondering if that resonates with you, if you’re able to really focus on creative leadership, because you partner with operational production-like leadership who you know you can trust to keep things running so that you can be a bit more of that visionary than we often see with people in design executive roles. The “Hammer” Tim: Yes, that’s a very, very good point. So, I talked to my wife about the role you’re talking about as my hammer, and I didn’t know I needed a hammer until just like understanding former roles. And so for me it’s the chief of staff and also, frankly, coming into Airbnb, my initial role was to sort of be the foil of Alex Schleifer at Airbnb. Alex Schleifer was the Chief Design Officer at Airbnb during my tenure, and I was the VP of Design. Alex loved doing the approach that we’re talking about and needed someone, and was less concerned and less, like, honestly, probably enthused about the other facets of leadership that are needed as well. And so I was playing that role just in terms of like operations, cultural, management, so forth, team morale, blah, blah, blah. And so now , I’ve sort of like reversed that a bit. And like my, I have an excellent chief of staff and along with the senior leadership team that helps out like evening out those more operational, administrative tasks of senior leadership too. Peter: Is that, is that Taylor? Tim: That is Tay– How do you…? That is Taylor. Peter: Taylor, who will probably be listening to this, is a friend and an active member of the Design Ops community. And, she is your hammer. So that’s almost like, like Rahm Emanuel was for President Obama. Someone who does some of the work to make sure the things that you are wanting to see done can get operationalized and implemented. Is that similar to how you’re imagining it? Tim: Indeed. Indeed, yes. Peter: Hopefully with less swearing. Inclusive Design Jesse: So, I know that you worked at Microsoft on their inclusive design initiative, and I know that inclusion in design has been a bit of a theme for you through your career, and I know that that has a lot of different facets to it. For us as an industry, you know, the way that we approach inclusion in user research, the way that we approach inclusion in the design process the way that we approach inclusion in hiring and promoting people, I’m curious about what are the aspects of it that you feel like are the most interesting opportunities for design as an industry to level up around inclusion? Tim: Yeah. Yeah. I, I’ll start out by saying I think the people that are most interested, and have moved inclusion forward the most are typically the people that have experienced the most exclusion. And so for me, exclusion has just been a part of my existence since day one. So I, I mean, I talk about the impetus first, which is, you know, I, I grew up in rural Japan. My father was in the military, so Okinawa and, and Iwa Kuni. And, you know, back then, I dare to say even now, growing up as a black child in rural Japan is like a very Jesse: Mm-hmm. Tim: isolating experience. And so, you know, my, my parents helped me through that. And so at a very young age, I understood like, yeah, I, I looked different. My hair is different. And it was quite a spectacle back then. And, and they just, my parents worked me through that. And you know, if you think about design school as well, I came into design school. No one looked like me. No one spoke like me. It was hard to relate to, to folks. I didn’t know what design was. I came into design school through a fine arts scholarship, and I’d never known what design was. I was a painter and like had my own like airbrush business in high school. I just like literally used that as my portfolio and, you know, landed in design school. Didn’t feel like I belonged. And then again, in the same way my parents helped me get through that, I had like a really great staff of instructors that helped me get through that too, which was like basically, hey, all the fear and uncertainty that you feel, and also the way you look at the world is extremely valuable. And like, we need that and it’s very valuable for you to get that out. And so it’s just flipped my mind into like all of that being a superpower rather than a disability. And so then now you talk about the word disability and what that means and so forth. And my focus is on how do you unlock and harness the breadth of human diversity through design and, and research to allow people to shine. And also not only altruistically, but you know, it’s been proven, but just in my experience, just to make like really, really kickass, like, products as well that are this magic combination of, like, viscerally, culturally compelling and, and emotionally engaging as well as, like, useful utility. Peter: I mean, It feels like we’re still so early days, so many companies are not approaching design with an inclusive kind of mindset or approach. Is that still where we’re at is like foundational or are you finding a better conversation happening farther along that curve? Tim: Yeah, I mean, shout out to like folks like Kat Holmes and like people that have like really, really dug into this wholeheartedly. But I do think we are in some of the beginning stages. I think the biggest challenge right now in my opinion, is moving from this, like, state of altruism and, you know, being a savior and things that kind of connote power dynamics into a very powerful strategic business tool. If you wanna talk about MAU and DAU and, you know, daily active users and, like, expanding the amount of people that use your product, thus expanding the financial impact into your business, then yes, you want to appeal to different types of people with different levels of ability and, and different cultural, you know, aspects. It just makes sense. For me, it’s turning the corner from like, oh, it’s so nice to like, understand these people’s point of view and like how our product is hampering people with mobility issues and like, and isn’t it so great that we can allow them to use our great product? In terms of like, what do these people need? What are their pain points? And like, how do we solve them in a way that makes our product better for everyone? It’s a different lens and also, like, we probably will make more money as, as well. Peter: This is interesting cause I think the history of design craft is somewhat ableist, right? The the things that have often been lauded are that which have served people who are able, and I’m wondering, you’ve talked a lot about craft and the importance of craft and practice, but those crafts and practices, a lot of those were developed for a pre-inclusive, let’s say, kind of approach to thinking about design. And I’m wondering how you’ve seen design evolve the practice and the craft of design evolve to incorporate inclusivity, where it’s not about the grid necessarily anymore, and visual hierarchy or whatever the concerns we might have had 20 years ago, but, it’s something else. How are you embracing, like, that fundamental change that is necessary? What does it mean to fundamentally change to embrace inclusivity honestly and authentically? Tim: Right. Well, I have a background in industrial design. And I think because that and architecture, for instance, are established practices that have to legally, and, you know, to a certain extent, yes, digital design as well, incorporate accessibility and inclusion into the very practice itself in a way that isn’t altruistic, that is in a way that is, like, crucial to just creating a product that is deemed successful at all. Product design, experience design, digital product design, I would say as a whole, and research, it’s just nascent, it’s not proactive. It’s very reactive for the most part. And it is based on, Hey, we made something. Oh, and a few people have missed out on it. So, like, let’s, like, accommodate them to, like, what we made as opposed to including everyone. Peter: You’re leading design and you’re an executive during what is a difficult time, in some ways, for many people, particularly our industry, layoffs, you know, those kinds of uncertainties. And I’m wondering what you found that you’ve needed to do, that you’ve needed to change? How have you been handling being a leader? What have you been doing to kind of help lead your team through these challenging and uncertain times? Managing through uncertainty Tim: Yeah, that’s a really great, great question. I have yet to experience an aha moment or any moment of like, really, really critical success that hasn’t been preceded by overcoming some level of hardship, difficulty, uncertainty, and fear. So you can go back, I, I talked about the design school thing I’ve talked about like just living, trying to like be a child in Japan. You know, coming into some of these legacy companies and so forth. So for me it’s just a growth mindset. And going back to that advice from design school of like this fear and certainty is where all the opportunity is. Peter: Hmm. Tim: Like literally. And, to me, that’s just the way I think, but I saw it be proved out before my eyes and was a part of it. At Airbnb when overnight we went from a business that was going warp speed, light speed to like zero miles an hour standstill overnight through the pandemic. Peter: Right. Tim: And the way that the leadership team led through that uncertainty making tough decisions, like, yeah, we did have to cut and reduce the workforce. But we approached it like a design challenge. What do people need right now? What are the pain points? What are the opportunities in this space? We just embraced the uncertainty and, and then we doubled down on the shared belief. And by, by the way, these are the steps I’m using right now as well. Embrace the uncertainty. It’s, it’s there. But just because it’s cold outside it doesn’t prevent us from, like, eating soup, right? Alright and what’s that shared belief? What’s the soup? For us right now, it’s the access to the food that you love and time to enjoy it with yourself, with your family. So with your loved ones. Once you focus on that belief, then visions start to, like, I think creativity just, like, abounds and that’s what allows you to adapt and I think disrupt. Jesse: So you have, over the course of your career, you have seen design go through any number of evolutions and transformations. How design is practiced now is very different from how design was practiced 10 years ago, which is even more different from how it was practiced when you started your career back in the nineties. So I find myself wondering from your perspective, what’s got you excited about the next stage in the evolution of design practice? Tim: That’s a really good question. I, I would definitely say the topic of inclusion. Not only product inclusion, but team inclusion as well. I feel like, you know, homogenous teams make homogenous products, for homogenous audiences using homogenous strategies, right? So… Jesse: yeah. Tim: …the output comes from the input. Enabling and having a priority to bring other voices to the table to not create homogenous teams and thus make less homogenous products and so forth and address that more diverse customer audience is what I’m super excited about. Working with a leadership team that believes in that as well. And, you know I won’t say that Having a female COO and CEO was not a part of my decision as well coming into Instacart. I think that’s, that’s been incredible for me. So yeah, that’s, the biggest thing for me. I mean, you can’t have a conversation like this without mentioning machine learning and AI as well. I think that’s fascinating and we’re starting to understand how to, like, incorporate that even more at Instacart. So stay tuned there. But yeah, that’s that’s amazing. Jesse: Tim, this has been great. Thank you so much. Tim: Thank you, Peter: Yes. Thank you. Tim: Thanks Peter. Peter: So Tim, where can people find you on the internet? Do you, do you write, do you publish? Where can people follow up with you? Tim: I’m active on LinkedIn probably the most. So yeah, just you could search for Tim Allen there. Tim Allen. Peter: Not that Tim Allen. The other Tim Tim: Exactly. Yeah. And you know, on the Gram and Twitter @TimAllenDesign. Jesse: Fantastic. Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too. As always, thanks for everything you do for all of us. And thanks so much for listening. I can’t believe we got through the whole hour before we finally got around to the Tim Allen joke. Peter: I’m sure it never happens. Tim: I knew it was coming. Jesse: Yeah.