Finding Our Way

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78: AI is Expensive, Teaming is Free (ft. Clay Parker Jones) Oct 24, 2026

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Show Notes Peter and Jesse are joined by organization designer Clay Parker Jones, author of Hidden Patterns: A Playbook for More Human Workplaces, who has led organization design work at Airbnb, Undercurrent, R/GA, and August. The conversation covers why roles persist, the importance of indexing on trust over role clarity, the difference between psychological and structural safety, organizational rule of law, and why demonstrating better teams beats trying to convince skeptics.Clay Parker Jones: https://cpj.fyi, Hidden Patterns book Jesse James Garrett: https://jessejamesgarrett.com/ Peter Merholz: https://petermerholz.com/ Transcript Jesse: I’m Jesse James Garrett. Peter: And I’m Peter Merholz. Jesse: And we’re Peter: finding our way. Navigating the opportunities- And challenges- Of design and design leadership. Jesse: On today’s show we’re joined by organization designer Clay Parker Jones And author of the book Hidden Patterns: A Playbook for More Human Workplaces. We’ll get into the untapped value that is unlocked through organization design, why teams might be better off indexing on trust rather than clarity, and strategies for overcoming organizational resistance to change. Peter: Clay, thank you for joining us. Clay: Happy to be here. Peter: You’re probably a little less standard of a guest- … on Finding Our Way, in that you’re not a UX design type. So for our audience who might not be familiar with you, how do you introduce yourself? Clay: Well, firstly, when I was young, I did want to become a UX designer. And I very much looked up to the both of you and the work that Adaptive Path did. So not being a good enough designer, I think, led me to be an organization designer. Peter: Which is something I, I now share myself. Clay: Hey, life brings us many changes. Okay. So how do I introduce myself? I’m an organization designer. I am now an author. I’m now also a dad. I live here in Brooklyn, New York, with my wife and son and cat, Ian. I’m a former bicycle mechanic. Defining Organization Designer Peter: Organization designer is one of those roles that I think people have heard but don’t really know what they do. Yes. What would you say an organization designer does? Clay: Like, the formal answer or the way that if I was trying to explain it to someone who’s going to be paying me would be something around the structuring of units to help people achieve a goal, or the reforming of an organization in its various constituent parts in order to deliver some improved outcome for stakeholders. That’s, like, a real nerdy example or a real nerdy way to talk about it. I think the way that I think about it personally is waking up with a mission of the people that you’re working with being able to get more and better work done today than they did yesterday, and continuing to do that over and over again. The idea of design is useful because it introduces, like, a category boundary. But I, I think so much of this work is actually just in… It’s in the margins. It’s in the meeting that goes well or goes poorly. It’s in the role that is well-described or poorly described. It’s in the team that knows that the other teams around them are gonna keep doing the things that they said that they were going to do and not always, or maybe increasingly so, not infringe on their territory or step on their toes. It’s in people feeling really excited about their work. And whatever mechanisms we might use in order to get there, it might be a PowerPoint deck containing a org chart. It might be a piece of software. It might be a prompt that somebody gets or a prompt that somebody gives to a intelligence. It’s all kinds of things. But it gets pretty narrowed into this idea of, oh, we’re making a deck for a senior leader that follows, like, this diagnose, design, deliver kind of pattern. And I think that’s increasingly unuseful or even unhelpful in the way that we define the field. Jesse: What are some of the other tools that you’d like to see come into play in how organization design is done? Clay: I think it’s more about the distribution of the knobs or the levers or, like, the palettes that we might paint with to more and more people. And I don’t mean that through terms or ideas like self-management necessarily. That may be something that happens, but mostly just that more teams are able to have more of an impact on the way that they are themselves designed, the way that they have agreed with each other that they’re going to work, and that more people are doing it more frequently at a higher and higher level over time. So it’s less about, like, the tooling exactly, and more about, like, more people adopting whatever tooling it might be. Peter: Mm-hmm. Correct me if I’m wrong, but org design, at least the way you practice it, is more defined by its outcomes of an improved org. Whereas while that had been the goal of UX design when Jesse and I were doing this 20-some years ago, UX design, over the last decade-plus, has been defined by its artifacts and its process and what it creates, less by its impact. And I’m wondering, well, one, an opportunity, I think, right now for UX design is to be less defined by its tools and process and artifacts, and more by its impact. And I guess with org design, I’m wondering, have you seen it defined by its stuff, or has it been able to stay a bit truer to an orientation on impact? Clay: I think that there’s, like, roughly two portions of the field. There’s this kind of like structuralist portion that gets paid for doing organization design, and that is seen by stakeholders as org designers. And those people are typically at one of the big consultancies, less so like an August, less so like The Ready, and more so like McKinsey or Kates Kesler, now part of Accenture. And they’re defined by outcomes, but they’re also very much defined by the actual artifact. There is a perceptible feel to one of their documents, that where even if it has the company logo at the bottom, you know who wrote this thing. And the outcomes are far, so far in the distance. They’re gonna come to us five, 10 years from now when we finally bring together all these operating units that have been operating on their own, with their own intention and with their own structure, and now we’re bringing them together and we’re gonna achieve some efficiencies. That’s gonna happen way far in the distance, and the outcome is not really even part of the conversation. It’s the output. It’s the thing that we all agree is, like, gonna be the effective transfer of power. And then there’s, like, this, I refer to as, like, a mutualist side of the practice, which is more about helping people define their work together and giving them the tools and the technologies and the language to actually be able to do that. And that is almost entirely outcome driven, and it gets paid a lot more reasonably than do, like, the structuralist org designers, right? And I think there’s a little bit of the mission kind of getting in the way there to a certain extent, if all we’re trying to do is get paid. But, at very least, there’s like these two sides. One is called org design, one is usually called, like, culture work or ways of working work, but it is org design. It’s changing the way that the organization is structured, intentionally, for good, usually, or that’s the intent or the hope. And then the other side is we’re trying to, we’re trying to hack it, and sometimes we get called in, sometimes we get brought in after the big consultancies get called in, and that is entirely always going to be sold. We always did at August, sell it in terms of the things that are, that our clients are going to be able to observe in the organization, not something that they’re gonna be able to hold onto, which maybe is a bad consulting strategy. Peter: Mm-hmm. Mm-hmm. Jesse: Some would say. Clay: Sure. The End of Role Clarity Peter: The impetus to have you join us on our podcast was something that you published in February called The End of Role Clarity, which I ended up responding to in a newsletter article of my own. But before we get into a dialogue, I think it would be good, for those who haven’t had a chance to read it, if you could just share the thesis. It’s a long enough article, so I’m sure you’re gonna have to elide some details, but what is your high order thesis when you were writing The End of Role Clarity? Clay: Yeah. In large organizations, so much of the conversation ends up being about, “Oh, well, we don’t have role clarity.” And it’s something people say when they are trying not exactly to avoid taking action, but it often allows people to do that. We’re not going to take advantage of this opportunity because we don’t have role clarity, because I’m not sure if that person over there is supposed to be doing that thing that they’re doing that I think I should be doing, and it’s getting in the way of us being able to make a good decision. And I wanted to offer with that piece this alternative view, which I think is more and more plausible or possible with, or maybe even required or will be forced upon us by the introduction of new technologies that allow more people to do things that they didn’t know how to do before. Whether or not they know if the output is good or not is sort of beside the point, but it is going to allow more people to be designers, be musicians. It’s going to allow people to do more things. So that means that individual roles as we have defined them today, like an engineer or a product manager or a designer, become less useful or interesting distinctions between roles because teams are able to just say, “All right, yeah, I can kind of be a software engineer if I’m a designer with an interest in artificial intelligence and figuring out, like wading through the process of like getting Terminal working for me and being able to work in the command line. Oh, I can actually be useful, and I can make a prototype with the design sense that I have.” Or if I’m a product manager, I can actually do some of the design work using some tokens that I’m pulling from a library that’s been well architected by actual designers. And that means that the more useful thing to be focused on is less, like, are they perfectly defined, and do they have no overlap between the two individual roles, or do they know how to work very well as a team because they have a clear team purpose, they have a clear sense of our focus areas, they have a clear understanding of how we’re going to be measured. They know where we’re going to work, they know and they’ve made an agreement together about how they intend to work. That’s much more useful than this idea of role clarity, which feels antiquated and stuck in this idea of the org chart being defined by the employment agreement, which I think, again, is going to be less and less interesting over time for the people who, I don’t want to say the people with the most talent exactly, but the people who are like really leaning into trying new tools and building with AI. Like they’re gonna want to be doing more, and that’ll change the way that we think about the team, and in ways that are in the near term probably not always so good and feel a little bit like, “Ooh, am I losing some of my identity in this?” So that was the piece. I think I’ve stepped away from the computer for a while to raise my now 12-week-old son. So hopefully that is mostly what I tried to say. And I know, Peter, you disagreed with me to a certain extent, and you emailed me right after I posted it. “We need to talk about this.” Which I knew then that I had done something good for the world in introducing something that people may find disagreeable, if not a little bit useful. Peter: The, the heart of your thesis is something that I think I tried to reflect on when I wrote Org Design for Design Orgs and in my own design leadership practice. And Jesse and I have talked about recently, even when we were back at Adaptive Path, where we tried to have just one role: You’re an experience designer. And in that role, there could be a range of skills, and different people with the same title might have different skills, and that’s okay. Because we wanted to kind of support what you’re talking about. It’s less about you being tightly defined in this way and someone else being tightly defined in that way, and more this group of people is joining together to solve some problem. As I’ve gone in-house, and then even after leaving, going in-house and becoming my own flavor of org designer, I found myself defining roles. But, like, when I create career architectures, I always start with skills and not roles, where when you see, like, how most people create career architectures, they start with roles and not skills. But I start with skills. I’m like, that’s the most important atom of effort, and then we can build a career architecture around that. And so I largely agree with you. I also thought it was funny that something I’m seeing is that AI, and I put AI in quotes, is enabling many of us to dust off things that we were saying 10 to 20 years ago, and be like, “Maybe now. Is there… if we… Will you listen now? Because it was true before, but it’s actually even truer now.” And I suspect that’s something of what you’ve got going on with what you’re writing. Why Roles Persist Peter: But the part that I wanted… that maybe I disagree is strong, but where I’m like, the hard part of it is, I think, there’s these three qualities of roles that are really hard to get over. Roles are human shaped, and I think as an anthropologist, I think we process the world, right, through heuristics, and one of the heuristics is things that are human shaped make sense to us. So a role makes sense to us in a way that a pile of skills doesn’t, and so we start there. It’s a human shaped thing. Thing two is, roles are, to use Seeing Like A State language, they’re legible by the bureaucracy, right? The bureaucracy loves roles. It knows how to post a job with the role title. It knows how to put you in an org chart. It knows what to pay you, right? There’s just something about roles that get taken up easily by these systems, that again, a pile of skills or, like, five people on a team doing a thing, whatever that is, what do we call them?How do we pay them? What do we… how do we reward them? How do they grow in that career or whatever? And then thing three is something you touched on, which is identity. This is something Jesse and I have been talking about, well, for 25 years, and pretty much since the start of the podcast, is designers… Like our industry, our colleagues, many of them went to design school. They’ve had design in their title. They see themselves as designers first and whatever else second, employees second, an employee at a particular company second or whatever. There’s something around design that has this connection or affiliation with identity that’s so strong. So my question to you, and this is a big one, but I’m curious your thoughts, like, how do we overcome these three kind of, obstacles isn’t quite right, but just, like, realities of role-ishness in order to achieve the nirvana of a post-role team-oriented future? Clay: Yeah. That’s, it’s a very good question, and I’m happy that you… It’s okay to disagree with a thing too. I appreciate that it sparked this, ’cause it is worth debating and it’s worth digging into. I think in the three things that you identified, two of them are really good and worth maintaining as we redesign a thing. Or if we move from where we are today to where maybe we hope to get, or where I hope to get with more of a team-oriented networked future for work, I think that’ll be better for more people more of the time. So human-shaped heuristic for understanding the work that’s happening in a team, that’s great. I wouldn’t change that. The identity thing I think can be, can be good for some people and limiting for others. Being constrained by the way that an organizatio…

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77: Automate All the Things!? A UX Reality Check on AI (ft. Dr Stefanie Hutka) Sep 19, 2026

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Show Notes Intentional Design Leadership Circle Are you a director-plus design leader looking to connect with others and grow your capabilities? Join Jesse and Peter for the fall cohort of the Intentional Design Leadership Circle, taking place on Wednesdays from October 7th through November 10th. Only 20 seats available for this live online program. Learn more and register. About this Episode Dr. Stefanie Hutka, design researcher, Berkeley educator, and author of What Your Machines Should Do, joins us to look to the history of industrial automation for lessons on AI transformation. From Toyota’s jidoka and the andon cord to Taylorism’s lingering grip, we explore why AI amplifies whatever conditions it finds, and why strategy and values must come before the tools. Dr. Stefanie Hutka: https://sendfull.com/, LinkedIn profile, pre-order What Your Machines Should Do Jesse James Garrett: https://jessejamesgarrett.com/ Peter Merholz: https://petermerholz.com/ Transcript Hey everybody, before we jump into the show, I wanted to share with you something that Peter and I have been working on. It’s kind of special. We have poured all of the thinking and all of the wisdom that’s come out of the last several years of this show into a six-week leadership skills development and support program that we call the Intentional Design Leadership Circle. It’s happening October 7th through November 10th, and there are only 20 seats for this live online program facilitated by Peter and myself. Find out more information and get your seat at findingourway.design. Now, on with the show. 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, we’re joined by Dr. Stefanie Hutka, design professor, researcher, and author of the book What Your Machines Should Do: The Science and Strategy of Human-Centered Automation. She’ll share lessons from the history of industrial automation to observe models to follow and models to avoid as organizations move towards AI transformation. From the humble loom to the factory floor to the values that underpin our processes, let’s go exploring with Stephanie Hutka. Peter: Stefanie, thank you so much for joining us. Stefanie: Glad to be here, Peter and Jesse. Peter: To kick off, I think it would be good just to get a sense of how you introduce yourself. I know you teach, and you write, and you speak, and you work, and so, who are you? Who is Stefanie Hutka in the world? Stefanie: Yeah. So I’ve been introducing myself by way of hats, that I’ve been wearing a couple of different hats. Hat number one, and arguably the largest hat, the top hat, if you will, is as a researcher. So I have even more sub-hats under that field. I go back, to early days, my PhD’s in cognitive neuroscience. I was very much an academic researcher. I worked as a research scientist, found my way into design research, and that is primarily the type of work I do today at my consultancy called Sendfull, that I’ve been running for about three or so years now. So hat number one, researcher, specifically design researcher today. Then hat number two is as educator. So I’ve been teaching at UC Berkeley, primarily at the School of Information, but also at Jacobs, the design school. I teach Introduction to User Experience Design. I just started my fifth year of teaching that to professional master’s students. I also have designed some new courses, including UX for AI and Designing Future Systems, which dove into some systems thinking mindsets and toolkits, as well as some strategic foresight. And then the third hat is as author. So I’ve written various things over the years, scientific articles, industry articles. But most recently, I have a new book that is coming out, my first book: What Your Machine Should Do: The Science and Strategy of Human-Centered Automation with Rosenfeld Media. That will be launching in November and currently on pre-order. What’s worth automating? Peter: Wow. Jesse and I have been exploring the subject of AI and design, primarily design leadership, for the last almost two years now. And when we found out about what you were writing about we’re intrigued. And so, unpack a little bit what the book is about for an audience of design and user experience leaders who maybe are still kind of grappling with concepts of automation. Stefanie: For sure. So the book is a field guide for product and design decision makers to navigate this question of how do we automate and closing what I’ve called the automation strategy gap, where you have these dreams of fully automated futures and running after let’s automate everything, versus the reality of what’s actually valuable to our users. How does this fit within their ecosystem? What is our organizational readiness? What is the actual capability of the tools at this time compared to that fully automated future? And so the book shares different frameworks and tools, some of which are derived from my own practice, some of which are derived from a synthesis of literature that I like to say is: it’s intended to be durable; it’s evergreen stuff. This is not a book about how to use Claude Design or whatever tool’s gonna shift by the time this podcast finishes recording. I’m really looking at what can we learn across human factors, human computer interaction, management theory, cognitive science, and acknowledge that we are in a very new territory. There’s many ways in which generative AI is unprecedented. Those three ways that I usually refer to that is: the unprecedented pace of development; the breadth of use cases that it can cover and what that means for human cognition and how much we can offload; and then the stochasticity of the output. So it is definitely, you know… it has unprecedented elements. That said, we have been automating stuff, we have been building autonomous systems, for quite some time, so what can we learn from those principles so it doesn’t feel like we’re completely, you know, flailing as if there’s no prior, priors plural. So the book is about those things. How much of a burger is this? Jesse: One of the interesting debates about this current wave of AI technology recently is the question of, well, how radical a change is this? And there is definitely this school of thought that holds that AI is, quote-unquote, “normal technology.” It’s just another wave of technological change. It’s not very different from the things that have gone before. And then there’s this opposing camp, which is very much on the side that this is so fundamentally different that there’s not a lot that we can learn from the past, and I wonder where you fall on that continuum. Stefanie: Yes. A little bit of column A or column B, or for my fellow design researchers listening, it depends. I think, you know, how are we, maybe how are we, defining AI, assuming we’re talking about generative AI, ’cause there are many types of AI. But yes, like the AI moment that we are in, I’ll start with maybe column B of what might be similar. So there’s something from one of your past episodes. I took notes on this ’cause I, I was excited about this conversation. Jesse: She’s a researcher. Stefanie: Exactly. I was doing research, secondary research. This is what I do. The Paul Ford episode from a couple months back, you talk about compilers as an example of, now you have the sort of translation layer of intent going into the ones and zeros, and, we’ve had moments like this where we can articulate our intent in different ways that speed up our processes. So from a technological standpoint, there have been big advances. We’ve had disruptive innovation. We’ve had mobile. We have had cloud. And those were definitely major events. We’ve had various tech bubbles before. We have navigated those. So we have, I think, from a disruptive innovation standpoint, we have some priors in terms of designing automated systems, like moving from human-in-the-loop to human-on-the-loop. I mean, there are planes flying over us right now with autopilot systems that we’re presumably pretty comfortable. We’re not too worried about, how will the pilot lock back in with situational awareness when they need to? And we have figured some of these things out, so maybe we can learn from some of that. So that’s what I’m talking about with some of those priors. Now, where I think AI is different right now is what I’ve called 10X cognitive offloading, and what I mean by that is, cognitive offloading is this just phenomena of delegating our thinking tasks to some sort of external device and often technology. The classic example is Google Maps. I give this example. I bike to campus, to South Hall. I’ve been doing that route for five years. I’ve got that locked in. But the moment someone invites me, say, to Cheeseboard, which if you live in the East Bay, both of you know this, it’s not far. It’s like a mile from South Hall, but I don’t do that trip very often, and I am entirely reliant on Google Maps. So I’ve offloaded my navigation capabilities to this digital map. And typically, when we’ve offloaded to technology, it’s been relatively finite in terms of our tasks, and I think the way, at least by default, a lot of these generative AI systems have been designed, like the phenomena of the prompt bar, it really invites kind of wholesale offloading, and we’re delegating the entire observe, orient, decision, act loop increasingly with agents such that if we are offloading, quote-unquote, “the wrong thing,” we can very quickly start to de-skill. If we haven’t learned the thing in the first place, there’s gonna be a gap in our learning. And I think that getting to those three things I mentioned at the top of the podcast around one of those being the breadth of use cases to which you can apply this technology, I think that is where it is different, and combined with the pace and the inability for sort of slower moving systems, governance layer, for example. We can’t build guardrails as fast as the tech is moving. I think that’s where things get unique. Grappling with the pace of change Jesse: It’s interesting to think about that pace challenge for organizations as they are trying to adapt themselves and adopt these technologies and actually get some meaningful value out of them, in that the technology is changing so fast that organizations hardly have the chance to orient toward one approach before the state-of-the-art changes. So if we put this in the context of a larger history of industrial automation, right? Where we’ve had increasingly more and more machines doing things that humans used to do, if we can define automation that broadly. We are now in a place where there is this kind of… this shearing force where the technology’s moving so much faster than the organization that the organization fundamentally breaks because of it. And I wonder about, in your research, from your perspective, what we can learn from the pressures that have been applied to organizations in the past, from past waves of innovation that might teach us something about what’s gonna make an organization resilient now in the face of what’s happening. Stefanie: Sure. So what immediately comes to mind is a contrast that I draw, in a chapter where I get into systems mapping, systems thinking, is contrasting Toyota production system with General Motors’ approach. So Toyota production system, one of the key sort of tenets of this is automation with a human touch, jidoka, comes from the Toyota founder, as a young boy, saw his mother working at a loom and saw that she constantly had to be monitoring this loom and invented this mechanism such that when the thread ran out or got stuck, the loom knew when to stop. And this was ultimately like, fast-forward, Toyota moves from textiles into auto manufacturing. Japan devastated after World War II. American automakers very, very resource rich and you get to Toyota saying, “Okay, how do we move forward given our limited resources?” And you have this approach to automation that’s very complementary to people. You have this idea of kind of the andon cord, you pull it if there’s an issue on the line and everyone comes rushing. And I think that’s interesting because it speaks to kind of the values that the company sort of organized around. Certainly there’s contextual factors, there’s different geographical, region, and cultural values, so on and so forth. And there’s a psychological safety when you’re pulling that cord that you feel like, “Okay, I can pull that cord.” So, that’s an example of maybe automation done arguably well versus a much more sort of Taylorist approach that I think we see with, General Motors as a contrast, but we also see in a lot of our thinking now. So in contrast, you have this mindset from like the early 1900s, if we can atomize work and, we can easily swap someone out to do it, and I think there’s an underlying mental model that there’s limits to our human capabilities and, if only we can sort of automate the human error out of things, we will be more productive. If you’re driving on the I-80, if you saw any of those Artisan billboards in the last couple of years, like “Stop hiring humans” with hiring intentionally misspelt to imply that we are error-prone fleshbags, I think you see a lot of that. Yeah, I just threw in fleshbags to wake up our listeners. You see some of that same sort of Taylorist mindset that’s very efficiency oriented, so you get this sort of trade-off between efficiency and effectiveness that comes down to the values in which the automation approach is grounded. So I think the shearing forces are coming from maybe this sort of Taylorist orientation, and this is challenging because this is like the paradigm arguably, like the underlying mental models that may be examined or unexamined that are influencing the values on which the organization moves. Learning from looms Jesse: You use this term in there, jidoka, which is a concept that I’m familiar with, but I think a lot of our listeners might not be, that is closely related to how this philosophy of automation was developed at Toyota, and I wonder if you can expand on that. Stefanie: The Loom example is the one I go to, like, the idea of, you still have humans in the loop, but you don’t need to have them constantly. There’s an element of there are things that are safe for machines, but there is a point at which the machine capabilities stop and, you need to bring the human back in. It’s not necessarily any sort of value judgment, just like this is what the machine can do, and there’s going to be a point where the machine ends its capabilities and the human needs to take over. Jesse: Yeah, I guess what I take from that is the idea that you build into the system the awareness of its own limitations and the awareness of when the system needs to stop and turn control back over to a human operator or a human intervention of some kind. Stefanie: Yes. I was asked this similar question. I gave a talk yesterday morning. It was a Agentic UX summit, and one of the Q&A was like, “How do you know when the machine should stop?” It’s like, well, I’ve got a historical anecdote for you. Like back to your earlier question about what’s different this time, maybe the capability for adaptation of the system as you’re giving it feedback, like loops are all the rage right now, and we’re building agents, and this idea of there’s still a human sort of building that loop. But if you’re optimizing the loop each time, the machine is doing incrementally more and you still need a human somewhere in there. But that dividing line isn’t static by any means. So I think that adds a new layer of challenge. Peter: As you were talking about the Toyota manufacturing process I was thinking and I was doing a little research during that. There was also the work of W. Edwards Deming, right? It wasn’t just one person figurin…

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76: Embrace the Chaos—Design Operations in the age of AI (ft. Z) Aug 14, 2026

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Show Notes Peter and Jesse are joined by Chengying “Z” Zheng, who shares her experience migrating a design team to be AI-first — off Figma and into code. She discusses how design leadership and operations divide the work, what happens to roles and titles when everyone becomes a builder, and how to make good design easier than bad design. Z on LinkedIn: https://www.linkedin.com/in/changyingz/Z’s Substack: https://changying.substack.com/Jesse James Garrett: https://jessejamesgarrett.com/Peter Merholz: https://petermerholz.com/ Transcript 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. On today’s show, Jesse and I are joined by Chengying Zheng, better known as Z, the design operations, or should I say experience operations leader with extensive experience in tech. She shares with us how she guided a design team through an AI transformation, setting aside Figma and building right in code, her thoughts on the evolution of roles and teams, how to maintain quality, and the new work of operations. Hi, Zee. Thank you for joining us Z: Thanks for having me Getting the team off Figma Peter: The conversation we’re having with you, for me at least, started, I wanna say, six to eight months ago, when you and I were in the offices of Figma at a gathering. There was a lot of folks there, but you and I had peeled ourself away from the crowd, and you looked at me, you looked around, you looked at me, and you said, ” It’s a little weird for me to be here because I just spent the last three months or so getting my team off of Figma and into AI tools.” And we talked a fair bit about that. You’ve been writing about it in your newsletter, but I’d love for you to share the, the highlights of that experience. Yeah, the highlights of that experience. Explain a little bit about where you were and what that journey was like and how you did evolve a team out of Figma and into more kind of AI-native practices. Z: Yeah, absolutely. It was a really interesting moment. I remember that conversation A lot of folks at the time were talking about AI transformation. Everyone was thinking about it. This was still last year, still a little bit early in this curve about AI transformation, so a lot of people were thinking about it, and people were doing it, and some, of course, AI-native companies were way ahead compared to the rest. They were already out there. And our team was interesting because we had this mandate, like any other tech company, right? So you will start to do AI transformation, to incorporate AI into your workflow. So for designers, the first thing that we looked at was how designers prototype. We weren’t even thinking about how designers ship, we were talking about prototyping. And of course Figma has been the de facto tool for product designers for many years by now, but in this new workflow, we were thinking about getting designers to prototype with the new capabilities, with all the vibe-coding capabilities. And a lot of our designers started to see that Figma, instead of a prototyping tool, which is what we used it for before, had now become a wireframing tool. Basically, you come up with ideas and then draw them out in Figma, but then you- the prototyping is actually happening in the coding part, in the vibe coding, whatever the tool was back then, whether it’s Claude or OpenAI, whatever. So I wrote about it. I audited our Figma. Of course, as the operations person, we look at our Figma usage and everything. I audited it one time, just on a random day, I looked at it. Out of our hundreds of licenses, there were 50-some people using it that day, and only five of them were from our product design team. Most of the others were marketers, PMs, everything. So that was a very interesting moment for us to look at tooling and at the designers’ tool stack. But that was months ago, actually, compared to right now. Everything moves so fast, and that feels like so long ago. Telling engineering what changed Jesse: I wonder about the cross-functional aspect of making this happen, because there is always this sort of ripple effect whenever one team changes the way it does things, on how that team then interfaces with the teams around it. How did you manage the cross-functional conversations as you were transitioning the team out of Figma as their primary way of doing things and into vibe coding? Z: Yeah, that’s definitely a lot of challenge and work. So I actually proposed it back in October last year, to our design managers, to design leadership. I said, “Let’s get our UX designers out of Figma.” Of course, everyone was like, “No freaking way. You are crazy. Designers are in Figma, that’s our tool,” and everything. But the reason I proposed it is that it wasn’t just a random proposal, like let’s get rid of tools or anything. At the time, we had a new design system that was entirely in code, and we were fortunate in a way, because instead of trying to continue building multiple design systems and trying to move them along, to modernize all those design systems, from the top down there was a mandate. This is the design system we’re going to use. That design system is in code. And that’s really what prompted this proposal. That didn’t happen, so by the time I talked with Peter, that was already three months after. I think we talked at the end of last year, and it was October when I was proposing it. But by then, just de facto, no push or anything, designers were already out of it. But there was a lot of conversation. If I could have done this all over again, I would do it differently. I would be reaching out to the engineering team immediately and talking about this transformation. At the time, this just organically happened, and then by the time I talked to Peter, this is… That’s when we started to realize, oh gosh, we need to talk to engineering a lot more. Some engineering teams still required our designers to give them a Figma file. Some other teams were more open, and you could do other ways of prototyping. And there was a lot of discussion about what designers were doing in code, and we also had to go out and talk about it. There are levels to “designers shipping code” There are different levels of designers in code. So there’s the- One, the basic thing about getting designers into code is engineering empathy, right? So engineers now, instead of just coding, they do a lot of reviewing code as well. So what it takes to- for an engineer to build something, that’s something designers should understand as well. And then another level is where we got our team to prototype, but then by the time February this year came around, our designers were actually shipping production-level code. It sounds so grand, production-level code or whatever, right? But by then we had worked with the engineering team, put a lot of guardrails in place, about what designers should not be touching in terms of code. If it’s an API, if it’s infrastructure, if it’s, say, if it touches a flow, these are things designers should not be doing. And what we’re actually talking about when we say shipping production-level code is paper-cut-level shipping of code, right? So change a piece of copy, change a wrong component, small changes. And so these are things people sometimes talk about, “Oh, designers shipping code.” They put it under a blanket umbrella that says, “Designers shipping code.” But there are actually really different levels of designers even touching code. People are not getting there because, “Oh, designers shipping code. Are we turning designers into engineers?” No, absolutely not, right? So same thing, we opened up Figma for other cross-functional teams to use. PMs using it, engineers using it. Are we turning engineers into designers? Probably not. Are we turning PMs into designers? No. But we’re turning everyone into a product builder, a contributor, in a way they’re passionate about, wherever they see a fit with the tool. Now we’re basically just giving everyone all the tools, not just keeping Git for engineering, Figma for design, or whatever the PM tooling is, but we’re actually giving the entire tool stack to everyone who is touching product and building, and they use the same tools we have. And so that’s where it is. But it takes a lot of talking, coordination, and it really does hit some nerves because everyone is jumpy, and designers say, “Oh gosh, engineers designing, PMs designing,” and the engineers say, “Oh gosh, designers coding, PMs coding.” So I wouldn’t say it was all smooth, but at least that’s something we put a lot of effort into, and we saw results from doing that. Standardization doesn’t scale anymore Jesse: One aspect of your story that I think really resonates with what I’m hearing more and more, and what I’m seeing in AI transformation efforts broadly, is the notion that you have to meet people where they are inside the organization. And imposing a kind of one-size-fits-all policy for this technology is not actually going to get you there, that you need to be able to find ways to leverage potentially a broad range of different skills across your team in a way that you haven’t before, and to be able to accommodate a diverse range of different kinds of workflows, and setting different kinds of expectations accordingly, cross-functionally, with how product and engineering interface with and interact with design. I wonder for you as an ops leader where your mind goes when you think about managing operations across a diverse, distributed set of work processes that no longer fall in line with a single paradigm anymore? Z: Absolutely. So I come from a very strong operator’s perspective, right? So in the past, as operators, you were the process wranglers, basically. That’s what it is. You want to… The word we used for the longest time was standardization. Standardize the process, and that will actually scale, right? So but right now we’re pitting speed versus quality. There are a lot of discussions in there, whatever. Like you just said, standardizing everything won’t work anymore because different teams move at different speeds, and different teams have probably started to adopt slightly different workflows. And some teams might… Some companies, some teams, might even allow them to use slightly different tools or whatever. So I wrote about it, and to talk about it now from an operator’s perspective, I push a lot for shared principles, and then giving people the agency to work out the details, how to execute it, and to have a little more flexibility instead of standardizing across the board. But shared principles are something every team needs to spend a lot of time aligning on, and also educating everyone and talking about, because if you think about shared principles, for designers, there are certain things, right? Accessibility is a, for us, something we care a lot about, and engineers care about that as well. And engineers probably care a lot about their code quality as well. So their APIs, nobody touches, and as long as we’re clear about what everyone can contribute and that everyone should reach out to the experts to contribute, that helps the team move in different formations, but still moving in the same direction. Should ops be leading the AI transformation? Peter: I’m, so, I’m gonna continue on this thread because when we spoke about this at that Figma meetup, the light bulb that went off for me is that this type of AI transformation might be better led by operations folks than design leaders. Whereas my kind of working assumption in the conversations I’d been having with clients and whatnot, design leadership was responsible for that. And, if they had an operations person, maybe would be leaning on them to help. But something that’s also happened over the last couple years is a lot of ops teams have evaporated. And so the, the irony being we’re in now in this moment that is so operationally heavy, and many teams don’t have operations folks to help them through it. And I’m wondering what is your relationship with design leadership through this type of experience? What are you responsible for? What are they still responsible for? How do you distribute authority? Who’s making what decisions? That kind of thing. Z: Yeah. So if you think about design operations in general, with your leader, it’s always a balance. It is always challenging to divide that responsibility and accountability. It’s just because different teams work slightly differently. So in my specific situation, it worked out really well because at the time, I reported to the head of design, and her mandate from the top down was AI transformation. And then my part of the work was actually getting that done. And then the design leader coming in down to the team, this AI transformation, you think about it as a gr- grassroots effort. Everyone wants to use something, build something. But to do it right, you absolutely need top-down support, to give people the time to do it and to give people the direction, where to go and what we want them to do. Do we want them to stop at prototyping? Do we want them to ship code? We do need to know what the end stage is that we need to get the team to. And as an operator, then we can actually help the team achieve that and figure out the logistics, scaffolding the team step by step, how do we get there, get the designers into code. I came from a very technical company. It’s extremely hard to get into our production code base, rightfully, and it should be. It shouldn’t be turnkey, where everyone can ship code. So there’s a lot of coordination. It’s my role and my team’s role to go out, reach out to our engineering partners, “Come on in, help us do it right, because you do want us to do it right. You don’t want to review crappy code. You want to teach us to do the right thing.” And then so in return it helps them as well. And also a lot of explanation as well, “Hey, we’re not trying to be engineers. We’re actually trying to take care of the design debt that engineers never have the bandwidth to take care of, and they are very small paper-cut things.” Leadership owns the what, ops owns the how So my goal is really to focus on the how. How do we get the team there? But design leadership is the what. Coming in with the what, and giving the team the mandate. That’s really important. With these things, if you just say, “whoever wants to get on the bandwagon, let’s do it,” it is really hard to move that fleet in the same direction. Those would just be sailboats, right? Everyone’s like, “I want to go. I want to go really fast. I want to do something.” And then someone else wants to do something else. “I want to use this tool.” “I want to use that tool.” So the design leader needs to come in and say, “This is where we’re going to get people,” the what, and then the operators come in with, how do we get there? And that worked out really well. And then also because we’re… We say it’s design operations, but on the other hand, nowadays my perspective on operations is that maybe we’re not design operations, we’re just operations, in a way. Experience operations, whatever. Reaching out to more teams outside the design team. And after our transformation for the design team, I ended up going out, because of our training, we had everything in place, documentation, recordings, process, all the things in place. Now other teams, these non-technical teams, came to ask us and say, “Can you train our team? Can you train our team?” So our team members, our operators, actually went out and thought more about how to leverage our knowledge to up-level the cross-functional, cross-board, company-wide AI transformation, everything. So I’m thinking and trying to figure out, do we still use this term design operations, and does it still have a meaning? There might be, but there might be more. Maybe design operations…

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75: The Steady State of Unsteadiness Jul 24, 2026

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Show Notes In this episode, Peter and Jesse compare notes from Config, Figma’s AI study, Lenny’s newsletter survey, and countless conversations to read the current state of design leadership. The signals: existential AI panic has cooled into exhaustion, organizational chaos and leadership churn are the new normal, and design still stumbles on business acumen. Their case for thriving—lead, don’t just design, and reclaim design’s unfinished mandate. For more from Jesse James Garrett, including his AI transformation practice: https://jessejamesgarrett.com/ For more from Peter Merholz, including his newsletter, his consulting, and thought partnership: https://petermerholz.com/ Transcript 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, Peter and I are listening to signals of the current state of design leadership. We’ll get into what we heard in our recent conversations with design leaders at events such as Config in San Francisco, and what recent research studies from Figma and Lenny’s newsletter reveal about the emotional toll of the current environment on leaders and teams. Plus, we’ll explore what leaders can do to keep the promise of design’s value alive with the rise of AI. Peter: I wanna start with this question. Jesse: Okay Peter: Have you seen the movie Backrooms? Jesse: I have not seen the movie Backrooms, Peter. Peter: I finally saw it four or five weeks after it was released, and it is easily the most interesting thing happening in cinema right now. Full stop, end of story. If you like movies, you need to see Backrooms. If you think it’s a horror movie, it’s not. If you don’t like horror movies, don’t worry about it. Go see Backrooms. Jesse: Okay. All right, thanks Peter: I haven’t walked out of a movie kind of excited about the form in a very long Jesse: Cinema yeah. Peter: In cinema. No, for real. But what’s on your mind, Jesse? Jesse: Well, you know You know, here on this podcast, Peter and I, we’re like the great psychologist Fraser Crane. We’re always listening. And we’ve been listening a lot over the last six, eight weeks, since the last time we recorded this podcast. We’ve been listening to the signals out there. We’ve been having conversations with folks. We’ve been together at a couple of events. We’ve been taking in what’s going on, and there’s enough going on out there that I thought it would be worth us getting together and talking about our reactions to some of the signals that we’ve been seeing out there. So, for example, you and I were at Config, the largest design event in the world now, it’s gotta be, in San Francisco just a couple of weeks ago in June. Had a chance to talk with a lot of different design leaders about their challenges and about what they were seeing, and of course, all of us were trying to read the tea leaves of Figma’s product strategy and what that meant for design teams and what they were maybe seeing about where all of this is going. They published the results of their latest survey of design practitioners and design leaders about the state of AI in their practices and had some interesting insights and reflections based on that. Config 2026: from existential dread to exhaustion Jesse: But I’m curious about what stood out for you. Let’s just start with Config. I mean, there’s been a bunch going on, but let’s just start with Config. What stood out for you about the conversations that we had and the experiences and the ideas that were in play in that gigantic gathering of 10,000 designers in San Francisco? Peter: What stood out from Config specifically for me was that AI was no longer seemingly an existential concern for design and design leaders the way it had been in the prior two Configs. It was two Configs ago when Figma was like, “We’re about product people,” and didn’t really mention design much. And designers started freaking out that they were about to be replaced by AI. I mean, yeah, so that was Jesse: Or simply product managers. Peter: Or product managers… Jesse: You decide which fate is worse. Peter: Sure. And then in 2025, Figma said, “Psych, we love design. Design is great. Here’s a bunch of tools for designers,” and that’s when they launched Figma Make as well. But the conversations I had last year were deeply existential, It was around that time last year that you and I started really hammering away on the kind of liminal concepts and the phase shift concepts and all that kind of stuff coming out of this dialogue that was occurring. This year it feels like folks have settled in. This AI stuff is real. They’re still figuring out what to make of it, but it’s real. It’s not going away, but it’s also not causing the kind of existential crisis it had before. It’s a tool. It’s a means to do their work. And yeah, so folks were far less hair on fire than they had been the prior two years. But what’s replaced that or what, has emerged, I think, as the dominant sentiment is they’re just tired. Everybody is fucking tired. Everybody is exhausted. I think a big reason they’re tired is that all this new stuff has simply been layered on top of whatever their existing job had been. And so folks are just expected to do more. Even though the promise of this new stuff is that you don’t have to do as much ’cause the machine does it, instead, the reality, at least right now, is, perhaps while people are figuring it out, it’s like you have to do your old job, which already maxed you out. You were probably already at Jesse: least… Exactly. Everybody was already plenty busy. Peter: Yeah. Yeah, you were already maxed out, and now we’ve just layered on this new thing you have to figure out, and we’re pretty much giving you very little guidance about that. So that’s my primary takeaway from Config. I honestly could care less about Figma and its product suite and whatever that indicates. I don’t think that’s nearly as much of a bellwether or harbinger as maybe it used to be. But yeah. The sentiment curve has shifted from fright to just tired. Jesse: Mm-hmm. Mm-hmm. Yeah, I think it’s interesting to note, first of all, the emotional tenor, I think the optimism is there, but it is I think somewhat muted relative to previous years. The people who are optimistic are a little more cautiously optimistic. It’s like the two sides are kind of meeting in the middle a little bit, that the skeptics are learning to appreciate a bit of what the technology can do and where it’s going, and the optimists have maybe had their irrational exuberance tempered a touch by the intervening year. But I think that one of the things, and we touched on this in the Liminal conversations as well, one of the things that is a recurring theme for these leaders is the emotional resilience required to continue to manage ongoing change, and the fact that none of this is gonna be settled soon. And in fact, the new steady state is an extreme unsteadiness for a lot of leaders in a lot of organizations. And in some cases, I feel like people, what they’re honestly looking for is something to anchor to that’s proving hard to find. Corporate chaos and the broken job market Peter: And I think it will continue to be hard to find for a while. Earlier today there was a post on LinkedIn that I ended up reposting with a bit of commentary. I forget the name of the woman who wrote it, but she was talking about her job hunt journey. She’d been… I don’t know if she’d just quit or been laid off in January. It is now June or July, she’s starting a new job. And she had statistics to go with her job hunt experience. Within those statistics was, she got through all rounds with 10 different companies, right? Which is a strong signal at least when I run recruiting and hiring. If you make it through that round, you’ve got a one in three or one in four chance usually, right? There’s not many candidates get that far. So 10 companies, she made it through all rounds. But then after getting to that point, she pointed out with four of those companies, something went haywire. The hiring manager quit or got fired, there was a reorg, there was layoffs, there’s something organizational occurring in 4 out of the 10 companies. So these are companies that thought they were stable enough to go through a recruiting and hiring process, get through, I’m sure, multiple candidates through many rounds, and oh, and then at that point it turned out they weren’t that stable. Some organizational chaos occurred and the job just disappeared, right? The requisition disappeared. And what that to me was a sign of, or is a sign of, it’s anecdata, but, I’m seeing other indicators, and it goes with the exhaustion thing, is that companies have lost their collective minds right now. The degree of instability within corporations, I mean, it’s been high for a while, and it seems higher now. When you talk about listening and signals, like one of the signals I’m getting is just a greater degree of uncertainty. It’s not necessarily layoffs, although that’s part of it. You and I have had friends recently who just found themselves without a job in the last few weeks that… Jesse: mm-hmm. Peter: At large, massive, otherwise seemingly very stable companies. Jesse: Stable-looking. Yeah. Peter: Yeah. And it’s just like, the analogy that just came to mind is, we’re all on a ship. That ship is just rocking, and we’re all just holding on to the ship for dear life as waves are coming overboard, and we’re just trying to make our way through this period until the seas calm down. Jesse: Trying not to get too sick over the rails. Peter: Well, yeah. Jesse: Yeah. Well, I think that, and you touched on some of these teams that have been really decimated in the last year, design teams out there that have been for whatever reason, one reason or another, they ran out of runway before they could get aloft and what these teams are facing now is, in some of these cases, you have these teams that have been so severely cut back that they have to renegotiate their mandates because they can’t keep doing what they were being asked to do before under these new structures. And the leaders are in the position of having to do that renegotiation of the value prop of their team, right? Of what we’re here to do and what we’re here to be measured for and what you can look to us to provide. The organizational and cultural shifts are as, at least as radical as the technological and process shifts. Leadership turnover and its ripple effects Peter: Well, y- yes, and I don’t think it’s necessarily just a matter of cutting back, though that’s definitely happening. So I conducted a listening tour, or I’ve been conducting a listening tour of design executives. It was something I was doing in May before I went out on a family vacation. And I talked to about 20 design executives. I’m still poring over the data. But something that was intriguing to me is of those 20 design executives, three or four were between jobs. Like I hadn’t realized when I’d reach out to them they weren’t working. But they hadn’t been laid off because of reduction. Each of them wasn’t working because there had been a leadership change in their organization, and the new leader didn’t want them in the org. Which, kind of, again, is speaking to a certain organizational chaos. The senior leadership are encouraging change within design organizations that involves just getting rid of current leaders. Not the whole team, just like, “That person doesn’t belong here anymore.” And sometimes it’s a new leader wanting to put their people in place. I just had something outside of the listening tour, but a friend just got fired really, not even laid off, because a new CTO is like, ” We’re gonna do things different now.” And I think as part of this chaos, something I believe is at the highest levels of a lot of these organizations, there is leadership turnover right, in the C-suite or just below. Jesse: Mm-hmm. Peter: That seems to be happening more often in the last year or two, and what we’re seeing is the impacts of that, the ripple effects of that within design. It might take three, six, nine, 12 months to finally get to design, depending on the size of the company. One firm that you and I are familiar with, had 50,000 employees, so it took a good nine months between the new CEO… Jesse: yep. Peter: …And the leadership shift. But in most of the cases I’m aware of, it’s not about reduction, it’s just about turnover, and, on the part of these senior-most leaders, a total disregard for the turmoil they are causing. Jesse: Hmm. Mm-hmm. Peter: Just disregard, disinterest. You’d think you’d want some degree of stability so that the business can do its work well, and there’s absolutely no interest in that from what I’m witnessing. Jesse: Yeah. Well, it’s interesting to think about just the sheer number of people who have some qualifications for leadership or management roles in a digital product development or design organization who have been turned out on the market in the last couple of years, which has really made it a buyer’s market, so to speak, when it comes to especially middle management. So, I’m seeing the same pattern that you’re describing of these wholesale leadership turnovers. You get a new CTO brings in a new CPO brings in a new VP of design, and the ripple effect goes all the way down. And just by virtue of having been in the organization a while, you become perceived as a liability to the new order, so to speak. And so for leaders, it then becomes this politics game of proving in that nine months, that you deserve to stick around. Peter: You used the word order. Jesse: I know, and you’ve been talking about chaos. Maybe executives are just bad at their jobs? Peter: Well, and I think concomitant with this upheaval is, at least for me, an increased recognition that the people running these companies, that m- many, I don’t know about most, executives are just bad at their jobs. They’re not accountable, right? They’ve had– they wouldn’t be in that role if they hadn’t had some success. I tend to, in private conversations with folks, just disregard this class of executives as dumb or stupid and that’s probably overstating it ’cause, again, they probably would not get into that role if they were categorically dumb. If they were just dumb. They clearly knew something, figured something out, got into a position of authority and influence. I suspect their wisdom is very narrow, though, and now they’re in this broad– they have the much broader mandate, and they’re trying to apply this wisdom from their narrow point of view to the broader mandate, and that’s where the stupidity is. And as I continue to reflect on that, design was probably never in whatever that narrow band was. Jesse: No, it never was. Yeah. Peter: And so the moment it expands to include anything that might include design, design will not be treated well because those executives, like we saw with Cloudflare where once the design system was put in an LLM, the CEO’s like, “We don’t need designers anymore.” Because he’s an engineer, and he just sees the world as, like, a machine you fiddle with or salespeople to sell it, and has no understanding of kind of the actual value that design was delivering, ’cause the only sense of value he perceived was the creation of assets or screens for engineers. Jesse: Yeah. Yeah. So again, it comes back to the value the design is delivering, the way that value is perceived, and whether it’s your AI transformation strategy or how you manage the politics of this kind of organizational change, it’s on the design leader to keep their eye on what that value prop is. Peter: Well, and to figure out how to communicate it in a way that resonates with, hopefully, people who are listening. Something I wonder, you said earlier that this is this new kind of unsteady state. Jesse: Yeah Peter: I was…

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LIMINAL—4: You As A Service (ft. Dave Gray) May 24, 2026

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Show Notes Dave Gray, author of Liminal Thinking and founder of School of the Possible, joins Peter and Jesse to examine what’s actually getting in leaders’ way right now: not the disruption itself, but the expertise that blinds them to it. The conversation moves from beginner’s mind to the compression of corporate work, landing on a provocative question — what does your value look like when you define it yourself? Dave Gray’s School of the Possible: https://schoolofthepossible.com/Dave Gray on The Practice Economy: https://schoolofthepossible.substack.com/p/the-practice-economyMore on Peter Merholz, his consulting, coaching, and training offerings: https://petermerholz.com/More on Jesse James Garrett, his AI Transformation Consulting and Leadership Coaching practices: https://jessejamesgarrett.com/ Transcript 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: This is Liminal. On today’s show, Peter and I welcome Dave Gray, veteran design consultant and author of the book Liminal Thinking. We’ll get his perspective on the mindset and skill set that can help leaders navigate this liminal moment. We’ll also examine the blind spots that result from too much expertise, the future of corporate politics in agentic companies, and defining your own value outside the terms of the corporation. Peter: Dave, welcome to the show. Thank you for joining us. Dave: Thank you for having me. I’m thrilled to hang out with you both. It’s been a long time, and we’ve had many experiences together. I’m happy to see you again. Peter: We have. I remember events going back almost 20 years now where we’ve talked together. But the reason we asked you to join our show is, we’ve been doing this series of sessions on this concept of liminal, liminality, the liminal moment we’re in. We remembered early on in that, that you wrote a book… called Liminal Thinking: Create the Change You Want by Changing the Way You Think. And so we know that you’ve been thinking hard about liminality and the role that it plays. And so, yeah, we wanted to get your thoughts on this matter. But maybe even before we dive into that, what have you been up to? I know what I last recall is you were a consultant at Xplane, and then you’ve been on your own, and you host communities. What do you do? The story behind Liminal Thinking Dave: Yeah, so before we leave the topic of the book, I don’t know if I ever told either of you the story of the book. I didn’t start out with some idea that I wanted to write about liminality. It started out as something totally different, and it evolved into that. So maybe we can get into that. But yeah for 30 years I was a design consultant, an innovation consultant. I did a lot of drawings and mappings for large organizations, helping them think through change programs and complex technologies and making them accessible, to sell them usually. And I exited that business, and I was faced with the question, what are you gonna do now? I sold my company and I just started thinking “Well, what is Dave as a service? What would that look like? What is it that people come to me for when I’m not selling anything? What is it that I like to do? What is it that people come asking me for?” The School of the Possible Dave: And yeah, so that’s what I’m doing right now. You could call it Dave as a Service. My name for it is The School of the Possible. It’s a company of one. Me doing the stuff that I enjoy doing in service to a community of creative people. It’s kinda like a Zoom version of a bar. Peter: Okay. Dave: I’m like the, you know, the bartender… Jesse: everybody knows your name. Dave: Yeah, everybody knows each other’s name. Make sure that everybody has a comfortable seat and it’s like a bar meets an art studio. Jesse: You know, one of the reasons that we wanted to talk with you is because liminality has been such a focus of our conversations lately, and you literally wrote a whole book about it. It’s not a new book. I was astonished to discover that this book is almost 10 years old now. But it is a book that has had some resonance over this last decade. It is a book that I continue to see people reference and call back to. And for people who aren’t familiar with the book, I wonder if you can encapsulate a little bit about the origins and the ideas that came out of that, and what were the big themes that you were trying to drive with writing a book on liminal thinking? Dave: Yeah. The story of the book, it’s not one that I tell very often, but I think it’s a really interesting one, because it started out with mutual friend of ours, Lou Rosenfeld, he’s, very good about remaining connected with his authors and prospective authors. And I just had been his friend. And he sent out a little note to his email list asking if anybody knew anybody who wanted to write a book about Agile, Agile software development. And I was like, ” I think that’s really interesting.” I had just finished a book called The Connected Company. A lot of it had to do with Agile kinds of approaches and techniques to organizing business. And I said, “I don’t really know much about it, but I would love to write a book in the kind of journalistic style. I’d love to go out and interview people and learn about it and write a book that way.” And he said, “Great.” So I started out to write a book about Agile and Peter: This is, like, 15 years ago or something now? Dave: Something like that. And so I started interviewing these people. Agile software development, coaches, professionals, experts, and I’d ask them about agile, and they would say “We know what agile is, but we can’t do it.” And I’m like, “Okay well tell me about that.” And I kept hearing from these people, who all seem to look like me. They’re, like, very homogenous from a diversity perspective. And I kept hearing the companies are structured in such a way that “We can’t do it. We can’t be agile.” And I thought, “Okay, that’s not agility then,” to me, because agility, to me, is you’re able to do things in spite of the environment, or you’re able to navigate within an environment that you don’t control in such a way that you can maintain some kind of balance or equilibrium. So I went back to Lou and said, ” I think we gotta think about this book differently.” And I expanded the group of people that I was talking to. It got much more diverse, much more interesting. Talking to people, soldiers, people who are in environments that they can’t control, literally, someone’s opposing their efforts. Humanitarian aid workers, firefighters. And I started learning about real, I guess, what I would call real agility. People who are able to operate these very complex, super volatile, rapidly changing environments. They’re able to achieve some kind of results without having control. And I think that’s very connected to what you guys have been talking about, this idea of, feeling like there’s rapid change going on. You don’t control it. You’re not in control of the situation, and yet you have you have things that you wanna try and achieve. And that’s where the book ended up going. And what was really interesting to me is a lot of it ended up being about mindset, and a lot of it ended up being about a lot of the stuff that gets in your way in operating in these kind of volatile complex environments is your own way of thinking about them. A lot of the barriers are inside your own brain, so to speak. The Agile Moment vs The AI Moment Peter: Before we got on mic, we were talking a little bit about the tenor of the discussion right now in places like LinkedIn. Where there’s a lot of people having a lot of feelings. They might be anxious feelings, they might be positive feelings, excited feelings. We’re in a heightened moment. Feeling like they’re out of control. And it’s interesting to me that those initial folks that you spoke with for the Agile book felt like they lacked control, because agile was seen as a net good, right? Companies were becoming agile, and, like we’re hearing about AI, there was, like, almost this mandate: We’re going to adopt Agile. And then people like, I’m assuming the ones that you were interviewing, are brought in to help us become agile. So these folks should have tailwinds, right? They’re the ones who are being seen as the ones who are gonna lead us to the promised land. But even those folks were feeling stymied, right? They got frustrated. They kind of threw their hands up. Which is a little different than what’s happening right now in a lot of organizations where we’re getting this top-down executive mandate about AI, but no one knows how to do it. Like, at least there was a group of people who could claim some expertise or some understanding of how to drive agility with some evidence in it. Right now, with rare exceptions, it just feels like we’re all making it up as we go. In the Agile moment there were these organizational or corporate constructions or strictures that prevented agility from arising. I’m curious, as I’m sharing, a little compare and contrast, what you make of these different moments. When agile was imposed on us, and we had the right people to help get us there, and we couldn’t figure it out, what hope do we have in this moment? Dave: Oh, wow. We’re all probably roughly somewhat near the same age, and we’ve probably all lived through a lot of different disruptions over the course of our lifetimes. I remember before the internet, at least before it was a thing that people used all the time. And I feel like I have a little bit of an advantage because I have been through so many of these that I’ve start to see a lot of common themes. And when you think about AI, the one that feels the closest to me as a designer was more like in the ’80s, when PowerPoint and graphical user interface, and suddenly everybody was able to make presentations and, PageMaker and, suddenly, you know, a lot of people who were in the design field were really freaked out because now my boss can make the whole magazine, like whatever. That was at least what we were afraid of at the time, and it’s like, there’re still designers, but there have been so many times when there’s been a prevailing idea that design is going away or that technology’s gonna take over that job. I forget who the painter was who’s, when photography came around, said, “This is great ’cause now we know what painting is not.” And I think it’s like, as we look at AI, one way to look at it is to see all the things that it’s gonna take away from us. But another way to look at it is to say, think of that as an editing out of the stuff that maybe we didn’t need to be doing anyway. Jesse: So you talk about identity. You also talk about skills, skills and tools, and the way in which we get attached to those things as a part of who we are. And we’ve talked on the show in the past about this same moment that you’re talking about here, where digitization starts to supplant really well-established practices that have been in place for a really long time. The example that comes to mind for me is in the field of accounting. Let’s go outside of design altogether. Accounting practices stayed more or less the same for hundreds of years until computerization started to change what your role was, and suddenly your penmanship didn’t matter as much. Whereas previously, like, this was part of how you got the job in an accounting office, was you could write clear numbers that other people could read, and these kinds of granular skills that then become much more fungible as the tooling evolves. But I wanna come back to the notion of the liminal mindset and what came up for you in your explorations of how people address these moments of change and what it takes for them to not get left behind, to not get left in that place where they’ve got the paste pot and the X-Acto knife instead of the mouse and the keyboard to be able to do their jobs back in the ’80s and ’90s. What You Know That Just Ain’t So Dave: I have a quote that I love. It’s from Mark Twain. It’s an old one, but he said, “it’s not what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” And for me, that’s such a great quote and so relevant today. Another way of saying the same thing is, Shunryu Suzuki who said, “In the beginner’s mind, there are many possibilities. In the expert’s mind, there are only a few.” And I think this is the thing. Over many years, you build up expertise, and the expertise enables you to be very effective and efficient, like ability to use certain tools, your penmanship, to your example, other things. Those skills, you start to think of them as part of your identity, of who you are. But all that focus, it’s kinda like horse blinders. It eliminates your peripheral vision, and it actually gets in the way of you seeing what’s actually going on if things are changing in a very fundamental way. And I think that’s what’s happening now. Things are changing in a massively fundamental way. To a beginner, someone new to the workforce coming in, they’re not gonna have all the knowledge that gets in the way of them seeing what’s actually going on. They’re gonna be like, “Oh, I can just get on AI and I can do this, and look at that, I made an app. Whoa.” And I think this is a common theme of a lot of these tools that come along. They create a new level of abstraction that wasn’t available before to the work. For example, when I started, before the Macintosh, before PageMaker and all this stuff, it was really important that you had to be able to use a ruling pen. Okay, a ruling pen is, you dip it in ink and it would make a very straight black line. With Adobe Illustrator or even MacDraw, that’s not a skill that I need to have with my hands anymore. And the people who are attached to the old craft are like “Yeah, but you don’t know how to draw a straight line. You’re letting the computer do that for you.” The Abstraction Ladder Dave: A good analogy for me is you go from walking, to getting on a skateboard, to riding a bike, to driving a car, to getting on an airplane. At each stage you’re losing some level of contact with the ground and the detail and the granularity. You’re not gonna see the landscape in as rich and detailed a way from a car as you are from a bicycle or from walking. But, you’re increasing your capability. So, what happens with the tool is they abstract you away from the ground. So now I don’t have to know how to write Python to code an app anymore. So there’s things that are happening that I don’t understand. Like, let’s say riding a bike. If you ride a bike a lot you have the ability to fix it yourself probably. You really understand how the whole machine works. You can look at it and understand it. When you’re in a car it’s a little more complicated, but actually, a car is probably easier than riding a bike, as you gain more power and control at a more abstracted level, you’re losing power and control at the more detailed level. You’re losing your attachment and your groundedness to the work, but you’re also increasing the scope and scale of what you can accomplish. And I think AI is just doing this at such a dramatic level. I’m not sure what corporations are gonna look like after AI’s finished, you know, burning its way through all the, all the- the shit, honestly, that we’ve been doing that is not gonna really matter that much when the AI can do it. It’s like the version of the ruling pen in a corporate world, a lot of it is, oh, just the politics. Think of all the political back rubbing or whatever you wanna call it that goes on in a large organization and the jobs that are honestly, not that hard. As a consultant going into large organizations, I felt, wow, there’s so much about just people’s egos and just making them feel important and so much political stuff about, oh, I don’t wanna p…

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73: Charting an Adaptive Path toward AI Transformation May 16, 2026

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Show Notes In this episode, Peter and Jesse compare notes from on how AI is reshaping design teams. The conversation moves through the operational chaos of proliferating tools, the urgent need to articulate a value proposition, why design operations got cut right before they were needed most, and the window of expertise power that won’t stay open.For more about Peter Merholz, his consulting, thought partnership, and teaching offerings: https://petermerholz.com/For more about Jesse James Garrett, and his AI transformation and leadership coaching offerings: https://jessejamesgarrett.com/ Transcript 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, Peter and I explore the emergent challenges of AI transformation for digital design teams. I’ll share insights from my seminar of the same name and compare notes with Peter on the larger trends we’re seeing. We’ll get into issues like renegotiating your cross-functional relationships and your value proposition, the cultural implications of running a team where everyone has their own custom tools, and just how long to hang on to people on your team who don’t want things to change. Peter: Hello, Jesse. Jesse: Hello, Peter. Peter: What’s up? Jesse: I thought it would be useful for us to get together and reflect a little bit on this last series of conversations that we’ve been having because for better or worse, there is one topic that is front and center in the minds of design leaders these days, and that is AI. How AI plays out in their products, how AI plays out on their teams, and how it impacts how design interfaces with the entire larger organization that it’s a part of. The Burger is Real Jesse: On this show, it has now been the better part of a year since this started dominating our conversations, going back to our conversation with Andrew Hogan back last August, talking about what he was finding out about AI adoption through his work leading research for Figma. Since then, we’ve talked with bunch of folks that are people who have been well-known to you and I for a long time. People like Christian Crumlish, Christina Wodtke, Jorge Arango, Paul Ford, Dan Saffer. People who’ve been really immersed in this work for a while and who have seen this cycle turn a few times. And we have been talking with them about the ways in which this current cycle evokes and reminds them of the cycles of change that we’ve seen in the last 30 years or so. And we’re also talking about how this time is different. And I’m curious where your thoughts have landed about those questions and what really genuinely is different this time? You know, Jorge brought up the idea that a lot of people are looking at this and questioning whether there’s a there there, you know. And it has been reinforced through the conversations we’ve been having that, as Jorge put it, this is not a nothingburger. This is a burger. Peter: Aha! Jesse: And that has implications. And I’m wondering, reflecting on the last several months of these conversations for you what are the patterns that you think leaders need to be paying attention to as they are trying to guide their teams through this change? Peter: You and I were part of a conversation last week that Jeffrey Veen instituted called the Design Futures Assembly, a half-day set of conversations and presentations on the intersection of AI and design, with some very heavy hitters in the room: OpenAI, Anthropic, Google, Microsoft, Figma, Adobe. Also, I’m doing what I’m calling a listening tour of design executives trying to get a pulse check of what they’re thinking and feeling in this moment. And so I’m bringing that to bear. And it’s not a nothingburger. Definitely a burger. And even if it was a nothingburger, the way people are acting, you can’t ignore it, right? There’s something there. You have to, engage the… Jesse: perception, if not the reality, right? Peter: The perception and just the overwhelm or something, right? There’s just so much about it. You can’t ignore it. The thing is, what is it? I think it’s an interesting question. And what I’m making of it, what we’re gonna definitely see, is how design operates will change. That is becoming truer, at least. That is changing. I just had a conversation with a VP, we’ve heard variants of this story recently, where they have their own Git repo’s. They’re committing to prod, right? We’re collapsing the distance between the work of design and the work of development. But there’s a potential risk when this happens, where when design gets associated with production, which has been the overwhelming mode for the last 15 years, the next step is to think you can automate design away because it’s more straightforward to automate production. Three kinds of designers Peter: The conversation I had with this particular design leader was interesting to me because she has, well, three types of designers in her team. Design strategists who were loving this. They’re able to imagine futures, visiontype, but do it in ways that feel more real. Quickly build things that you can put in front of users, get that user input, iterate. It’s just this unlock for these more strategic designers who are quite generalist in terms of strategy, research, content, design, to, with just one, maybe two of them, just do a lot more than they could have ever done before. So that’s at one end of the spectrum. On the other end of the spectrum were designers on her team that also wanted to play with code, but maybe in the past couldn’t quite get there. They probably built their own prototypes and stuff in code. But now, with these tools and technology, they’re in code, they’re partnering directly with engineers. They’re able to kind of bleed into that realm. So it’s a different kind of generalism, right? You have design strategy as more of this, let’s call it first diamond generalism, and I don’t know if she had a term for it, but let’s say the kind of design technologist as the second diamond design generalism. And what she pointed out is, there is a population in the middle that’s getting lost. Like she wanted to make it clear that it’s not all wine and roses, that there is a population getting lost. But something else that she did, actually, that I think you would appreciate based on the talk you gave last week about AI transformation. As it was becoming clear that AI was going to be important, she took two people on her team and turned them into a AI enablement squad. They got removed from their product work and their job was to figure out how this team was going to embrace AI, figure out the tooling, figure out matters of process, figure out how do you get repos, be the bridge to engineering, talk to them, understand what all those things are. And that ended up spurring the creation, essentially, of this platform design team that’s dedicated to UX excellence. So if it’s not AI, it’s design systems. If it’s not design systems, it’s defining quality, right? She’s realized there’s a role there for this team, even beyond AI, to help set standards for how the team operates. And I say that as a story. You know, it’s clear that the edges of design practice are blurring, and there’s a lot of opportunity for design to evolve and blur into those edges. And that is the part that, I think, is the burger, is navigating these adjacencies. At least– It’s a big part of the burger for me. Jesse: Yeah, I would say there are two things that stood out in what you talked about. Last week I did this online seminar that I called AI Transformation for Digital Design Teams, where I talk about the patterns and the strategies that I’ve been employing in my work as I’ve been helping teams and supporting leaders in developing strategies for tackling all of this stuff. And you touched on a couple of things that I think are really key from what I’ve seen. First of all is, like you gotta clear the decks for somebody, whether that is leadership within your team, whether those are, again, like maybe the principal IC level might actually be a sweet spot where you can really offer an opportunity to people in the organization to leverage their hands-on skills in ways that can benefit a larger organization. But if you don’t have the ability to clear the decks for people and get them engaged with a team like you’re describing, then to bring in a fractional leader from the outside, somebody like me, who can take a view of all of it and get it all organized for you, can really help to accelerate things. The second piece of it, though, which I think is really key, is that the opportunity is not just to do what you’re already doing better. The opportunity is to take a step back and look at what design is and means for an organization and how this tooling can support that. Articulate a value proposition Jesse: And I think that the challenge and the opportunity for leaders is to apply a bit of a quality filter to all of this technology that’s being thrown at them and to ask themselves, “How is this supporting the value proposition that my team already has in place and/or How does this support the extension of my team’s value proposition towards something new, towards something bigger, and towards something that is maybe having more impact than we’ve ever had before? Peter: You said the words value proposition. You said the phrase, “How do I use this to act upon the value proposition I already have in place?” It turns out, I would argue, most design teams haven’t articulated their value proposition… Jesse: oh, sure. right? Peter: I suspect it’s those teams that are having some of the biggest struggles right now, ’cause they don’t know to what end they would be adopting this. It’s just whatever they’re doing, keep doing more of that faster, as opposed to this one leader that I was talking to, you know, there had been some strategic mandate, there had been desires for vision, there had been a recognition of how this group can be maybe more horizontal, looking across an end-to-end experience, while, you know, product and engineering is more vertical, focused on specific applications. I was surprised how energized this leader was when I was talking to them about AI, but I think it was because they had conditions, right? They had the conditions in place to enable flourishing with these new tools and approaches. Whereas I suspect most design organizations lack those conditions to enable that flourishing. Perhaps an… adaptive path? Jesse: Yeah. So one of the things that I called out in the talk that I did was just the fact that every company is gonna have its own unique path toward how this new tooling gets implemented, because every company is bringing its own legacy into it. The ways that things have been done in the past, the expectations have been placed on design teams in the past, the data structures, the decision-making structures, the organizational structures that constrain what’s possible within any given context. And I think that’s a big piece of the task for leaders, is to figure out what’s actually gonna work here, as opposed to what works at the big companies in Silicon Valley or what works at the little startups in Silicon Valley or, you know, what’s working for our competitors or what is the standard that’s been set within our particular product category or industry segment. But to ask ourselves based on what we have in place, because I think your point is right on. If you don’t know what your processes are It’s gonna be really hard to upgrade those processes in any kind of consistent way to incorporate this tooling. If you don’t know what your value proposition is, if you don’t know what the expectations are that your cross-functional partners are bringing to the table, you might be investing a whole bunch of energy in AI initiatives that have nothing to do with what is actually being asked of your teams. And so for the leaders, the responsibility then becomes, again, to be this filter, to be the evaluator of where these investments make the most sense and deliver the most value and deliver the most impact both within the teams and cross-functionally. Peter: You said something along the lines of every team charting their own unique path. You might call it an adaptive path. Jesse: You might call it that, yes. Peter: But, one of the risks, I think, of the direction that you’re suggesting, is that every organization starts building digital product differently. In some ways, it sounds great. Purpose-built, totally bespoke, this process for this context, this company, this time, dial it right in and boom, they can just flow. And that sounds good in some theory, but it doesn’t allow for mobility, interoperability, translation. And so if I’m a designer who’s working in a team that’s operating in its own unique way, and then I get reorged, and we know this happens all the time, and I’m now reorged into a team that operates totally differently, they charted their own unique path, now I have to spend a lot of time figuring out how I work there. Whereas a year ago, by and large, design worked the same in most contexts. Used the same tools in roughly the same order. One of the things we’re hearing now is not just the proliferation of AI-empowered tools that are out in the world, Figma with Figma Make, or Lovables and Cursors and Replits and v0s and Claudes and all that kind of stuff. But I’m talking to design leaders who are like, “Oh, yeah, and we’re building tons of custom internal tools to solve problems that we have.” Which sure, ’cause of Claude, it’s relatively cheap and easy to build internal tools. But then you leave your company and you go to work for someone else, and they have a totally different internal tool suite that has nothing to do with the kind of internal tool suite you learned… Jesse: right. Peter: are you spending three months before you’re useful in this new context? That doesn’t make sense to me, right? And so I foresee some shaking out of some patterns, some stable patterns of ways of working, and input and output of tooling. Jesse: I can see that. At the very least, I think that you have to have two things. You have to have consistent internal expectations just to be able to compare the work of different designers across the team and be able to evaluate who’s actually delivering and who is bringing a sophistication of craft to their work. And then secondarily, there are those external expectations, your cross-functional expectations, your expectations at the executive and leadership levels, your expectations with your business owners that also have to be managed in here. And you’ve touched on one of the big open questions, which is, like, how standard can it get while still embracing the inherent flexibility of the new tooling itself, which is literally a world where software costs nothing, a world where you don’t need to figure out how to build the custom tool. You don’t have to get a developer’s time to build the custom tool. All you have to do is describe the outcome that you want, and a robot will make it for you. I think that fundamentally changes the role that software itself plays in people’s workflow. Peter: We are in a very active period of discovery about exactly this, right? The more I think about it, the more I talk to folks about it, it’s not just about design when we’re talking about digital product. It’s design connecting with product, connecting with engineering, possibly other teams, right? The workflow is not just one function, it’s a cross-functional workflow. And if, the design team has some combination of seven to 10 externally created tools plus 10 to 20 internally created tools that they’ve got going on, you could multiply that by all the other teams, and it starts getting out of hand. But it’s a bit like that university landscape that was part of the inspiration for th…

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72: The Worst Technology Rollout in History (Ft. Paul Ford) May 09, 2026

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Show Notes Journalist, technologist, and Aboard co-founder Paul Ford joins Peter and Jesse with the perspective of someone running a services firm in the middle of being remade by AI. The conversation covers the collapsing cost of software, blurring roles, what machines do well and badly, what design’s value proposition becomes, and Paul’s practical advice for staying upright through indefinite change.Paul’s company: https://aboard.com/; Paul’s LinkedIn: https://www.linkedin.com/in/ftrain/Peter’s website: https://petermerholz.com/Jesse’s website: https://jessejamesgarrett.com/ Transcript 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, journalist, technologist, and agency founder Paul Ford joins us to share his perspective from all of those perspectives on the tidal wave of change from AI. We’ll talk about shifting expectations, shifting identities, holding onto the human in the face of rapid change, and a whole lot more. From the pages of Wired and The New York Times to your ears, here’s our conversation with Paul Ford. Peter: Paul, thanks for joining us. Paul: Oh my goodness. Hello friends. It’s good to see you. Peter: It’s good to see you. I’ve been following your work on the internet for probably 20, 25 years. Paul: This is it’s just ridiculous at this point. Like it just… the three of us, anyway, it’s great to see everyone. I don’t even know if we’ve even met half the time. Peter, I think maybe you and I have been in a room a few times, but Peter: yeah. Paul: It’s lovely to see everyone just getting our career started, getting stuff moving. Peter: Career. I think we’re getting our career restarted. And maybe that’s a place to begin. It appears you’ve been going through it the past few years, and I’m curious how you introduce yourself, how you talk about what it is you’re up to now. Getting Our Careers Restarted Paul: It’s changed from time to time, but essentially I am the president of a services company. It works like a services company. People come to us and they say, I want you to build my thing, just like the industry I’ve been in forever, except the nature of building a thing has changed really fundamentally. You can spin up software very quickly and, I’m the president of Aboard. We are a AI, sort of, delivery org. We help you get your head wrapped around a lot of these changes. And we help you ship software very quickly. Sometimes with our custom tooling, sometimes just using Claude Code or whatever. And so I come from that background. You’ve all been in and out of services, like I have throughout your career, and actually it’s, kind of relaxing for a minute because a lot of times I’m talking as someone who is also a former journalist and I have to be on and know everything. In this case, you understand where I’m coming from. I don’t know what the hell’s going on. Like I used to charge a certain amount of money. I used to, I used to be like, Hey, I’m gonna do this and I’m gonna get a product manager. I’m gonna get a designer. Maybe a junior designer too, and a couple of engineers. One for back end and one for front end. And then I’m gonna give you a thing and it’s gonna break, and then we’re gonna figure out how it needs to work. And then about six months later, you’re gonna gimme a lot of money, like hundreds of thousands of dollars, and you will have your thing and it will be good. And that was 20 years of my life. And that is not the case anymore. And I think you guys are probably dealing with this just in the exact same way. I’m curious what, where you’re at. Peter: Before we answer that, I have one specific question. No. ’cause you had an agency, you had Postlight, Jesse and I also had an agency in ye olden times Paul: What was it? No, you gotta, you gotta name it’s for the people. Jesse: Name it for the people, Peter: Oh, they know Adaptive Path. Paul: There we go. From Product Company to Agency (Again) Peter: And the sense I got, and correct me if I’m wrong, ’cause I’m witnessing this from afar, you left Postlight, you started Aboard, which I got the sense was started as a product company, you had an idea for a thing, you were gonna build a piece of software to put into the world. And that was my operating assumption until literally three days ago when I went to your website and I was like, wait a minute. They’re an agency. Why? What happened? And I’m curious what that story is, ’cause based on what you were just saying, I think it’s probably illustrative of something going on right now. Paul: Yeah, no, fair enough. So I was the CEO with my co-founder, Rich Ziade, who was the president of Postlight, which was a product focused software development firm in New York City, very New York based. We did a lot of work for big banks. We did a lot of work for the MTA. And so everything that you would expect about boutique and it scaled, it grew pretty quickly. And it got to about a hundred plus employees many in the US, a few globally. Especially in Beirut, which is where Rich is from. He’s from Lebanon. And all those things selling all day long, so on and so forth. We, during the pandemic, stepped back, new leadership took over and it felt like time to move on. The company was purchased by NTT Data Americas and became part of a big product group. And I was contractually obligated not to sell services because my power as a salesperson is so incredible. Jesse: Yeah. Paul: Just, Just, if you’re not careful, I will sell you a six month product engagement while you’re not even looking. Peter: Alec Baldwin has nothing on you. Paul: No, exactly. I’m just ready. I’m ready at all times. I love to close. A, B, C. Jesse: A, B, C. Paul: Exactly. But Richard and I really like working together and we didn’t go with the acquisition. It was one of those where they were just like, cool, we’ll take it from here. And so what we sat down to do was to build, and it’s now been through many iterations, a kinda white label…. We were like, let’s take the advice everybody always gives you. Let’s build a version of what we used to do at the agency that we could license. So every project you sit down and you build Kanban and you do user authentication and integration with Microsoft a lot of just the basic data and scaffolding stuff. And so we built that. That was version one. And then we were thinking, there’s just a series of decisions that you make when you’re building something, some of which are good and some of which are bad. So we made a version that was a little more open to the world where people could manage data, but the theme has always been from day one that we would take this to organizations, and organizations would use it to accelerate software development. And so that felt good. And we had leads and we had clients customers really, because you’re selling a product and they were using it internally and all those things were happening. And then ChatGPT showed up and started writing code. And I was like, whoa, this is gonna change everything. And we all kind of agreed. And so then the last couple years have been about iterating in reaction to the fact that the cost of software is going down. And the need for acceleration, even as a concept, is becoming commoditized because you can just deliver stuff all day long. And so a lot of the things that I thought I was way in the future on, I’m not anymore. Nobody is. Because what the hell is a Kanban board? Or like sales or a CRM if you can build a credible one in two hours? And so we’ve been riding that wave and what’s happened is that you react to your inbound. And our inbound has been orgs saying, help us get organized around this. That’s great that you have some custom things that you’ve built that help us build. We love that. That’s really nice. Good for you. But we’re just trying to get this going here. Can you help us solve this? Can you help us integrate these three things? And by the way, could we also make sense of AI while we’re doing it? So we’ve backed into kind of consulting plus custom tooling as opposed to custom tool with consulting around it. Jesse: I think that one of the challenges that’s going on for enterprises right now is that they don’t know what they do know, and they don’t know what they don’t know. Paul: There is a great Reddit thread now, where I think it’s in just like the Claude Reddit where an engineer is just like, CEOs keep giving us code in engineering, and I’m losing my mind. right? Jesse: terrible. It’s like the worst case scenario. And so it is this interesting sort of tension that teams find themselves in where the walls are collapsing. And the gap between thought and reality is shorter than ever. Paul: Which we should be excited by, given our careers. Jesse: We should be. Yeah. exactly. And then I wonder about these teams, your clients, our clients, the people who are inside these organizations who are trying to get things done inside these much slower moving cultural environments, Patrick Swayze in Ghost Paul: I gotta tell you, I don’t know if you have this experience, but you’re dabblers, we’re all dabblers because we were early in this technology and that was what kind of got us into it. And I just wrote a post about this for our newsletter. I feel like Patrick Swayze in Ghost: I’m telling everybody what’s happening. Like, You’re in trouble. There’s danger. And everybody’s like, wow, it’s cold in here. I keep having that experience and what I realized is that what has happened is so weird. It’s so weird. And we’re used to weird things, but most of the world is organized…. i don’t know if you guys had this experience, I’m gonna be another web old timer, but like, there’s a lovely program. I taught it for a while and it was with people like Jeffrey Zeldman at the School of Visual Arts, the MFA in Interaction Design. And there was a point where I went in, and it’s like me and Jeffrey and Karen McGrane and I’m like, oh, we’re the older weirdos here. We’re, like, the early ones because there were these just very put together graduate students who were like, I’m gonna learn interaction design, I’m gonna build a really good career. And then they would go to FAANG companies like right away. They were good product people. And there’s that moment when you realize oh, this is becoming professionalized. That’s really good. That’s actually healthy. People are seeing this as a stable thing, as opposed to a wild wave to ride and figure out. And I feel that that gulf has never been more profound in my life. Like, it’s very hard to see something so transformative. And then you take it to people and they’re like, yeah, but what about those Mets? Like they’re just kind of like, they just would like, please, can we not discuss this anymore? Peter: in my experience, it’s one of two things. Either, this is the only thing people want to discuss or this is the thing everyone’s trying to avoid. It’s hard to have just a casual conversation that might touch on it and then discuss other things. Jesse: It’s got a gravity well, right. Paul: Yes. Peter: It is the gravity well. It reminds me Paul, I don’t know if you know Matt Jones, from the UK, one of the people behind BERG. I remember his frustration in 2004 or five, where all anyone wanted to talk about was the web. And he is like, there’s more to the world than the web. And he was right. And I’m sure there’s more to the world than AI, but right now, like this is the actually intellectually interesting thing as well. There’s something here that’s forcing us to reconsider stuff that we felt was maybe assumed. You outlined it. And that’s been a theme that Jesse and I have been pursuing how for 20 years, from about 2000 to 2020, 2022, there was just this nice, steady kind of pace of growth and development and reliability. Jesse: It felt like we were building a stable new thing Paul: That’s right. Jesse: For about 20 years, right. And then suddenly it wasn’t stable at all anymore. The Tinkerers and the Professionals Peter: Right and something’s happened. Even pre-AI with the layoffs and stuff in 23. But it’s definitely kind of timed to the AI moment. You were talking about professionalism and you were talking about how we started as tinkerers. And I wrote on the whiteboard behind me the word humanities because the three of us went to school at around the same time, and all studied, I studied anthropology. Jesse was a journalist, and you studied English, the famous degree of futility. But with our generic humanities backgrounds and not being afraid of technology, we were able strike out on these emergent technology of the web and the internet. And now there’s a group of folks who… It got professionalized at places like SVA or bootcamps and other things in the last 15 or so years. And the thing I’m seeing, and I’m wondering what you’re witnessing, Paul, is that folks of our vintage are in some ways less rattled by what’s happening now because we came up in a discombobulated moment and in fact many of them are excited because it’s like, Hey, this feels like the late nineties again. Whereas folks who arrived when it professionalized are the ones who are maybe the most off kilter because their assumptions are now shattered. Paul: I think that there’s a few ways to hit at that. I’ll take two angles. So angle one is, there was a great quote. They asked Linus Torvalds, who created Linux, who’s a little bit older than us, but not much. And they’re like, what do you think about AI? He is like, oh, it’s wild. All the vibe coding, it’s really interesting and it’s gonna really, it’s a real accelerator. Like he’s just vaguely into it as a technologist. He’s not shocked, he’s not an open source purist about it. He is just oh, there’s gonna be vibe coding. It is what it is. But he is, like, but let’s be clear, nothing was as transformative as compilers, which was a really funny thing to say. But then when you think about it, until compilers, you had to literally put in the code that the CPU runs in like hexadecimal numbers and, like, you were flipping switches and then one day you could issue a list of English-like instructions. And that’s like at a thousand times cognitive speed up. Like, so many people, we just take it for granted. We take it for granted that you can have something that looks like Python or JavaScript and that will run, or even HTML and it will do something on the computer and you can learn that and you can teach it and so on. And that, that actually wasn’t there for a really long time in the history of computing for all sorts of reasons. And so I really liked that framing because I was like this is another transformative thing. It is accelerated, it is different. But we’ve been through major transformations before. That said, what’s different is it was not a, multi-trillion dollar, 30-million-person industry as it is today. And so the change is being felt really radically. And so, we are very interdisciplinary by nature. It’s what attracted us to the medium because it was the first time that you could smosh the humanities degree with the technology, with the visual, with the written. Like, It all started to congeal and you could kind of mess with all of it. And nobody could tell you no, you know, nobody could be like, you’re not allowed to do that. ‘Cause there’s the web, you can do whatever the hell you wanted. And so I think that is always very attractive to us. But most people really want a little stability in their lives, like they really do. And we’re the freaks here, right? Like, we’re like, ah, well more chaos. Let me just huff it up. Boy, that’s some good disaster. Get me more. Peter: I dunno, I think I’ve reached a certain age where I’m fine with stability. Paul: This is the thing… Peter: Maybe when I was younger, chaos I could thrive on. Paul: But think about actually, Adaptive Path is a good example. It was a tra…

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71: Finding Our Way Live! (ft John Gleason) Apr 19, 2026

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Show Notes For more about The Future Of… Design conference: https://www.thefutureof-conference.com/. Use code FINDINGOURWAY for 26% off the registration price. Find out more about Jesse James Garrett and his upcoming live session on AI Transformation at https://jessejamesgarrett.com/Find out more about Peter Merholz at https://petermerholz.com/ Transcript 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, it’s our first ever live broadcast on YouTube. Recorded April 3rd, 2026, design consultant and industry analyst John Gleason returns to the show to explore the ideas behind his forthcoming design leadership event: Are you ready to lead? We’ll talk about the role of boldness and vulnerability in design leadership, how leaders can position their teams for greater strategic impact, and how to advocate for a larger value proposition for design. Now here’s our unedited live conversation with John Gleason. Peter: Hi everybody. Welcome to an experiment in, for us, at least in podcasting, not that others don’t do this already, and, that’s what we’re doing right now. Jesse: We are finding our way in more Peter: We are finding our way with live streaming and get, kick us off here. Just a quick, introductions. Most of you will know Jesse and myself as the hosts of your podcast, finding Our Way, and we have with us our returning guest, John Gleason. John is a, I think of you as a, you can change this, if you choose, but I think of you as a design and business consultant. You have a background, primarily in business, but you were at Proctor and Gamble during their design revolution. And we got to know you because about a year ago this time, you hosted an event called, the Future of Design, where you posed the provocative question is design dead? Jesse and I didn’t attend that event, but we heard the things that came out of it, were intrigued, and we had you on our podcast last June to talk about it further. And we know that you are planning a new forthcoming event, for the future of design in, mid-May, but now you’ve got this subject, are you ready to lead? And so we thought this would be a good opportunity to dig into what’s going on with design leadership, what you are seeing with your background in packaging and brand design and industrial design, what we’re seeing in the worlds of UX and digital product design, and see where this conversation takes us. We are live. I will be checking the chats because, you know, at some point we would love to engage some audience involvement. John, anything else you want to say, before we dive into the conversational part of our discussion? John: Part of the context that I wanna offer I’ve known about the two of you for a long time and then became a long time listener, first time caller when you invited me to join the podcast last June. Peter, if recall, part of it started with, oh, I’m glad those things don’t happen in our world. This idea that design’s dead and declining, a decoration station, and then you and I talked and chatted and we both had some revelations and realizations that maybe there’s more commonality across the types of design activity, than differences, because the activity is different or the outcome or the artifact or the thing being created. So I’m delighted to be here in part, to open up some dialogue for me to have a chance to continue to learn, but also expand the dialogue and the discussion around the ability for design to influence growth and culture and other things. Jesse: So John, I’m curious about this year’s event and the direction that you see the conversation heading. Here in the tech space, it continues to feel like a lot of bleakness, a lot of uncertainty, a lot of doubt about what the future holds. And I guess I’m curious about where you see the conversation headed that helps to resolve that. John: I think one of the, I guess it’s an aspiration that we had last year when we, the three founding partners for the future of conference, decided to do the silly, crazy, stupid thing of, let’s produce something that gets people together, was born out of observations that I’ve made as I’ve had a chance to peek inside 150 or so big companies in the last 15, 20 years. And that is… most design and business leaders, and this is true of marketing or supply chain or finance, they’re in their world, inside their company solving problems and managing challenges. But because they don’t often get a chance to get out and meet with their peers they think that those problems are unique to their own circumstance. And then because they think it’s unique, they think it’s confidential and sensitive, so they can’t talk about it. And then because they can’t talk about it, they have to go try to solve it themselves without help, without guidance, without a roadmap. So part of the original ambition was, let’s create a forum that gets people together first to build awareness that their problems are probably not as unique as they think they are. And then use the power of the community to help solve for some of those things collectively, to accelerate the ability to change the trajectory or direction or arc of where and how design contributes to business impact, to career development, to cultural dynamics. So that is a foundation. One of the things that came up during the conference last year many times, which led to the theme that we have this year of, are you ready to lead, is there’s all kinds of training in schools and university degrees and the like for the craft of the businesses that any of us are in. Jesse: Right. John: But there’s generally nothing that teaches those people how to navigate complex organizations, how to influence people with more power and more stripes and more influence than themselves. How to set a vision for something and get alignment for that vision. And so part of that is let’s use the forum that we started to create with the future of and begin to use, step two or round two of this as the opportunity of people sharing what they’ve learned on their journeys. The hard knocks. The things that that maybe they did really accidentally or on purpose. Again, as a way of trying to accelerate the ability for people to use some of those tools and frameworks and roadmaps and checklists and principle what, whatever that people are willing to lead with as a way of trying to arm the industry more broadly as a way of trying to elevate design more strategically and more profoundly. Peter: It’s interesting you say that. I’ve been having a similar thought where… So as Jesse suggested, in, in the field that we’re primarily in, this UX and digital product design, there’s a fair bit of consternation and uproar. AI is feeling like it’s being imposed on people as opposed to them organically adopting it. And that’s causing people to feel like they don’t have autonomy or agency in their own work, which causes people to stress out. There’s layoffs, there’s a whole bunch going on that leads to anxiety or even fear for some folks. And the realization I had was, I think everybody is dealing with this on their own. And we need ways to enable folks to deal with it collectively. So my, my initial thought was, I’ve been writing a little bit about this, for design leaders to, I think, we, we need design leaders to be more vulnerable right now. I keep coming back to that. People look to their leaders for answers and solutions. But this is a moment where many leaders just don’t have that. They’re figuring it out like everybody else. But I think those leaders aren’t comfortable acknowledging their lack of awareness or their lack of understanding of exactly what to do. And so they’re pretending like they’ve got it together. And, but then they ask me, my teams are anxious and frustrated, and what would you say to help unlock those teams? And I’m like ,you need to unlock, right? You need to show that you don’t have all the answers, that you’re figuring it out, so that you’re modeling for your teams that they can be open and vulnerable. I have the Brene Brown book here, ’cause I’ve been thinking about this. So that they can be open and vulnerable and so that you are all operating with more full information about one another. And then once you do that, once you share that, or once you discover you have shared kind of challenges, now you can work together to address them instead of everyone feeling like they have to do it on their own. And I’m wondering, John, how, what you’re seeing in your world when it comes to some of these kind of more existential crises, like last year, even pre AI, you were asking, is design dead? Now in this, not, maybe not specifically pre AI, but AI has definitely accelerated since then, what are you seeing? What are you seeing that’s working maybe in terms of, kind of, leadership approaches that you’ve witnessed that are causing, maybe the temperature to come down a bit? John: Let me take a step back and build on the point you just made Peter around vulnerability and consternation and fear and those things, those are feelings that don’t only exist in design. Marketing, finance, supply chain, CEOs, CFOs, all the people that are supposed to be the proud leaders all have their own set of fears and uncertainty. And part of the challenge, there’s not a school or a training program to teach design leaders or anybody for that matter, how to navigate complex political organizations. Part of the reality around one, one of the reasons I believe vulnerability doesn’t exist broadly in corporations and even agencies and consultancies, by the time people get to a certain level in their company, they feel like they can no longer admit they don’t know something. So there’s a lot of faking going on. Oh yeah, we’re gonna go do this and we’re gonna go do that. And, or they’re hedging their bets and they’re waiting to make a decision until, the clouds part and the angels sing. So part of this is if you think about… vulnerability is one of those characteristics that infers psychological safety… Jesse: right. John: And design and designers are the pent-ultimate people and organization that, that are wired to experiment. If there’s not the safety to explore, they won’t explore and you’re not gonna get the best of people. And so part of this is basic psychology, basic human resources. But most companies today, especially today with the economic circumstances we’re facing, are faced with the belief that they can’t fail. And this quarter, next quarter is the planning horizon, which doesn’t play well to a designer’s vision horizon, if you will. Jesse: Right. John: And so some of this is, it really does take individuals, unless the culture is so good systemically, and as time goes on, I find that there are fewer and fewer of those that have a systemic positive growth oriented culture, because everyone’s trying to cover their backside. Jesse: Yeah. I think that’s a big piece of it. I think it’s important to acknowledge the emotional reality of the position that the leaders find themselves in now, because I’ve talked with a lot of people in the last year, since the last time you were on the show, John, who have had to figure out how to cut a third of their team and then be the one to deliver that message, even though it wasn’t their idea. And then they still have to turn around and justify their value proposition to their executives as well as to their cross-functional partners. And the idea that in a circumstance like that, somebody is just gonna blossom into vulnerability as a leader, I think it’s a pretty big ask. John: And vulnerability is, and perhaps I’ll be a little bit sharp. Vulnerability is viewed as a weakness in many corporate cultures. That’s a big thing that reasons why people don’t go do that. But I’ll talk about one, one point that you make. Again, Jesse you talk about these people who are being mandated that they need to go make these big cuts and then deliver those messages. Again, not unique to design. And so part of that is, is I think because there is the perception and a great deal, the reality that there is a higher emotional quotient among a design community, that there is more empathy and understanding in those circumstances than, somebody that might sit in a in a more linear, numbers oriented, kind of business function, where it’s, okay, these are just numbers. We’ve gotta go do this. And I think the one, one of the topics that came up in, in last year’s conference was the question was posed: it was first posed as a framing. Look you designers, you play in this empathy space every day. I don’t hear you talking about having empathy for your CEO who has to go deliver some things and the bosses of people who are perceived not to understand what design might contribute. And it, it really was interesting how many people in the room went, oh yeah, could benefit by trying to better understand fears and the pressures and the things that they’re under, even though most of those people don’t seem to openly show and outwardly show fear. Jesse: Right. John: And so part of it is, how do we build the tool set so that people have the confidence to be able to stand up and offer okay, we can make these cuts, but here are the likely implications and consequences of those actions. Just so you’re clear, hierarchy, I’m happy to go be a good corporate soldier and go try to do these things, but if you’re trying to grow, if you’re trying to innovate, if you’re trying to disrupt, if you’re trying to create a culture of curiosity and openness and vulnerability, you probably sever most of those things when you cut a third of your organization. And I know part of this is about survival. Jesse: right. John: About hitting your, the numbers that Wall Street expects. And again I’m being facetious in some of these comments, but part of it is most designers aren’t armed to be able to have that business implication conversation, or they’re not confident in being able to have those things. And so I, I think it would surprise a business leader if a design leader were to step up and say, okay, here are the business implications if you go do that. Peter: So generally, I agree with the need for design and user experience leaders to have empathy for the challenges that others are facing and that yes, we’re not alone in this situation. But a couple thoughts that I’m tying together, one is something you said John earlier, which is like, how it feels like in… Our organizations are decreasingly safe. Like something shifted in, in the last, I don’t know how many years, three, five years where things have become less safe. And then something that Jesse and I have discussed on a forthcoming podcast, it’s in production, but hasn’t been pushed, is ’cause you mentioned empathy for the CEO, and at least what we’re witnessing is that once you get above a certain level of executive-ness, it tends to select for sociopathy, right? People who do not care about other humans. People who do not see people as people, but as resources, right? I think part of the reason they succeed is they can make a decision, a spreadsheet decision, and they see people cost x and chairs cost y and facilities cost Z and they’re like, okay, let’s get rid of people. That’s a cost we can now reduce or whatever. And so I want design leaders to demonstrate empathy for their leadership, but sometimes their leadership is toxic and broken and there seems to be a wave of that, like in tech, right? Jesse and I primarily work in tech or tech kind of adjacent spaces, and that those folks have ripped the mask off and demonstrated their toxicity. I’m curious, again, I’m looking to you to give us a kind of parallel perspective. Are you seeing similar things? Are you seeing different things? Like how is that playing out in, in, in your world? John: I think the things that you desc…

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LIMINAL—3: The Waves within Waves Apr 10, 2026

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Show Notes As of publishing this episode, the Intentional Design Leadership Circle starts in 5 days, on April 15. https://www.eventcreate.com/e/intentionaldesignleadershipThere are still a few spots left. Also, Jesse announced “AI Transformation for Digital Design Teams,” a new online event taking place April 30. For more information and registration, head here: https://www.eventcreate.com/e/aitransformation4design For more about Jesse James Garrett, and his coaching and AI consulting practices visit https://jessejamesgarrett.com/For more about Peter Merholz, his organizational effectiveness, leadership development, and coaching practices, visit https://petermerholz.com/ Transcript 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: This is Liminal. When everything is subject to change, how can leaders choose a destination and set the right course? On today’s show, Peter and I return for part three of our exploration of liminal leadership. We’ll get into extracting the signal from the noise of the liminal moment, the role of shared values and collective action in setting direction, and how to make good choices when you can’t predict the outcomes. Hello, Peter. Peter: Hello, Jesse. Jesse: So today we are resuming our liminal conversation. There are little bits of these ideas that have been coming to the surface for us that have led us to this particular conversational series. And now after having spent a little bit of time on the show exploring it, you know, I had gotten to a place where I felt like there are some definitive statements that we can make about all of this. And then I saw something on YouTube the other day that really kind of shifted my thinking about it, which is that for some reason, sort of out of the blue, YouTube started serving up to me surfing videos unasked for not part my usual rotation… Peter: Are you sure YouTube hasn’t been listening? Are you sure YouTube hasn’t been listening our podcast? Jesse: I can’t be sure of that. None of us can be sure of that, can we, Peter? And I found myself watching just, like this stream of live beach footage, which was just, not a big tournament and not your best pro surfers or anything like that, just the beach in a place where they have some really big surf and there are a bunch of people out there on any given day trying to catch those waves. And what I noticed about watching it was how little of it looks like success in the ways that we would frame success. How much of it is struggle and failure and catching up and compromise. Because what you’ll see out there, if you watch just, like, raw footage of a beach… Maybe there’ll be 10 people out there with surfboards. A big wave comes up and let’s say six of the 10, the wave just rolls right under them. Like they don’t have a chance, they’re not there and they’re just going to fall off the back of the wave. Of the rest of them, three are gonna go, not over the wave, but under the wave. They’re gonna get swallowed by the wave. They never get a chance to get their feet on the board because the wave takes them down before they get that chance. And then that 10th person out of 10 is the one who gets their feet up on the board and they’re up on the board for a minute. But there’s no such thing as a soft landing in surfing. And it becomes a question of, okay, now you are riding that energy, how do you create an exit that feels natural from what you’ve been doing? And so, the way that I really started to think about it is, first of all, the wave’s not for everybody. This wave might not be your wave. Like how many waves of technological innovation would you say that you and I have seen in the course of our careers? You started out working for a CD-ROM company, my friend. Waves of Technological Innovation Peter: Careers? We could even go back a little bit further, I started as an Apple IIe kid. Got a Mac for college. So I went from, command line interfaces into GUI interfaces. The desktop revolution when I was in college, I had jobs where I used Freehand or whatever to make stuff. And, Microsoft Word, figuring out how to lay stuff out really precisely in Microsoft Word of all things, right? You had to figure out how to hack all the spacing and kerning and all that kind of stuff. And anyway, sorry. That’s a bit of a, I’m getting, getting nostalgic. Jesse: Peter. Hey Peter. Get back. Come back to the 21st century please. Peter: Come back. But you had GUI, and then it was when I was a student at Cal, the web breaks. Actually I had a job doing multimedia work in school, pre-web. I saw the web. I didn’t work on the web for a couple years, though. I did work at a CD-ROM company. I then helped that CD-ROM company get on the web. I then worked for a design firm that was moving from traditional design to digital design and web design. So you have the web, you have Web 1.0, you have Web 2.0, you have mobile, and people forget even before mobile, you remember WAP? Remember when people thought Nokia phones and the Palm Pilot was the future? Jesse: Hey, I did a bunch of design in that space during that time, so dude, that was real work. Peter: Yes. I’m I’m sure. You had iPhone, obviously tablets, the move to the cloud. I already mentioned Web 2.0. And then it’s interesting because, as you talk about waves, there were these actual waves and then there were attempts at making waves. Right. Jesse: Waves. Yeah. Peter: Well, yeah, ’cause because pretty much very little meaningful evolved after mobile with the possible exception of things moving to the cloud. People tried to make something called Web3.0 a thing. People tried to make blockchain a thing and crypto a thing. And the metaverse a thing. Jesse: NFTs. All the stuff. Yeah. Peter: Yeah. But yes, to your point we’re definitely now on a wave. It’s a wave that feels possibly as meaningful as the shifts to web and mobile. Definitely as meaningful, as say, the shift to things like desktop publishing, and putting the ability to create directly in the hands of creators as opposed to needing a chain of labor to get from somebody’s idea to some produced thing. Jesse: Yeah. Let’s come back to the notion of liminality and the fact that there’s always another wave coming, right? That the waves themselves just keep on coming. And in fact to be a surfer is not to find your one perfect wave and then step off the board. It is not just dust off your hands and declare a job well done. It is more of matter of finding the waves and the waves within waves. You touched on a couple of things. There are always these technologies that are coming to the surface, or techniques that are coming to the surface. One of the big things that’s happening with AI is that the technology has reached a relatively stable state, but the techniques around the technology are continually in rapid evolution. And the big open question, as people look around at these allegedly AI driven layoffs and things like that, is what have those guys figured out over there that we haven’t? And in fact, the answer is probably not much, but it’s enough to give them a sense of what the future of their organization looks like. And so surfing the liminality means acknowledging the trajectory of the data that’s right in front of you, right? To be able to read the wave and see where the wave is going so you don’t get drowned by it. Waves of Practice Change Peter: There’s a parallel here because you’re talking about the kind of these techno waves of technology and change and AI is the most obvious, latest example of it. I stated how we haven’t really seen a meaningful technological wave since probably the combination of whatever was happening with Web 2, mobile, and maybe a shift to the cloud in the late two thousands, early 2010s. But that’s not totally right in that in parallel… So those are waves of… Jesse: Right. Peter: Society-wide impact. But within our industry, within our field, someone was referring to the waves of design tools that we have embraced going back to whether it was, obviously Photoshop and Illustrator, some of us using diagramming tools like Visio and OmniGraffle. Then you have prototyping or like early, like some of those, yeah, prototyping tools. Your Dreamweavers or whatever or, earlier web tools… Jesse: Page Mill. Peter: But then I… so I got off the design tool train sometime in the Photoshop, OmniGraffle era. I never embraced Sketch. I never embraced Figma. Though I know those have been waves, right, that people have had to ride. I use Keynote when I need to design something. Jesse: Yeah. Peter: That’s my little wave off to the side. But I’m bringing that up to suggest, ’cause you said the word waves within waves, and I think something that maybe gets lost is things can feel very unitary or global or monolithic, right, it’s AI and it’s everything and it’s this one thing that we’re all dealing with. But the reality is probably that this thing of AI is obscuring a lot of little waves within it that we’re having to figure out and navigate. One of the things that’s coming up for me a lot in this liminal moment, what’s clear in the discourse is anxiety, and a just a generalized anxiety. Attention and Anxiety Peter: And part of me wonders if that generalized anxiety is because it’s not one monolithic thing, it’s a thousand little things, and your attention gets frayed. You don’t know what you should be investing your time in to understand and explore. You. start down one path and then you hear this other thing that comes up and you’re like should I do that, or should I finish the thing I started? And like how to handle all the potential, not noise, but all the potential sources of your attention. And I think a not unreasonable response is just to peace out. Jesse: Oh yeah. Oh, for sure. Just, yeah. Give into the overwhelm and go to bed. Yeah, I think that’s real. I think that one thing that I notice in this is the question of what the transition asks of us. Because some of these transitions these past waves of technological change, some of these transitions for some of us asked very little of us, because it didn’t really require us to change our lifestyles. It didn’t really require us to change how we did our work. It didn’t ask a lot of us. Some of these transitions have asked quite a lot of people to let go of and give themselves over to in terms of… Just think about the digitization of various industries over the course of the back half of the 20th century, and what that asked of every worker in every facility doing every job to engage with different technology that didn’t work the way that they expected, that they basically had foisted upon them by some central authority. And so this is how automation gets a certain kind of stigma because it feels like something that is enforced upon people rather than something that is offered up as an opportunity or a genuine enhancement to their abilities. I keep coming back to what this means for leaders, because as you pointed out last time we talked about this, they are the leverage point. They are the point of influence to not just to embrace the new, but also to acknowledge what is potentially left behind that somehow needs to be kept up, right? the fear of this highly automated world is that the soul is lost from the work, that the human voice is lost in the work. And if no one else is there to defend it, like it’s got to be the leaders who make it happen. They’re the only ones with the influence. Peter: To defend what? Defending Humanity in this Liminal Moment Jesse: Defend the soul, the spirit the human element. If it does turn into a wall of automation, it’s because we chose to automate things that shouldn’t have been automated. And so it takes people with the thought and the feeling and the expertise, and as we talked about in the last episode, the background in understanding human beings and the sociological and the psychological grounding to understand what inhumane practices look like in order to instill that understanding in the systems we create. And I think that applies both internally and externally in terms of not just like what constitutes automated abuse of customers, but what also constitutes automated abuse of your employees, right? Peter: This is making me realize something that I hadn’t, I guess, acknowledged, come to terms with, which is that I’d been thinking of liminality as something that happens to us, right? That as you go through life, as things shift and evolve, there’s going to be moments… I think one of the theses of our conversations is that liminality is always there. You’re always going from something to something else, but there are definitely moments where it feels more heightened and this is one of them. And that’s just the way of the world. Liminality is a common anthropological frame, rites of passage, certain points in your life where you’re about to step into some new… Jesse: Seven ages of man, right? Yeah. Peter: I was bringing some of that thinking to what it means to how we show up as people in our liminal moment and thinking about other themes that we’ve discussed, which is that this uncertainty that we are in can cause anxiety, but is also opportunity, right? Because discombobulation means people are looking around for someone with some answers to settle things, right? And there’s voids that folks with ideas can fill. But something you’re saying, and I don’t know the implication of it, but I think it’s definitely worth calling out, is that liminality isn’t simply something that happens to us. Much of the liminal moment that we are in has been imposed upon us by folks who are acting out of their own self interests, but are dismissive, neglectful of the impacts of that decision making on others. And we’re all having to navigate that. And because when you talk about leader, you talk about power dynamics, and we live in a society where a relatively small number of people wield outsized influence that we all then have to react to. And figure out our reaction to… Jesse: Yes. Peter: and that seems to be something different about this moment, maybe than prior liminal moments. There’s an arbitrariness to it. Jesse: There are a couple of sides to it. One thing I’ll say is that I called my business Intentional Associates. You called your business Humanism at Scale. We are both in the business of driving more intentionality in these organizations because I believe that we both believe that if we don’t stand for humanity within these systems, then no one else will, because it is Design, more than any other function, that is invested in bringing humanity to internal decision making. And that’s what we have seen in our careers as the opportunity for design to create broader cultural change, both internally as well as at the larger social scale that you’re talking about. So there’s that piece of it, first of all Secondarily, there is a certain friction associated with the liminal moment that requires a grace, a fluidity, an adaptive path, if you will, that goes against the way that a lot of people think about their roles. And the way that a lot of organizations think about what success looks like. And in some ways, when we’ve talked about creating that semi-permeable membrane, that bubble around design, it is in part to enable design to continue to keep that torch lit for humanistic practices. But it is, I think, a question of that multiplier effect because the perception, the real perception at this point, is that major enterprises are going to start shedding thousands of jobs because they will figure out how to automate away a lot of the work that’s being done by human beings right now. Regardless of whether we think that’s actually possible with the technology that exists, these technology companies absolutely want us to believe that’s possible because that’s how they keep their i…

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69: In a World of AI, What is the Work Really About? (ft. Jorge Arango) Mar 27, 2026

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Show Notes For more about Jorge, visit https://jarango.com/ For the Claude skills he discusses, visit: https://github.com/jorgearango/llmapper-skill To learn more about Jesse and Peter’s Intentional Design Leadership Circle, starting April 15, visit https://www.eventcreate.com/e/intentionaldesignleadership To join the first Finding Our Way Live! on April 3, visit our event page on LinkedIn: https://www.linkedin.com/events/7442678896506068992 Transcript 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, consultant and author Jorge Arango is our first return guest, five years after his last appearance. We’ll talk about his current work in AI transformation, how AI has evolved his thinking on the craft of design and where information architecture still plays a role in this new landscape. Peter: Jorge, welcome back. It’s been five years since we’ve last had you on the show. Jorge: Fortunately it’s not been five years since we’ve talked. But I’m so excited to be back in the show. Peter: Awesome. You are our first return guest. Five years ago, it was deep in lockdown, heart of the pandemic. We talked to you about some themes that are still relevant today, craft, practice. We were interested in your architectural background and how that was helping you think about design and design processes you were teaching at the time. So you were very meta around your thinking and we wanted to tap into that, but it’s five years later. Which feels like a lifetime, particularly after the last couple of years. So what’s going on with you? Where are you at? What you up to? How do you talk about what you’re doing right now? Jorge: You know, talking about five years, it makes me think that about five years ago people were tossing around the phrase “the before times” to talk about like the before the pandemic, you remember that? It’s like, “Back in the before times…” Jesse: Right. “Before what?” anymore. Jorge: Yeah, that’s the thing, right? Like that phrase is, like, we keep using it. It feels like we’ve left the world behind, right? Things started changing significantly back in 2020. I mean, I feel like things had been changing even before then… Jesse: Oh yeah. Jorge: 2020 was a big inflection point with the pandemic. It moved so many people and processes that maybe had resisted going online. It moved everything. We were working remotely and all that stuff. We still are. Getting Excited with the Work Again Jorge: But then obviously, the breaking of AI into the mainstream as a thing that people are concerned with, interested in, trying to find how to use, is the latest catalyst, I think, in casting the past as the before times. And as many people have, I’ve been trying to find my way in this new world, and I find that for me it’s about coming back to fundamentals, to first principles, to what is it that I’m uniquely suited to help add value with? And I’ve been on a path of rediscovering that, and I’ll say this right up front, I’m more excited about the work than I have been for a long time, as a result of all these changes. Peter: What do you call the work? What do you mean by “the work” when you say that? Jorge: Y’all know that Harry Max and I are doing a podcast. And Harry has this definition he’s used this in a couple of episodes. He has this definition for stupidity that I really like. He says that, I’m reading now from one of the transcripts here, “Stupidity is a result of a series of decisions and actions that lead to results that are the opposite of the intended outcome under conditions of self-deception.” Peter: Okay. Jorge: So basically self-sabotage, right? Like, it’s like… we, Peter: I didn’t realize your podcast was about our current United States Jorge: Well, this is like the discovery for me. You asked what’s the work? I’ve realized that my work boils down to helping people and organizations, particularly the people who have the most leverage, act intelligently. Like, I bring up Harry’s definition of stupidity because that’s what you don’t want, right? You don’t want self-sabotage. You don’t want to declare that you are trying to do something and then end up with the opposite outcomes. And we have this catalyst in our midst, AI, which can either help or hinder our efforts to act intelligently. And my work now is focused on… the way that I describe it in my website is, like, What’s the architecture of intelligence? Like how can we use this information that we have available to us to act more skillfully? And you won’t be surprised to hear that I think that, first of all, letting in the right information and then carefully structuring that information is a big part of how we act skillfully. AI and IA Jesse: So, you know, the three of us all met through the information architecture community back in the early two thousands where there was a real energy and focus building around the idea of, if we could just structure enough data in the right ways, we might be able to create systems that were better for humans. And that, I think was the, continues to be the, innate promise of information architecture as a discipline. Now, and honestly, this was predicted by IA people. It’s so funny because I can’t remember who said it. I think it might’ve been Lou Rosenfeld. I think it might’ve been Peter Morville, I can’t remember which of them it was, but I feel like it was one of those two guys who, at some IA Summit said, we’re not going to crack the AI nut until we crack the IA nut. And the idea being that if we master the structuring of information itself as a human discipline, then we will be capable of creating the intelligent systems that we actually need, that will actually serve us. And it feels like a lot of your work in the last year or so has really been moving toward that. I don’t wanna project onto your career something that isn’t there, but I’m curious about, like, how do those ideas resonate with the work that you’re doing now? Jorge: Yeah, they absolutely resonate. the way that I’ve articulated it, at least in my website, is that information architecture can be done more skillfully with AI. But conversely, AI can be better if the information that it’s fed is carefully architected, right? So, I’ve been trying to play kind of both sides of that. Say, it’s like I work both sides of that loop, right? I’m trying to like understand how AI changes the work of structuring information with the understanding that the better a job you do at structuring the information you feed, particularly language models, the better the outcomes you’re going to get. There’s work above that, which is like trying to figure out, like, what are the outcomes that we’re trying to get out of this? And you talked about, like, human goals that ostensibly you want to design systems that produce better outcomes for people and for society and that help drive us forward, and there’s a technical conversation about like, how do we structure systems to help us achieve our goals? And then there is a broader conversation about what are our goals, you know, what are we trying to do here? And that has to be informed by a clean read on the context. Like where are we? What’s going on? What are our competitors doing? What is our organization aspiring to? Like, there’s all these things that stand above the technical discussion about how do we architect information, how do we architect AI or what have you? A Lot Depends On Your Definition of Design Jesse: I guess when I think about our audience and I think about design leaders and the pressure that they are under, in a lot of ways it is about simply having a story to tell about where this tech fits in as you see it as a leader, within your organization, within the boundaries and the constraints of what is expected of your team. And in some design teams that expectation is super tactical. It is pixels and Figma and, moving the data into production. And on other design teams, it’s not that. There’s a lot more sort of strategic permission to engage with the bigger ideas behind the product. And I’m curious about your perspective on how those things play out in the choices that design leaders have to make around where they focus their attention because their attention is spread so thin, right? It’s like, where can I pay attention to this tech where it’s actually gonna matter and it’s actually gonna create some traction for the team against an actual value prop. Jorge: I think you framed the question correctly by stating upfront that there are different understandings of what design is, right? And I suspect that in a large number of organizations, design is seen as a production function that involves cranking out screens. And if that is the sense in which design is understood in a particular organization, the design leader will have a different engagement with these new technologies than in an organization where design is more, I’ll be judgmental here, more correctly seen as a more strategic discipline. So let’s acknowledge that right up front. There’s an information architecture labeling problem there with the word design. My sense is that it might not be worth a leader’s while to try to reframe the organization’s understanding of the discipline through rhetoric, through persuasion, right? You’re working in an organization where design is seen as a production function, your best strategy forward might not be to try to convince your colleagues that’s not a good reading of what design is. You might be better served by trying to prove designs value within the constraints that apply to that particular organization, right? If the organization sees it as a production function, then try to produce it as effectively and efficiently as possible. Jesse: So this suggests tuning your approach to AI tooling toward the value prop that is already expected of you, right? On some level. Jorge: There’s a step before that, which is, taking for granted that the design leader understands the context that they’re operating in. That might not be true, right? Like you might have expectations of what design is that are misaligned with how design is actually expected to function. And again, you two have worked more closely with design leaders than I have, coaching them and stuff like that. So you might have more to say on that. Peter: I have a lot to say about that. Jesse: Yeah. Peter: I wanna set aside the understanding context bit, which is important. Jesse: For sure. Peter: So Jorge you mentioned the challenge of rebranding design, it is commonly understood in some fashion internally. This is a challenge that nearly every design leader I work with faces, it’s at the heart of my masterclass and one of the core tenets of my class is you need to meet people where they are at in their maturity. You as the design leader, are always gonna be way more mature than the rest of the organization about design. And if you try to accelerate or put forward your design approach into an organization that’s just not ready to receive it, you won’t get anywhere. This gets a little bit back to something Jesse and I used to talk about years ago. When Jesse had this idea of the three maturities. Jesse: Right. Peter: I don’t think the idea though is simply to then give the people what they want and stop there, right? That’s where you start, because folks around you have a set of expectations. If you don’t meet those expectations, they will then just dismiss you. So you need to meet their expectations, but you also then need to have some idea of where you want to take things, which as you meet their expectations, the theory goes, you demonstrate your credibility, the more credibility you’re demonstrating, the greater trust you’re earning, the greater trust that you earn, the more that you can then start bringing people with you. But there’s a journey you need to go on. You can’t just again hop the queue or hop the maturity model and say, we should be operating at maturity level five. We’re at two. Let’s just go. You need to take the steps. You need to take the steps through it. The Need for Clarity Peter: I wanted to actually get back to something else you talk about, which is related, which is something that’s becoming clear as I read about AI and talk to my clients about these AI tools, is that perhaps the biggest gap, shortcoming, that teams are facing is a lack of clarity on the part of their organizational leadership, their senior most leadership. And without clarity as to goals, outcomes, mission, vision you get a lot of chaos with AI, ’cause you basically accelerate the current chaos. Jesse: Amplify the noise rather than the signal. Right? Peter: Yeah. And I think that’s starting to stress people out as, like, a lot more stuff is being done. But you also hear that people don’t feel like they’re doing better work. They’re just doing more work. And I think the reason they’re not doing better work is there’s a lack of clarity as to what are those goals, what are those outcomes? What are we aiming for? And so I’m curious, Jorge, it sounds like you’ve been doing a fair bit of work consulting with Greg and your practice with organizations. Are you, how are you helping them achieve clarity, or what is your relationship to the clarity story here? Jorge: The three of us were working when the web happened, right? And that was a time of big change. Like now, that was a time when people were excited about a new technology and looking for ways to apply it. There was a lot of hype, there was a lot of misunderstanding. I remember, like, trying to explain the web to people and getting glazed looks, right? Like, what are you talking about? And it was a time when there were a lot of solutions in search of a problem to solve, right? And people were putting the technology forward because it was like an exciting new thing. And in many ways, I feel like we’re in a repeat of that, but even perhaps more impactful than what the web was in that this feels like the ultimate general purpose technology that we can now apply to anything, right? Like, it’ll just solve all your problems because it’s artificial intelligence and it’s so much smarter than people and all this stuff. And there’s a lot of misunderstanding about what the technology is that is very similar to the kind of a misunderstanding that we saw in the early web. Recently, I reread, do you remember John Perry Barlow’s Declaration of Independence of Cyberspace? Jesse: Oh very much. Yeah, sure. Jorge: Right? You go back to that and you read it and you’re like, man, you remember that kind of naivete that we had at the time? It’s like it’s going to change the world, like nations of the world, stand aside. Here we come. There was this notion that this technology was going to somehow overcome human foibles, it’s like technology never really does that, does it? Technology can amplify human Jesse: Yes. Jorge: You know, it’s understandable that we are now in the thrall of this new thing and therefore acting unskillfully in many ways. I suspect that needs to burn out and it will burn out. What I wanna do is, I want to help organizations and the people who are leading organizations use this new technology as skillfully as possible. So like, how do we speedrun the path to a skillful use of the technology, meaning free from the delusions that come from our projecting into the technology capabilities that it doesn’t really have. Which in this case are quite tempting because it is, first of all, there’s been a lot of hype, and second of all, frankly, we work with the technology day to day, and I’m continually impressed by its capabilities, right? Jesse: Yeah, no, the line is really fuzzy, right? Between what it can do and what it can’t do. In part because we are still exploring the boundaries of what it can do, but also because that’s changing. It’s been fascinating. S…

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