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100 / The Emergence of Product + Design Leadership, with Jesse James Garrett

Hosted by Sean Flaherty & Paul Gebel




Jesse James Garrett

Design Leadership Coach

Marking 100 episodes of Product Momentum — Check out our special Book Giveaway!

Jesse James Garrett has been one of the most prominent voices in digital product design for more than 20 years. His career highlights include co-founding the groundbreaking UX consultancy, Adaptive Path, and writing the foundational book, The Elements of User Experience, whose iconic five-plane model has become a staple of the field; and defining Ajax, the dynamic interaction model that transformed web technology and design in the Web 2.0 era. His work has been published in more than a dozen languages and he is a frequent keynote speaker on making designers and organizations more human-centered in their work. 

When UX design guru Jesse James Garrett first started out, user experience as we know it today wasn’t even a thing. Yet he remains among the most prominent voices in digital product design. As both witness and catalyst for more than 20 years, Jesse’s work in this space triggered much of the UX evolution and inspired the cultural change we’re now experiencing within our organizations. The emergence of product and design leadership has accelerated the ‘professionalization’ of traditional roles and has empowered teams to deliver better products and user outcomes.

As Jesse explains in this – the 100th episode of the Product Momentum Podcast – “The exciting thing is that many product leaders are finding the way to gain the empowerment and the support and the leverage to drive not just good product outcomes, but organizational outcomes that fundamentally shift the way these organizations approach and think about what they do.”

Product leaders are forever balancing the technical realities of what it takes to deliver a good product with the market realities of the business model, the competitive landscape, and customer realities, he continues. “And what I’m seeing are product leaders turning to design as a way to deepen their expertise … around that customer piece of the equation,” Jesse adds. “The designers who are elevating into those more senior leadership roles are the ones who are able to frame design in terms of its ability to deliver value around user insight more than around delivery.”

Sean and Paul chat with Jesse not to wax nostalgic about the early days of UX, but instead to discuss the growing influence that human-centered design is having on human-centered decision-making, which eventually brings about a human-centered culture within organizations.

Listen in to hear more tips from Jesse James Garrett about strategic leadership and the role of design in delivering value in this 100th episode of Product Momentum.

Paul [00:00:19] Hello and welcome to Product Momentum, where we hope to entertain, educate, and celebrate the amazing product people who are helping to shape our community’s way ahead. My name is Paul Gebel and I’m the Director of Product Innovation at ITX. Along with my co-host, Sean Flaherty, and our amazing production team and occasional guest host, we record and release a conversation with a product thought leader, writer, speaker, or maker who has something to share with the community every two weeks.

Paul [00:00:43] It’s great to have you with us again. Not only do we have the legendary Jesse James Garrett as today’s guest, but our chat with him also commemorates the 100th episode of Product Momentum. When we started out, Product Momentum was really just an experiment. We wanted to see if there was room for ITX to support a community of product people and create a forum for sharing knowledge. So when we think about 100 episodes, it’s really a nod to you and to the amazing guests that we’ve met along the journey.

Paul [00:01:08] But before we get into our conversation with Jesse, we wanted to tell you about a little giveaway. It’s a small token of our gratitude for helping Product Momentum get to 100 episodes. So we’re going to select ten winners to receive a book authored by one of our actual podcast guests. Could be from Jesse, could be from Jake Knapp, could be John Zeratsky. But really quick, here’s how to enter. Head over to That’s Take a two-minute survey and get yourself entered to win a book and it’ll arrive sometime in mid-January. All right. Let’s get back to business and onto the conversation with Jesse.

Paul [00:01:47] Today, we’re really pleased to be joined by Jesse James Garrett. Jesse has been one of the most prominent voices in digital product design for more than 20 years. His career highlights include co-founding the groundbreaking UX consultancy Adaptive Path, writing the foundational book, The Elements of User Experience, whose iconic five-plane model has become a staple of the field, and defining Ajax, the dynamic interaction model that transformed web technology and design in Web 2.0. His work has been published in more than a dozen languages, and he’s a frequent keynote speaker, making designers and organizations more human-centered in their work. Jesse, thanks so much for joining us today. Happy to have you.

Jesse [00:02:24] Thank you for having me.

Paul [00:02:25] Absolutely. The zoom-out question that I want to kind of get started with is thinking back to the beginning, back in the days when that layer chart was a staple in cubicles walking around, thinking about the early days of user experience. What are the biggest differences that come to mind as you look back over the beginning when user experience began to coalesce in the late nineties? What are those things that are different?

Jesse [00:02:48] You know, it’s interesting. The first thing that comes to mind in response to your question is professionalism, that the field as a whole and our practices as product developers and designers have elevated and professionalized so much over the course of the last 20 years that there are whole careers in this that kind of didn’t really exist before. I remember really product management itself even starting to emerge as a standalone discipline in the late nineties. And the idea that you had someone who was just thinking about how to manage the delivery of a product was a radical idea. Never mind the notion that it could be formalized and standardized to the extent that it is now.

Jesse [00:03:38] So we are a much more professional bunch than we used to be. And at the same time, there are more amateurs than ever because the field is gigantic. I mean, if you think about how much product development, how much digital product development there is going on right now, today compared to this day, five years ago, this day ten years ago, this day 20 years ago. I mean, certainly, you’ve got the explosion of just tech startups, to begin with. You also have the fact that there are so many individuals and entrepreneurs and kind of like one-off little projects happening all around the edges. There’s so many people making software now. And in fact, in almost any kind of other business that you happen to have been in, if you’re at any kind of scale at all, you are now also in the software business. And so sort of at the high end, you’ve got these extremely mature, extremely professional practices in product management and in product design. And at the same time, that is the tip of a very large iceberg of hundreds of thousands of people who are doing this work. That just wasn’t the case 20 years ago.

Paul [00:04:47] Yeah, I love that perspective.

Sean [00:04:49] I’ve been a software product consultant since the beginning of the Internet in the late 90, similar to you. And in the beginning, I’d sell a project, and I’d be not only the salesperson, I’d be the developer, the designer, product manager, the tester, the deployer. I’d have to figure it all out, you know, and now, I mean, the jobs have gotten so specialized and so complex, you couldn’t imagine one person trying to do all of that stuff, you know?

Jesse [00:05:14] Yeah. Yeah. We’ll hire a web guy, right? Not anymore.

Sean [00:05:18] Yeah. We’ve come a long way.

Jesse [00:05:21] Mm-hmm.

Paul [00:05:21] I have a quick curveball follow-up from my first question. What do you miss about the proverbial good old days? What do you look back on when the tectonic shifting hadn’t settled out and things were still brand new?

Jesse [00:05:32] Yeah, well, it’s hard not to be nostalgic for the newness of it all, right? The unknown-ness of so much of what was happening in the late 90s and early 2000 is as we were unpacking and discovering and inventing so much of this. But, you know, again, on my point of professionalism, in the absence of professionalism, anybody doing this work was somebody who found their way into it because they were really motivated, because they were really interested, or they were really good at it. And so what that meant was that in those days, when I was engaging in these projects, when I was fortunate enough to have a team around me and not just be a solo do-it-all guy, I was meeting some really interesting people who came from a really wide range of different perspectives, who had all read different books and had different philosophies and different influences in the work that they did because nobody could go to school for any of this stuff. There were no textbooks, there was no conventional wisdom. There were no best practices to fall back on. So everybody had to sort of survive by their own wits. And that made for some really interesting and vibrant and dynamic working environments that are a little harder to find these days, I would say.

Paul [00:06:47] Hmm. When it comes to the need for the domain management and leadership, sort of the maturity, the professionalism that you’re alluding to, what would you tell folks that are aspiring to become maybe director level and above, you know, leaders of designers, leaders of product people? What are some ways that you’re looking at the future and saying, how do we cultivate leaders in this space that are more than doers, creators, you know, thinkers, creatives? What are you coaching and leading people through in those kinds of conversations?

Jesse [00:07:14] Well, across the board, in my work as a leadership coach working with leaders of design teams these days, what I am hearing from people is, “I wish we could do more; I know there’s more value we could deliver as a design team, if only we could get to a place of more support, more empowerment.” And the exciting thing that’s happening is for some of these leaders, they are finding the way to gain that empowerment and to gain that support and to gain that leverage to drive not just good product outcomes, but organizational outcomes that shift the way that these organizations approach and think about what they do. And so when I think about product management and product leadership, I feel like product leadership always has to sit at this balance point between the technical realities of what it takes to deliver a good product, the market realities of our business model, our competitive landscape, all of those kinds of things, and the customer realities: “What’s going on with the user base? What’s going on with user behavior and user psychology?”

Jesse [00:08:18] And what I’m seeing more and more are product leaders who are turning to design as a way to deepen their expertise and to deepen their savvy around that customer piece of the equation. And the designers that I’m seeing who are elevating into those more senior leadership roles are the ones who are able to frame design in terms of its ability to deliver value around user insight more than around delivery.

Sean [00:08:51] Yeah. You used a term in there, customer psychology, and this is leading to another conversation or question I have about what the future of this industry looks like. So you have people on the project team going to the designers to look to them for customer psychology. And I see on the product side of the house a lot of great product leaders doing the same thing. It’s almost like there’s this convergence happening on the creative side of the house. And I’ve always seen it as you got to deliver the thing predictably, and then you’ve got to deliver what’s possible. And that’s the design/product side of the house.

Jesse [00:09:21] Yeah, I think that’s true. You know, I think there’s an interesting parallel too here in the relationship between product and engineering. You know, how deep does a product manager’s engineering expertise need to be in order for that product manager to make smart, well-founded technical tradeoffs? Because that’s part of the job. And so there’s that element, which there are a lot of product managers who come into product management from an engineering background, from a deep understanding of engineering practice, engineering processes, what it takes to deliver solid code, but who don’t have that same level of sensitivity on the customer side. And the evolution of the role, I think that, you know, as we start to look at product management elevating from a more operational sort of a function the way that it was 20 years ago toward more of a strategic leadership function, those product leaders are going to have to incorporate that customer perspective into their decision making, into their prioritization, into their envisionment of the products that they’re leading.

Paul [00:10:19] Yeah.

Sean [00:10:19] Right, so if I can rephrase that, the strategic leadership of the future is really about digging really deep into who it is the product exists to serve. And from what I gather from the very beginning of this conversation, it’s not just about the product. It’s also about, you said organizational outcomes.

Jesse [00:10:35] Yeah.

Sean [00:10:36] Which I find really, really intriguing. So when you say organizational outcomes, you know, these leaders need to not just be thinking about the product.

Jesse [00:10:44] Right.

Sean [00:10:45] They need to be thinking deeply about their teams, how they’re structured and how they’re growing and learning and the skills of the future, right?

Jesse [00:10:51] Mm-hmm. And some of those are organizational and operational considerations. So I know of and have worked with multiple design leaders for whom they did a whole bunch of user research, customer insight, deep psychological analysis stuff, and developed some models out of that to help them get inside the heads of their users and what was going on with user behavior, and then they reorganized their design and their development teams around their behavioral model. And in their mind, this is going to make them more effective at going to market. And as those kinds of processes become more sophisticated and become more mature, you’re really going to start to see some significant differentiating in the market between the organizations that have developed this capacity to do this deep core analysis of user behavior versus the ones who are flying by the seat of their pants, who are making it up as they go along, who are making all their decisions according to the fiat of a product manager who may or may not have any exposure to or sensitivity to these kinds of customer insights.

Paul [00:11:54] Yeah. I’m going to ask us to maybe take a quick sidebar down a thought experiment on exactly this topic. Twenty years ago, no one could have imagined that we would be as mature or as professional as we are today. But looking back, it almost couldn’t have happened any other way. It was always going to happen this way.

Jesse [00:12:10] Yeah.

Paul [00:12:10] Taking out your crystal ball for a minute, I’m going to ask you to do something dangerous and predict the future. Looking another 20, 30 years down the road, you started to talk about these organizations that have the maturity and the depth to understand these things versus those that fly by the seat of their pants. What kind of things do you see coming down the pipe in the next decade or two?

Jesse [00:12:32] Well, we are continuing to evolve our understanding of how to apply analytics effectively in our work. And there’s been a lot of investment in trying to find universal or semi-universal metrics that every product can be managed against. I see that evolving into something more sophisticated where you have a range of different philosophies of product strategy and product management, different points of view on what matters most. And I would not be surprised a bit to see some factions arise as we sort through the best way to do it. Because as it’s getting bigger and bigger and more and more professionalized, we’re realizing more and more that one size doesn’t fit all for this kind of stuff.

Paul [00:13:17] Yeah.

Jesse [00:13:18] The other part of it, in addition to the organizational and operational piece of it, is the cultural piece of it. And this, I think, is where the real potential for cultural change of a type that we haven’t seen before is really there. I think that what we’re going to see as you see organizations that start to build these robust, mature customer insight practices to drive product strategy, maybe that sits in product, maybe it sits in design, maybe it sits in a third place that product and design are participants in some way. But imagine an organization that has dialed in its process for understanding its customers and has been executing that process repeatedly for 10 years, for 15 years, for 20 years. You now have a level of institutional knowledge that hasn’t been possible before. You also have the presence of that body of knowledge in the organization in a systemic way that didn’t exist before, which means potentially you now have an organization that operates culturally in different ways because people are making different decisions because they have awareness of different factors in their decisions. So the potential here is for human-centered design to drive human-centered decision-making, which eventually brings about human-centered culture within organizations.

Paul [00:14:42] I love that. It’s such an aspirational, yet approachable take on how we work and where we’re going. You used the words guiding people’s attention and intention when we were chatting a bit before the show. I’m curious, are those the levers that you’re trying to help people most with? What do you mean when you talk about attention and intention in the work that you’re doing today?

Jesse [00:15:02] Yeah, well, it’s been so fascinating to work with design leaders and help them improve their leadership skills through the one-on-one coaching that I’m doing because there are so many other people that I meet and I work with for who leadership, design leadership was never something that they set out to achieve. It was something that almost accidentally kind of fell in their laps because they happened to be the most skilled design person in the building at the time that a leadership need was recognized by the organization. So they’ve had no preparation. They’ve had no mentorship. And they may not have even had the intention to go become a leader. But now they find themselves in this position and they’re asking themselves, “How did I get here?”

Jesse [00:15:44] And what I’m helping them with is bridging the gap between the way that they saw themselves as designers and the way they need to see themselves now as leaders, which is less as designers of products and more as designers of systems that bring products to life, and less as masters of technology and materials and more masters of relationship and orchestration. And all of that requires figuring out who you are, what are you trying to accomplish, what are your intentions here. And then based on your intentions, where do you need to direct your attention? What do you need to be aware of, both inside the organization and outside the organization, to inform the choices that you’re making, to continue to move you and your team toward your goals?

Paul [00:16:29] That’s amazing. We just have a few last questions while we have your time here. I’d like to bring things back down to Planet Earth for just a minute. I’d love to stay on Strategy Mountain and talk about all these, it’s my favorite. But one thing that I often reflect on is that these lessons are best learned through story. So I’m wondering, do you have a favorite story of how a leader has come to either realize or make an impact differently in an organization about where they didn’t either realize how they got there, as you said, or maybe took maybe a page out of your playbook and made a difference. What’s the story that comes to mind when you think about how all this great aspirational stuff gets made out in the practical sense of the term?

Jesse [00:17:06] You know, when I talk with the leaders that I work with about what makes them feel the most successful in the work that they’re doing, it is almost always when they feel they are changing the conversations that are happening around them. More even than hitting their deadlines or hitting their metrics or getting that promotion or building that team, what they really want to do is influence and they want to influence the people around them toward a place of more thoughtfulness and a place of more inquiry. Less assuming that everybody has all the answers, and more helping people to ask the right questions. And more than I think the specific anecdotes of happy stakeholders and good ratings on the App Store is that internal impact that is really resonating with the leaders that I’m working with.

Paul [00:17:55] That’s so powerful. Thanks for sharing that.

Jesse [00:17:57] Yeah.

Sean [00:17:58] All right. This has been an incredible experience having the opportunity, you’ve been one of my heroes, I’m just going to put that out there for the audience, since the beginning of my career in this space. So I’ve been waiting for this conversation for a while and thank you for joining us. But beyond that, I’ve collected a bunch of takeaways. I think I have a record number here. I’ve got like nine solid takeaways, so I’m going to state them, give you a chance to respond to each of them if you don’t mind.

Jesse [00:18:20] Okay, yeah.

Sean [00:18:21] We’ll go through that little process. The first thing I captured was that leaders need to drive not just product outcomes, but organizational outcomes.

Jesse [00:18:29] Hmm. Yeah. I would say in a lot of ways that’s the big difference between management and leadership. You know, when people talk about what’s a manager versus a leader and authority versus soft power and all of those kinds of things. But I think that that, what you just described, is really what it comes down to.

Sean [00:18:45] Cool. The second one I captured, and some of them are interrelated here, the second big thing I captured was this need of product and design leadership, and I’m going to merge these terms product and design leadership because, you know, we’re building products together. So you stated there were three sorts of realities that these leaders have to balance, and they’re the product realities, the business realities, and the customer realities.

Jesse [00:19:08] Mm-hmm. Yeah.

Sean [00:19:08] The third thing I captured was balancing, like strategic leadership is about keeping the focus on what’s possible. The term you used was envisionment.

Jesse [00:19:16] Hmm.

Sean [00:19:17] You know, the evolution of really customer insights and really deep understanding of our customers with predictability and actually getting something out the door and that whole conversation around engineering. So that’s another key job of product design leaders, yeah?

Jesse [00:19:30] Yeah, absolutely.

Sean [00:19:32] Fourth one, I love this one, is that the products that will succeed in the future will be those that have teams that deeply understand their customers and users.

Jesse [00:19:41] I think along with that, a culture that is willing to listen. It’s not enough to gather all the data and you just have an army of research teams who are constantly churning out reports. You’ve got to have a way that that data gets integrated into your decision-making.

Sean [00:19:56] It’s that integration that’s important. Because if integration doesn’t happen, it’s not valuable. Yeah.

Jesse [00:19:59] Yeah.

Sean [00:20:00] The fifth thing I captured was that one size does not fit all when it comes to team organization. And one little snippet that I captured was about maybe even organizing teams around customer insights.

Jesse [00:20:11] Yeah, it’s a real strategy that is working with real success out there.

Sean [00:20:15] All right. So along with number four, number six, how we adapt in the future. So the most adaptable, most probably strategically successful firms, products of the future will be those that create systems for learning how to better collect deeper customer insights. That’s next-level.

Jesse [00:20:32] That’s exactly so. Yeah, systematize it.

Sean [00:20:34] All right. Seven, we need to focus less as designers of products in the future and more as designers of systems that build relationships.

Jesse [00:20:43] Hmm.

Sean [00:20:44] Those weren’t your exact words, but that’s what I had captured.

Jesse [00:20:47] Yeah, I think that is true. It’s especially true for leaders. I would say that if you’re a product designer, you probably are, you know, pretty focused at the product level. But once you’re elevating to the leadership level, your vision needs to extend beyond the product that is your domain.

Sean [00:21:02] And you used that word relationship, leaders of systems, leaders of relationships… number eight was learnings need to come from both inside and outside of the organization. And this is a thing I’ve seen a lot, like teams either are so focused on going and learning from the outside that they forget that they have a place to experiment in their normal day, or vice versa, they get so focused on trying to get the job done that they end up navel gazing and forget that there’s a whole world out there that’s learning around them.

Jesse [00:21:28] Mm hmm. Yeah.

Sean [00:21:29] And that’s, that’s an important balance to strike.

Jesse [00:21:32] You know, the tendency to double down on what has worked in the past rather than attempt to push beyond it towards something new, I think is also a big cultural factor there.

Sean [00:21:43] For sure. And the last one is that when leaders feel successful, that’s when they have the opportunity to, and do, influence the quality of the conversations that are occurring when they’re not around. Because you can’t be in every conversation that’s occurring.

Jesse [00:21:57] Oh, yeah, that’s very true. If you’re only influencing the conversations that you’re in, you’re probably not effective as the leader.

Sean [00:22:04] Awesome. So with that, we’re going to wrap up with just a couple of quick questions. One is, Jesse, how do you define innovation?

Jesse [00:22:10] How do I define innovation? Innovation is about creating new things that meet people’s needs in unexpected ways.

Sean [00:22:21] I like that. I like that introduction of the word unexpected.

Paul [00:22:25] Last thing before we let you go, what are you working on? What are you thinking about? Maybe, what do you recommend a product manager or design leader pick up and read?

Jesse [00:22:33] Well, so I have a podcast of my own. It’s called Finding Our Way, and I do that with my friend Peter Merholz, who co-founded Adaptive Path with me. I’m a coach, he’s a consultant. We both work with design leaders and we have some really enjoyable, stimulating conversations there, sharing our perspectives and kind of bouncing off of one another. And so that’s something that I recommend people check out if they’re curious about more of my thinking.

Paul [00:22:57] Yeah, we’ll link that in the show notes for sure.

Jesse [00:22:58] And beyond that, if you want to know more about my coaching, my website is

Paul [00:23:03] All right. Well, thank you very much, Jesse, for joining us. It’s been a pleasure. I learned a ton.

Jesse [00:23:07] This has been so fun. Thank you.

Paul [00:23:09] Absolutely. Cheers.

Jesse [00:23:10] Take care.

Paul [00:23:13] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.

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