Leading with Design: The Reality and Challenges of Being a Design Leader with Jesse James Garrett

Aurelius Podcast – Episode 62 highlights with Jesse James Garrett:

  • Discussing The Elements of User Experience and its impact
  • Defining and communicating the value proposition of design
  • What being a design executive and design leader actually looks like
  • Steps for success in a design leadership role
  • The importance relationship building in design leadership

Boy do I have a special treat in being able to say that this time around we spoke with Jesse James Garrett, author of The Elements of User Experience, co-founder of the hugely influential design and strategy consulting firm Adaptive Path and world renowned speaker on the topics of UX, design leadership and strategy.

It is not an understatement to say that his work can be credited to the careers of many of us in the UX field as it exists today. Jesse’s been doing this thing we call user experience for 25 years, meaning he’s seen it from inception to the evolution of what we call UX today. Lately, he’s been spending his time helping define design leadership and mentoring others in becoming the best design leader they can be for their respective organizations.

We talked about “the book” (Elements of User Experience), the evolution of UX design and where we are today. From there we focused a lot on what being a design leader really looks like, even day to day, as well as many of the challenges that exist for someone in that role. A great deal of that discussion included thoughts on the value proposition of design, aligning it with business objectives and finding your own personal growth and place as a design leader.

Amazing conversation with one of the most celebrated individuals in our field that I know you’ll take away key learnings from.

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Jesse James Garrett – Leading with Design: The Reality and Challenges of Being a Design Leader

Episode Transcript

(this transcript was automatically created using our very own transcription feature in Aurelius and has been minimally edited, please excuse any typos or weirdness 😀 )

Hi, Jesse. How’s it going? Great, Zach. How are you? I am excellent.

As I was telling you a little bit before we officially started recording, I am personally, selfishly very excited for this because it is not an understatement to say that your work, and specifically your book, is quite literally what got me into the field of UX and everything that I do now. So this is a real treat for me. Really appreciate you coming on to join us on the podcast. Thank you so much. That is so great.

That’s so gratifying to hear. I really do appreciate it. Absolutely. So this feels weird for me to ask, because, again, I feel like you’re one of the OGS of UX, right? As our show goes, we like to keep consistency in this, where every time somebody comes on, I say, why don’t you start by talking a little bit about your background, kind of who you are, the work you’re doing.

And thinking about as a means for people to understand sort of where you’re coming from and in the in my opinion, crazy circumstance, that maybe somebody hasn’t heard of you or your work up to this point. Well, thank you for that. And what I’ve found is that the field has been through such an explosive period of growth over the course of especially the last ten years that I find that I meet a lot of people these days who haven’t heard of me and haven’t heard of my work. Because people are coming into the field by so many different paths these days and by following so many different threads of ideas. So for people who have been in the field for more than ten years, it’s very likely that you’ve heard of me.

I’m Jesse James Garrett. I have been working in the field of digital product design for about 25 years now.

Among the things that people know me for are the book that you mentioned that I wrote, the Elements of User Experience, which was first published as a one page diagram back in the year 2000, and then I turned into the book in 2002, which has subsequently been, for a lot of people, their very first entry point to the field. In addition to that, I co founded one of the very first UX Consultancies, a company called Adaptive Path. We spent 13 years doing what I think of as some groundbreaking consulting work, helping to define some of the practices and the philosophy of user experience design, and then turning around and teaching those practices and those philosophies to other designers all over the world. So that’s me. That’s a bit of why people know me.

For the last while, I’ve been an executive leadership coach working with leaders of design teams. As design has become a more potent, a more powerful force inside these organizations, it’s placed greater and greater responsibility on the leaders of these design teams. And I am, these days, devoting myself to supporting those leaders with all of the experience and the knowledge and the background that I have. Perfect. That was very succinctly said, giving the breadth and depth of in the field, at least in my opinion, perfect summarization of that and definitely some stuff that I wanted to ask you about on the show.

I don’t think there’s more than maybe a couple of handfuls of people who are as well qualified as you to be able to speak to that sort of here’s UX kind of where it started, here’s where we are, because there weren’t even these leadership opportunities available back then. We were still talking about what it even was. A lot of people, and I know that this conversation still happens today, but there was a lot of people still even wondering what place this has in a business or any product organization really. So I would like to kind of COVID that from point A to point B. But the one thing that I did want to ask you too, in terms of the book, the Elements of User Experience, because I know that I’ve read and heard you say before that you never expected it to have sort of the reach that it ended up having just really quickly.

I would love to hear some anecdotes from you personally to say sitting here now, even hearing me and others still say this that influenced someone’s career their whole life. How does that affect you to just say I wrote this thing that I thought was pretty useful and here we are 20 years later. It’s absolutely extraordinary. It is such a gift. I meet people all the time who tell me that they found a purpose in their careers through their connection with my work, which is just about the most gratifying kind of feedback you could possibly have.

It’s fascinating too, to see the ways in which people have taken the work and taken it into different corners. I’ve heard about people who have taken the basic model of elements and taken it into areas that go far beyond digital product design into other kinds of systemic problem solving, which is really kind of what the model lays out for people are some ways of thinking about problems in digital product design systemically? Yeah. It has really been an extraordinary thing and it’s been extraordinary to see the evolution of how we define what this work is and how we define the value of this work. And I think that that’s one of the most interesting things is that our context has changed so much in part because of what we’ve done.

The sophistication of design practices is very, very different now from when we started Adaptive Path back in 2001. The sophistication of the clients, the sophistication of the users, the sophistication of the tools, the technologies, all of it is in a really different place. But the value proposition of UX, I think is the piece of it that has remained true, which is how do you make sure that you’re investing all of this effort in software development towards something that actually is going to connect with people and how can you be sure that that investment is well placed? And this, to my mind, is the value proposition of user experience design, the idea of connecting what you build with what it means to people. And if you’re able to do that, then you’re able to set priorities from a product strategy perspective.

You’re able to craft experiences from a user interface perspective in ways that make products more successful. Yeah, I really love that you bring that up as the persistent value prop of UX, because translated into sort of quote unquote business speak, it’s basically risk mitigation, which has never gone away. It’s never gone away and it is arguably especially given the year that we’ve had the market and economic conditions that we’ve seen in 2023 as a whole. I think that that’s still top of mind, regardless of the health of that business. Yeah, I think that’s really true.

And in my work these days, as a leadership coach, working with design leaders, one of the challenges that I’m frequently helping them work through is how you communicate that value proposition, how you find alignment around design’s value proposition, because as I said, the field has just exploded in the last ten years. We’ve just been up the hockey stick of that exponential growth curve, which means that there have been just a ton of people who have piled into the field bringing lots of different perspectives, lots of different background, and very little consistency in terms of the experiences that they’ve had that have brought them into these roles. And so what that means is that as a design leader, when you’re stepping into conversations with your peers, with product leaders, with engineering leaders, or whether you’re engaging with your business stakeholders or others, at the executive level, there’s always that open question of is their understanding of the value that user experience design brings the same as mine? And finding that alignment and finding that agreement. Because a lot of times the breakdown actually is that the executives don’t see the value in the same way that you do, because they don’t see the risk in the same way that you do.

So when you say the value proposition of user experience is risk mitigation, that’s awesome, as long as the executives believe that there’s an actual risk. And that, I think, is the challenge that a lot of leaders are wrestling with these days. Yeah, I mean, that makes sense to me for sure, based on what I’ve seen. And it’s fascinating for me to hear you describe it that way, especially given your perspective, because it was very much a thing for a very long time, where it was finding alignment between business needs and customer needs. And that was the focus of UX as a profession.

And now sort of this subset of that, which you’re focusing on, which is the leaders of that profession finding alignment between the business and the meaning, the value of user experience. I mean, I just think that that’s fascinating, the evolution that you personally have had in dealing with that. So let’s take a step all the way back and just what is it? What is the alignment between business and user experience? Because I think that that’s the million dollar question.

If we start there, and I think we could start to pull apart how it gets out of alignment, how there’s 100 questions about that, but what is there? Yeah, well, so I think that part of it has to do with just crafting great products, which is old fashioned, hands on with the tools, really solid visual design, really solid robust interaction design, really clean and crisp and logical flows, all of that kind of stuff. That stuff is really critical. A lot of design leaders, I think, come into the role thinking that that’s the job is to deliver high quality craft, and then they get frustrated when they get sort of boxed in to that craft role, when they aren’t given the permission to kind of spread their wings beyond that. Because there’s this other element that’s underneath that, which is the idea that all of those decisions are driven by customer insight.

They’re driven by an understanding of behavior and psychology and the way that the experience unfolds for people. What happens in a lot of organizations is that there’s so much emphasis on that first value proposition that becomes difficult to make the case for the second value proposition because the connection between them, that third element, hasn’t really been articulated for the business. They haven’t really made the case for why the same organizational function that ships your pixels ought to be the one that talks to your customers.

Yeah, this is an interesting trend that I’ve personally observed over the last, let’s say, ten years, with the proliferation of tools and systems that allow you to ship more faster in design specifically. I mean, this is true also in development and technology. The focus has sort of become that. And yes, I think there’s been a separation of well, it’s actually all the same thing to your point, right? Yeah.

And one of the things that I want to ask you about what you say when leaders get into these roles and they realize that either I’ve been painted into a corner or I see the light, but everybody else doesn’t, and there’s that sort of disparity. Are we talking about managers, directors, VPs, executives, all of the above? Is there different challenges there? I think it happens all the way up and down the chain. What happens is that the senior most leader of the design team has to put forward a value proposition for design as a function that that person’s, peers and leaders above them can all agree on.

That’s the sort of constituency, if that group of people agrees on the value proposition of design, then the design team is set up to execute against that value proposition. Right. If there’s misalignment, if there’s disagreement on the value proposition of design, let’s say this is probably the most common situation. You’ve got an executive level design leader who has an executive level product peer and the product peer does not see the connection between customer insight and shipping pixels. And so the value proposition of design that gets communicated down.

The product organization then informs the thinking of people at all of those levels, from the C level to the VP, to the director, to the senior manager, to the manager. And so all the people on the design side who have to interface with all of those people at every level are now all facing the same disconnection because now that individual misalignment between two executive level leaders is now cultural misalignment across two whole organizational functions. Yeah, that’s very wise observation in the way that that’s put I don’t know that I’ve heard it articulated that way, but that makes a ton of sense. Right? Like if functionally, we don’t agree.

Culturally, disagreement manifests whether you intended it to or not. Right? Yeah. So if every conversation that I have as a product manager with my boss is all giving me the message implicitly or explicitly that design is good for these things and keep them out of those things because they’re not useful over here, that’s going to be how I behave. And if you as a design leader, as a design manager who has to interface with that product manager, you’re trying to bring a different value proposition.

You’re going to find yourself running into roadblocks. Yeah. It’s going to feel like you’re beating your head against the wall, making no progress. This created a question in my head. It’s kind of twofold.

The first one is how do we fix this? If you find yourself that situation, which I think is the obvious question, but even prior to that, it makes me wonder, how do you prevent yourself from getting into that situation to begin with? I can imagine that there’s some folks listening to this who are maybe eyeing that job and applying for something or they’re looking for that promotion and they think that once I get there, I’ll be fix all these things. One of the things that I would personally like to ask because I think is useful, is how do you identify before even taking that role, whether or not this is the case? Because then you can at least choose to say, I want to try and solve and address that friction because of whatever personal professional reasons or maybe that’s not the right place for me.

Yeah, well, I will say that based on what I’ve seen, very few design leaders ascend to executive level opportunities because the organization has already got everything squared away as far as the value of design goes, it is usually a bid to grow the value proposition of design by appointing an executive level leader. So then the question is, what’s the promise of that role for the organization, not for design as a function? Yeah, the promise of having an executive level leader for design as a function is profound, but it doesn’t matter if there isn’t also a value proposition back to the business for even having an executive level leader there. So first of all, to understand what that is, and then secondly, to acknowledge that that job is going to involve some degree of wielding influence and persuasion in order to create change beyond design as a function, in order to enhance the understanding of that larger value proposition.

So I think that a lot of leaders, or a lot of people who want to be leaders, they look at those executive level positions and they go, man, if I could just have that title on my business card, I would have the authority to get everything that I want. And then they get there and they find out that that business card literally just gets you in the door. It does not buy you any influence. Authority is not the same thing as power, and all it does is give you a starting point for building that power. And acknowledging that that is the task is, I think, one of the most important things about stepping into a role like this.

I’m really glad you took it there because the way I asked that question, I feel a little bit like I was leading the witness because I was kind of hoping that you would illustrate that fact. Because I think we’ve all well, not maybe not all of us, but those who’ve been in or around those types of roles have heard these stories where exactly what you just described, if I’ve got that title, then I’ll be able to do these things. And that’s not the case at all. That just gives you the opportunity to do them. But there’s a different skill set aside from being a great designer that allows you to do those things.

Absolutely. I think that some designers look at design leadership as being, like, designer plus plus they’re going to have the same level of sleeves rolled up hands, dirty hands on, driving creative design decisions. And they get there and they discover that there’s no time for any of that stuff because you’ve got to do all of the work to clear the way for those design decisions to be made. And for the most part, you’re going to be supporting a different group of people who are going to be the ones actually making those decisions. So, yeah, you’re absolutely right.

Turning the corner from design to design leadership means shifting your context pretty significantly. That said, what I say on my website is design is just let me see if I can quote myself correctly, leadership is just another design problem. And that is the way that I have seen so over the years at Adaptive Path, all of my clients were design leaders. I worked with dozens and dozens of them over the years, side by side in the boardroom presentations, in the team meetings, in the stakeholder workshops, all of those kinds of contexts. And what I’ve seen makes them successful in taking on these leadership challenges is when they are able to take their design mindset, their design skill set out of the context of delivering design work and bring that mindset, bring that skill set into the realm of leadership and to basically design their way out of their challenges.

And when you can learn to do that, it unlocks a whole lot of things for design leaders that, honestly, I’m not sure that you see in other organizational functions because of the creativity that design leaders naturally have to cultivate in order to get good enough at design to be considered design leaders. I love the fact that I feel like you’re like a half a step or a step ahead of everything I want to ask. It almost seems that I want this is perfect because I was going to ask that, which is do you feel like people who excelled in a design role, we’re talking hands on, hammered and nailed kind of role, also do well in design leadership? Or do you feel like it needs to be sort of a hybrid, somebody who maybe has done some design but was also already successful in some sort of business role or function in the past? It’s definitely a range.

It’s definitely a range.

I think what it comes back to is how attached are you to your identity as a designer and how does that inform how you tackle problems day to day?

I think that for some people who get into leadership positions in design, they look at a lot of what that job entails and it doesn’t look like design to them. And it gets under their skin. It’s like, I must be in the wrong place. I must be doing something wrong.

Something here is amiss because I am not doing design work as I understand it. And so releasing that notion of yourself as a designer, but continuing to engage with creativity as a part of how you do your job, how you live your life, I think is a big part of the shift that has to happen there. Yeah, it makes me think of that one song. I don’t actually remember the band or the name of it, and Shame on me, but it says, and you wake up in this big beautiful house with your beautiful how did I get here? It kind of reminds me of those lyrics, right, where you say, indeed, this is everything you said you wanted, but how did I get here?

I don’t belong here. And it makes me think of something else that you said earlier, which is if you were to accept that your role as a design leader or executive is actually to pave the way for great design to happen, that is a design problem. Yes. You are actually still, by extension, designing best work that you want to happen to done with relative autonomy or whatever the case, whatever the organization needs. Yeah.

So you’re not creating artifacts anymore, you’re not creating things, you’re creating organizational structures, you’re creating processes, you’re orchestrating relationships within the context of the organization. That is absolutely all design work. Yeah, I would agree. It makes me wonder because I think we’re talking about all the things that a design leader or design executive maybe ought to have. What is a case that you’ve seen where design leadership failed for one reason or another, and this might be something that you’ve seen more than once, sort of a pattern as to why design leadership or an executive leader at that level wasn’t successful.

It doesn’t have to be specific to the person, but maybe even situationally. Here’s how that doesn’t go well. And considerations to avoid. Yeah, I think that we’ve touched on some of them earlier.

Misalignment of understanding of design’s, value proposition, too much attachment to the design side of the design leadership equation, hands on function. Yeah. Too much reliance on authority to get your way rather than persuasion.

And I think that an inattention to the relationships you need to cultivate to get what you want when you get to the executive level, power is not so easily compartmentalized and is a very sort of fluid and dynamic dance among the executive leadership that is constantly unfolding. And power can shift dramatically from day to day in that dynamic environment. So it requires a degree of adaptivity, it requires a degree of really kind of not assuming that things are going that the status quo is going to remain as such. Sure, I think is a big part of what makes design leaders successful and conversely, ignoring that is what leads them to fail. Yeah, I think that’s really fair.

There’s a couple of things that you said with that answer that I definitely want to dig into. The first one, which we kind of started with misalignment of the value design will bring to the organization. That is certainly its own topic. But you also talked about authority versus persuasion. Then you follow that up with relationships.

And I might argue that those are all sort of rolled up into one consideration challenge in and of itself. So let’s start there and talk a little bit about that because I think that’s also, even if you’re not in a design leadership position, I have seen even successful or unsuccessful designers have ignored that at their own peril even. Absolutely. Yeah. Well, so within design is a craft discipline.

And the way that you prove that you’re good at it is through the quality of your craft. Early in your career, it’s absolutely necessary that you show people that you have those skills and you can deliver on that. And then as a result of that, we get so attached to that notion of creating value by making stuff that even in a role where our job on paper is to make the stuff.

I’ve met over the years a lot of junior designers who were not attentive to elements of communicating the design that were necessary to actually get people to agree to go along with their ideas. And so, yeah, absolutely. That potential to neglect your relationships, to assume that because you are the lead designer on the project, that your authority is going to enable you to win every argument, those kinds of breakdowns happen at every level in the career path. Yeah. And that sounds like it definitely touches all the way back to something you said earlier with your identity of yourself as a designer and as a person who may become in that leadership role, too, where if your identity is through the quality of craft, maybe leadership isn’t for you.

But if it is, you just got to learn to let that go. I think that’s right. And there is a degree of introspection, reflection and self knowledge that I think is essential for any creative professional to chart a path for themselves. Whether you are early in your career and you’re trying to figure out what are the elements of design practice that you want to deepen your expertise in, or it’s later in your career and you’re trying to figure out how to invest in an organization that is going to provide you or a product that is going to provide you with a sense of meaning and purpose and accomplishment in your work, or even at the leadership level once you get to that place. And you’re not touching pixels too much, but you are there to hold a vision in some way.

So to know for yourself where your strengths are, where your interests are, and where your path is taking you as a creative professional is a big part of finding the right role for yourself and engineering a place for yourself in your organization where you can be successful. Yeah, it’s probably useful to let people know, to have permission to almost grieve of losing that part of themselves like that’s. Okay. You should feel a certain sense of loss, but as you say, it is growth and evolution. Okay.

Yeah. I really appreciate that. It is sort of a bittersweet coming of age that happens, I think, as people transition into design leadership. It does mean letting go of some things. In a lot of cases, that people were very attached to that at one time meant everything to them.

Right. But it also means finding new opportunities to embrace a new vision of yourself, a new vision of your potential, a new vision of what you have to offer the world. Yeah, really useful to copy the word you’re applying there, embrace that you’re actually making space for others to also do that work well and you have a new ability to serve. Yeah, I think that one of the challenges where we are right now in the evolution of the field is that our current crop of design leaders have mostly had to operate without good models because before them there were no design leaders in digital product delivery. So basically what that means is that we have the senior.

Most people who are leading this field right now are all people who have been wandering in the dark, basically and making it up as they go along. And the rest of design leadership across the board is following in their footsteps as best as they can. But all of it is very new territory that we are all discovering together. Yeah, very true. That’s also useful perspective for people who work for those folks in the organizations to just understand that most of the time people aren’t being maleficent, they’re just doing but maybe they don’t just like none of us do.

One of the things that I wanted to ask you with that too, because there’s an interplay between people doing the work and the leadership and regardless of what role you’re in, you always are going to feel like there’s a disconnect between that does make me curious. And asking you, somebody with so much experience, can somebody who’s not a great designer hands on making the pixels become a great design leader? That’s an excellent question. I think it comes back to that question of what’s the value that you provide and how do you prove it? If you are not demonstrating your value through the craft, if you’re not demonstrating your value by shipping design work, there must be some other way in which you can demonstrate to an organization the value that you bring.

Maybe that’s about driving operational excellence, maybe that is about driving alignment around vision. Maybe that is about orchestrating partnerships. There are lots of aspects to what it takes to deliver design far above and beyond the craft of it. So I think, again, it’s a question of where is the place where your particular orientation, background, skill set, mindset are best applied to create those results? Yeah.

In your answer I hear you talk about some things we already touched on. Are you good at communicating design or vision or strategy? Are you good at creating relationships where people are more receptive to the value of design?

Are you good at taking two competing visions and reconciling them? There are lots of different roles to play. Yeah, very good. So with that, going to go back to one of the other things that you mentioned, and we’ve been talking about this on the periphery, this alignment or lack thereof, understanding of value design plays in an organization. How do we get there?

I think we need better partners. And by better, I. Mean partners who have more sensitivity to the types of value that design delivers, the types of value that design leaders see themselves delivering. I think that I would love to see more people out of design backgrounds in nondesign roles in these organizations. I think that if you were stepping into a design leadership role and you knew that you had a product partner who had a design background and you had an engineering partner who had a design background and your business stakeholder also had a design background, I think you’d be pretty well set up for success there.


Have you seen situations where that was the case? I think the interplay between what we might call product management and UX or design leadership. I have definitely seen people either straddle that line, myself included, back when I was working in house. But have you seen that in other roles, business? Yeah, well, I mean, to varying degrees, I definitely have seen people move from design into more sort of operational and people leadership kinds of roles.

Again, anything to do with orchestrating process is something where a designer potentially has a lot to offer.

I will say I don’t really see people moving from design to development too much unless there’s a particular technology that has sparked their passion.

But definitely the crossover into product I see happening more and more. I’m meeting more product managers who have at least had some design training or been in some kind of a design role in the past. So yeah, I think those possibilities definitely exist out there. Sure. So let’s say I’m somebody who is coming into a design leadership role, either up through the ranks of the company that I was in or I accepted a new role.

And one of the first things I have identified is I need to create that alignment between the business and what we can deliver on the value of what design is for our organization. Let’s even assume that I’m walking into an executive role or a very high level worship role where I’m the person tasked with that. What would be your first, next step for that person? Yeah, well, I would approach it exactly as a user researcher would. You’ve got some user needs you need to identify, go find out, make a model, do some profiling of your major constituencies, your stakeholder groups, ask yourself what they need, ask yourself what they care about, ask yourself what motivates them and then ask yourself what you can do for them.

Exactly. As a user experience designer would, I. Love how simply you put that. I’m also very biased because I’ve been having that kind of conversation for a long time as well, where I tell people these are people just like any other people you would speak with. They have fears which are very powerful driving forces, especially at high level business executive.

They have motivations, sometimes maybe less, sometimes unsavory, but most of the time, well, intended. Right. Most of us well intended, understand them well. And then more importantly, there is often, especially at that level which I’m sure you’ve seen firsthand, a lot of unspoken goals and expectations to come in and just lay down the plan without understanding of that it’s not going to be well received. Yeah, absolutely.

And getting at that unspoken stuff is not something that happens in one stakeholder interview. And so this is where you have to go above and beyond user research methods toward actual relationship building. If you really want to understand what drives and motivates these people, you’ve got to get them to open up to you and they won’t do that if they don’t trust you. So creating that trust, earning that trust from folks stepping into the role is where you have to start. Definitely.

And you said that earlier, authority versus persuasion and building part of that in order to help craft a vision of here’s what the value is. And by the way, it sounds to me like doing that successfully isn’t just crafting your vision of what the value is, but rather turning the mirror around and saying here’s what I’ve heard is important to us either as an executive leadership team and or company. And here is my I’ve sprinkled my ingredient of design on how they helps fulfill that. Absolutely. The design leader is not a singular visionary.

The design leader is a synthesizer of perspectives. And when the design leader has been really successful, they’ve created a point of view that people can align to. Yeah. And going back to that relationship building thing, when you say hey, you’re going to have to go above and beyond. I don’t think that always is as elaborate as maybe somebody might hear that buy somebody lunch, buy somebody a coffee, buy somebody a cocktail if that’s your thing and they’re open to that, whatever.

But it is those things where you take it out of the we are now doing business context. If somebody can get to know you again as a person, just like doing a great user interview is making the participant comfortable. Absolutely. Same thing with somebody you’re going to be working with, right? Yeah, absolutely.

It’s taking the skills that you’ve already developed out of the context in which you’re used to operating and reapplying them in this new context. That’s the challenge. Yeah. So I’m curious if folks are sitting here listening to this and say I think that I’m right for a role like that, maybe now or in the future, but they don’t feel like they have the applied experience to start chasing that down. What are some things that they might be able to do to get better at that or maybe provide sort of build up their resume, so to speak?

Well, I’ll say again that it’s an extremely discontinuous environment out there. Design leadership means many, many different things in different organizations. A lot of it has to do with the age, scale and maturity of the organization itself. A lot of it has to do with the scale and maturity of your partner functions in the organization, how mature your product function is, how mature your engineering function is.

A fair amount of it has to do at this point with what the organization’s past history with design is. If you’re coming into an organization as their first executive level design leader, your challenge is a little bit different. If you are their second or third, and if they had one three years ago but haven’t had one for the last two years, that’s another challenge still. Right. So all of that stuff, I think, is just to say that there probably isn’t a simple checklist of design leadership qualifications that can put out there that would capture such a diverse range.

I do think it’s about really understanding what the organization that you’re joining or the organization that you’re a part of wants to get out of that role. What’s the value that they see in having a design leader in place and aligning what you have to offer with that. Yeah, that’s such a great point in terms of the history of that role in the organization that I didn’t expect you to answer with. But I’m really glad that you did because I can say personally that I came. Into not at executive level, but I came into an organization once as a design leader, a higher level that had no experience with this in the past.

And that was a lot of education work. That’s what that was a lot of education on this practice can be and the way that we get there. Whereas to your point, potential landmine, if you say, well, they actually had a chief experience officer and then they didn’t have one for two or three years, there is more than a story there and that’s really important to understand. It actually could have been a change in leadership as well. This is just a whole host of thread and all of a sudden you find yourself in a whole different area of the world, so to speak.

Yeah. So regardless of whether you’re joining a brand new organization or you’re elevating into a design leadership role inside an organization for the first time, you are always stepping into the collective projections and expectations of your peers and the executive level leaders that you have to tease apart. Figure out which ones you want to play to figure out which ones you don’t, and get in alignment with all of that stuff if you’re going to make progress. Yeah. When you say find which ones you’re going to align to, I think really finding yourself in the middle of that is absolutely, really important.

Because I don’t think that you mean to suggest not that I’m putting words in your mouth, but I don’t think that you mean to suggest learn what everybody expects of you and just fulfill that role, because you wouldn’t be successful in that, because that’s basically an impossible task. But what you can be successful in, right, is yeah, really understanding the context and expectations everyone has, being really clear on where your vision of design and how it fits the organizational model can do that and where it can’t. So that very least expectation setting is. Absolutely nice. Well, I could easily take several more hours asking you questions about this and having conversations about anything in the world of UX.

But of course, as with all things, we are running towards the end of our time here, and I definitely want to be respectful of that for you.

One of the things I like to do at the end of every show is I ask if I got temporary amnesia and somebody came to you and said, well, what was that podcast all about? I couldn’t answer that. You would have to just answer in a sentence or so. How would you summarize the chat that we had today?

I think this might be a job for Chat GPT. No, run it through afterwards. Yeah. Well, I think it comes back to that notion that leadership is just another design problem. And this conversation has really, I think, touched on a number of the ways in which the skill set of a designer is perfectly applicable to the challenge of leadership, but it does require a reframing of that value proposition in order for designers to turn that corner and really embrace the opportunity.

Nice. Very good. So you’ve been doing this a long time, you’re still in it and you’re still helping people figure this out, specifically design leaders and executives. Is there anything else that you want to share with folks about that and your work and maybe where to find you if they want to continue this conversation? Yeah, I love the work that I’m doing these days.

I do one on one leadership coaching, skills development, work with leaders, helping them unpack the challenges that are in front of them and figure out how they need to evolve their practices as leaders in order to face those challenges. I work with people all around the world, and I am having a blast because the opportunity to help a leader grow their skills pays off, not only just for that leader and for that organization, but for their entire team and hopefully for every team that they are a part of for the rest of their careers. So it is really powerful work that I’m doing. If you want to learn more about my work, you can find more about that at my website@jessejamesgarrett.com. Awesome.

We’ll have a link to that in the show Notes as well. I’m really curious with regard to that, is it mostly individuals that reach out to you for that, or are they organizations, say, hey, we could use your assistance in our design leadership practice here? It is usually individuals, although they are individuals in executive leadership roles, so they have organizational objectives, but it is their personal growth that I’m really here to support. And so often that is the motivation that brings people to me. Perfect.

Well, we’re going to have a link to your website in the Show Notes. Folks can find you. I can’t say thank you personally. Huge, huge joy and honor to be able to have this conversation with you. Really appreciate you coming on.

Jesse James Garrett, thanks for coming on and chatting with us. Thank you so much. Zach all right, everybody, we’ll see you next time.