Discernment and Defining 'Good Enough' with AI

Show Notes

When the ground is shifting and the destination isn’t clear, how do you lead? Peter and Jesse explore the mindset and skills required to navigate the liminal moment—when old ways have dissolved but new ones haven’t taken shape. From core mindsets of maintaining situational awareness and striving for balance, to core skills around communication, persuasion and connection to build lifelines, this is a conversation about what it actually takes to lead through uncertainty.

More about Jesse: https://jessejamesgarrett.com/

More about Peter: 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.

This is Liminal.

Change is hard. Leading others through it is harder. In this episode, Jesse and I probe what it means to lead through a liminal moment. The mindset you need, the skills and behaviors that will carry you through. Designers have spent decades pushing organizations to embrace change. Turns out that’s easier to advocate for when you are not the one being disrupted.

Jesse: Hello, Peter.

Peter: Hello, Jesse. So last time you used a metaphor of surfing. Uh,talking about how when you are surfing, you cannot set it and forget it, that it requires this total presence, total attention, constant awareness of what’s going on, constant adaptation to the signals in order to stay on board.

And you were saying that as a parallel to the mindset that leaders need in this liminal moment or the liminal circumstances that they find themselves.

And I wanted to pause there and then pick it up now, because I think, you know, in that last conversation, we, we set up a lot of the context of why we think we’re in this liminal moment and what it means to be navigating liminality.

The Liminal Mindset

Peter: But I think there’s an interesting conversation to be had around, I guess two areas, maybe more. The liminal mindset, which I think is your surfing metaphor, addresses, and kind of a liminal skillset, right? What are the practices that you can undertake that enable you to succeed when things are liminal?

And so one of the things, you know, you’re pointing out with the liminal mindset is that, vigilance, right? That, that need to maintain alertness, awareness…

Jesse: Yeah.

Peter: To not be rigid, right, and, and stuck in a particular mode or mindset, but to recognize the context in which you’re operating, the seas on which you’re bobbing up and down and, and to act accordingly.

That actually puts me in mind of Ed Catmull’s book Creativity, Inc.

Jesse: Mm-hmm.

Peter: Where he argues against rigidity and stability in favor of balance and equilibrium, right? He credits Pixar’s success as not doing the same thing every time and not being really rigid around how they do things, but always being able to return to a equilibrium. But, but allowing themselves to bob and weave a bit, and to go with the flow, again, to continue to use that metaphor.

And so, yeah, I’m, I’m curious, as I reflect that back on to you where this is taking your brain.

Jesse: Yeah. Well, I think that you point out a few important pieces of the puzzle.

So first of all, just to think about it as a mindset rather than as a skillset. What that entails is an attitude, a stance, a way of setting your own priorities within your own mind about what you pay attention to, what you give focus to, what you give energy to, and what you don’t.

And so that first piece of it, the mindset piece of it, I think is really critical.

And then layered on top of that, you have, you used the word vigilance, which sounds to me a little, perhaps a little harsh because vigilance can sound like taking a defensive posture, which I don’t think this is actually what this is.

Peter: I’m talking Charles Bronson, Death Wish, here, yo.

Jesse: Yeah. But rather, in our conversation with Colt, he talked about the concept of situational awareness, which is very commonly applied in military context, where it simply is about, are you on top of what’s going on right now? Not what was going on five minutes ago or an hour ago or yesterday, but are you on top of what’s going on right now?

And are you paying attention to the things in the present moment that are actually the most relevant things. And that is this notion of maintaining situational awareness that I think is really critical.

A lot of it is about operating in real time, being able to be in a real time, tight feedback loops, you know, between perception and action. Allowing yourself to kind of iteratively refine your judgment as you go, rather than, you know, committing to the master plan front and then driving that forward no matter what the waves do, because then the waves are just gonna put you under.

The Liminal Skillset

Peter: Yeah. And it’s, it’s interesting because I always forget exactly how the phrase goes, but, you know, plans are useless and, but planning is essential, right?

So you mentioned the liminal mindset, and I agree there is a state of being, a state of showing up that’s important. But I think there’s also a liminal skillset.

Jesse: Oh, yeah. Mm-hmm.

Peter: And I think designers, design leaders can embrace a set of skills that they are good at, or should be good at,

Jesse: Mm-hmm.

Peter: And apply them to navigating liminality.

And so when you talk about not being beholden to plans, there’s something around the value in having a vision, you know, in these liminal moments, the value of, like, having some sense even in the confusion of where things might be going and, and being able to lean into that.

But it’s, I guess it’s not having a vision, it’s having visions.

And…

Jesse: Well, and it’s interesting for design because of the way in which this kind of pulls against this auteurist view of the designer as the master planner, as the architect, as the orchestrator of every detail, in that the liminal moment doesn’t permit that. It requires you to respond in designerly ways, but not in ways that look like delivering against the master plan.

Peter: That reminds me of, you know, a challenge that some designers have and have had for decades working in digital media where you can’t specify to the nth degree exactly, you know, your layout and your typography and your color scheme and all that. And the frustration that many designers would have.

But instead to recognize that the role of a design leader is more one of orchestrating elements in a context towards a desired goal or outcome, as opposed to fixing some presentation you know, in some kind of snapshot of time.

Jesse: Form, right? Yeah.

Peter: I guess a lot of this is getting back to this notion of fluidity, of feedback loops of, well, flow.

But, but you want it to be directed, right?

And that’s where I think even if you don’t want to be beholden to a vision, a specific point on the horizon that you are death marching to, come hell or high water, I guess what I’m realizing is a lot of the leadership practices that I discuss, you know, generally are highly applicable here.

And the one that’s coming to mind is having an agenda, right. You know, having a point of view, having a perspective of, Yes, I don’t know where this is going, but I have a sense of where it should head, based on my experience, my perspective.

And just knowing, I’m having a hard time articulating this clearly, right?

But, like, by having an agenda, having principles, having a sense of purpose, having a sense of your own value.

I think you talked about this last time, the difference between values and value, really, like, having your own value system as a foundation upon what you’re standing, will help you make better decisions as you’re trying to figure out how to navigate this uncertainty, this ambiguity.

Jesse: Yeah, yeah. As a leader, especially, because of the volume of information you are consuming and processing and making decisions based on, you have to have rubrics. You have to have heuristics. You have to have rules of thumb that can guide you through these situations where the data is imperfect and the picture is ambiguous.

And if you don’t have that, you are very easily led astray by red herring signals.

So you need to know what you’re kind of listening for, especially as a leader, because of the multiplier effect that you have in your role, because of the ways in which, not just the levers that you have your hands on that other people don’t that influence the way entire organizational structures move, but also because, when it comes to mindset, the leader sets the tone for the entire organization. And the mindset that you instantiate in your role ends up becoming what the people on your team model themselves on, and what you end up creating.

AI Tooling Forcing Change

Peter: Since our last discussion, I’ve had a few conversations with design leaders around embracing AI tooling…

Jesse: hmm.

Peter: …that feels relevant here. Well, and it feels relevant here, especially as you’re talking about modeling the mindset, because I think, you know, this uncertainty is opportunity.

And it’s a positive opportunity. This is a, you know, we can charge into this breach and come out the other side having made a positive impact. But only if we approach it with some spirit, if we have an agenda, have that point of view of what to make, how to make sense of, of the mess that, that we’re maybe currently operating in.

Whereas I was talking to one design leader and, and reflecting on how, you know, in a near term future, her team might no longer need Figma, right? Put a design system inside an LLM and, and design right out of that in production-ready prototypes that use live data that collapse the distance between what design is doing and what engineers receiving.

And as I said this to this design leader, they reflected how it was triggering them to think about how their team would not be working within that tool. Even though this particular design leader is rarely themselves in that tool, right? The team’s identity has been aligned with this tool. And, you know, what does it mean when this thing that has been our identity is taken away from us.

Now, on the other side, was this other design leader I was speaking with, I told this last time, where it took two to three months to get this design team comfortable not using Figma and going straight to the AI tools.

And it was two or three months of misery for this design team where they’re like, we don’t like this, this isn’t what we signed up for, we didn’t expect this to be our job. But then once they came out the other side,

Jesse: Yes.

Peter: They, they embraced it.

And I think in part that leader, because again, they weren’t a craft leader, they were this ops leader, there was something about that relationship that allowed this leader to see these people through this challenge, without getting caught up in their own identity getting caught up in it as well.

Jesse: Right, right. Well, I think that this is one of those situations where success requires optimism about change. It requires the leader especially to go, You know what? We don’t know what we’re doing. We don’t know how we’re going to get there. It’s a mess right now, and it’s going to get messier. But I believe there is a place that we can get to, that is a more positive place for everybody.

And you know, as we talked about last time, I think it comes back to, what do you think the value of design actually is in your organization, and how do you optimize for that with this new tooling and with these new processes and new ways of thinking about what a designer’s job is day to day?

Because again, if you think your designer’s job is to be hands-on with a mouse in Figma every day, you might be looking at a really different future.

Peter: Well, and it was funny ’cause that first design leader I was talking about we, we had this conversation ’cause on, on one side, there’s this expectation to embrace AI in their workflow.

Jesse: Sure.

Peter: And then this kind of, resistance or almost dismissal of that within the design organization.

But then, as we were talking about what we were going to cover in our session, another topic was how do we elevate design, and how do we help design really be seen as a force to be reckoned with within the organization? And I’m like, these two things are connected.

Jesse: Yeah. Yeah, exactly.

Peter: Right, right. And one of the places we ended up was, like, you need to define design on the impact and the outcomes it’s driving, not on the artifacts it’s producing.

Jesse: Yeah.

Peter: That’s going to be how you elevate it, but that’s also how you’re going to then be comfortable embracing, you know, other kinds of tools to solve these problems because you realize it’s not about the tool so much is about the nature of the change that you’re trying to drive.

Jesse: Right. Yeah, I think that’s really true. And I think that also it points to something, going back to having an agenda and taking a stand, which is that these things are gonna get defined for you because of the collaborative nature of your work.

So if design teams are not, and design leaders are not, taking the initiative to define for themselves what a design process looks like, that both leverages these tools and leverages the value of what the humans bring to the process, if they are not able to put forward ways of doing this, that advance the human-centered values that they, as teams, say they stand for, they’re gonna get lapped by product, by engineering.

If you continue to define what you’ve done in the terms that you always have, you’re gonna stay in the box you’ve always been in.

Responses to Liminality

Peter: Well, right. Getting back to this concept of liminality, right, there’s maybe three, kind of, outcomes.

What you’re talking about is, is people who, when they engage in the liminal moment are like, oh, hell no. And just back out. They’re like, not for me, don’t wanna deal with it. It makes me uncomfortable, makes me uneasy. And those folks are gonna be the ones left behind, right?

I suspect a significant number of the designers who have found themselves disempowered these past few years, you know, who had maybe been in executive roles, had been promoted, had been given opportunities, and who are no longer, I think many of them it was a self-induced circumstance because when offered this way potentially through, they’re like, Nope, not me, and, you know, maybe unintentionally inadvertently, but found themselves getting rolled back, ’cause they did not embrace that moment.

There’s a second response, which is you kind of remain in the liminal moment…

Jesse: mm-hmm.

Peter: And, I think there could be a type of, like, chaos adjacent design leader who doesn’t mind the discombobulation or maybe they are just getting, it’s like they’re in the clothes dryer. They’re just getting tumbled around and, like, every time they try something, they’re just getting kind of knocked around and knocked around and knocked around.

And that’s a space to be in for a period. You don’t want to dwell there. That’s, that’s gonna lead to burnout. That’s gonna lead to, as I’ve heard from some friends of mine, heart troubles or other kind of, you know, problems as they can’t figure out

Jesse: Just sort of

Peter: kind of how to, how to na-, how to, how to surf it.

Jesse: boiling pot. Yeah.

Peter: Yeah. I mean, to use your surfing metaphor, they’re just getting tossed repeatedly by those waves. They, they can’t get on top of it.

And then the third, right, is surfing that liminal moment such that you’re finding yourself on top of the wave and leaning into a bit of that chaos, but in a way that that ends up being, I don’t wanna say productive, but positive, you know, with some positive outcomes.

You mentioned the positivity earlier. This is something I think a lot of design leaders actually struggle with, is maintaining positivity for, for many reasons.

But, you know, it’s a non-negotiable for a leader to have a positive affect. It doesn’t mean wearing rose colored glasses or being pollyannish or saying things are fine when you know they’re not.

But it does mean having a relentless optimism, having a point of view that there is a way forward. It’s James Kirk-ian, right?

Like there is a third way, you know, the, the, the, the, the, the, the Kobyashi Maru is telling you the only result of this is death. But you have to help people, you have to believe, and then you’ll bring people along by being able to articulate potential positive outcomes that you all can move towards, right?

And having…

Jesse: If you don’t believe that, if you don’t believe that, then that just becomes a self-fulfilling prophecy for yourself and the team. Like you, as the leader, have to be the one, even if you’re the only one, who can see a path forward toward some elevation of the team’s value I think is probably what’s the long term result of that, right?

Peter: And kind of perhaps to that point, something that I’ve, you know, thinking about the liminal skillset, right? So you have a liminal mindset of positivity, [garble], liminal mindset of, if not vigilance, at least awareness and, and iteration and, and you know, kind of checking your priors every

Jesse: Yeah.

Peter: so often.

Liminal Skills are Leadership Skills

Peter: The liminal skillset, as I’ve thought about this separate from our conversation here…

One of the keys to liminality is, is the same as, as keys to leadership. Two really come to mind actually.

Relationship building, right? You are going to get through this liminal moment by having advocates throughout whatever organization you’re in.

That there are people that you are connected to in different places in different functions such that as these seas are roiling, you have lifelines or however you want to think of them, to someone in finance, someone in HR, someone in product, someone in marketing, that, that you’ve set up your own shadow network, support network, whatever, of folks who you’re aligned with, who have similar thoughts in terms of where things can go, and through those relationships, you can better together, as a collective even…

Jesse: right.

Peter: …make your way through to the other side.

And to that something I find myself returning to, and it’s one of the skills, leadership skills that I’ve let go of when I do my teaching, that I think I need to bring back, which is communication.

Being a really good communicator. The leaders who will be followed during these liminal moments are those who can articulate a compelling story of where this is going, right? And then getting people excited by that compelling story to then help you realize, actually realize this story, right?

Jesse: Mm-hmm.

Peter: It might start as a story, but that story is what’s gonna capture interest and engagement and want them to come along to make that story real.

And so to really hone those communication skills that in a way that allows you to communicate a compelling narrative that people are excited by.

Because they’re looking for it, right? And when you’re in a liminal moment, it’s all chaos. It’s all confusion. People are looking to hold onto something that feels real and exciting, energizing.

Jesse: Yeah, yeah. And this actually connects back to something from the surfing metaphor that I wanted to call out, which is, you might be really good at reading the wave. But you’re still gonna fall off the board if you don’t know where you stand.

Which is to say you have to feel a sense of connection to the board that’s holding you up. And in that case, it’s the leader and the team.

And the sense of how you position your feet and how you, you know, maintain your center of gravity, and all of those kinds of things on the board are choices that you’re making moment to moment, but they’re all based on your internal sense of who you are and where you stand.

And so if you wanna get your team excited about a vision, it has to be something that they genuinely believe in, which means it has to be resonant with their values. It has to be resonant with their intentions. It has to be resonant with their own dreams of what this product could be, what their own careers could be.

And if you can’t connect any of those things, you’re trying to get people excited about a bunch of things because they’ve got a whole bunch of important business outcomes attached to them, that’s probably not gonna go far enough.

What If People Don’t Want to Liminal?

Peter: I am wondering, as you were talking about the team, I’m wondering your thoughts on what to do when team members just aren’t getting on board.

They’re the board, but now I’m gonna have them get on board.

Jesse: Yeah.

Peter: Right. You’ve done the work. You’re articulating a positive future. You’re trying to provide some space so that they can get from wherever they are to this future in terms of, you know, maybe some re-skilling, new tools, we’re gonna try different ways of working.

You’ll likely face some resistance within your team, you know, that’s not what they thought they were setting up for. They don’t believe in it for whatever reasons. It doesn’t align with their individual value systems that they’re bringing into this conversation.

What do you say to the leader who’s, who’s, I’m now thinking, so you were talking surfing. I’m now thinking rafting, right? And I’m thinking rafting because the raft is made up of a set of pieces of wood and maybe not everyone in your raft is aligned. You’ve got a piece of wood that’s not willing to be quite tied together to the others to create the raft.

Like how do you just jettison that piece of wood? What do you, what do you do with folks?

Jesse: It’s really hard. It’s really hard and it’s not yet the crisis that I think it will be in 12 months, 24 months.

I think that as these teams processes continue to evolve… Right now, there’s a lot of permission to do things a lot of different ways. So again, I’m talking about AI transformation here specifically, but I think that the example is more broadly applicable to other kinds of liminal moments where what you have is: new technology comes in, everybody looks at it, and it’s very clear that this is going to be in some way useful to how we do our work.

And I think about other kinds of major workplace transitions that happened in the late 20th century when PCs came into the workplace. And all kinds of processes suddenly were done on screens in ways that they previously were done with paper and pencil, and sometimes a knife and a bottle of paste, right? Like, we continue to keep those metaphors because that was the work that was being replaced, the cutting and the pasting.

And so similarly, I think that we’re in this space now where maybe not right away, but somewhere down the line, you’re gonna find yourself in the same position, as a designer in 2026, 2027, as an accountant might’ve found themselves working inside an accounting firm in 1979 or 1981.

Where, you know, this new technology is rolling out that is going to vastly change how you do your work. You gotta decide whether that is something that works for you.

And then to compound that we have the particularly problematic history and ongoing practices associated with this technology. As we talked about in our conversation with Christina. Where, like, there’s no like good guys in the AI space, there are only degrees of malfeasance.

And the question for you as a practitioner is, like, can I still use this tool and feel okay about who I am and what I’m contributing to the world? And on some level, ultimately that has to be a personal decision and a personal choice. Meanwhile, the processes are going to continue to evolve around you.

I imagine that there will continue to be this overlap period. I worked in publishing during the overlap period where publishing was partly done digital and partly done through manual paste-up work. And so I got exposed to both of those practices back in the nineties.

I’m imagining that this is gonna be a very similar kind of thing where there’s gonna be some overlap, and teams that continue to produce results on the timelines that are expected of them are gonna continue to be able to do things their own way. But that is going to continue to evolve.

And for leaders, I think it is a matter of hearing those concerns with genuine sensitivity and grace, while also acknowledging where the whole raft ultimately has to go, in your metaphor.

Peter: Yeah, the reason I ask that question goes back to the conversation we had with Kaaren Hanson a few years ago now when, shortly after she had started working at Chase Bank, and when we asked her order of operations when she inherits a team…

Jesse: mm-hmm.

Peter: When she moves into a new executive role,

Jesse: Mm-hmm.

Peter: At the very top of her order of operations is getting the team right.

Jesse: Mm-hmm.

Getting Your Team Right

Peter: Because as a leader it’s really difficult to advance whatever agenda you have and to see through your plans if the team isn’t capable of that, right? Isn’t ready for it, isn’t skilled for it, et cetera.

And it calls into question, what does it mean to have a “team right,” when you’re in these liminal moments, right? When she was talking about it, at the time, she joined Chase Bank in 21. And it was just at the end of that, just, like, we kind of had a sense of where things were going, right?

And so you knew what the team looked like that you wanted to grow because it’s the same kind of team you would’ve been growing for the last 15, 20 years.

Whereas right now, it’s unclear… you know, as a design leader, and we’re now primarily talking about kind of on the management track. So, you know, hiring managers, design executives, people with responsibility for recruiting and hiring and resourcing and all that, what does it mean to be a design leader in a liminal moment when the role that you’re hiring for today,

Jesse: Right,

Peter: the nature, the shape, the work of that role could be quite different in definitely two years, possibly one year.

We talk about the blurring of roles between design and product management, and do you need designers who are more product-y or not? There’s still this weird, on many leaders part, kind of, fetishization of craft.

Where is that going? Is that actually valuable, increasingly valuable, come what may, because there’s a longevity to craft, right? Craft has been with us for hundreds of years.

Like, is that actually the right thing, or is it part of that rigidity that creates a kind of brittleness that, you know, you get somebody who’s really good, I mean, kind of, to use the metaphors, that maybe they were really good at paste-ups and mechanicals. They were the high end of their craft there, but, you know, they couldn’t translate it into a computer paradigm when the desktop publishing revolution came.

So yeah, how, what are we looking for as we’re staffing up teams that can be resilient through these liminal moments?

Jesse: Yeah. So the people who are gonna come along are the people who are already embodying some elements of that liminal mindset that we talked about.

They demonstrate a kind of an ability to maintain a broad awareness of a situation and not just kind of, like, execute against a brief. They demonstrate an ability to, honestly, to be fluid with their tooling, to be flexible in their approaches, to have more of a tool kit than a rote process that they follow in the work that they do.

And who embody that optimism that, like, whatever the change is, we together are the right people to see it through.

Peter: That’s interesting. ‘Cause that’s, I guess, not necessarily difficult to hire for, but it’s a different process, I think, to identify those types of candidates, then, at least, what I see most teams are using to figure out who to hire,

Jesse: Hmm.

Peter: …right? They’re doing a lot of looking at case studies and portfolios and what did you do on this and what was your process?

And it’s a different set of questions and a different set-up…

Jesse: mm-hmm. Mm-hmm.

Peter: …to understand how someone bobbed and weaved.

I think so often, like, the portfolio presentation skews towards what sounds like a happy path. Like you don’t often hear of the blind alleys that someone went down, especially when they only have 30 minutes to talk about it or whatever, right?

They’re gonna give you the high notes, they’re gonna give you the highlights, and it’s gonna sound like one thing just led to the next, that led to the next, and it was all good.

Jesse: Right.

Peter: Whereas what you want to hear from your candidates is how many blind alleys they went down, how many difficult conversations they had,

Jesse: show me the failed concepts

Peter: What it took to overcome,

Jesse: Yeah. Yeah. Yeah.

Peter: …obstacles, resistance on the way to get to a solution that was good. Might not be the best, but that was pretty good. And, given what was thrown at them throughout the process, that they got to a generally positive outcome should be seen as like a huge success.

But I can tell you for certain our recruiting and hiring processes would filter out someone whose end result was good, not great, but that they got to good, given the process they had to go through is a sign of their…

Jesse: competence.

Peter: fortitude, alacrity, ability, right?

But that’s kind of, you know, thinking about it, that’s the reality that, that so many people, so many designers are operating within.

Jesse: Yes. Yeah.

Peter: Along with some of the stuff that we talked about when we did the conversation about organizational health, my research and report that I did, where so many senior designers, probably even lead designers, are operating from a stance of disempowerment, right?

They are one or two levels below the people that they are partnering with and all that kind of stuff. So, so any success they have should be, you know, confetti should be thrown if they’ve made it out the other side with something that’s good.

Jesse: Yeah. Yeah. Yeah.

It’s interesting to think about the skillset separate from craft.

So, like, just asking the question, what is the non-craft skillset that, ’cause if we assume that the craft is a bit of a moving target in this liminal moment, then what do people bring if the rug is pulled out from under them and the organization suddenly goes, you know what, we don’t need Figma anymore. We’re covered with Gemini or Codex or this or that, or whatever the thing is.

How many of your people can adapt to that circumstance, and what did they bring that isn’t their ability to find a particular command in a particular menu that continues to deliver some value?

Foundational Skills

Peter: Well, when I’ve thought about liminality and in my frame as an org designer, and thinking about how we define roles and responsibilities and skills, it feels to me like we’re getting very fundamental when it comes to skill sets.

Like, like the skill sets that matter most are communication.

Jesse: Mm-hmm.

Peter: You know, that ability to connect with others to clearly articulate what’s in your head in a way that other people can receive it.

Kind of related to that, some persuasion. How do you bring them along towards a direction that you think matters, right? So very basic communication skills.

Relationship skills, as we were saying before. How do we connect with others? Bring them along, demonstrate care? Demonstrate that trust or build that trust that allows us to connect with and align with a group of people.

So, trust building skills, communication skills.

Some, for lack of a better phrase, business skills, right, strike me as foundational.

You know, a little bit of what Leslie Witt talked about. You know, just what are the fundamental business mechanics in the space that you’re operating in, and some awareness of that, and how they work, the knobs and dials that your particular company cares about, and that you can be able to speak to that, because that will be kind of the lingua franca, thinking back to communication, right?

The common language of that organization will be likely rooted in some probably simple business realities. But still, whether or not they’re simple, you still need to have some familiarity and a nimbleness with them.

And then when I think about it from, okay, so, those are like, everything I’ve been saying is just kind of like core professional skills. And I think there’s a lot of value in design and user experience people bolstering those core professional skills.

Not Taste, but Discernment

Peter: What makes design and user experience interesting is we think about those craft skills. It’s not can I choose the right item in a menu in this tool? You know, this is something we talked about, I think, when we were first thinking about AI and its impact on design and user experience. And sometimes the word taste is used. I’m not a huge fan of taste ’cause there’s a, not just subjectivity, but a luxury quality to that that…

Jesse: It’s is a snobby word, isn’t it?

Peter: It can be a little snobby.

Though the word I’m about to say also can be construed as snobby, but there’s a snobbiness to it. The word that comes to mind is, and I think this is something that you talk a lot about, yeah, when you gave your talk on AI and IA, is discernment, right?

I don’t know if that’s a skill. It’s a bit like what Christina talked about. She gave one of the best explanations of product sense of anyone I’ve heard, right? And it’s, you’ve done a lot of reps, you’ve seen a lot of things. You’ve witnessed what works and what doesn’t over the course of career…

Jesse: A highly informed intuition that you apply…

Peter: And, and that gives you this informed intuition that allows you, regardless of tool, whatever that tool is producing, you have an ability to understand and appreciate how that tool will perform, in a heightened way and better than those around you.

So again, is that a skill? It’s hard to articulate that as a skill. But it’s, it’s something you can develop, right?

It might not be a skill, I was gonna say a manual skill, but, you know, it might not be something with like process and methodology and practice and whatnot, a craft behind it that you are developing in a very conscious way, like you are piano playing, right? Or, or something like that.

But it’s something you can get better and better at.

Jesse: Yeah. It’s interesting because I do think this comes back to one of the things I said in that elements of UX AI talk which is that by definition, because it is a probability machine, what it will always be best at is mediocrity, which means that you cannot rely on the system itself to tell you what good enough looks like.

You have to be the one to say what good enough looks like, which means you have to have a point of view on it. And that point of view needs to be informed.

And as we talked about last time or the time before that, a lot of the bad stuff that gets out there in the world right now, in terms of people’s AI projects, is bad because the person who was doing it didn’t know what good looked like.

And the more people we have who know what good looks like, who are working with these systems, the better the quality of the results we’re gonna get.

Peter: Related to that, because what bad and good look… bad and good are subjective-ish. You can create assessment frameworks that help you understand what bad and good are, but in order to tune those frameworks, I think another skill would be, I’m trying to think of a way to, to put it that isn’t wonky, but it’s, it’s, okay, understanding humans.

Jesse: Mm-hmm.

Peter: Right? From a sociological, anthropological, psychological standpoint. Having a robust understanding of people, how they behave, what motivates them, their abilities, how they process information, all those things, will be useful regardless, right, of whatever’s coming, right.

Because, at least until it’s just robots talking to robots, you know, the things we are involved in, there are humans using them.

It does, you know, beg a separate question, which is, if what I’m saying is true, why is it that UX researchers continue to, it feels like they continue to be increasingly marginalized.

Jesse: Yeah, we’ll have to see how that plays out.

I mean, I think the question of, to what extent UX research has proven itself in a lot of these organizations, I think is a big one. They may be producing all of the insights in the world, but unable to get traction around them because of the way they’ve been set up.

But, you know, all of that notwithstanding, I agree with you.

I think that it does come back to the ability to bring a level of discernment that the robot can’t bring, right? So if it’s always trying to hit the middle of the bell curve, you gotta go upstream if you want to deliver some additional value.

And so that’s what this is gonna turn into.

What I’m imagining in the future, is much smaller design teams in which most of the production work is being done by one kind of a robot or another. And you have humans who are engaged in setting up those requirements as robustly as they can, and reviewing the results to fill in those gaps in terms of actual human behavior and actual human psychology and the things that the robot doesn’t know.

And then, you know, those things eventually finding their way to the light of day. But I think that that gap will always be there to close.

Many Possible Futures

Peter: So you, you are putting forth a hypothesis, maybe a speculation, right, of much smaller design teams. And I want to, I don’t know if challenge is the right word, but maybe interrogate it in the context of the conversation around liminality…

Jesse: oh, sure.

Peter: …right? Because a supposition of liminality is that we don’t quite know where this is going.

Jesse: Yeah. That’s fair.

Peter: Right. And, and I don’t mean to say you’re wrong. I’m just like, you, you put forth a, this is where things are headed..

Jesse: Trajectory…Well, I didn’t say that.

Peter: And, something that we’ve discussed and I feel is likely of use, and I guess it’s a skill. It’s definitely a practice.

There aren’t that many liminal practices, and one of the few that I could identify is scenario planning.

There’s a company from ye olden times called Global Business Network that created an approach to figuring out where the future was going, that they called scenario planning.

There’s a book called Art of the Long View by this guy Peter Schwartz. They tended to work with, like, oil and gas folks who need to make 30 year plans, often involving geopolitical uncertainty because oil and gas is in places that are uncertain themselves. At a crossroads.

And so this practice of scenario planning is born to help companies think about what are, you know, I think usually around three potential futures, right.

And the word scenario, meaning you’re telling stories, right? You’re like gathering a bunch of information, all the wisdom that you can. And then you’re looking at three futures, n number of years out, 10, 20, 30 years out, where different things are kind of dialed up and down, you know, in going back to the oil and gas, right?

And one you might have oh, that’s, anything I say is gonna be politically fraught,

Jesse: Ooh. Yep.

Peter: right? But you know, what if there is a war, you know, a, a war is in play. And that would be one turn of the knob. But what if peace is in play? That would be another turn of the knob, right? Like, it doesn’t have to all be doom and gloom.

But you want to prepare yourself for these various exigencies and unknown outcomes.

And then when you do that mapping, when you do that scenario planning, sometimes what you can find is like, oh, there’s a way that we can behave today that will kind of set us up come what may…

Jesse: right.

Peter: …and that’s what I’m trying to get at is, like, you made a hypothesis of small design teams.

You can make a different hypothesis theoretically of larger design teams, or you can make a hypothesis of the evaporation of product management and its designers and engineers working together, and tooling is doing what most people who have the title product manager or product owner are doing. What is that future?

You could make a future of no designers, or people with that title, and instead, you know, it’s product managers working with engineers.

And so, what does that mean?

I guess, given these possible futures, I’m curious, as I’m reflecting on that, what does that suggest to you, in terms of the moment we are in now, not knowing exactly where this is…

Jesse: Yeah, yeah. No, you’re absolutely right. I don’t think it’s inevitable that every design team is gonna get boiled down to three people.

I can see situations in which you’ve got design teams getting larger, potentially a scaling up of certain kinds of design activities that involve more customer engagement, design activities that involve deeper exploration, design activities that involve other kinds of things that design teams don’t have the time or space to do right now because they are on the hook for production work. So I think all of these possibilities are on the table.

Coming back to what this asks of leaders, I think it is about keeping the possibilities open and not letting yourself be paralyzed by that.

You know, when you were talking about the leaders who find themselves kind of tossed about on the waves stuck in the liminal moment, I was thinking about how, you know, the animals have the instinct when under threat to fight, flight, or freeze. And that freeze response is often, you know, a, a natural place for people to go when there’s nothing to fight and nowhere to run to. So what do I do? And just kind of like sit still until something changes in a way that I feel like I can take action on.

But then you have to be able to take that action. So it comes back to our old friend “strong opinions, weakly held,” right, that you want to have a point of view that you feel really confident about, that you feel is the most informed point of view you can muster at this moment, and then be willing to shift it.

The Liminal Leader

Peter: I’m curious what you think of the responsibility of the leader, ’cause they have some usually greater influence, authority, and leverage. What’s their responsibility to define that future? To put shape to the ambiguity, to be the engine of de-liminalizing, right, and bringing clarity.

Or is the liminal moment outside of their control, right? Is it about navigating forces beyond your ability to have that kind of impact? And so it’s about readiness and resilience. And then as things become clear, being able to lean into that.

I’m, I guess I’m trying to, I’m curious your thoughts on, on the responsibility of leaders and their agency in this moment.

Jesse: Right, right. Well, yeah. So last time I talked about how I felt like for a lot of leaders, this was kind of the shoe on the other foot, in that instead of being the instigators of change and the creators of disruption within their organizations, they now find themselves having to respond to change and respond to disruption from outside.

But you’re absolutely right. It’s a balancing act. It’s a dance.

You know, you can’t necessarily shape the wave, but you can shape the trajectory of your board on the wave, and that’s where the surfer’s agency comes into play.

Otherwise you’re just floating.

It is I think, an ongoing question for leaders as to what they can push, and how far and how hard they can push, their own agenda within the liminal moment, because it always has to respond to the liminal moment, so…

Peter: There’s a Heisenberg Uncertainty Principle. Like, like as you push on it, it’s going to affect it and you have

Jesse: Yeah. You can’t measure the velocity and the position at the same time, so Yeah.

Peter: Your action on it will have some effect on the system.

Jesse: Yes. Exactly. Exactly. And needs to therefore be responsive to the system. And this might bring us to what might be actually an interesting stopping point for this conversation, which is, how do you get out of the liminal moment? How do you know you’re out of the liminal moment? What is the leader’s responsibility to try to drive the liminal moment toward closure? And how do you set yourself and your team up for what comes after the uncertainty, you know?

Peter: Hmm. I like that. Let’s see where that takes us.

Jesse: All right. Fantastic. Thanks Peter.

Peter: Thank you, Jesse.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

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