Captain of the Ship: Leadership Awareness

Show Notes

As of publishing this episode, the Intentional Design Leadership Circle starts in 5 days, on April 15.
https://www.eventcreate.com/e/intentionaldesignleadership
There are still a few spots left.

Also, Jesse announced “AI Transformation for Digital Design Teams,” a new online event taking place April 30.

For more information and registration, head here: https://www.eventcreate.com/e/aitransformation4design

For more about Jesse James Garrett, and his coaching and AI consulting practices visit https://jessejamesgarrett.com/
For more about Peter Merholz, his organizational effectiveness, leadership development, and coaching practices, visit https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. When everything is subject to change, how can leaders choose a destination and set the right course? On today’s show, Peter and I return for part three of our exploration of liminal leadership. We’ll get into extracting the signal from the noise of the liminal moment, the role of shared values and collective action in setting direction, and how to make good choices when you can’t predict the outcomes.

Hello, Peter.

Peter: Hello, Jesse.

Jesse: So today we are resuming our liminal conversation. There are little bits of these ideas that have been coming to the surface for us that have led us to this particular conversational series. And now after having spent a little bit of time on the show exploring it, you know, I had gotten to a place where I felt like there are some definitive statements that we can make about all of this.

And then I saw something on YouTube the other day that really kind of shifted my thinking about it, which is that for some reason, sort of out of the blue, YouTube started serving up to me surfing videos unasked for not part my usual rotation…

Peter: Are you sure YouTube hasn’t been listening? Are you sure YouTube hasn’t been listening our podcast?

Jesse: I can’t be sure of that. None of us can be sure of that, can we, Peter? And I found myself watching just, like this stream of live beach footage, which was just, not a big tournament and not your best pro surfers or anything like that, just the beach in a place where they have some really big surf and there are a bunch of people out there on any given day trying to catch those waves.

And what I noticed about watching it was how little of it looks like success in the ways that we would frame success. How much of it is struggle and failure and catching up and compromise. Because what you’ll see out there, if you watch just, like, raw footage of a beach…

Maybe there’ll be 10 people out there with surfboards. A big wave comes up and let’s say six of the 10, the wave just rolls right under them. Like they don’t have a chance, they’re not there and they’re just going to fall off the back of the wave.

Of the rest of them, three are gonna go, not over the wave, but under the wave. They’re gonna get swallowed by the wave. They never get a chance to get their feet on the board because the wave takes them down before they get that chance.

And then that 10th person out of 10 is the one who gets their feet up on the board and they’re up on the board for a minute. But there’s no such thing as a soft landing in surfing. And it becomes a question of, okay, now you are riding that energy, how do you create an exit that feels natural from what you’ve been doing?

And so, the way that I really started to think about it is, first of all, the wave’s not for everybody. This wave might not be your wave.

Like how many waves of technological innovation would you say that you and I have seen in the course of our careers?

You started out working for a CD-ROM company, my friend.

Waves of Technological Innovation

Peter: Careers? We could even go back a little bit further, I started as an Apple IIe kid.

Got a Mac for college. So I went from, command line interfaces into GUI interfaces.

The desktop revolution when I was in college, I had jobs where I used Freehand or whatever to make stuff. And, Microsoft Word, figuring out how to lay stuff out really precisely in Microsoft Word of all things, right? You had to figure out how to hack all the spacing and kerning and all that kind of stuff.

And anyway, sorry. That’s a bit of a, I’m getting, getting nostalgic.

Jesse: Peter. Hey Peter. Get back. Come back to the 21st century please.

Peter: Come back. But you had GUI, and then it was when I was a student at Cal, the web breaks.

Actually I had a job doing multimedia work in school, pre-web. I saw the web. I didn’t work on the web for a couple years, though.

I did work at a CD-ROM company. I then helped that CD-ROM company get on the web. I then worked for a design firm that was moving from traditional design to digital design and web design.

So you have the web, you have Web 1.0, you have Web 2.0, you have mobile, and people forget even before mobile, you remember WAP? Remember when people thought Nokia phones and the Palm Pilot was the future?

Jesse: Hey, I did a bunch of design in that space during that time, so dude, that was real work.

Peter: Yes. I’m I’m sure.

You had iPhone, obviously tablets, the move to the cloud. I already mentioned Web 2.0. And then it’s interesting because, as you talk about waves, there were these actual waves and then there were attempts at making waves. Right.

Jesse: Waves. Yeah.

Peter: Well, yeah, ’cause because pretty much very little meaningful evolved after mobile with the possible exception of things moving to the cloud.

People tried to make something called Web3.0 a thing. People tried to make blockchain a thing and crypto a thing. And the metaverse a thing.

Jesse: NFTs. All the stuff. Yeah.

Peter: Yeah. But yes, to your point we’re definitely now on a wave.

It’s a wave that feels possibly as meaningful as the shifts to web and mobile. Definitely as meaningful, as say, the shift to things like desktop publishing, and putting the ability to create directly in the hands of creators as opposed to needing a chain of labor to get from somebody’s idea to some produced thing.

Jesse: Yeah.

Let’s come back to the notion of liminality and the fact that there’s always another wave coming, right? That the waves themselves just keep on coming.

And in fact to be a surfer is not to find your one perfect wave and then step off the board. It is not just dust off your hands and declare a job well done.

It is more of matter of finding the waves and the waves within waves.

You touched on a couple of things. There are always these technologies that are coming to the surface, or techniques that are coming to the surface.

One of the big things that’s happening with AI is that the technology has reached a relatively stable state, but the techniques around the technology are continually in rapid evolution.

And the big open question, as people look around at these allegedly AI driven layoffs and things like that, is what have those guys figured out over there that we haven’t?

And in fact, the answer is probably not much, but it’s enough to give them a sense of what the future of their organization looks like.

And so surfing the liminality means acknowledging the trajectory of the data that’s right in front of you, right? To be able to read the wave and see where the wave is going so you don’t get drowned by it.

Waves of Practice Change

Peter: There’s a parallel here because you’re talking about the kind of these techno waves of technology and change and AI is the most obvious, latest example of it.

I stated how we haven’t really seen a meaningful technological wave since probably the combination of whatever was happening with Web 2, mobile, and maybe a shift to the cloud in the late two thousands, early 2010s.

But that’s not totally right in that in parallel… So those are waves of…

Jesse: Right.

Peter: Society-wide impact. But within our industry, within our field, someone was referring to the waves of design tools that we have embraced going back to whether it was, obviously Photoshop and Illustrator, some of us using diagramming tools like Visio and OmniGraffle.

Then you have prototyping or like early, like some of those, yeah, prototyping tools. Your Dreamweavers or whatever or, earlier web tools…

Jesse: Page Mill.

Peter: But then I… so I got off the design tool train sometime in the Photoshop, OmniGraffle era. I never embraced Sketch. I never embraced Figma. Though I know those have been waves, right, that people have had to ride. I use Keynote when I need to design something.

Jesse: Yeah.

Peter: That’s my little wave off to the side.

But I’m bringing that up to suggest, ’cause you said the word waves within waves, and I think something that maybe gets lost is things can feel very unitary or global or monolithic, right, it’s AI and it’s everything and it’s this one thing that we’re all dealing with.

But the reality is probably that this thing of AI is obscuring a lot of little waves within it that we’re having to figure out and navigate.

One of the things that’s coming up for me a lot in this liminal moment, what’s clear in the discourse is anxiety, and a just a generalized anxiety.

Attention and Anxiety

Peter: And part of me wonders if that generalized anxiety is because it’s not one monolithic thing, it’s a thousand little things, and your attention gets frayed. You don’t know what you should be investing your time in to understand and explore. You. start down one path and then you hear this other thing that comes up and you’re like should I do that, or should I finish the thing I started?

And like how to handle all the potential, not noise, but all the potential sources of your attention. And I think a not unreasonable response is just to peace out.

Jesse: Oh yeah. Oh, for sure. Just, yeah. Give into the overwhelm and go to bed. Yeah, I think that’s real.

I think that one thing that I notice in this is the question of what the transition asks of us. Because some of these transitions these past waves of technological change, some of these transitions for some of us asked very little of us, because it didn’t really require us to change our lifestyles. It didn’t really require us to change how we did our work. It didn’t ask a lot of us.

Some of these transitions have asked quite a lot of people to let go of and give themselves over to in terms of… Just think about the digitization of various industries over the course of the back half of the 20th century, and what that asked of every worker in every facility doing every job to engage with different technology that didn’t work the way that they expected, that they basically had foisted upon them by some central authority.

And so this is how automation gets a certain kind of stigma because it feels like something that is enforced upon people rather than something that is offered up as an opportunity or a genuine enhancement to their abilities.

I keep coming back to what this means for leaders, because as you pointed out last time we talked about this, they are the leverage point. They are the point of influence to not just to embrace the new, but also to acknowledge what is potentially left behind that somehow needs to be kept up, right? the fear of this highly automated world is that the soul is lost from the work, that the human voice is lost in the work.

And if no one else is there to defend it, like it’s got to be the leaders who make it happen. They’re the only ones with the influence.

Peter: To defend what?

Defending Humanity in this Liminal Moment

Jesse: Defend the soul, the spirit the human element. If it does turn into a wall of automation, it’s because we chose to automate things that shouldn’t have been automated.

And so it takes people with the thought and the feeling and the expertise, and as we talked about in the last episode, the background in understanding human beings and the sociological and the psychological grounding to understand what inhumane practices look like in order to instill that understanding in the systems we create.

And I think that applies both internally and externally in terms of not just like what constitutes automated abuse of customers, but what also constitutes automated abuse of your employees, right?

Peter: This is making me realize something that I hadn’t, I guess, acknowledged, come to terms with, which is that I’d been thinking of liminality as something that happens to us, right?

That as you go through life, as things shift and evolve, there’s going to be moments…

I think one of the theses of our conversations is that liminality is always there. You’re always going from something to something else, but there are definitely moments where it feels more heightened and this is one of them. And that’s just the way of the world.

Liminality is a common anthropological frame, rites of passage, certain points in your life where you’re about to step into some new…

Jesse: Seven ages of man, right? Yeah.

Peter: I was bringing some of that thinking to what it means to how we show up as people in our liminal moment and thinking about other themes that we’ve discussed, which is that this uncertainty that we are in can cause anxiety, but is also opportunity, right?

Because discombobulation means people are looking around for someone with some answers to settle things, right? And there’s voids that folks with ideas can fill.

But something you’re saying, and I don’t know the implication of it, but I think it’s definitely worth calling out, is that liminality isn’t simply something that happens to us. Much of the liminal moment that we are in has been imposed upon us by folks who are acting out of their own self interests, but are dismissive, neglectful of the impacts of that decision making on others.

And we’re all having to navigate that. And because when you talk about leader, you talk about power dynamics, and we live in a society where a relatively small number of people wield outsized influence that we all then have to react to. And figure out our reaction to…

Jesse: Yes.

Peter: and that seems to be something different about this moment, maybe than prior liminal moments.

There’s an arbitrariness to it.

Jesse: There are a couple of sides to it.

One thing I’ll say is that I called my business Intentional Associates. You called your business Humanism at Scale. We are both in the business of driving more intentionality in these organizations because I believe that we both believe that if we don’t stand for humanity within these systems, then no one else will, because it is Design, more than any other function, that is invested in bringing humanity to internal decision making.

And that’s what we have seen in our careers as the opportunity for design to create broader cultural change, both internally as well as at the larger social scale that you’re talking about. So there’s that piece of it, first of all Secondarily, there is a certain friction associated with the liminal moment that requires a grace, a fluidity, an adaptive path, if you will, that goes against the way that a lot of people think about their roles. And the way that a lot of organizations think about what success looks like.

And in some ways, when we’ve talked about creating that semi-permeable membrane, that bubble around design, it is in part to enable design to continue to keep that torch lit for humanistic practices.

But it is, I think, a question of that multiplier effect because the perception, the real perception at this point, is that major enterprises are going to start shedding thousands of jobs because they will figure out how to automate away a lot of the work that’s being done by human beings right now.

Regardless of whether we think that’s actually possible with the technology that exists, these technology companies absolutely want us to believe that’s possible because that’s how they keep their investments flowing.

I think that it is for us to answer that question as the upholders, the flame keepers for humanism within organizations, as to how much of this story we buy into and how, much of a counter narrative we offer and what that might look like.

Responding Collectively

Peter: Yeah, and as you talk about a counternarrative, that connects with something I’ve been thinking about.

Our past two conversations have been very much about what you as an individual can do, or the impact of liminality on you as a person, as you as a leader. How do you develop your own resilience, how do you ride this wave?

And maybe, as a leader, how do you bring others with you?

But it’s still been centered on this kind of individual, not just responsibility, but locus of action.

Jesse: Yes.

Peter: And personal choice, personal decisions.

I’m wondering what the role of collective action plays.

So at the end of the last episode we teased the idea of coming out of the liminal moment. And I think what we’ve realized since then is we may be not quite there yet, but, when you’re in a moment like this, I sometimes call it the Great Discombobulation, right?

You are not the only one being discombobulated. Literally everybody is, at least everyone you know…

Jesse: True.

Peter: …is. And we could all choose to address it on our own, or we could try to connect with others with similar ideals, values, to work together to shape an outcome that is aligned with those values.

You touched on our values of humanism and intentionality. And I think a little bit about the Margaret Mead quote, “Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has.” Right?

What does it look like to group, to connect, to look beyond yourself, to realize that others are in a similar situation?

Something I’m starting to see that might be a response, here in the city of Oakland are a bunch of communities springing up, primarily in storefronts, but in other locations as well, right, as a response to a collapse of some structures of community that, perhaps we’ve relied on in the past.

And trying to find ways that people can connect, particularly in a sensitive moment for community, at least in the United States. How do we connect and support one another better?

The Leader’s Role

Jesse: As we pointed out a little while ago, the leader is the leverage point in so many ways because they have the microphone, they have the leverage, they have, in some cases, the direct authority, the check writing authority, which counts for a lot. Money talks, bullshit walks, and if you have the opportunity to spend the money, then you are the person who gets to decide how things go in a lot of ways.

And so if we think about it in that classic up, down, and sideways like you teach in your masterclass, that if a certain amount of the relationship energy is going down, it is creating alignment, creating trust within your team around shared intention. Coming back to intentionality, right?

Intentionality is the way through the liminal because the intentional can hold you together cohesively as a team. When it comes to those sideways relationships, those cross-functional relationships, then it becomes about a desire for certain shared outcomes, right?

We might not have the same worldview as a Chief Design Officer and a Chief Technical Officer, right? We might have different ideas of what the priorities ought to be, but we do have a shared sense of the outcome that we want to create, or hopefully we do.

And that’s part of what a leader can create in the liminal moment that can guide the difficult conversations that unfold in there.

And then, when you’re talking about the relationships upstairs, then you’re talking about, are you reading the same signals that your boss is reading? Are you aligned to the same things that they are actually paying attention to? Because if you’re a Chief Design Officer reporting to a CEO, they are probably dealing with a whole bunch of stuff that is pretty far off the radar of design and you might need to be aware of in order to be able to effectively stay in alignment and not get thrown off the surfboard in that liminal moment.

Peter: As you were sharing that framework, and you mentioned developing relationships cross-functionally, you’re a design leader partnering with a technology leader around shared outcomes, I do believe that potentially a more fruitful path, if you can find it, is to connect with cross-functional partners who do have shared values.

I don’t wanna suggest that the design org is the only one with a certain set of values that others wouldn’t share.

Actually, I was having this conversation with a friend of mine who I used to work with over a decade ago who is a product person. I’m a design person. We had a really strong partnership because we both like to nerd out about organizational solutions to product development problems. And I was talking to him recently, not about liminality, just about, frankly, the broken state of tech.

And so he’s a VP of product and in his org there is a chief product officer. And the chief product officer was leaving and so there was an opportunity that he could ask for a promotion or apply for the role, right?

They wanted to replace that role and he was making an explicit decision not to, and when I asked him about it, what kind of revealed is, there’s kind of a waterline in a lot of these organizations between the senior executive staff and the folks below it. And below the waterline, even across functions, I think you tend to find more commonality, more desire just to like, let’s do some good stuff. Let’s put some good stuff out in the world. Let’s ship good product or whatever. Like an honest and authentic desire to deliver good stuff.

The Sociopathy of Executives

Peter: But above a water line, it starts getting weird and starts getting, frankly, sociopathic. Right? Where there seems to be a selection bias for senior executives around sociopathy. That I believe is because a way that you can be a successful executive is by looking at your organization as not a group of humans, but a group of resources, right?

That’s a sociopathic mindset. And to manipulate those resources, whether they’re people or money or capital assets or whatever, to manipulate those resources for some gain. And you consider people and computers and chairs and buildings to be basically the same. They’re just things on a balance sheet. And those who are willing to go there, are the ones who end up getting promoted into the senior leadership roles because they can succeed in a way that those unwilling to go there find themselves hitting a ceiling where they’re, like, that’s not how I want to operate.

Jesse: Yeah.

Peter: And so I think there are likely folks that you might not realize you have shared values with outside of your organization I think the prospect here is that in a liminal moment where stuff is uncertain and unsettled, if you can find fellow travelers, particularly outside of your function, you can band together, propose things, while folks are in this, ‘we don’t know what’s best’ mode.

If you can bring together a group of folks with a plan for meaningful, positive change, I believe, I might be wrong, but I believe something like that is likelier to be successful now than it would be in a relatively stable context where…

Jesse: Oh, sure.

Peter: …you would just be like, business as usual.

Jesse: Yeah, no, there’s just more on the table right now. If I were the head of product overseeing a product management organization of what I understand to be a typical product management skillset, I’d be terrified about what these new technologies meant for my team, because nobody on my team can actually write requirements to the level of specificity required to actually execute.

But you know what? My design partner’s team might. So I think it’s a very real opportunity to build bridges, especially at the leadership level. But I think that to your point, it might not be at that, like, the sociopathic C-level, which I have to completely agree with. It feels like that’s what gets selected for, right?

And what you end up with is that, yeah, everybody with a more humanistic bent hits a ceiling somewhere along the way that prevents them from gaining more authority.

But you mentioned shared values and I think that’s an important piece to bring into the conversation.

I talked about shared intentions with your own team. I talked about shared outcomes cross-functionally, and I talked about shared awareness with executive leadership to show that you were following the same signals that they were following.

But I think there is this deeper question of, are we on the same page in terms of where we see this going? Not just from a metrics perspective, but in terms of the shape of the organization that we’re leaving behind.

There is I think, not enough attention to legacy in leadership broadly. But especially in navigating the liminal, like if you are genuinely trying to set a team up for some future, regardless of how clearly you can see it, it’s still on you to leave it in a shape that they can actually execute on, right?

Broaden Your Horizons

Peter: Agree. I don’t have much to add to that.

And I find myself realizing that you and I might be falling into a bit of a trap with an assumption that the path forward is within the context in which you’re currently operating and trying to make sense of that space, and to navigate that space, and in this liminal moment maybe set direction within your current organization to help bring clarity to all that uncertainty.

But that could be a trap, right? A potential way forward, and we’ve seen this pattern in prior cycles, is that small group of people with shared values in your organization, leave that organization and do their own thing.

And there’s an opportunity theoretically right now, right? Given what we were told about these tools, to let a thousand flowers bloom, right? And maybe, the outcome, or an outcome of this liminal moment, well, an outcome of this liminal moment is…

It was with Jorge, we talked about the K patterns, right? Where the, the poor get poorer and the rich get richer.

A similar thing… ish? Is we see either: Fewer massive enterprises, right? Those that can just capture the space we’re in and the value therein and it becomes, Weyland-Yutani type shit.

And or a thriving marketplace of three to seven person businesses solving problems in a way that they couldn’t have sustainably done before for whatever the economies were, but now maybe have a greater ability to do so, to opt out of a giant corporate ladder climbing game and into a… I mean, I’m starting to sound solarpunk or something here, right? But, into a more emergent, I don’t wanna say the word artisanal, but I’m saying the word artisanal, distributed, hopefully gloriously chaotic as opposed to painfully chaotic, flourishing.

And I say it’s happened before, right after the dot bust. It took the dot bust and the wounds licking and the playing around with technologies. Adaptive Path emerges from the dot bust. Core early technologies, Flickr comes to mind, Facebook, a lot of the things that have now are dominating, kind of emerged from this period of firmament that occurred in that downturn.

I don’t want our thinking to be constricted, to playing forward the current situation or the current context, and instead recognize because we don’t know where this is going, we are freer to imagine other potential outcomes that might be more aligned with our values.

Discerning Which Wave

Jesse: Six outta 10 people don’t get on the wave, and maybe they wanted to get on the wave and they just couldn’t build up the energy necessarily to catch the wave. Maybe they just realized it wasn’t their wave and they let it go under them, and maybe the wave that’s happening in your company right now isn’t your wave right?

Maybe they are deploying these technologies in grossly irresponsible ways because they haven’t intentionally developed an AI transformation program and maybe they are advocating for things that don’t align with what you signed up for, what you even thought your job was going to be.

All of that is okay. It’s okay in a couple of ways. First of all, this is gonna be something that is gonna take a long time to make its way out. The ripple effect is going to continue from these organizations that are closer to the center, first of all, which are these organizations that are frankly under VC pressure to adopt certain technologies and meet certain metrics in their own growth.

And then you’ve got the companies that model themselves on those guys, which we already know about. Regardless of the right or wrong of how they’re actually doing things.

So then from there, you’ve got a whole long tail out from there of other organizations that are gonna be adopting these technologies at their own pace. I can imagine you can continue to basically, continue with business as usual, in the exact same way that you’ve done the job as a design leader for the last 10 years.

You could probably do that for five to 10 years more, easily, before it gets to a place where you start to run out of places that do things that way, because the tooling has evolved. Maybe not 10 years, maybe that’s too optimistic, but.

Peter: I think this is important; overlooked. We’re in a moment of such kind of anxious intensity where it feels like we have to change now, or in the next three months, and if we’re not, we’re gonna fall way behind.

To remember that these things take time, that every change that has felt like it was going to be immediate took time. As you were talking, I was reflecting on how most businesses still don’t build software well, even though we’ve known for 20 years how we should do it. We just ignore it.

That and, like, the agile revolution was some similar kind of upheaval internally for a lot of organizations.

How’s that borne out?

Jesse: Mm-hmm. Mm-hmm.

Peter: Many companies still really aren’t.

Not Burning Out

Peter: And the thing though, that we haven’t talked much about, is if this is gonna take time, people can’t maintain their current level of anxiety, energy, whatever that buzz that we’re all, that we’re all feeling.

It’s gonna burn them out.

And this is something that in my own, just personal kind of thinking through what it means to show up in this liminal moment, I’ve been wondering about, which is, how do you not burn out when everything is always feeling anxious?

Now you’re telling me that we’re gonna be doing this for five years or something. That doesn’t make me feel better. I’m gonna feel like I’m feeling today for five years. Is that what that means? There’s something about…

Jesse: That’s not what I meant.

Peter: I know it’s not what you meant, but there’s something about this, like, navigating liminality is frazzling, right?

Because of that uncertainty.

Jesse: It’s exhausting. Yeah.

Peter: I feel that as a solopreneur, operating in six or seven spaces and I’m constantly task switching and I never quite know what the next thing is that I’m going to be working on.

And so I have to be ready for a lot of potential opportunities depending on what turns up in what direction, and that’s exhausting.

And I’m curious, this might be something that you have some more formal, or at least mature thinking about, born of a coaching practice. ‘Cause I’m sure this is something leaders deal with all the time, which is managing their energy, managing a pace, cadence.

Right. A leader always has, even before a liminal moment, leaders always had more work to do than they had time to do it.

In a liminal moment that feels like it’s like everything else: accelerating.

How do people manage their own, energy, resources, so that they don’t burn out. When they’re in an environment that just feels like it continues to apply pressure.

Jesse: I think prioritizing your attention is a fundamental skill for leaders.

The ability to, as much as possible, shut out everything that isn’t the decision that you need to make right now, and be able to really let go of it until it’s time, and to trust yourself that you will create the time and create the space for that decision, and that you’re prioritizing the right things.

And if you don’t have the mental systems in place to prioritize the right things, yeah, you’re gonna be constantly scared that you’re spending too much time on the wrong things.

So I think that’s a huge piece of it.

To go beyond the surfing metaphor and look at something like sailing. Imagine that the leader of a team is the captain of a ship, right? And you’re standing on the deck of the ship and what are you paying attention to?

You’re paying attention to the information that’s coming up through your feet as the boat is rocking in the water, and you’re paying attention to what you’re seeing from the waves and the clouds and the other stuff that’s coming in, and you’re paying attention to, what you’re feeling from the wind that is gonna tell you how much attention you have to give to where we put the sails and where we put the rudder and where we, how we deploy the team to get the ship to where it’s going.

So if you’ve got calm waters, if you’ve got people that you can trust to keep an eye on the mainsail and all the rigging and the stuff, yeah, you can go downstairs and you can take a nap.

But if you don’t have those people, you can’t.

Peter: I like naps.

Jesse: I said Peter’s magic word.

Peter: Thinking about navigating this moment collectively.

A week or so ago, I wrote in my newsletter, what I’m calling the design management quality cascade, and it’s a response to witnessing VPs of design reviewing, like, delivery work in an organization of more than a hundred people, right?

It’s not like it’s a 10 person organization, that makes sense, but when there’s 150 people in the organization, the VP should not be reviewing delivery work.

But it was happening and it was happening for a number of reasons.

What the design management quality cascade lays out is how to locate the appropriate responsibility at the appropriate level, right? So you’re talking about the captain of the ship and there’s a certain set of things that they’ll be responsible for, and then they’ll have, I don’t know all the terms on a ship, but they’ll have their leaders reporting into them who’ll have their responsibilities, and people reporting to them…

And on a ship, this I do know, everyone knows exactly what their specific responsibility is. the ones I know In a design organization that almost never happens.

And so what ends up happening is that VP, that captain, ends up doing a bunch of work that they probably shouldn’t be doing. They’re not prioritizing well, to use your language, because they don’t know… they either don’t know or they don’t have the confidence in the people in their organization that they’re actually doing the thing that they should be doing.

And so they feel like they need to do it all.

Jesse: Yeah. Yeah. They don’t have people that they can turn their backs on. They don’t have people that they can trust to make decisions without them. And that’s what it comes back to is, like, how many decisions can you actually let go of so that you can give the maximum time and space and attention to the decisions that actually matter that only you can make.

Peter: Well, and that becomes exceedingly acute in a…

Jesse: Exactly so, yes.

Making Informed Decisions

Peter: Right? Because… because, a liminal moment, you’re going to be making new decisions, right?

Most of the time when you are making decisions, you’re making decisions where the outcome is somewhat predictable, right? And it’s usually choosing between trade-offs. We could go path A, we could go path B. Path A has this, path B has that. We know where both of those paths go. And your job as leader is to help figure that out.

In a liminal moment, you don’t know necessarily the results of those decisions.

Jesse: Door number three.

Peter: Though you are probably best situated to hypothesize, right?

Actually, probably the nature of the decision depends on the level of the organization, right? But at that senior level, because of the context you’re in, because of the information that you have access to, you understand a likelier outcome of decisions at a certain altitude.

Jesse: The more you expand your awareness as a leader, the better informed your decisions are. Full stop, right?

The more different sources of data that you are taking in, the broader range of the organization that you’re in connection with, you’re just gonna be more broadly informed.

And that’s what I mean about building shared awareness with your executive leadership because they have to be informed about everything. And if you are ignorant of two thirds of what’s going on in the company, because you’ve been paying attention to your own little corner, your value prop isn’t there as a participant in actually guiding the organization.

Peter: There’s gonna be multiple reasons of your ignorance, but if, a reason for your ignorance of what’s happening in the C-suite is because you are involved in decision-making in the, lower levels of your organization, that’s a bad use of time.

And so delegating responsibilities, placing trust in those people within your team, empowering them to make the decisions that they are closest to and should have full information on, frees you up as a more senior leader to tackle a kind of decision making, a different kind of decision making, where there is a risk involved, because there is an uncertainty and an unknowingness.

I’m thinking also about… it should be at that executive level..

Jesse: Yes.

Peter: Because you mentioned the power of the purse, right?

And this is something else, too many design executives don’t understand the power that they have, but that you get with being a vp, that you should have budget and budgetary authority. You get to make decisions, you get to carve out time to do things.

And I know that in many organizations, VPs have become disempowered. That’s a separate conversation. It’s an unfortunate one. But not just design VPs, like VPs across the board, like the C-suite holds very tightly to all kind of meaningful decision making.

Let me get back to my original thread, which was as a VP, as an executive, you should be able to initiate programs of discovery to sense your way through the liminal moment, right?

You don’t need to know where you’re going. None of us know where we’re going. But you have the means to…

Jesse: Read the wave.

Peter: Better hypothesize, to read the room, better hypothesize, and then place some bets. Yeah. To put probes out there, and then based on the information you get back from those probes, do the work of directing the organization towards healthier outcomes.

Shift from Reactive to Proactive

Jesse: That’s what I think is central to a leader’s value proposition, is the ability to generate from their own perspective, from their own point of view, those sorts of explorations.

If you don’t have the power and the permission to do that, I don’t know.

I don’t think any organization really just wants reactive leaders. I think on some level it has to be a part of what you do, that you scout for opportunities for your team to deliver new value and different kinds of value, and to continue to drive and explore that.

I don’t know, that’s me.

Peter: No, I think you’re right. I think you’re right. I think too many design leaders are reactive. They’ve gotten in a do what they’re told mode. That started with this mindset… I still hear from design teams that use briefs. ” We gotta receive a brief and then when we receive the brief, we now can respond to that, we know what to do.”

And I’m like, What? What…uh, briefs? No, no briefs. Full stop. Because briefs mean, you’re in service to, not in partnership with.

And when you’re in service to, you are not leading right? You are only reactive.

And if you want to make change, you need to shift that posture to one of problem identification and exploring solutions.

And as you were talking, a theme that’s been true about all this AI shit since we started talking about it is, because AI is an accelerant, kind of more than any other thing, what it does is it reveals cracks in…

Jesse: Mm mm-hmm.

Peter: …Organizational practices, that maybe had been filled in, or you could paper over or you could kind of ignore. But now with that accelerant, those cracks are starting to strain and break, if you haven’t been doing the right thing.

And I think what you’re talking about, what we’re getting to here, is that basically nothing we were saying about what a VP should be doing is new. This is what VPs should have always been doing. The difference now is when VPs don’t do the things that they should have been doing, the outcomes are magnified.

Because, let’s say, you’re that VP who’s looking at work, is too focused in the weeds. And thanks to AI, the amount of work that your teams are doing is accelerating. So now you’re just gonna be in the weeds more, right?

Which means you’re spending even less time with the executive leadership that you should be partnered with, right? That kind of thing.

Jesse: Yeah. In the same way that, as we talked about when we talked about the Elements of UX in the Age of AI talk it’s not just that it amplifies the existing value proposition, but it also magnifies the places where the process is not optimized. And those things are gonna continue to be coming to light for teams within their own processes.

You know, when I think about what all of this means for the liminal leader, so to speak, it does seem to entail a willingness to hold your own perspective while continuing to listen to others. Maintaining those connections with other viewpoints because, to your point about collective action, the organizations that are going to hold together through this are the ones that have the strongest shared values and shared practices and shared beliefs.

Otherwise, I think you’re right. People will spin off and do their own thing and maybe some of them will see this as an opportunity to move to a smaller place that is gonna be really lazy about adopting all these new techniques and technologies. And they can continue to build websites with Quark Express for as long as they want.

And there are other people who are just gonna get the hell out, right? And go open a pottery studio in Alameda or something like that.

Peter: And that’s been happening. Bakeries.

Well, Yeah. And a thought I wanted to make sure that got out, that I think captures a bit of what you were just saying, but something that I’d written down before we spoke: liminality is not about a destination.

You’re talking about: what does it mean to be a liminal leader? To be a liminal leader is you don’t know exactly where you’re going. So it has to be about the journey.

But, and this is tricky. It can’t just be random. You’re not just stumbling around. There is a direction that you’re moving in.

Liminal leadership needs to have confidence that even though you don’t know exactly where you’re going, you’re moving in generally the right direction, wherever that is.

Jesse: So this is where the three out of four people who get on the wave, get swallowed by the wave, because they misjudged where they were relative to the wave and weren’t paying attention to the right things. And they went under instead of over and didn’t get up on the board.

And what you’re talking about is really the ability to get up on the board, so to speak, to be able to calibrate yourself to the moment and activate in the moment when the moment arises.

Am I overextending the metaphor? Maybe.

Peter: No, and I think this is good place to end.

The thing I just realized, and I don’t know if that was always part of your intent, was that of those 10 people, it’s not the six who never got on the wave that are struggling. It’s the three…

Jesse: Thought they could catch it!

Peter: …Who thought they were ready and weren’t. Those six are actually better off having let that wave go by ’cause they weren’t ready for it, right?

Jesse: Yes, that’s exactly right.

Peter: So it’s having that, we talked about discernment with Dan, right? There’s a discernment here of your moment, right? And this is that prioritizing conversation as well. You need to be self-aware of what is your moment and what isn’t and with some of those surfers there was a misfit between what they perceived and their ability to take advantage of it, and they didn’t succeed.

Whereas those other six on subsequent waves might have been able to have a perfectly good ride.

Jesse: Yeah. Yeah.

Thank you so much for the conversation, Peter. It’s been fun.

Peter: Yeah, this was great. Thank you, Jesse.

Wow.

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.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

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