4: Management Leadership Jazz

In which reflections on the coronavirus pandemic spark a freeform conversation ranging from Trump to Jobs on management, leadership, power, uncertainty, and more.


Welcome to “Finding Our Way,” the podcast where Peter and Jesse welcome you to their journey as they navigate the opportunities and challenges of design and design leadership.

As always, I’m Peter Merholz, and with me is Jesse James Garrett.

Jesse: Hello, Peter.

Peter: Hi Jesse. Good afternoon. How are you?

Jesse: I’m, I’m, doing well, all things considered. Yeah–

Peter: And there, there’s a lot to consider… 

Jesse: There is a lot, there’s a lot of context. Just a lot. We’ve got some extra context these days for everything.

Peter: It’s funny. I haven’t had enough time to go meta on the current situation, but I think there is, there’s something about this situation that is interesting and revealing. My normal mode would be to reflect on it and I just haven’t had time to do that. Have you been able to step back and think about what we might be learning through this uncommon experience?

Jesse: Oh, wow. That’s a, that’s kind of a big question. I, so just as a point of reference, for our listeners’ context, it is Thursday, March the 26th, 2020. And so that’s where we are in the overall timeline of this extraordinary year, as it has just begun to unfold for us. And you know, I don’t think anybody really can get enough distance on any of this yet to extrapolate learnings from it, except for some very broad learnings about the systemic nature of cause and effect in our modern globalized world. The ways in which systemic structures and the choices that we make in our individual lives are actually intertwined in terms of the outcomes that they create. And, I think that when we look at the differences in how the Covid–19 virus has propagated across cultures and across societies, and the dramatic differences that we’ve seen across the various countries in which the pandemic has taken hold, come back to issues of culture, issues of governance. Frankly, a lot of the stuff that we’re interested in talking about here at the scale of design and design leadership, but really at the global scale. There are these factors at play that influence how an event like this unfolds, that are hard to see in advance because they are these second order, systemic kind of effects. And then it ends up expressing itself in these really unusual ways.

Just before we started recording, I was watching video of, you know, in cities all over the world, there are parks and plazas and public squares that have resident populations of feral animals that rely on the presence of humans to sustain their populations. And now there are these packs of animals kind of roving the empty streets of cities around the world looking for tourists to give them bread.

And there are none coming. And so it’s a schooling in unintended consequences that has really just begun. Yeah.

Peter: Raccoon apocalypse.

Um, one of the things that this has done is make evident different kinds of leadership, and different responses that leaders can have in situations that are kind of revealing. There’s the leadership as demonstrated by President Trump,

there’s the leadership demonstrated by Governor Gavin Newsom here in California.

As Covid was starting to land in the United States, Trump’s leadership mode was to tell people what he thought they wanted to hear, which sometimes can be an okay strategy depending on the seriousness of the incident, but in this case was not the right strategy because telling people what they wanted to hear did not allow them to prepare as they needed to for the reality.

This was in marked contrast to here in California, governor Gavin Newsom, who came out in front of this very early on and started talking about the seriousness and how we’re going to need to start shutting things down and that this is going to take awhile and, his leadership approach was to be upfront with the citizens of California, and he told us stuff we didn’t want to hear. I don’t want to hear that I’m going to have to be in my house for weeks, if not months, on end. But it is good for me to hear that if that is the reality, if that is a reality that I need to get accustomed to and start preparing for.

Right. And thinking about design leaders, I was in a session yesterday where we were talking about “radical candor.” And, there’s a book by that title by Jill Scott. And, you know, the idea behind radical candor is that you are forthright, you are frank with people, with the situation, the issues in play. You are respectful. You are not aggressive. You are not rude or mean, but you are direct, because it is through that communication of information that we are able to understand the situation and then develop strategies for getting better.

Whereas a more common approach, probably the most common approach that I’ve seen in design teams and with design leaders is what she refers to as “ruinous empathy,” which is, because we want to be nice to one another—and designers, at least the ones I’ve worked with, often tend towards the nice, the polite, the pleasant—because we want to be nice to one another, we don’t tell people what they need to hear. We instead tell them what they want to hear, and they don’t realize that they might be underperforming or that this work could be done better or that somehow they are not reaching their potential. And so then these folks end up stuck at a particular level and they’re not growing because in order to get them to grow, we would have to critique them and tell them that they are not measuring up, and that would be not nice. And we kind of get in our own way in doing that, and so it was interesting to think about these leadership styles, both at the micro level of teams and at this macro level of states and societies.

Jesse: You know, and I would argue that, what all of that comes back to is, how effective are the interpersonal skills of the leader. You know, obviously there’s a lot to be said for, you know, vision and operational acumen and all of those kinds of things that are, that are asked of leaders.

But I think, in order to mobilize people around a common cause, people who have a diverse range of skills to bring, a diverse range of perspectives, to mobilize them around a common cause requires being able to speak to them in ways that resonate with them and bring them along. And that’s something that design leaders get used to doing in the context of defending design work as designers, and then as they are elevated to leadership, they sometimes kind of lose their way a little bit, in terms of knowing how to bring people along with ideas that aren’t design concepts.

Peter: I would say there’s a difference there. I guess it’s easy to react in a situation and provide a rationale as you said, a kind of defense of something that you have created. It can be harder to proact, right, when there isn’t a thing to react to, but you have an idea of where things should be headed. 

And it can be very, disconcerting for folks to make that kind of commitment.

And I think particularly for design leaders who often feel disempowered, feel like they don’t have access to enough levers to ensure that they are able to see what their vision is forward. To that, I guess I would say don’t worry about that disempowerment. Our job, particularly as design leaders, is to articulate a clear vision forward, and work with our peers and in the organization to figure out how to rally towards that goal.

Jesse: I’m interested in this idea of reactivity because I think that it is something that can be a challenge to navigate as one is moving into leadership for the first time or early in the journey of being a leader, of figuring out how much to react versus how much to push against the organization or against your team.

Right. How much are you a first responder there to put out the fires and clear the path for design, like you’ve talked about in your work as a design leader, versus how much do you push. So you’re a leader, you have some authority. That means you have some permission, some latitude, to take steps as you see fit.  But if driving organizational change is a necessary part of driving success for your design team, then you have to be sort of working at the edges of that permission.

You have to be working along the boundaries of your authority as it is currently defined in order to orchestrate the new, to draw the organization toward what it is eventually going to become. And so there’s a balance there that I see leaders having to walk between. Being what has been asked of you versus being what the organization actually ultimately needs.

Peter: I think what you highlighted, which I hadn’t quite thought of in this way, is that most design managers are design managers and probably a very small subset of them are truly design leaders, because I think that leadership is about

pushing against those boundaries, taking people into, if not unknown territory, less well known territory, less well understood territory, taking them to someplace uncomfortable, with the idea that that is where ultimately success will be realized. 

Leadership can kind of happen almost at any level as long as that person is demonstrating these qualities of pushing, of challenging, of coercing, persuading, bringing people along towards something new that they might not be familiar with.

Jesse: Yeah, I definitely agree with that. At Adaptive Path, we saw inside a lot of organizations, where the power in the room and the power on paper were two very different things. And it had to do with the level of respect and trust that people had for the viewpoints of certain people and how effectively those people use their power.

And people who were able to cultivate a broad base of respect and trust and were able to use their power in responsible ways, were able to maintain that power without necessarily being in a position of authority. Power may be a different thing again, I guess that when I’m talking about power here, I’m talking about the ability to influence an outcome.

Peter: Right. A manager’s impact is through their granted authority, and a leader’s impact is through the adoption of a new mindset that continues without them needing to be around.

Jesse: Yeah. When we talk about, maybe not the manager versus the leader, but management versus leadership, there are management oriented responsibilities that people have. And then there are leadership, I think, opportunities.

I think in a lot of cases people can be set up to fail if they are, given a management mandate for a leadership problem, it’s like having the ops team lead your strategy development. They’re great at a different thing, and this is not that thing.

Peter: This actually reminds me of an experience I had last year, in support of Kaiser Permanente. One of the things I learned, and I was working with a consultant there, who had a master’s degree or a certificate in change management. And when we work in design, we often think about change management, right? As designers, one of the things we are doing is helping people imagine new futures and then figuring out how do we get to those new futures. So there’s actually a reasonable connection or overlap with the act of design. But one of the things she pointed out, is that oftentimes people apply change management practices to what is actually transformation management. And this speaks to kind of what you were saying before, where you will apply management approaches to what is actually a leadership problem. People will apply change management approaches to what’s a transformation problem. And there’s a fundamental difference between change and transformation.

Change management is going from a to B, where B is known. They call it agile transformation, but it’s an agile change basically, right? We are currently working in waterfall. We’re going to work in agile. We’re going to now change to people broken up into squads of eight. They’re going to work in these two weeks sprints, et cetera, et cetera, et cetera, right? So you’re going from one known to, another known, even if you haven’t practiced it yet, you generally know where you’re headed.

Transformation management is where you’re going from a current state of known to, you don’t know, it is unknown where you’re headed. And, If you apply change management practices to transformation management, what you end up doing is trying to, I think you said, kind of operate your way towards a new future and that just doesn’t work.

It ends up getting rejected because you don’t know where you’re headed and you need a different set of practices to transform. But the uncertainty in transformation ends up often running contrary to an organization’s desire for certainty. So they apply the change management approach, because there’s a certainty implied in the change management approach.

Transformation management, you don’t actually know where you’re going to end up. That’s kind of the point. So you get this conflict of certainty and uncertainty fighting one another. And the certainty usually wins, right? Cause the certainty is part of the dominant existing culture.

And the attempts to create something new gets squashed because it requires an organization to live in the uncertain for longer than they’re comfortable.

Jesse: Right.

Peter: And then, it just gets rolled back and it never happens.

Jesse: Yeah. Certainty wins out because certainty is comfortable and certainty makes the fear go away and executives carry a lot of fear around, all the time. It’s just sort of the nature of the job. This is interesting though, because this connects back to something that you were talking about earlier when you were talking about the design leader pushing the organization into the unknown. And what I got from what you were saying was that it is always the design leader’s role to be pushing the organization in these ways.

And I wonder how true that actually is because I can see that being true in a startup environment, where the goal is to invent the product as you go and to discover your market opportunity as you go. And certainly that same pushing into the unknown was an important part of Adaptive Path’s value proposition to its clients as well as a part of our internal culture to continue to innovate our practices and keep inventing new stuff.

But I find myself wondering if it’s not mostly the case for most design leaders that the job doesn’t really ask for this kind of boundary pushing stuff. It asks for them, you know, to run the team and to run the team really well. Do you think that’s true?

Peter: Yes, and that’s fine, especially when you get to a larger organization in a more stable organization. It’s about keeping that organization humming and running, and so you’re tweaking and you’re fiddling and you’re trying to, you know, continue to improve effectiveness. But if we’re going to be talking about leadership as we did last time, as a practice and a craft, I think we have to recognize that leadership is distinct from management in terms of that pushing.

And in my experience, and I think this is true of most of the design managers I know, while most of their job is management, for most of them, there’s at least 10%, 20% of their job that should be leadership. They might not all be embracing that opportunity, which is a separate issue, but I think that opportunity does exist.

One of the things I’m starting to see a lot more is design managers, directors, senior directors, who are bringing on principal designers. So, these are kind of director-level designers, but who are not expected to manage people, but expected to be a creative leader in a realm of work. Because I think these design managers and executives even recognize that they don’t have the time, the bandwidth to do the creative leadership as well as the executive engagement and the people management and all the other things that are expected of them.

Jesse: It’s interesting because there are some leaders that I think really start to run up against limitations in terms of their potential to grow and to move up in organizations because they are able to practice the relationship building and the management and the alignment and the orchestration and the leadership within the context of their own teams. But then when they have to do that outside of the context of design process and design decisions as they are representing design on a larger stage, they become uncertain about where their power is and they become uncertain about, “How do you use it effectively?” 

It kind of comes back to something that we were talking about earlier about how people end up becoming design leaders in the first place, which is that the skills that got you the job aren’t necessarily the skills that are gonna let you keep the job.

Peter: Right. a challenge that many design leaders have that might be somewhat unique to design compared to other functions, is that their peers and their bosses say they want new thinking, new ways of working, the creation of new value that design can bring through its practices.

But then, as designers or design leaders attempt to deliver on that, it pushes the organization into this uncomfortable and uncertain realm. And there’s this snapback, where it’s like, “Wait, whoa, whoa. When I said we wanted innovation, I didn’t mean that. I meant something that I could put on a spreadsheet and better understand and you’re giving me something that is different than that.” And I think this is in part because companies are still trying to figure out what to do with this function that is design, and how to, for lack of a better phrase, capitalize on it. I think there’s this internal conflict where like they want one thing and they asked for one thing, but then when you give it to them, they pushed back and they get upset.

And so you don’t do it, and then they’re mad at you because now you’re not delivering the innovation that they asked for. And, and, they don’t realize that the people outside of design don’t often realize that they’re getting in their own way when it comes to what they’re asking for. And that leaves design leaders who are often not particularly well versed in navigating these types of things, their heads are just spinning, trying to figure out what is expected of them, and then it becomes easy to retrench or retreat into that which is safe, which would be the management aspects of their role.

Jesse: I feel like the things that you’re describing are almost artifacts of this stage in the development of UX as a practice, if you are a design leader in an organization that hasn’t had design before and you are trying to engage with a whole bunch of peers and stakeholders who have never had to engage with design before.

You are, by definition, trying to pull the organization into a new place, which by definition is going to be uncomfortable for people and it’s going to require a great deal of diplomacy. 

I wonder at what point we start to turn a corner where those fights become less and less relevant because you don’t have to do so much of that educating, bringing people along, helping them figure out how to talk to you in a way that helps them get what they want from you.

Peter: I appreciate and wish for what you say to be true. I am dubious of that happening anytime soon and I’m dubious for that to be happening anytime soon because a challenge that I believe design has in these organizations is that it is a function unlike literally any other in that it is this kind of creative function, that is being granted some measure of real influence and authority.

There’ve been creative people in organizations for a long time. But often, it was designers maybe in a marketing context who received a brief, executed on the brief, and weren’t really driving the business in any meaningful way. They were

executing on a fairly narrow remit, in some small part of the business as needed.

And now design as a function, and it’s a practice is being brought in one or two levels below the CEO with real executive authority, with large teams that cost a lot of money to hire, and with real influence over the success of a business in terms of the nature of their output driving core fundamental business value. 

The issue there though is that the dominant cultures of these businesses tend to be mechanistic, analytical, reductive, business driven, numbers driven. Engineers and MBAs, frankly, share a mindset of how to approach problem framing and problem solving, which is, which is fairly analytical and rigorous and, and detail oriented and predictable and certain.

It’s a lot about removing uncertainty and, and being certain, but I think there’s this feeling in many organizations, it might even be unconscious, that those approaches have reached their limits. And design seems to offer an opportunity to unlock new value. And so they’re bringing design in ‘cause they, they want that innovation. They want that magic. They want whatever design has to offer, but they don’t recognize that when they’re asking for design to enter into these contexts that they’re bringing in a fundamentally, deeply different way of looking at the world, approaching the world, framing problems and solving problems that isn’t analytical.

it tends to be more, synthetic, more generative, more creative, more experimental, less certain. It’s not blasé, it’s not dismissive to business realities and a need to generate value. It’s just a different way of getting there. And it is deeply in conflict with that dominant culture.

And so, I am hopeful that we can get to what you’re asking for. I think the way we get there though is when more and more people with design backgrounds are in senior enough positions of leadership and recognize, the opportunity and the potential of this, what can feel uncomfortable, approach and give it the space

to deliver as it can. And until then, design is going to find itself straitjacketed.

I don’t know how much education you can do of existing broader organizational leadership, versus, is this one of those things that we just need kind of a new generation of leaders…

Jesse: Right.

Peter: …be okay with this lack of certainty, right? I mean, we’re coming out of 120 years of Taylorism, and management science, that was all about breaking things down to their details and creating repeatable, efficient processes, and design runs highly contrary to that. And it’s going to take a while before this more creative, generative, uncertain approach to value delivery is appreciated by these organizations.

Jesse: It feels like what you’re describing is, this thing of, like, caging the wild beast. Right, this natural creative force of design that we’re trying to figure out how to, like, fit it into this Taylorist mechanistic metropolis like, sorry, mega-machine, that we can take this wild organic element and kind of plug it into somehow.

And I find myself wondering whether the wild beasts can ever be truly tamed, or if it is always like, “Are you the zookeeper from now on?” Basically, regardless of how the organization’s changed, and is design always going to bump up against the practical mindedness that is necessary for successful management of a business.

Peter: I don’t think so because I think much of that wildness can be practiced safely; practice safe wildness. 

You know, thinking about Apple, particularly under Steve Jobs, because he obviously understood design, had a passion for design, and was willing to let that uncertainty manifest as long as necessary until the uncertainty eventually turns that corner and becomes something that is now more certain and feels real.

There’s a way to approach it where you do it in a safe context where you’re not, you’re not launching this stuff. You’re not shipping this stuff. but you’re trying a bunch of stuff. You’re iterating on it. You’re weeding out 99, possibly 99.9% of the ideas until you get to those germs that catch on and then you’re building on that. And, that requires a degree of patience, a degree of confidence that most leaders simply don’t have. But, if you can see it through to that point, Apple demonstrates what the potential is of allowing that unbridled energy to be realized.

Jesse: You know, one of the adjectives you’ll see most frequently associated with his name is mercurial. In that, yesterday’s great work is suddenly not good enough today. and the ways in which he would let people know that, not necessarily the most constructive…

Peter: No, I, and I’m not going to, I have no desire to be a hagiography of Jobs…

Jesse: …and, and this is I, yeah, no, I know that that’s not–. And my point was simply that, Jobs often, famously, couldn’t tell you exactly what he wanted until he saw it. But as soon as he saw it, then he knew and was, was very decisive in that respect. But it’s almost like the vision was actually sort of a created out of the best little bits of work of many different people rather than Steve Jobs being able to picture the whole thing in his head and then just like giving direction to a team, which is how I think people thought he was working. 

Peter: That’s right. One of the interesting things about Jobs is how little vision he actually had. He was not imagining…

Jesse: Yeah. 

Peter: …these crazy futures. He didn’t come up with the graphic user interface, but when he saw it at Xerox PARC, he realized that is where things are heading, and figured out a way to take something someone else had come up with, and he figured out how to evolve that into something that would be accessible for everybody. But you’re right. He needed other people to show him that vision.

And this kind of gets back to designers, right? When they’re working best, they are creating visions, most of which are bad. Maybe not bad, but, but, but, but ineffective or infeasible or not going anywhere…

Jesse: Not right. They’re just not right in one way or another. Yeah.

Peter: One of the challenges that companies that want to quote “be like Apple” have, is that their leaders aren’t able to navigate all these quote, “not right” ideas, to realize what are the right ones, the pearls within there, that are worth investing in.

Jesse: Yeah. Well, one of the things that comes through in the various anecdotes about Jobs is, that one of his superpowers was discernment that, in a wide range of different areas, whether that was visual design or industrial design, or the nuts and bolts of software and hardware architecture, he had the ability to wrap his head around a problem well enough to be able to tell the difference between a good solution and a bad solution in a wide range of different areas. And he was able to use that skill to orchestrate the work of all of these different people toward something that eventually added up to a compelling product.

So I think that that cultivation of discernment, that development of taste on the part of the leader, is an essential part of that orchestration of vision.

Peter: I would like to think that, that quality of discernment exists in the world in many people. Jobs had developed it and refined it. I’d never considered discernment, as you phrased it, as its own skill, but, it is, there’s a quality there that can be developed though some people probably have a higher amount of it or a higher degree of it than others, as an inclination and, how can an organization identify its higher discerning individuals and engage with them, grant them some degree of influence and authority to practice that discernment, in value to the business.

Jesse: That is an interesting question and I think an excellent place for us to leave off and…

Peter: The biggest question we’ve had so far, and we’re just… 

Jesse: …something deep to think about. I’m just going to let it hang there. I’m going to sleep on it. For, for a bit. Thank you so much, Peter. This has been wonderful. I think it’s probably time for the outro.

Peter: I believe it is. So, once again, Jesse and I thank you for listening to another episode of Finding Our Way. As always, we are interested in hearing from you, whether through Twitter, email, carrier pigeon, whatever means you have at your disposal, let us know what you think about the show, or let us know what you would like us to talk about.

We want to be open and responsive to this community, as we feel it’s not just Jesse and I finding our way, but all of us finding our way together.

Jesse: Finding our way. Thanks, Peter.

Peter:   Nope. Nope. That just didn’t work. That didn’t work. Fuck, fuck, fuck. I feel like Orson Welles yelling… 

Jesse: I thought you were doing, I thought it. I thought it was… 

Peter: It was going for awhile and then I, I spun out and feel again, like Orson Welles…

Jesse: We know a farm in the South of England. Sorry…

Peter: What is this fucking drivel! Why am I reading this shit? 

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