Design | 12 min read

Design leadership as a subversive activity

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Design management can be a strange beast. On the one hand, you work your butt off to stack your team with the most creative, curious and diverse individuals you can find. On the other hand, it’s your job to, well, manage them and keep everyone pointed in the right direction and behaving as one coherent unit.

If you’re anything like me, you’ll probably attempt to achieve this by inventing some form of process for everyone to follow. But as I’ll discuss below, this approach has its roots in archaic management methodologies that have more to offer the assembly line of yesterday than the open plan office of today.

The essence of design leadership is the inverse of what I had assumed

Unfortunately, I learned this the hard way. As our Product Design team at Intercom scaled through various stages of growth, I carefully put in place new processes that were just right for where we were at each stage. I thought that’s what my job was and I put a ton of time into it. So it was a bit of a shock and a bigger disappointment to find that without fail and often dramatically, those processes would break soon after.

I eventually came to realize that the essence of design leadership is the inverse of what I had assumed. More than adding new structure, it needs to be about subverting existing structures before they fail. Not to teach, but to listen.

To achieve that you need to monitor the role of entropy in how your team operates – a kind of early warning alarm system that will give you a heads up before everything’s gone to hell.

So how can design leaders and teams approach this riddle? What’s the meta-process behind designing an effective team process? As with any design problem, let’s begin by unpacking the underlying factors in more detail.

The perils of a curious mind

Who tends to do well at Intercom? That is, what traits are common to people we’ve hired who have gone on to be really successful? That was a question we recently asked ourselves when thinking about improving how we recruit and interview new candidates. When it came to Product Designers, one trait emerged more clearly than any other – curiosity.

We poor distracted souls attempt to survive the ravages of the internet by putting in place various rules and processes

It stands to reason that curiosity would be an asset for designers. It helps them generate new ideas by building connections between existing ideas, understand how their designs are received so that they can iterate and improve upon them, draw on other parts of the business and keep learning in an industry where everything is constantly evolving.

All of the best designers I’ve worked with have been innately curious and yet, curiosity can be a liability as well. All of us who choose to dine at the trough of the newsfeed know this only too well. I am not here to deny that videos of Japanese marble runs and Wikipedia articles about Austro-Hungarian con artists are fun. In fact, that’s just the problem, they are like catnip for the curious mind. But we all know what curiosity does to cats.

BTW, have you seen this little jungle cat? OMG.

Anyway, we poor distracted souls attempt to survive the ravages of the internet by putting in place various rules and processes to keep ourselves focused. The Pomodoro technique, Getting Things Done, bullet journalling, todo apps (so many todo apps), inbox zero … Welcome, my friends, to the wonderful world of productivity porn.

Delivered with earnest intent to protect your precious productivity from the instant gratification monkey in your brain, the general idea here is that having a process and sticking to it is the only way to get real work done. Not to mention the warm and fuzzy feeling that comes from having a checklist of shit you’re definitely going to get done. Maybe just after a quick check of your Twitter mentions …

What does this have to do with design leadership?

I’ve noticed a similar tendency amongst design managers who take over a new team. Faced with a group of creative, diverse and curious individuals whose work may either beautifully cohere or spiral unpredictably at any moment, design leaders see the need to bring focus. So they react in a similar fashion to checklist-makers. They apply productivity thinking to their team and how they go about their work. They implement a – pause for dramatic effect – Design Process.

But wait. Before the inevitable design awards start rolling in, you need to choose a process to follow. Just like the world of productivity porn, there’s no shortage of well-worn solutions to choose from – iterative design, Stanford d.school’s Design Thinking process, the double diamond approach, Google Ventures’ design sprints, a full third of all Medium posts ever written.

design thinking

Yet despite this embarrassment of options, most of us can’t help but roll our own solution that’s just right for how we work. Incidentally this is also why, despite the hundreds of todo apps that already litter the App Store, developers can’t seem to stop making new ones.

I thought I needed to come up with one-process-to-rule-them-all

Confession time. This is the approach that I fell deep into as I started to build out the design team at Intercom. I thought I needed to come up with one-process-to-rule-them-all that everyone should conform to. Like I said, I thought that was my job. Looking at Medium, I don’t think I was the only design leader who felt this way.

It’s not surprising that new design managers, many of whom come from a background of being practitioners themselves, tend to rely on their established skills to tackle these problems. Good designers see basically every element of existence as a design problem to be solved. It’s an affliction. So of course how a team should work is reducible to being yet another design problem to which there can be an elegant solution. I used to design products, now I design teams that design products. Same thing, essentially.

It should be said that this is entirely reasonable at some level. You do need some structure in place in order to keep everyone on the right track. In fact, if you don’t have some form of process in place, you’re negligent as a leader.

It’s all about finding a balance. If taken to the extreme, a process-heavy approach runs the risk of managing designers in the way factory workers of old were often regarded as resources to be optimized, rather than the creative problem-solvers they really are.

A short history of management

Conceived by factory manager Frederick Taylor, scientific management was the first big idea to sweep the corporate world in the early 20th century. Its big idea was to maximize efficiency by setting precise targets for workers and rewarding them accordingly. In contrast to previous models, workers were paid for their output, not their time. Their every action was monitored and their output was measured with military efficiency.

Whereas earlier factories were chaotic, collaborative workshop-like environments, the scientific management method found its physical manifestation in the form of the assembly line. Since the mass-production work in factories was, by definition, repeatable and identical, small tweaks to this process could lead to massive efficiency and productivity gains. This approach was the catalyst for much of the 20th century’s industrial successes: an explosion in global economic growth, the creation of a large and comfortable middle class, and unit affordability that enabled regular people to own cars instead of carts.

Design leadership as subversive activity - A history of management

It is, however, worth noting the effect on the individual and the changing nature of work. Under this new approach, efficiency was paramount, and workers themselves became like cogs in a giant machine. Many went from building things to building one small slice of a thing. It’s hard to imagine that an eight-hour-a-day bolt-tightener on the Model T assembly line felt the same sense of job satisfaction as his father may have felt after building a cart by hand. Not exactly the sort of environment that catered to the naturally curious.

Design leadership as subversive activity - history of management

Even as the workplace evolved beyond the factory line and the era of the office worker came about, many of the same attitudes towards management persisted. Faced with the task of managing large numbers of people towards a common, operationally complex goal, the simplest option remained to create strict rules and processes for everyone to follow. Once the machine is thus primed, you just need to run it.

But wait, it’s not all grim. You’ll notice that photograph of a factory is in black and white, and that’s because this is the past I’m talking about. So who shall save us from the bean-counting, TPS report-filing, boring-at-best, oppressive-at-worst regime of scientific management? Peter Drucker, that’s who.

Design leadership as subversive activity - Peter Drucker

Peter Drucker

Kirk to Taylor’s Spock, Drucker was also a management consultant, but he wasn’t all that much of a numbers guy. Instead, he emphasized managing by objectives, creating clarity for workers about the end results that management want and then getting the hell out of the way. Teams are the ones closest to the work, so it makes sense to give them the freedom to figure out the best way of achieving results. As Drucker put it, you’re all smart people, you figure it out.

Of course, there are many jobs, like building cars, that still benefit from a scientific management approach. These are, however, the jobs that will most likely be automated out of existence in the coming years and fine-tuned to extract even more productivity gains. It turns out that treating humans like humans and machines like machines is a pretty good management approach.

Drucker’s real insight was that being outcome-driven makes a great deal of sense in the modern office environment. He even coined the term “knowledge worker“ to define a role where creativity and problem-solving are more valuable traits than rote execution.

Minimum viable process

And so we return to curiosity. As we discovered when we looked at people joining Intercom, those most likely to succeed in an outcome-driven environment are those who are equipped with the curiosity and initiative to examine a problem and define their own path. Their job is not only to deliver an end result, but to figure out the most appropriate route by which to get there.

As for managers, their role is to set teams up in a way that permits them to be creative and curious. Even the most well-intentioned managers who are desperate to avoid accusations of micro-management, dutifully talk about “managing for outcomes, not outputs.” Their job is apparently to hire great people and empower teams by describing a mission, vision and clear a path.

You want guardrails, not a train track. It’s a balancing act

So why is the reality often different? Why do these endless design processes still exist? It’s not because your manager is a terrible person (and this is especially true if you work on the Product Design team at Intercom). It’s more likely because it’s so damn tempting. As I said, designers gonna design. But mostly it’s because it remains necessary.

Humans are most comfortable communicating with small tribes of other humans, not processing dozens of non-stop Slack channels. Coordinating successful modern companies requires massive levels of alignment and communication. Beyond a very modest scale, getting everyone pointed in the same direction requires some process, Drucker be damned.

Therein lies the art of process design. Not too prescriptive, but not too permissive either. Just enough direction to keep everyone on the right path but still enough slack to allow the innovative folks to go off piste. You want guardrails, not a train track. It’s a balancing act.

If that sounds tricky, the good news is that you don’t need to worry too much about getting your process exactly right. The better a process works, the more inevitable it becomes that you’ll need to change it anyway.

We’re getting close to the bedrock now. But there’s one last trick to this balancing act. You’re going to have to pull it off while sitting on the startup roller-coaster and that means that you’re not going to have to just get it right, you have to keep readjusting as you go.

Anti-entropic feedback

The only thing worse than no process is a static process. A static process ignores the fact that your company, team and product are changing all the time. A static process means you’re stuck doing the same thing over and over, while the world moves on around you. Ultimately, it means ignoring the fact that entropy exists.

“Entropy is the general tendency of all systems – natural and manmade – in the universe to ‘run down,’ to reduce to chaos and uselessness.”

What worked at one stage of our growth won’t work at the next stage

When I first read that definition I had a mini-epiphany. It was exactly what I was seeing with our teams at Intercom. Every time we scaled, our processes would break. It’s frustrating but I’ve come to learn that it’s also natural. Of course, what worked at one stage of our growth won’t work at the next stage.

I read that definition in a book about education by technology critic Neil Postman. The book describes “subversive teaching” as an approach oriented more around students questions than teachers answers.

Students are encouraged to question the status quo so that the teaching may respond to changing needs and doesn’t submit to entropy. The process looks for ways to break itself by constantly being submitted to anti-entropic feedback.

This flips the model. Here the role of the leader isn’t to teach, but to learn. Not to define process, but to facilitate evolution.

Design leadership as a subversive activity

So what might design leadership as a subversive activity look like? First, accept that nothing is set in stone. Reject dogma. View certainty as a bad sign. Focus on the outcome. Remind people of the bigger picture and what you’re trying to achieve, why you think your current methods are the best way to get there, and that they are just a means to an end. It’s the end that’s important.

Ultimately, it’s about leaders casting themselves as learners

Solicit change. At Intercom we perform company-wide surveys where we ask everyone how we should improve or change. Then we assess the responses and the leadership team puts together an action plan to outline the specific steps we are going to take. We publish the answers internally, describe what we’re going to change and then do it. We repeat this process twice a year.

It also comes from just listening to people. Whether it’s in a 1:1 session or our group design critiques, it’s often about just asking questions and being attentive to what’s no longer working so well.

Ultimately, it’s about leaders casting themselves as learners. Because just like a good designer should be curious about how their design performs so that they can iterate and do better next time, good leaders should be curious about how their teams work so that they can iterate that.

There is a crack in everything, that’s how the light gets in

As with most things, it’s about achieving balance. Lack of focus will have you noodling forever and an unchecked process will lead to entropy.

Grinding on efficiency can certainly get you pretty far but you need to leave room for curiosity to emerge and for new ideas to shine through. You need to be open to subverting what you just worked so hard to put in place.

And the best way to do that is as simple as constantly asking yourself: “How could we do this differently?”


Does this sounds like the sort of environment that you would enjoy? We are actively hiring – check out our openings.

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