The Courage of Despair

Leadership calls for making tough choices. They’re often unpalatable; this is part of what makes them tough. People dislike change, especially when it requires trading predictable (even if less than ideal) outcomes for the unknown. But sometimes progress calls for a bold leap forward, regardless of how terrifying it seems. What to do?

In The Art of War (5th century B.C.), Sun Tzu wrote:

When you surround an army, leave an outlet free. This does not mean that the enemy is to be allowed to escape. The object is to make him believe that there is a road to safety, and thus prevent his fighting with the courage of despair.

The courage of despair. Archetypical image: Cortés’s ships burning off the coast of Veracruz; his men’s choices reduced to pushing into the unfamiliar or dying alone, marooned. A powerful situation that instigates coherent action; not a hectic, desperate flailing, but a single-minded drive towards a particular direction.

A tricky move to pull off. Cortés’s men probably hated him after he eliminated their path back to “safety.” How do you get people to continue following you after such a gesture? You craft a new identity. No longer a group of rag-tag mercenaries with disparate aims; we’re now a tribe hell-bent on survival. (Again, Sun Tzu: “When I let go of what I am, I become what I might be.”) For this to work, everyone must be committed to the new path — the leader included. After his order was carried out, Cortés, too, was stranded.

I’ve most often experienced the courage of despair in its opposite: the irresoluteness of confidence. A formerly successful team continues operating as before, even when their context has changed radically. Instead of facing the facts and starting in a bold new direction, the leader hedges his or her bets. Unable to grasp — and act on — the urgency of the situation, the team continues in “business-as-usual” mode; their options gradually whittle away; their former cash cows become emaciated. When the moment of reckoning arrives, they’re unprepared. Catastrophe ensues. (I’m ashamed to admit: I’ve been the waffling leader.)

There’s no fighting “as if” your life depended on it. It either does, or it doesn’t. In today’s world, most leaders will not be called on to turn choices into literal life-or-death scenarios. But fostering courage and action will sometimes call for closing off comfortable choices in favor of moving towards new, unfamiliar directions.

Dealing With Organizational Politics

For some kinds of problems, it’s essential that you think through what you’re doing before you work out how you’re going to do it. Common sense, right? Unfortunately, it’s not the norm. Too many designers still start projects by formally exploring directions before they’ve nailed down answers to key questions:

  • What distinctions will this solution impose on the situation?
  • How do those distinctions help/hinder the path to user satisfaction?
  • How do the organization’s governance structures affect our ability to create distinctions that support the user’s journey?

This last question is the most challenging for designers since it requires that we delve into territory many of us would rather leave unexplored: organizational politics.

Political struggles result when individual groups try to further their own agendas while serving the organization’s overall goals. Groups (and their leaders) compete and cooperate with other groups for resources and attention. Through the choices they make, they try to position themselves to achieve influence and power. Given enough scale and resources, all organizations exhibit some of these power dynamics. In some cases — but not all — these struggles can become toxic, affecting the performance of the organization and the people in it.

Many designers complain about having to deal with political forces. But dealing with politics is not only part of the job; it’s also a sign of maturity: The point of design is effecting change, and the only designers who don’t have to deal with politics are the ones who aren’t causing real change in their organizations.

Note this doesn’t mean designers should merrily go along with highly dysfunctional situations. Life is too short to deal with that sort of thing. But it’s important to acknowledge that design can disambiguate complex situations, leading to clarity and better decision-making for everyone involved. Understanding how power dynamics work — and embracing the reality of politics — is essential for designers who seek to effect real change in their organizations.

The Role of Design in Strategic Decision-making

People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.

— Steve Jobs

Strategy calls for making choices. That means saying “yes” to some things and “no” to others. The latter is the harder of the two.

Leaders often face options that seem equally compelling but are mutually exclusive; choosing one means forgoing the other. Economists talk about the opportunity cost of a decision: the potential value we give up when we choose one option over another. Let’s say you have enough budget to invest in one of two promising projects. The opportunity cost of choosing project A is whatever value project B would’ve generated. If it turns out B’s value would’ve been higher than​ A’s, you made a poor choice.

How do you know?

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Design Strategy Inside Out

Today, design is seen as a key function inside many organizations. For recently-minted designers, this statement may seem trite. “Of course design matters,” they will wonder. “Why wouldn’t it have a key role in the creation of products and services?” Well, design wasn’t always as central to business as it is today. Many people (including me) attribute design’s current prominence to Apple’s resuscitation in the late 1990s, its emergence from the ashes, and eventual domination of the tech market and beyond.

Wired magazine cover from June 1997.

Design played a central role in Apple’s comeback, and the business press gave it its due. But before this, many people inside organizations saw design as being in service to either marketing or surface decoration. One result of Apple’s back-from-the-dead story is that many large organizations today value design — and not just in the superficial sense of making things more attractive, but in the deeper sense of design as engine of coherence, engagement, innovation, and brand loyalty.

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The Value of Mapping Semantic Environments

You hear about it all the time: an accomplished designer joins a large company to lead their design efforts, only to leave disillusioned and frustrated after a relatively short stint. These are smart people and great designers. They’ve come into the situation with the best intentions and have put their credibility on the line. This is not the outcome they wanted.

When you talk to them, they’ll tell you corporate politics ground them down, or that there’s too much inertia in the company, or that design isn’t as valued in the organization as they thought it would be, or that they’ve lost executive support. These things may all be true, but they’re all symptoms of a deeper issue: the leaders (and their teams) haven’t mastered the organization’s semantic environments.

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Fielding Ambiguity

When I was a student, I had a very dualistic understanding of how the world works. Architectural projects were either the-best-thing-ever or utter shit. There was no in-between. I venerated the designers of glorious projects, overlooking their flaws. I assumed the people who made shitty ones were completely clueless. Why would they make such crap?

Now that I’ve been working for a long time, I understand designers don’t have complete control over the work. Ambiguity is the norm; the “right” answers are often only right in retrospect. Some people leave; new ones join. People change their minds. Teams get reorganized. Conditions change. Incentives change. Learning to be effective under such conditions is not easy. We crave clarity and resolution, and often they’re not on offer. But learning to deal with ambiguity is essential to maturing as a professional designer.

Whenever I find myself in an ambiguous place, I take a step back to make an inventory of what I do know about the situation. (This will often take the form of a mind map or other such visual information dump. Stickies and a whiteboard are useful tools in this context.) I look for specific areas where I lack information. What has changed? What do I know I don’t know? How can I find out? What can I infer from the things I do know? (Of course, there’s also stuff I don’t know I don’t know. Knowing that offers some relief.) If other people are in the same situation with me, making these inventories together can help relieve some of the uncertainty, and remind me I’m not struggling alone.

Taking steps towards clarifying the situation is always preferable than letting it paralyze you. The process can even prompt you to reframe the problem you’re dealing with, bringing some degree of relief — if not closure.


Responsibility. How does this word make you feel?

I suspect many of us find it heavy and burdensome. If something goes wrong and somebody says you’re responsible, you don’t feel very good. Suddenly a weight is on you; it’s “on your shoulders.” If you’re responsible, you’re expected to work towards resolving the situation. It may cost you — time, money, cognitive effort, reputation, etc.

On the other hand, responsibility can be liberating. If you’re responsible, that means you have agency over how things turn out. (By definition, you can’t be responsible if you can’t influence outcomes.) Choosing to act responsibly means acknowledging your power over a situation. It also means complying to wield that power within a series of constraints agreed with others. For example, we say people are “responsible citizens” when they choose to fulfill certain civic duties. When given a choice, they act in a way that may inconvenience them but ultimately benefit the community. (E.g. serving jury duty.) Responsibility requires clear choices.

When you design an information environment, you create an architecture of choices. You give the people who use your environment agency; response-ability. Do they understand the degree to which they’re responsible for their experience within the constraints you’ve established? How does this make them feel? Are you working to empower them or burden them?

What Are You In Service To?

“What are you in service to?” This is one of the most important questions I’ve been asked. I was taken aback the first time I heard it. “I do my job, right?” Nope. That’s not what it means. What are you (ultimately) in service to? Bigger picture. As in, what’s the change you want to instigate in the world? How will your contribution make things better?

I’m in service to enabling healthy societies that serve the needs of people in sustainable ways. My area of expertise — where I can contribute to making this vision real — is crafting information environments. Every year, more of our social interactions move from physical environments (such as buildings) to information environments (such as websites, apps, and other such digital systems.) I help design these things so they create contexts that serve human needs. This is what I do, but not why I do it. I do it because ultimately I’m in service to well-functioning societies.

My “in service to” statement motivates me. I want my children to have rich, long, fulfilling lives. For the world to be better for them, it needs to be better for everyone. The work I do can help move us in that direction. But the direction must be clear if we’re to move towards it. (As the Lewis Carroll wrote, “If you don’t know where you are going any road can take you there.”) I’m lucky to have found what I’m in service to, and aligned my skills towards it. It gives my work purpose and meaning — essential for going the distance, especially when things get tough.

What about you? What are you in service to?

Team Moods

I was once part of a team that was going through a rough patch. We’d been through two reorganizations in eighteen months — not good for morale — and now we’d had a sudden change in leadership. (Which is to say: we found ourselves with no leadership.) There was no vision of the future, no clear lines of responsibility, no accountability. People were leaving — out of their volition and otherwise. It was a mess.

This team included some of the brightest people I’ve worked with. All of us found it very difficult to get anything done. We’d spend more time talking about the state of the team than about the work. We were worried about the future of the company and — of course — our jobs. It was an unpleasant experience for all; I remember the sense of relief when it ended. (The team was dissolved.)

If you’d been able to travel back in time to when I first joined the team, you would’ve gotten a very different picture. We were cracking then! We had a clear vision of what we were doing and who was responsible for what. We had competent and committed leadership. We had deadlines. We had the support of the company. It was exciting work! I have vivid memories of a celebration party the night we launched our first release. Everyone was exuberant.

Same group, two very different situations. In one, we were paralyzed; ineffective. In the other, we were at the peak of our productivity. What changed?

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