Learning leadership in a design thinking workshop

When I first fell for design thinking, I fell hard. In the third month as a civilian, after 14 years of buttoned up service in military structure, and two days into our fellowship at Stanford’s d.school, we got our first taste of a design thinking workshop. It was a relatively simple challenge — something like, design new programs for Stanford student centers — and their version of structure to tackle this challenge felt like sweet freedom to me. The environment they created, the diverse team they brought together — fellows from the medical school, journalism school, and the ten of us from the d.school — and the process they modeled were all meticulously crafted to mine the best out of our creative and critical thinking capacity. Over the past few years of practicing design thinking as a participant and facilitator, I’ve come to find that it doesn’t just guide a group to develop more creative products and services, it is also a great incubator for developing the character traits of a leader.

Great facilitators change the assumed power dynamics in a group. From the traditional model where the teacher, or person standing at the front of the room has complete authority and absolute knowledge, to a more egalitarian model where the facilitator moving around the room is there to moderate a process, but the participants can all step into leadership roles throughout the activities. Typically, design workshops are a lot of fun. People ‘warm up’ — the group may start the workshop playing games, establishing familiarity. Improv activities are a personal favorite. But this appearance of breeziness and fun, the sprawling on bean bags, the casual dress, the ephemeral post-its, doesn’t tell the whole story. There’s a lot on the line in these workshops. Businesses use them to develop new products that have to result in an increase to the bottom line, governments use them as a way to improve services and show a material improvement in the lives of their citizens. During that first workshop with my peers at the d.school, the games and foam chairs and the relaxed attitude of our facilitators was necessary to help us bring our best. Smart people were competing to look the smartest, and simultaneously not sound dumb. The improv games helped us through a lull in brainstorming. The instructions to go listen to the users of the student center — the students themselves, helped us place them and their needs at the center of conversation, and decenter our own sense of self-importance, or the need to author the best plan.

Over that first year in the design thinking community I found that the best participants in workshops — those who were the lynchpins to teams developing the best prototypes for products and services — were the people who best embodied the traits of curiosity, selflessness, humility, and courage. When a mentor asked me what about the fellowship might be applicable to leadership education in the military, it made me think about those four character traits, and how design thinking workshops might be a place to hone them.

Leaders use a commitment to curiosity everyday. They are curious about what they don’t know, they’re curious about the biases or pre-conceived beliefs that prevent them from spotting great team members, market busting ideas, and even the problems that could sideswipe them if left unseen. Curiosity can be fun discovery and painful self-awakening, but it’s never dull. The more curiosity a leader has, the wider and more diverse the ideas and friends they have, the more successful they are likely to be.

The initial phase of a design thinking process should alway starts with user research — in person. Building empathy for users through interviews with them and observation of the context of the challenge you’re working on is the best way to really understand a problem. Getting out from behind a desk and into the field builds empathy, or, at least it should. Designers who have a deep curiosity for their users and the problem they are solving will be able to push past their own biases of the roots of the problem and how a user might experience it. Building one’s muscle for curiosity, means that as a designer you hold a state of wonderment and intrigue for people and challenges, rather than default to promoting your own opinion or needs.

The second phase of a design thinking project involves a set of exercises to synthesize the findings from the user research, drawing insights from the experience with users to refine the team’s focus on a specific need. It’s really easy for teams to draw quick conclusions, and instead of looking from their users point of view, frame a need that echoes their own. The synthesis stage is generally when the biggest pivots happen. Sometimes teams have to face the uncomfortable reality that their users don’t need them, and they might be actively harming their users. This has happen often in the international development community. Outside teams come into a country, intending to do good, and often decide themselves what the local community needs and deliver ’solutions’ that actually make conditions worse. Great designers cultivate a sense of selflessness as they approach this work. They work to keep their focus on the users’ needs — no matter the implication to them or their team. Ultimately, that honesty is a service both to the users and the designers.

Teams find the third phase — brainstorming ideas to serve the users’ need — to be an extremely experience — fun and joyful, or the opposite, dull and terrifying. The teams that find joy in coming up with ideas for solutions often look like they’re performing improv. In fact, improv exercises are routinely used to ‘warm up’ a team, to get them in the frame of mind and body to start riffing on ideas related to the design challenge. You can’t try to look good in improv by coming up with some awesome idea and saving it for when it’s ‘your turn’. Brainstorming can make fools of us all, but the genius of it, is that one person’s silly idea can be the inspiration for another person’s genius solution. Designers have to come to the work with a sense of humility. They’re not focused on their individual performance, but rather the production of the team.

In the final phase of design thinking projects, teams develop prototypes of the most promising ideas and test them with users. Great teams orient themselves toward learning, not a performance of perfection. Learning as much as possible, as fast as possible, usually means making the first prototype with cheap materials like cardboard, putty, and colored paper. Learning means asking users to see where the prototype fails them, listening to their perceptions of their experience. This is really hard for most people. We want to explain to someone why they should love the thing we built for them, we want to show off something beautiful. But in order to develop a solution that really works for users, the design team has to have the courage to try out different ideas knowing full well they will fail in some way. They celebrate the ways in which a prototype fails — that teaches the team so much more, in a phase of their work when they can still make adjustments, than if they had hid away for months trying to make the ‘perfect’ product. It takes courage to stomach the sense of risk and volatility in opting for stress testing iterative prototype versions, but the result is a far more useful and adaptable solution to the user’s needs.

Having a lived experience of leadership in a lower stakes setting, like a design workshop, is the equivalent to sparring before boxing matches. No fighter entered the ring for a real, scored match without several sparring sessions. Learning leadership by lecture is like akin to imagining you’re prepared to fight after talking through different punch combinations. Learning leadership is a physical, emotional, social set of lessons as much as it is cognitive. I remember sparring the guys on my Naval Academy team. They were super friendly and really welcomed me on to the team, and that meant they were happy to beat my ass when we were in the ring together — it made me better when I went to the tournaments. In the sparring sessions I learned where my weaknesses were — getting stunned with a few power punches to the face is a real motivator to go back to the mirror and practice, to get out on the track and keep growing my cardio base. Sparring was where i learned how to read an opponent and adapt my fight strategy. And besides, no girl ever hit me as hard in a fight as those guys did during practice. They made me ready.

Leaders need settings to practice challenging their ego’s, reading a group’s nonverbal signals, identifying their own biases and pushing past them. Design workshops are especially good for that, because it’s a space where the highest level performance won’t emerge based on demand. You can’t order a group to produce creative work. There must be a culture of trust and respect in order to create the kind of environment where people feel simultaneously vulnerable enough to voice even crazy sounding ideas, and confident enough to play with and consider crazy sounding ideas even while holding legitimate criticisms.

Over decades, Pixar has consistently produced movies that hit #1 at the box office, which is an incredible run considering the extremely unpredictable nature of their work. It takes years to make a movie, millions of dollars, and it can’t be taken back and tweaked after its release into the world. The pressure riding on each project to be perfect, and perfect in ephemeral ways — funny, entertaining, widely appealing — is stunning. Their founder and CEO, Ed Catmull, wrote about his job as a leader of this team, “The way I see it, my job as a manager is to create a fertile environment, keep it healthy, and watch for the things that undermine it. I believe, to my core, that everybody has the potential to be creative — whatever form that creativity takes — and that to encourage such development is a noble thing. Instead of saying, ‘The writing in this scene isn’t good enough,’ you say, ‘Don’t you want people to walk out of the theater and be quoting those lines?’ It’s more of a challenge.” He models the epitome of curiosity, selflessness, humility, and courage leading his team to creative success. Design workshops are a microcosm of Pixar’s creative environment, and an ideal setting to practice living in to those leadership traits.

I would love to hear your thoughts and feedback.

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