collaborative design, wilderness, and the call to lead

For the most recent project in my bootcamp, I was in a group with two other designers and we had three weeks to execute a re-branding and re-design of a government agency’s landing page.

At the end of the three weeks, each group presented its work. In the whole class, there were only two groups of three. The rest of our cohort worked in pairs. At the end of each presentation, my instructors asked each person one of two questions:

Where did you compromise? What was the greatest challenge?

The responses orbited around differences of opinion about certain styles - button color, typography, navigation elements, etc.

And while competing opinions on aesthetics might have been the largest hurdle for a pair, in the group of three, we had a challenging enough time sharing interface elements that we didn’t reach the point of discussing aesthetic differences.

Why was it so difficult to collaborate? At 29 years old, I am proud to say that I am still reflecting on group dynamics and honing my leadership skills. Every time I learn a new lesson in this essential soft-skills area, I am reminded that human to human interaction, very much like human-computer interaction, is a lifelong process.

The first time I learned something distinct and significant about leadership was in 2009. I was with a group of twelve other young men (17-22 year olds) in the desert. We were trekking through Grand Staircase-Escalante National Monument along the Escalante River. (Side note: this is an area with immense cultural and historical value to American indigenous peoples and it is in danger of natural resource exploitation. I would like to point out that this anecdote is a testament to the power of wilderness in shaping leaders and cultivating values. Grand Staircase-Escalante National Monument deserves our protection. Let’s move on.)

This final expedition along the Escalante River was the capstone of the Semester in the Rockies, a program with the National Outdoor Leadership School (NOLS), and it was a thirty-day backpacking trip consisting of mostly cross-country (off-trail) travel.

Around day ten or eleven, our NOLS instructors were giving us more freedom. Often, we set GPS coordinates for the next day’s camp, then split into two smaller groups, each with a designated leader for the day, and the instructors and the two groups made their way independently across the desert, through side and slot canyons, up and down the mesa, to the designated rendezvous.


The most essential feature of these independent travel days was the group structure. Every night, a leader either volunteered or was appointed by the instructors. The leader planned the route for the day, wrote a description of the various features that would act as navigational cues, and had to be prepared to make decisions in case of any unexpected situations or emergencies in the execution of the route.

One evening, after we had eaten a fulfilling dinner of backcountry Pad Thai - spaghetti noodles lathered in a homemade peanut sauce of Jiffy and Sriracha - it was time to pick leaders for the following day. One of my peers volunteered for group A, but group B didn’t have a leader. I had already volunteered some days before and I was reluctant to lead again, mostly because I wanted to stare up at the crystal clear Milky Way with a full stomach and a Nalgene bottle of hot water tucked into my sleeping bag with me.

“Come on, Tom. It’s going to be a good day to be a leader.”

A phrase that will live in my memory forever, spoken by the leader of Group A, convinced me that I ought to take the opportunity to exercise the leadership muscle.

So I shrugged off my star-gazing laziness and wrote up a route plan. In the morning, I set out with five others down the canyon from where we had camped. The goal was to navigate the canyon as long as we could, until it narrowed to an impasse or an opportunity to scramble up the few hundred feet to the mesa presented itself.

One of my team members was lagging behind for most of the morning and when it came time to make the scramble up to the mesa, he revealed why he had been so slow. Earlier in the morning, just before leaving camp, he had vomited and then had diarrhea in quick succession. Now, three or four hours later, he was dehydrated. Not ever a fan of heights, my team member’s vertigo was amplified by his queasiness and the dizziness that accompanies dehydration.

Getting him out of the canyon and up to the mesa would be time consuming, but the risks were manageable. We shuttled his pack from bottom to top, so he could manage the scramble without the extra weight, a couple of us double-running three hundred feet, first with our own gear, then with his.

The mesa was exposed to the sun’s full majesty, which didn’t help with his exhaustion. We found a lone juniper, and made him comfortable in its shade while he rambled somewhat nonsensically (not a good indicator).

All of a sudden, I found myself leading of a group with a dynamic medical scenario that was nearing an emergency.

Like my friend had said, “A good day to be a leader.”

In the end, by leveraging the unique qualities of every member on the team, we were able to rendezvous with Group A and the instructors. Over the course of two days, we scheduled an emergency evacuation and our peer was flown out of the desert to the nearest hospital. He recovered in a week. No harm, no foul.

This memory sticks with me because it is a testament to the nature of leadership, a nature that the speaker and intellectual Simon Sinek makes very clear in a number of his lectures: leadership is not about power or control, it is about sacrifice. A leader’s responsibility, first and foremost, is to her team.

If you are going to lead, you had better really want to lead, because when it comes down to the brass tax, leadership is work. More work, in most scenarios, than any other position on a team.

Flash forward nine years. I’m out of the desert and back in a classroom. I have eight years of group facilitation behind me and I am in a group with two men around my age, both of which I consider pretty cool dudes and would gladly have a beer and shoot the breeze with. Our task is to redesign the website for the United States Department of the Interior.


We got off to a great start. The phases of the project that relied on a single deliverable created as a group, such as red-lining the responsive states of the site, a heuristic analysis, brand strategy exercises, and building a style guide, we completed easily and without conflict. Opinions were shared and discussed. Decisions were made. All in all, we meshed well. None of us were too laid back or too uptight.

This ease of interaction had a flip-side. Not one of us volunteered to lead our group. Even as the project grew beyond our grasp, none of us expressed concern that we should pick a point person to act as a project manager.

And as quickly as a day’s cross-country mileage turned into a medical emergency in the desert, our website redesign became a complicated mash-up of three different versions of every interface element: three headers with different drop-down menus. Three footers with various content hidden or on display. Three container styles. Three caption styles. Various hamburger mobile navigation patterns, bottom tab-bar navigation patterns, slide-out and pop-up animations across three different prototypes.

We were all reluctant to step into the leadership role because we progressed far enough along without one.

We were hesitant to inject hierarchy into our very laid back dynamic.

The idea of a group leader appeared to threaten the organic nature of our group. But a purely organic ecosystem, like a jungle or a rainforest, is not a place with clearly identifiable patterns or atomic elements. We let our creative juices run amok, touched base as we felt we needed, and at the end of three weeks we were tangled up in three different species of vines and flowers and frogs and macaws, all of our own creation.

Having worked in and with groups for a majority of my twenties, I have developed an eye for group dynamics. I can see when an individual is hungry to be a leader, when a group is resistant to structure, and when a team is in need of an organizer or an organizing principle.

I could see our group needed a leader, but I was reluctant to step into that role. In the end, the mess we ended up with was more work to correct than the minor amount of friction it would have taken to elevate our trio from “super chill” to “well organized”.

Sometimes, I am waiting to see who else is interested in the leadership role.

Even if you’ve been a leader in ten groups, it is a mistake to assume a priori that you should lead the eleventh.

Other times, I hold off volunteering for a leadership role to contemplate the true responsibility and sacrifice necessary for success, and whether or not I have the capacity to fulfill the leader’s duties for the full length of the project. This time around, I was adverse to taking up the leadership mantel because I honestly thought if we communicated well enough, we could do without it. As it was, we threw together a presentation the night before our class and crossed our fingers.

To walk away from this project with the lesson of “It helps groups to have a leader,” is too thin of an analysis.

Upon reflection, I realized that the pitfall for me was thinking about the group and leadership in a binary way.

In my mind there were two options, “Step up as a leader” or “Let the group continue without structure.”

The double-diamond design thinking diagram emphasizes the use of convergent and divergent thought. Bringing aspects of a project together, blending and compromising (convergent), but also challenging ideas, breaking them apart, and presenting counter-arguments (divergent). I was only thinking about convergence and thinking about it from my perspective, “How do I bring this group together?” What would have been useful, and divergent, would have been to illustrate how far apart each group member was, and encourage a conversation about leadership to bring us back into one another’s orbits.

To start a conversation about leadership within a group is just as useful, if not more so, than stepping up as a leader. I assumed that my team was waiting for me to take the reins, when all of us as a group were really just in need of a good conversation about whether or not we needed someone to take the reins at all.

We are living in the golden age of design tools and collaborative software. It is easier than ever before to share wireframes and prototypes, to make notes in real time and iterate elements in a shared pattern library.

Without someone to direct all of that potential, these tools can end up serving as silos instead of creative meeting places.

At the end of the project, I wasn’t elated with the level of fidelity of our redesign or the story of our process that we presented to our class. Nevertheless, the most coveted characteristic of design thinking rings true here: in failure we learn our greatest lessons. And the most important aspect of UX design is clear: think beyond your own perspective to empathize with others. And that’s not limited to your users. It’s something we should all do, all the time, for every member of our team or organization.

✌️Last updated 
November 13, 2021