Took over a design team losing two people a month. Eighteen months later, no one had left.

At 7:30am on January 13, 2022, I thought he was joking. His second text told me that two other peers of mine were also laid off. Then, as if on cue, an invitation came for a 1:1 with our Director of Product that started in 10 minutes. I joined the call feeling like I was about to empty the contents of my stomach, to learn that my fate was not only safer, but the opposite—I was getting promoted.

In fact, I was getting promoted into my past manager’s job… sort of.

When I was hired at WHOOP, the design team was in hypergrowth. I was designer number 7, interviewing other candidates on my second day, and we grew to 21 designers within my first two months. Our design director quit after six months, the talent she hired began to quit in droves, and we started losing two designers a month. In January, a restructure laid off three more people to bring us back down to 12. The design manager role was abolished in favor of 4 hybrid player-coach roles, including myself.

Despite my forced pathway into management, I found a new fire in my gut helping other designers regain their confidence and their relationships with stakeholders. I wasn’t great at it at first—I was too empathetic and not holding the line on quality—but those turbulent times made me realize I wanted to fully lean into the role. In June, I made a case to our new VP of Product for a full-time management role and a backfill for my IC work, tied to a 30-60-90 day plan we co-designed. I was promoted in July, and slowly regrew the team over nearly two more years.

Starting in the full-time management role, I ran workshops with our team to define a crisper vision of how our work serves a greater goal to advance the business, and how we as individual designers seek to show up in our work. I finalized these statements after gaining that input, to mobilize us around.

This person just told an amazing, user-centered story in under two minutes. With about 25 of us crowded in a room covered in an explosion of post-its, markers, and sketch pads, I excitedly started going off about what a perfect example his story was: how well he distilled the complexity of his group’s ideas, with a storytelling arc that got us excited about the impact we could have on their main character’s life. He told me later it was one of the first times he felt he genuinely learned something from a brainstorm.

This workshop took three hours during one of our quarterly onsites in Boston, when the remote team synced travel to be in HQ for planning. I started running these workshops as a senior designer when I saw room to push our creative confidence in front of the whiteboard. As my role grew, it became an exciting expectation that we would always spend a couple of hours a quarter stepping away from the daily grind to speculate wild futures, retrospect on hardships, experiment with a new skill, or consider new ways of working.

Before WHOOP, I worked at large companies where I could pull from established design practices. At IBM, the collaborative approach was ingrained long before I was trained on their take on design thinking. That meant no need to explain why we did things a certain way, but if you broke from the standard activity list, eyebrows went up for doing it “the wrong way!”

Coming to WHOOP, I embraced the creative freedom. Folks certainly did not lack creativity, but I saw patterns of complaints: teams lacking focus, ideas not getting actioned, and quieter voices feeling they couldn’t get a word in. I see workshops as a way to invite structure to how we collaborate.

The pushback I got was that I was sometimes too structured, and needed to invite more flexibility and nimbleness.

So I brought in feedback requests after every session, and each quarter a group of managers and I adapted our onsite schedules to it. All in all, I facilitated over 30 workshops with a huge share of the company, with teams like Software, Performance Science, Strategic Finance, Marketing, and Business Partnerships.

WHOOP had embraced continuous learning through weekly rotation calls between PMs and members, but we weren’t better off in how we supported the researcher function. After losing our third UXR in less than a year, leadership put a hold on hiring any more, inside a hiring freeze across most of the company.

I’d rather take on the weight of conducting research first-hand than see us innovate without a collective understanding of user needs. But this wasn’t just about getting research onto the roadmap. It was about inspiring every decision-maker to feel ownership of hearing what users think and do, so our next UXR would join a team that matched their excitement.

Here’s the road I took to make continuous learning a habit at WHOOP.

This spin on “teach a man to fish” was shared during an interview with a prospective senior designer. She didn’t choose us after a landslide approval from our panel, but I’ll never forget how great her interview cycle was. I conducted over 100 interviews as a hiring manager, and created an abundance of resources to help scale our team with focus and structure.

After assessing skill gaps early in 2023, I pitched a hiring and career development plan that highlighted an imbalance: we were highly capable at visual design, yet only a few could go deep in UX methodologies. That created an obsession with how things look over how they work. The last hiring cycle I led introduced a new distinction, UX Designers, with more emphasis on critical thinking and human-centered practice. Drawing on my time building talent acquisition technology at IBM, I built the system below.