Thrown Into Management: Lessons Learned Leading Thumbtack’s Design Team

I joined Thumbtack in July of 2015. I’d been at a consulting firm for seven years, and Thumbtack’s mission of connecting people to local small-business professionals really spoke to me.

But six weeks in, my VP of Design decided to leave, and I suddenly found myself in charge of leading the design team. On top of that, I became responsible for tripling its headcount by the end of the following year.

Over the next 14 months, my team would grow from 5 to 18, from single-discipline to multi-discipline, and from flat to stacked. But with just six weeks at Thumbtack behind me, I had no idea how I was going to get through that next year.

I learned many lessons, but two stand out as the most important ones that helped me and the team get unstuck and get moving: build trust (quickly) and keep the team engaged once that trust is in place.

Here’s a cheat sheet of Audrey’s tips for new team leaders:

Build trust (quickly)

1. Listen to the team and generate a shared set of priorities instead of creating plans solo.
2. Invite candor with your own honesty and ask for honest feedback in return.
3. Connect as humans by learning about one another’s lives.
4. Be humble and vulnerable, and admit it when you make a mistake.

Keep the team engaged

1. Find your pulse-takers to tip you off to your team’s emotional state and where your energies are needed most.
2. Provide perspective on the great work that individuals do and your team’s impact on the world.
3. Remove friction in team processes so people know what to expect as you grow.
4. Reconnect with rituals that support camaraderie outside of work.

Here are a few stories and tips that helped my team find its footing and gain momentum after such a big change.

Build trust (quickly)

The team had only known me for six weeks, which means they didn’t know me at all and didn’t have any reason to trust me. There was no way they were going to rally just because I told them to. I needed to build trust quickly, and these four basic principles helped me gain their confidence so we could all get to work.

1. Listen

When I first took over the team, I wanted to jump into action right away. I wrote up my 30/60/90-day plan and was ready to go. There was so much to do! But one of my colleagues had the foresight to stop me and say, “Audrey, you’re missing a really important step. I think you need to just listen to them.”

I took that advice to heart because, in the past, I’d been on the receiving end of leaders who didn’t listen. I knew that if I wanted to get my team to a good place, solutions couldn’t just come from me. So I put my plan aside and scheduled one-on-one conversations with everyone on the team. I asked each of them: What’s been frustrating to you? What do you think could be better? What’s something that you’re excited about right now? Then I summarized that feedback in a team meeting, and together we looked at the short list of things they liked and the longer list of things they thought could be improved. Together, we brainstormed solutions to the highest-priority items, and that became our new, shared 30/60/90-day plan.

The team felt like they had been heard and, most importantly, they felt shared accountability for getting our team back on track.

2. Invite candor

Early on, a few designers were still reeling from the sudden change in leadership and questioning everything they knew, including me. There was one meeting when I saw eyes darting back and forth, and I felt their skepticism so deeply. When it was over, I just thought to myself, “Ok, what’s going on?” I dragged the designers into a room, sat them down, and said, “I really want your open and honest feedback. I can sense your skepticism, but the only way we’ll get better is if we do it together.”

I started by sharing some of my own observations, fears, and concerns, and they quickly followed with theirs. Sometimes it’s difficult for leaders to know when to be completely candid and when to soften things, but in this case, candor opened up an important conversation. I demonstrated that I would be open and honest with them and expected the same in return.

3. Connect

A few new designers joined around the time I did, and as a team, we hadn’t yet connected outside of our day-to-day work. I wanted us to be able to relate as people, so early on, I asked each designer to create a slide about themselves and present it. They talked about where they grew up, why they became a designer or a writer or a researcher, and what kinds of things they loved.

I also took a tip out of the oldest playbook there is and broke bread with them. The team came to my home for dinner, and I introduced them to my husband, my son, and our small dog. It seemed like a small thing, but it went such a long way that now I try to do it at least once a year.

In another example, we once started a team offsite with an artifact exercise where everybody shared an object that represented a pivotal moment in their lives. One team member brought in an old, tattered letter from his mom that he keeps folded up in his wallet to remind him of who he is and where he’s from. Another team member brought in a headlamp from when her parents shipped her off to Outward Bound to rid her of some bad teenage habits—a trip that changed her life forever. I brought in my son’s first footprints and talked about how being a mom changed how I wanted to show up as a leader.

All of these moments added up, giving us empathy for one another as people and not just coworkers.

4. Be humble and vulnerable

This is a tough one. Over the last year and a half, there were many moments when I had to embrace humility and admit my mistakes. And learning to do this is especially hard when one can already feel so vulnerable as a leader.

At one point, our team had grown so much that I was completely underwater. I knew my next hire needed to be a manager to help share the leadership load. I wrote up a job req, posted it, and updated the team in a quick two-minute snippet in our weekly meeting. I didn’t think for a moment that anyone would question it because, to me, it was such a no-brainer.

But I was wrong. About an hour after the meeting, one of the designers came up to me and said, “Audrey, that wasn’t great. People are pretty upset that you glossed over such a big decision without getting their input. This decision will have a big effect on their lives too, and you didn’t even bother to have a conversation with them.” I knew he was right. I immediately called a meeting in the design studio, and the first words out of my mouth were “I was wrong. Let’s talk about it.”

We spent 45 minutes talking about the role and what it meant for everyone. I also shared how much I needed a manager’s help, describing what my day-to-day was like and why a manager would be beneficial to the team as well. Being able to say “I was wrong” helped me regain some of the trust I had so casually cast away just hours earlier.

These tactics are nothing new, but they were exactly what helped my team gain momentum in those early days.

Keep the team engaged

Once we got moving, I needed to keep it that way. Thumbtack was growing and changing so quickly that my team would get lost if I wasn’t careful. So I shifted my focus to keeping the team engaged.

5. Find the pulse-takers

When you’re leading an organization, your calendar doesn’t allow for a ton of one-on-ones all the time, and it was difficult for me to maintain a constant read on the emotional pulse of the team. So I picked a few of the more tenured members of the team who were tapped in, and I regularly checked in with them. How was the team doing? I relied on my pulse-takers to give me an honest take on how the team was feeling and what I might be missing. And in doing so, not only could I learn where my energy was most needed, but they also became more aware of and felt more accountability for the team’s well-being.

6. Remove friction

Team engagement can’t happen when there’s friction. When we were a small group, it was okay that we were a melting pot of patterns and processes, all approaching things in a slightly different way. But as we grew, we needed to establish patterns that took the guesswork out of how we do things as a group.

For example, we documented our best practices for giving and receiving feedback to relieve some tension that had been growing among team members. Once we wrote down our best practices and had a conversation about them, people were able to align around shared expectations.

We also wrote out our team values: a list of things we expect from one another as we show up as team members and approach our work. Again, by documenting these, team members—old and new—were able to rally around a common set of patterns and expectations.

7. Provide perspective

Teams can get lost in the day-to-day details. They lose perspective. So one of the most important things a leader can do is to show them that they’re doing great work and that it has a significant impact on people’s lives.

A designer once told me he felt like he hadn’t done much in the eight months he’d been on the team. I couldn’t believe what he was saying because I had the perspective to see how many great things he’d created. I immediately went on the team’s shared drive and pulled a bunch of the design work they’d finished that year. Those images went into a huge slide deck, and I clicked through each one during our end-of-year offsite. As I did, I could see their eyes light up. They’d actually forgotten all they had accomplished, during a year of immense growth and change, no less. Creating this moment to stop and reflect is now a yearly ritual.

We also instituted a design showcase every other Friday where designers can share their work with colleagues. It’s not a crit, there’s no feedback, there’s no time for Q&A. It just lets them get excited about the work and see their contribution to the team.

And most importantly, I help my team members connect their work to its significance in the world. They have to hear firsthand that their designs are allowing a first-generation immigrant to make a living as a plumber and support his family. Or that our product allowed a man to quit his HR job at Yahoo and become a landscaper full-time to pursue his passion for plants. These are true stories. I try to connect our designers’ work to a greater bottom line, one that helps the company have an impact on a national scale.

8. Reconnect

The last point I’ll make about engagement is that it’s not just about the work. It’s about building ongoing camaraderie and affinity with the people you spend so much time with.

When we onboard designers, we ask them to sketch a bit about themselves: their favorite food, their secret vice, their superpower, what they believe great design to be.

Every Monday, we do a creative ritual as part of our weekly design sync. It’s about 15 to 20 minutes long and has nothing to do with the work. Whether we’re sketching blind contour portraits or designing a space cruise ship together, the team gets a moment to just have fun and laugh together.

And like most design teams, we love our field trips. Right? We love reconnecting with our creativity and with design in general. We also just like to hang out without an agenda.

When I think back to those first 14 months as Thumbtack’s head of product design, I learned so many lessons—almost all of them the hard way—and there are sure to be many more down the road. But building trust quickly and keeping the team engaged were by far the most important because they served as the foundation for everything going forward.

Even today, we continue to build on the practices above, and I find myself coming back to them often. Because with trust and engagement in place, we can maintain the momentum we’ve gained and make the mark we’ve always wanted to as a team.