I Worked In Construction. You Learn To Just Fix Problems And Move On.

Tracy Young, the co-founder of TigerEye, a sales technology company, shares key leadership insights with Adam Bryant in this “Art of Leading” interview.

Q. What’s your approach to leadership? 

A. My leadership style is authentic and vulnerable. It wasn’t always. I made enough mistakes early on in my last company, PlanGrid, where every single day I was in the biggest job I’d ever done. I was trained as a construction engineer. I knew more about HVAC systems and the tensile strength of steel than I did business. I felt like I had tricked the whole company to be able to lead them, so I suffered from massive imposter syndrome.

I would spend days prepping for our all-hands meetings. I made beautiful decks with crazy animations, and I would even write in jokes because I thought it was my job to entertain the team. At some point, we were experiencing so many problems that I didn’t have time to prep for the all-hands, and I had to go up on stage.

So I just talked about the problems we were experiencing. I talked about what I didn’t know, where I thought the risks were, and I asked the team for help and they responded. That was the best all-hands I ran over the four years I was leading the company.

I learned so much in that moment—that the team just wants to hear from me. It really taught me that this is actually the leader I need to be. And it was a lot easier because I didn’t have to spend all this time preparing. I could just talk openly with them.

Q. There is a balance that you have to strike of being open about the challenges while also inspiring confidence. How do you think about that?

A. There is a balancing act. I remember when I was pregnant with my first child, and after four months, when I was starting to show, I told the team that I was going to have a baby. Everyone said, “Tracy, we know.” I asked, “How did you know?” Because I wasn’t showing that much.

One of my teammates said, “I watched you eat two bagels this morning.” I realized in that moment that the team is always watching their leader and trying to figure out their mood. They’re trying to figure out whether they should answer a recruiter’s call. They’re trying to figure out if this business is still viable and whether to pour their heart and soul into it.

For me, it’s about bringing the team on the journey.

So the balancing act is to be willing to talk about the problems but also be willing to listen to potential solutions and then showing the team that we can make decisions. For me, it’s about bringing the team on the journey. When I do make a decision, I explain to them how I got there and what we’re going to do, and then I give people an opportunity to push back. Otherwise, the expectation is that everyone is on board for moving the company forward this way.

Q. How else has your leadership style evolved over the years?

A. I listen a lot more than I used to. I probably tried to talk more early on to compensate for something. But I learned that I’m just a better leader if I am able to listen to people on the team and understand what their obstacles are and whether I can unblock them or connect them with someone else on the team to help them move forward.

Q. At a tactical level, how have you become a better listener?

A. Our first core value at TigerEye, my new company, is wholeheartedness. When we feel overwhelmed or when we’re trying to juggle too many things in our minds at once, we aren’t really listening. So it’s about being present in whatever we’re doing at the moment.

Q. What are your other core values? 

A. Humility is one. We are all experts at something and we are amateurs at everything else, and so there is no room for big egos or showboating. Kaizen, the Japanese philosophy for continuous improvement, is another, and we use it a lot for when something is not quite there.

Trust is a core value. Trust is everything. Without it, we can’t build good products together, and we won’t work well together. We have to give each other trust by default and do everything we can to protect the trust that’s been given to us. And simplicity completes the list. We have to make the simplest possible version of our products so they are intuitive and beautiful. And that includes internal processes. Why have ten steps to do something when we can do it in two steps?

Q. What were important early influences for you?

A. I’m the first one in my family to be born in America. My parents are refugees of the Vietnam War. While I was growing up, we were often just slightly above the line that separated being really poor and homeless.

They worked hard and saved enough to move us into middle class. I watched my parents work seven days a week and they had two jobs for many years so that my siblings and I could have a better life than they did. I didn’t know what a vacation was until I was 18 years old.

Q. How do you hire?

A. I’m looking for our core value of humility. People work remotely, and so I’m also looking for excellent communication skills down to the emails that are coming back to me. Can you stay present as you hear my questions and answer them simply? Those are really important beyond the technical interview. I also like to ask about their parents. What do you admire about them? What did you learn from them?

Q. There’s so much disruption and uncertainty now. What prepared to be able to lead in this kind of environment? 

A. I learned a lot from my time working in construction. You diagnose problems and you just fix them. There’s no point in spending much time talking about them. Yes, you always need to be searching for the lessons, but it’s so unproductive to beat yourself up over things. There’s just no point. What is our reality today? If there’s a problem, you fix it and move forward.

We have to allow ourselves to be human, of course. These negative things happen all the time and it’s okay for us to feel sadness or anger or other negative emotions. But what we can do is shorten the duration. Let yourself go through those feelings, and then it’s game time to fix the problem.

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