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Art of Leading

Owen Tripp

Talent “Beyond What Money Can Buy” | Owen Tripp, CEO of Included Health

April 16, 2024

Owen Tripp, co-founder and CEO of Included Health, shares his key leadership lessons, the importance of hiring for cultural fit, and why the hardest part of leadership is doing what’s unpopular.

This interview with The ExCo Group‘s Adam Bryant is part of our Art of Leading interview series. 


Q. What is your leadership playbook?

A. Number one is that I want to communicate with people in the same way I would want to be treated myself. I’ve had the benefit of working in much larger organizations and in individual contributor roles. What I’ve always admired about certain leaders and desired in all contexts is clear communication, where I get treated like an adult and understand why we’re doing something.

Second, surround yourself with the best people that money can buy, and even beyond what money can buy. The “beyond what money can buy” part is important because when you’re an entrepreneur and don’t have a lot of money, you’re out there with your tin can and your stock options, and you’re trying to get anybody to pay attention to you.

You have to make a level of personal commitment and investment in people that they will experience, in effect, as their own form of treasure. It’s saying to somebody, “I’ll give you a salary and some stock options. You can probably make more elsewhere, but I’m going to invest in you as a human being, and I’m going to try my hardest to make you better than where you started.”

Q. How do you hire? What questions do you ask in the job interview?

A. Once we determine somebody has the skills, I focus on how people show up around ideas and challenges. People have described working on our executive team as being on the set of an Aaron Sorkin show like West Wing. It’s very fast, very debate-driven, very witty, very logic-inspired. So knowing that people can process at that speed with us is really important.

You want to have different styles on a team—and a lot of research and literature supports that—but we have found that people need to operate at the speed of the rest of the executive team because our pace of work and decision-making is very fast.

I also want to know how people have responded and will respond, to stressors in life and what qualifies as a real stressor. I want to understand what constitutes a bad day for you and what constitutes a moment where you had to change and think about something in an entirely new and different way. One of our company values is that we value change. We accelerate through change curves. Understanding people’s comfort with that sort of transformation is really important.

So, I will ask people for examples from their lives. It could be a professional or personal change because, in this dynamic, I think people show up the same way at work and at home. So I will ask, when did you have your plans changed? When did something work out differently than you expected?

Having a little adversity in your life is not a bad thing. You wouldn’t wish that on people, but you also want to see how they channel it. I’m highly allergic to folks who think that the world is conspiring against them and that the only reason they haven’t gotten something they want is because things have been thrust upon them.

Q. What were important early influences for you?

A. I’m one of the two middle kids in a four-kid family. You can probably draw your own conclusions on negotiating at the dinner table to ensure that I got enough food and was keeping my parents’ attention in all the right and most healthy ways. We were a family of very high academic expectations.

My parents were and are in fields highly connected to the community’s social good. My dad was a doctor, and my mom was an educator. I saw them actively reinvesting in their communities and showing that their work had a purpose.

My social circles were quite different. I had two groups of friends. I had my highly science-driven, slightly nerdy crew. We did a lot of taking things apart and rebuilding them. Then I had my sports friends. I was a big baseball player. I can point to a lot of inspiration from both those groups today. I felt more at home with my nerdy friends, but my philosophy around leadership comes from sports and playing on teams.

Q. What are a couple of themes that come up most often when you are mentoring other executives?

A. The first one is that I often see a bit of a superhero complex in people newly promoted to senior executive roles. Earlier in their career, they were probably rewarded for doing what nobody thought could be done—they led the team into a particular conquest and emerged victorious.

Rarely in those early stages are leaders recognized for letting other people lead, investing in their growth, and developing a leadership philosophy. Yet that’s exactly what you need them to do for their next phase of growth. You must learn not to play “hero ball” anymore and look for ways to bring people along.

Second, you must move on quickly from talent that isn’t performing for you because they will hold you back like a boat being chained to the bottom of the ocean.

Q. What do you think is the hardest part of leadership?

A. It’s doing what’s unpopular, especially now. We have many mechanisms in society and inside corporations to quickly vote on whether we like or feel good about something. Yet some of the most important things that need to be said aren’t going to get a lot of reactions like that.

They may not feel comfortable or agreeable, probably because they’re not particularly provocative or opinionated. But sometimes, the important things that need to be said are sort of neutral. They’re not really that spicy.

It’s about setting a moderate tone and being pragmatic and practical, which isn’t necessarily going to drive a lot of engagement. So that’s what I think is the hardest thing about leadership—doing what’s unpopular or being willing to deviate from what’s in vogue.

These lessons from Owen Tripp, co-founder and CEO of Included Health, are part of our Art of Leading interview series featuring powerful insights from top leaders. 

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