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Art of Leading

Jim Hollingshead

“I Look For People With Mental Agility” | Jim Hollingshead, President and CEO of Insulet Corporation

May 6, 2024

Jim Hollingshead, President and CEO of Insulet Corporation, a medical device company, shares his key leadership insights, offers top advice to executives, and emphasizes the importance of hiring people with mental agility.

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


Q. What are the qualities that you value the most in the people who work for you?

A. I’m looking for people with mental agility who can connect the dots. Obviously, they will have their area of expertise. But I want people who are enterprise thinkers—people who are curious about how the whole business works so that they can think broadly, have a fresh set of eyes to ask good questions and engage with the team in a highly collaborative way.

You want somebody who doesn’t need to get their way but has an opinion. I tell everybody on my team that when you come into a team meeting, you should have an opinion and be ready to voice it, but you’re not trying to win an argument. We want to know what you think. I’ve seen executive teams where some people want to focus on their patch and don’t feel like they have a right to have an opinion.

But at the top level, everybody should be thinking about the whole business. One of my mantras with my executive team is that we’re all in the whole business all the time. We’re not running in silos. We’re all marching to the same goal, and we’re all coming to the room with a point of view about whatever topic we’re talking about. And we’re here to have a conversation and collaborate to get to an answer that is the best possible answer. We may not all agree with it, but it’s the best possible answer we can get as a team.

Q. Given that you want those kinds of executives on your team, how do you hire them? What questions do you ask?

A. I usually start by saying, “I’m a lousy interviewer, so what I want to do is just get to know you. I’ve got a couple of questions for you, but mostly, I want to chat and get to know you a little bit. Tell me how you got where you are and why you’re interested in us, and then let’s leave some time so you can ask me whatever you want to ask.”

It’s a little disarming for people. For me, it’s about getting a gestalt of the person, like how they talk about themselves and what they’ve accomplished. Are they very hierarchical and like to lead from positional power? Are they claiming a lot of credit or giving credit to other people? I hire people who want to be collaborative.

Q. What were the early influences that shaped who you are today?

A. My dad was an engineer. We lived all over the world when I was young, including Japan and the UK, and I started to see the world through different sets of cultural eyes. Then, my parents divorced when I was ten. I learned to pretty much fend for myself from an early age, and I started living on my own when I was 16 because my mother moved, and I wanted to stay at my high school. I wasn’t on the street or anything. My rent was paid, and I had an allowance. But living on my own helped me build a kind of stubborn resilience, a resilience to almost prove people wrong.

So that made me pretty tough-minded. If we set a goal, we’re going to hit the goal. Although we all have our moments of insecurity, I have pretty strong self-belief and a healthy disrespect for authority. If somebody says, well, this is the way it’s always been done, or this is what experts think, I’ve always reacted with, “I need a better reason than that.”

Q. What was a key leadership lesson from early in your career?

A. I’m very analytical, and I’ve always been able to quickly connect the dots and see what’s wrong with something so that we can fix it. As a young consultant, I would almost get mad if something wasn’t as efficient as it should be. At one point, a partner I was working with closely approached me and said, before we had one of our European operations meetings, “Every time you walk into that meeting, you come across as so negative. When you walk into meetings, I want you to focus on your emotional stance. Focus on how you want to come across.” That has stuck with me, and it’s made me more effective.

Q. And when you give advice now to other executives, what theme comes up most often in those conversations?

A. Generally speaking, I often coach people to be aware of the other side of the coin of their strengths. Somebody may have risen to their role because they’re super analytical, but now they must pay more attention to emotional leadership. And sometimes, I see that people need my permission, as CEO, to shorten the list of stuff their team is trying to do. Often, I see senior executives who have their teams working on 50 things when they probably should be doing four. So I’ll help them see that focusing on a shorter list of stuff that you nail is better than trying to do more things and not getting them all finished. It’s better for the team, and it’s better for the business.

Finally, sometimes executives lack self-confidence, even at senior levels. It’s interesting how often my job is to say, “Hey, you’re doing the right thing. Keep going, I’ve got your back, and you’re doing great.” I might add some specific coaching, but often, they need somebody to tell them to be courageous and go do that thing they’re pushing on.

Q. How would you complete the sentence, “The hardest part of leadership is…?”

A. Because of social media, you’ve got massive scrutiny in an environment where our culture is more sharply divided than at any time in my life. Social media throws gasoline on the division and immediately broadcasts anything anybody wants to say.

As an executive in a public company, you are under so much scrutiny all the time about so many issues, and social media is like a minefield. It’s true for anybody in leadership, but it’s especially true for public company CEOs. The way to manage it is to be clear about your organization’s purpose so you can say, this is the issue we’re focused on here.

These lessons from Jim Hollingshead, President and CEO of Insulet Corporation, are part of our Art of Leading interview series featuring powerful insights from top leaders. 

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