Corner Office

This interview with Mark Nathan, C.E.O. of Zipari, a health insurance software company, was conducted and condensed by Adam Bryant.

Q. What were your early years like?

A. I grew up in a small town, Delmar, outside of Albany, N.Y. I was always building stuff, like forts and BMX trails. They were big projects. We would spend weeks building a trail, or forts with two or three stories. It would always take a bunch of people to get them done.

I was pretty industrious as a kid. When I was around 10 years old, I would take a wheelbarrow and wagon and go door to door to collect people’s old newspapers. This was back before people recycled in their homes, but there was an industrial market for recycling newsprint.

I had my whole garage filled up with newspapers tied into bundles. And I put them in the back of our station wagon to take them to the port. I’d get about $15 per carload, which was a lot of money back in 1978.

I then created a company when I was 16, selling high-end stereos directly to people. I’d deliver them, set them up, and people would still pay 30 percent less than they would in a store.

My core values come from my mother and father. My father was a brilliant man, and could have been a doctor or lawyer or anything. But he wanted to work 9 to 5 for the state so he could be home more with his family. They both were involved in all sorts of charities. My mom really taught us about networking. She can talk to anybody.

What were some early life lessons for you?

I had a philosophy teacher in 11th grade who said something that always stuck with me. He said, “There are all these definitions and types of intelligence, but the one that I like the most is the ability to adapt to an environment as quickly as possible.”

I always think about that and look at people that way when I’m hiring. Can they adapt into this different environment? Can they step into a role where they’re not necessarily comfortable, and how long does it take them to adapt?

What about your college years?

I wanted to do liberal arts, but I studied electrical and computer engineering. I figured I could pick up literature on my own. So I set a goal for myself, through all seven years of undergrad and grad school, of reading 50 literature books a year — Kafka, Balzac, Dostoyevsky, all the classics. Doing that helped me get a particular job later on, because I was able to show them I wasn’t just a technical guy.

When was your first management role?

It was in my first job out of college. I was 24 and managing about a dozen people. That’s when I first started developing my style. In the morning, I would go around to people and ask if they needed anything to help them do their jobs. And I’d do that again in the afternoon.

Tell me about your leadership style now.

I don’t really believe in firing people. Although it’s necessary at times, nine times out of 10 it’s usually a hiring problem. Nobody likes to fire people, so I try hard not to have to get to that point.

I see it all the time, where somebody is brought into a role because we needed to fill it quickly, and we kind of take a pass on checking whether they’ll fit into our culture.

But when you fire someone, not only does it hurt the person, but it hurts their family, it hurts the co-workers who liked that person, and it creates fear. So there’s all sorts of damaging ripple effects.

I like to say that nobody ever comes up with a brilliant idea while they’re being chased by a lion. You need to create an environment where people can be themselves. So now when we hire, we’re really cautious. We have a hiring manager, and there are also four of us who screen for cultural fit.

I look at people’s aspirations, such as where they want to get to, and then I figure out how to get them as close to that as possible. Once I do that, then their productivity goes up dramatically because all of a sudden they’re doing something they like.

I’m also very direct about what I expect from people. People know that I’m going to say it how it is, and I’ll tell people how I think they should be doing better.

I found that I learned the most from managers who told me the really tough things that I didn’t want to hear. So I tell people I’m mentoring that there’s one rule when we meet: Put on your Teflon. Because if you really want to grow and you want to learn, put on your Teflon because I’m going to tell you things that nobody else is telling you.

But some people do take that kind of feedback personally.

I don’t mentor those people, because I know it’s going to go in one ear and out the other. It’s going to affect our relationship, and it’s going to make it awkward at work. If you don’t want to learn, don’t learn. But you’re also not going to be a leader. You’re not going to be growing.

Tell me more about your hiring process.

I always use the same question when I meet people after they’ve interviewed with others at our company. The first thing I say is, “So what have you learned today?” And that’s it. Their answer could be about the technology, the product or the company.

I’m looking for two things: how they communicate, and whether they’re honest with me. Being honest with me is important, especially when you’re in a technology company. If you have 10 people working through a problem on a whiteboard for two hours, you can’t have the whole premise of the work be wrong because of a bad assumption at the outset. So I really need people, especially engineers, to keep things factual. If you don’t know, no problem. Just say you don’t know.

What career and life advice do you give to new college grads?

I’m a big believer in grabbing new opportunities, especially if it’s a new challenge that will add to your repertoire. You’re going to switch jobs many, many times in your life.