Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Shawn Jenkins, chief executive of Benefitfocus, a benefits technology company. He has found that being a C.E.O. resembles a flight instructor. “I’ve got to be willing to let you fail a pretty good amount, almost to the point of danger,” he said.

To read the complete interview as well as Bryant’s interviews of other executives, please click here.

Photo credit: Earl Wilson/The New York Times

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When you were a child, were you in leadership roles or doing entrepreneurial things?

I’m a single-mom kid, and my mother was a real estate agent — her pay was based 100 percent on commission — and we didn’t have much money. I don’t want to overplay that; everybody’s had to deal with things in their lives. But I do think about this a lot. Even in the speeches I give to our staff, it comes out — this sort of survival instinct that we needed to have in our family.

So, whatever leadership I might have had as a kid was probably shaped a lot by a sense that, “We have to work in this family, and things have to go really well today for tomorrow to be pretty good.” There’s no doubt that a fair amount of my willingness to step out and do something uncomfortable, which is an aspect of leadership, is born out of that necessity.

So what kind of jobs did you do outside of school?

I grew up in Daytona Beach, and as a teenager, I worked on deep-sea fishing boats. I was the third mate, then the second mate and worked my way up to first mate. It was hard work, and a bit dangerous, but it was immensely fun.

There’d be times when we’d be done fishing and heading back to the dock, and the captain would want to take a break. I got to a point where they would let me drive the boat. When I got my hands on that wheel, and the captain would go downstairs, and I was standing there by myself and driving the boat, even for 10 minutes, it was thrilling. It was addictive. I thought, “This is what I want to do.” In a sense, that’s what I am today. I like having the responsibility, and if something goes wrong, I’ll be held accountable. I’d rather be the one who picks the direction.

Other lessons later on?

I enrolled in an aviation program in Pennsylvania. I really enjoyed flying, and I learned a lot from the people who were testing my skills. One time, I was taking my check ride with someone from the F.A.A. to fly a twin-engine plane. In these kinds of tests, they do all sorts of things to see how you react to different problems, and you have to cope with them. I was probably 22; the test wasn’t going well. I had passed every test before then, and I thought I might not pass this one. I got mad at myself, and I got mad at him. “Let’s just go back,” I said. “This isn’t working.”

He said: “That’s not how this works. You don’t just say, ‘We’re going to stop.’ We’re in the air right now, Shawn.”

I said: “I know that. I can get the plane back. I just want to stop the test.” He said, “You’re not going to stop the test.”

I didn’t pass. After we landed, he said, “Now tell me what went wrong,” and he talked me through the whole thing. He didn’t discourage me; he didn’t beat me down; he didn’t make fun of me. But he didn’t let me off the hook, either. He said, “If you want to be a safe pilot, that can’t happen again, ever.”

In the work we do now, there’s a lot of pressure. And my leadership style with people is to be like a flight instructor, if you will. We’re both going to fly this plane, because there are two sets of controls. I’ve got to be willing to let you fail a pretty good amount, almost to the point of danger. You don’t yell at people, and you don’t pull the yoke away from them. The people who imparted a lot of wisdom to me never touched the controls. They kept letting me fly the plane myself, and just gave me little nudges.

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Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times’ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.comthat he started in March 2009. In his book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews with more than 70 leaders. To read an excerpt, please click here.

His more recent book, Quick and Nimble: Lessons from Leading CEOs on How to Create a Culture of Innovation, was also also published by Times Books (January 2014). To contact him, please click here.