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 Richard D. Fain, chairman and C.E.O. of Royal Caribbean Cruises. During the interview he observes, “I always find that you learn more by arguing with someone than by just agreeing.”

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

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Want Clarity? Learn to Play Devil’s Advocate

Bryant: Do you remember the first time you were somebody’s boss?

Fain: Yes, I had just moved to a company called Gotaas-Larsen. I was treasurer. It was 1975, and I was 28 years old.

Bryant: And you were put in charge of a staff of how many?

Fain: Forty, so for me that was a big change.

Bryant: Was it an easy transition?

Fain: Actually, I didn’t find it a particularly difficult transition for me. In my job before that, I had had a fair amount of responsibility but no direct reports. That actually proved to be good training, because I got things done by working with others, and had to beg or cajole to get what I wanted, since I was dealing mostly with people who were either my peers or my superiors. Because I essentially had no line authority, it was a question of gaining people’s willingness to work with me in most cases. So that served me reasonably well when I actually found myself in a position of some authority.

Bryant: So what was your strategy for getting people to work with you before you had direct managerial responsibility?

Fain: I’ve always believed in communication. Everybody has their own style, but what’s worked for me is just to be quite open. If you have an objective, you try to get others to share that same objective. I probably communicate more than most, and I would try to be explicit about what I was hoping to accomplish, and I also listened to what they wanted. I think people are always surprised if you actually listen to what they say.

Bryant: You find that most people don’t listen?

Fain: I’m often shocked at people who will get a question and don’t answer the question that was asked. And usually there’s a very specific question. It’s very much “this is what I would like to know.” And people very often respond with something quite different — “What I think you really must have been asking,” as opposed to answering the actual question.

In grammar school, I did that assignment where you make a peanut butter and jelly sandwich at home, then write an essay on how to make a peanut butter and jelly sandwich. And when we came to class the next day, the teacher had laid out peanut butter and jelly and bread and knives. “Now, exchange papers and follow the instructions.” And of course only about half the class was able to make a sandwich.

It was an interesting learning experience about how much you take for granted. So I listen carefully for exactly what people are saying, what they’re asking about, what their concern is, and I try to be direct when I answer them.

Bryant: What were the most important leadership lessons for you?

Fain: I’ll name a couple. I had been the chief financial officer at Gotaas-Larsen, and we were going through a bit of a transition. So for a period of time, I felt that I was really running the show. I didn’t have the title, but I really felt that I was making the key decisions. And then I was actually put in charge, and I thought, “Well, nothing is different.” And it was really quite shocking to me what a difference it made between being almost the boss and being the boss.

Bryant: And what was the difference?

Fain: There was a sense of responsibility, and the other thing was that everyone was looking to you not just for guidance but for responsibility. And so, when things go wrong, and they always do, you have to maintain your composure and not allow yourself to wallow in the problem. You have to show the confidence that gives everybody the sense that we’re all working to a conclusion and that there will be a good conclusion. And being able to convey a sense of confidence, even in difficult times, was quite a challenge.

One of the things that really brought this home to me had nothing to do with business. We took a group of bankers on a salmon fishing expedition to Laerdal, Norway, and Laerdal is just a magnificent place. It’s beautiful and the river is gorgeous. But this summer was particularly cold and damp. There were no salmon in the river. It was drizzly and miserable. And my wife took me aside after the first day and said: “Richard, you’ve got to stop apologizing for this. This is a beautiful place. Life is good, and you’re bringing all of us down.” And she was right.

Bryant: What about mentors?

Fain: One of my mentors was Jay Pritzker [the Hyatt Hotels founder and a former director of Royal Caribbean Cruises]. Jay was an extraordinary man. In all the time I knew him, I don’t think he ever agreed with me on any subject, ever. When we would have an important decision at the board level, Jay would be my No. 1 antagonist, and he would argue vociferously against whatever I was proposing and question me in a highly skeptical tone. He was good at it, and he would ask the penetrating questions for exactly as long as it took for any other member of the board to agree with him. And the minute anybody else started to pick up the cudgel and continue along the same path that he had just been on, he would say, “You know, I think he’s crazy, but we’ve got to follow Richard on this.”

It was fascinating. He loved to play devil’s advocate. I love to play devil’s advocate, so we were on much the same wavelength. I always find that you learn more by arguing with someone than by just agreeing with them. And I also realized early on that having to explain something to someone is often the best way to make sure you understand it yourself.

And so part of my management style is to play devil’s advocate. There are people who think that I sometimes forget the second part of the term, but I do find that I learn by arguing with somebody. I learn more about whether somebody really believes their point of view and has thought it through, and it also helps me clarify in my own mind the direction I’m going.

Bryant: There’s an art to doing that, though. You have to make clear you’re challenging people, not criticizing them.

Fain: The first prerequisite is that the person you’re dealing with has to be good at their job and has to have confidence in what they know. I actually find that I will argue more strenuously with those whose judgment I respect more. I’m fortunate that the people I work with are really top of their league. They have the self-confidence to stand up for what they believe. And, in many cases, I’ve worked with them for a long time, and they understand that’s how I work. I do my homework, and I will be challenging.

But assuming they’re successful in presenting their case, they won’t have a stronger supporter, and so it’s worth it. They’ve also seen me switch sides, when it is necessary to provoke a dialogue on the other side.

Bryant: How has your leadership style evolved over the years?

Fain: I understand better now that people sometimes have to make their own mistakes. I’ve always been a bit of a perfectionist, but sometimes messing up is one of the best lessons. And so I’m perhaps less likely than I was 10, 20 years ago to jump in and fix something.

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To read the complete interview and others, please click here.

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 Sunday Business section and on nytimes.com that he started in March 2009. To contact him, please click here.