Bob Pittman (chairman and chief executive of Clear Channel Communications) in “The Corner Office”

PittmanAdam 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 Bob Pittman, chairman and chief executive of Clear Channel Communications. “There’s always another point of view somewhere, and you need to go back and find what the dissenting point of view is.”

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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Were you in leadership roles when you were younger?

I started as a radio disc jockey at age 15. I needed a job to pay for flying lessons. That was my passion. I tried to get a job at the men’s clothing store in my small town in Mississippi, because that’s where all the cool people worked and hung out. I was too young. I tried to get a high-paying job bagging groceries for the Piggly Wiggly grocery. There were none. Then I went to the radio station. Bill Jones, who owned it, said: “Do you have good grades? Do you stay out of trouble?” I said, “Yeah.” He said, “Go read this copy.” He listened to me and said, “O.K., you’re hired.” I got completely hooked on radio, and my first management job was in Pittsburgh when I was 19. I got to program a radio station there.

How many people were you managing?

Maybe 10 or 12. I didn’t know how you were supposed to manage people, so I was not bogged down by the conventional wisdom. What I realized I was doing was becoming a team leader, not a general. We were not going to have the military model, because when you’re 19, no one’s going to accept you as the big boss. I was the team leader, so my job was to sell them on my idea, and to keep selling them, and then listen really well, let everybody have a voice and let there be some dissent. That really developed the style that I’ve had forever.

Tell me more about how you encourage dissent.

Nobody’s in an ivory tower, and let’s figure this out together. Often in meetings, I will ask people when we’re discussing an idea, “What did the dissenter say?” The first time you do that, somebody might say, “Well, everybody’s on board.” Then I’ll say, “Well, you guys aren’t listening very well, because there’s always another point of view somewhere and you need to go back and find out what the dissenting point of view is.” I don’t want to hear someone say after we do something, “Oh, we should have done this.”

I want us to listen to these dissenters because they may intend to tell you why we can’t do something, but if you listen hard, what they’re really telling you is what you must do to get something done. It gets you out of your framework of the conventions of what you can and can’t do.

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

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