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The New Hollywood Leader

Oprah Winfrey on Leadership

by David Brownstein

Hi there, Just saw this interview with Oprah in The Hollywood Reporter. I’ve excerpted the most interesting parts.

What intrigues me is that she outlines the changes that occur when creative people start a business, that becomes successful and impactful. We’re all challenged with learning new skills and habits as our organization grows. Read on for what Oprah learned from her 29 meals with Nelson Mandela.

PS: I’ll be curious to see what any of you think about this. Agree, Disagree? I’m not sure I agree with her final comments about doubt. What do you think?


Hollywood Reporter: As you grew up, did anyone mentor you, especially in the business arena?

Winfrey: I didn’t have a lot of mentors, you know? I happened into being a businesswoman. It has never been a goal of mine, and I wouldn’t necessarily even say it’s a strength of mine.

But you’ve been so successful in business.

I have to really work at it. I have to work at disciplining myself. The business of the business tires me out. What I would rather do is just stand out there, in front of the camera — or not in front of the camera, ‘cause it doesn’t matter to me if I’m talking to a flight attendant or an audience of 10 million people — about concepts, ideas, principles that cause people to have these "Aha!" moments. That is what I am. At heart, I am a teacher. But I’ve made a lot of mistakes.

Can you name any?

The biggest mistake in the beginning was not understanding that you need infrastructure and systems in order to run a business. And that there’s a reason why there’s a hierarchy in reporting systems in business. You can’t handle a business like friendship. I started out with four or five of us, and then there were eight, and then there were 22. And I kept trying to manage it as though there were still the four of us. And it wasn’t until 1994 that I actually brought in someone to be president and organize the systems. I was a crazy person, trying to do it all.

How do you find the right people?

I used to do for every employee — now I have 700, so I can’t — but I used to do what I call "the gut check." I would just spend a few minutes doing my own emotional check of how I felt about this person, whether I sensed their honesty. Now, honestly, there are people in the company I probably haven’t met. Our building, Harpo, is like a campus. We have a main building where the studio is, and then I have five other buildings. So it’s possible that you’re working in the dot-com (Oprah.com) and I’d never see you.

How do you keep good people?

People tell me the reason they stay here is because of, uh … me. And also because of the mission. A vast majority of the people understands that we’re not just doing television and haven’t been for quite some time. And a vast majority of the people is here because of the principles by which we do television.

Do you have an inner cabinet?

Well yeah, I call it my kitchen cabinet, composed of people who’ve been here over the years, who have grown to be more than employees. People whose opinions I trust. Maybe six or seven people. Whenever there’s a major decision to make, I gather those people in the conference room.

Have you been in a situation where one of them really strongly disagrees with you about the direction of the company?

No. Because, there really is only one direction, and that is to keep getting better. (Pause) Well, let me think about that. … Well, you know, we’re constantly debating around here (about) the balance of the shows. For example, I’m not keen on celebrities, and celebrities sell. That would be, probably, in terms of disagreement (the main arena). My whole career has been based on being truthful in the moment. And if I have to pretend to be interested in something that I’m not interested in, it doesn’t work.

Who, as a moral authority, guides you?

Elie Wiesel would be a person that I actually consider a friend and a moral authority. Nelson Mandela. Years ago, I was asked to come stay at his house. I spent 10 days and had 29 meals! And I was a nervous wreck.

It’s very interesting that you counted the meals.

Twenty-nine meals! And I was so nervous about it. "Oh my God, what am I going to say?" And Stedman (boyfriend Stedman Graham) brilliantly said, "Stop worrying about what to say. Why don’t you just listen?" And that’s what I did. And my favorite moment with Nelson Mandela was sitting alone with him, for an hour or so, in his study, reading the Sunday paper, both of us having tea and not saying a word.

Did he teach you anything about leadership?

His humility is transforming. I don’t know if it taught me or if it solidified what I already knew. The greater the power, the more humble you can afford to be.

Do you have doubts?

About what?

Yourself? Life?

No, I don’t have any doubts. I really don’t. Because I live in a very spiritual space — not a religious space, but I live in a spiritual space where I understand the connection that we all have with each other. It’s not just rhetoric for me. I really do understand the common denominator in the human experience.

What'd You Think?

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