What Oprah’s Leadership Journey Reveals about the Power of Authenticity

Oprah Winfrey isn’t just a public figure—she’s the wealthiest woman in the entertainment industry and the first African-American woman billionaire. But how did she rise from a daytime talk show host to a media mogul? What leadership skills did she develop along the way?

In this episode, Harvard Business School executive fellow Bill George explores the challenges Oprah faced on her path to success and how she overcame them. He explains how she shifted away from people-pleasing, found her unique voice, and embraced vulnerability as a key leadership strength.

Key episode topics include: leadership, entrepreneurship, race, media, TV, entertainment.

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• Listen to the original Cold Call episode: Black Business Leaders Series: Oprah’s Path to Authentic Leadership (2018)
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HANNAH BATES: Welcome to HBR on Leadership—case studies and conversations with the world’s top business and management experts, hand-selected to help you unlock the best in those around you.

Oprah Winfrey is not only a public figure—she’s the wealthiest woman in the entertainment industry and the first African-American woman billionaire. But how did she rise from daytime talk show host to media mogul? And what leadership skills did she cultivate along the way?

In this episode, Harvard Business School executive fellow Bill George breaks down the challenges Oprah faced on her leadership journey. You’ll learn how she overcame her tendency to try to please other people and found her own voice, rather than emulating other media personalities. And you’ll learn why she leans into vulnerability as a leader.

This episode originally aired on Cold Call in January 2018. Here it is.

BRIAN KENNY: See if you can name this person: North America’s first multi-billionaire black person, and the greatest black philanthropist in American history. Serial entrepreneur who combined business savvy with showmanship to revolutionize an entire industry. Recipient of the Presidential Medal of Freedom and honorary doctorates from Harvard and Duke. Author, publisher, Oscar nominee. But before all of that, rural Mississippian born to an unmarried teenage mother who endured poverty, abuse, and prejudice in the deep south. This is a true rags-to-riches tale about a person known and admired throughout the world by one name only: Oprah. Today we’ll hear from Professor Bill George about his case entitled, “Oprah!” I’m your host, Brian Kenny, and you’re listening to Cold Call.

SPEAKER 2: So we’re all sitting there in the classroom.

SPEAKER 3: Professor walks in …

SPEAKER 2: And they look up and you know what’s coming. Oh, the dreaded cold call.

BRIAN KENNY: Bill George is an expert on leadership, a topic that he teaches and writes about extensively, including numerous books, articles, and business cases. Bill, thanks for joining us today.

BILL GEORGE: Thank you, Brian.

BRIAN KENNY: I’m going to ask you to start by stating the obvious who’s the protagonist in this case and what’s on her mind?

BILL GEORGE: Oprah Winfrey, and what’s on her mind is being responsible for your life and how you use your crucible for personal growth to achieve a great life.

BRIAN KENNY: Mm-hmm. And so what prompted you to write this case?

BILL GEORGE: Well, I was writing concurrently my book, True North now called Discovering Your True North. And we had a whole section on crucibles and it seemed this captured it perfectly. And I had a chance to interview Oprah over dinner in 2005 at the Nobel Peace Prize ceremonies.

BRIAN KENNY: Wow.

BILL GEORGE: And it was a rather unique opportunity to spend three hours alone with her. Photographers were coming by and snapping photographs. She didn’t even look up from them. And she wanted to tell me her whole story going all the way back to her childhood, all the way to the fact that she had chartered an airplane filled with books to take to Africa where she’d started a home or school for children and spent 30 million of her own money.

BRIAN KENNY: So when you talk about a crucible, can you sort of put a definition on that? What do you mean by a crucible?

BILL GEORGE: Crucible is that really difficult time in your life when you come face-to-face with who you are at your most basic form, the things that are really important in your life, but you only discover it when you’re faced with existential questions like, who am I, what’s the purpose of my life, why am I here?

BRIAN KENNY: Mm-hmm. So let’s talk a little bit about Oprah’s past. I’m sure everybody would love to hear what she was like over dinner, and I’m sure she was lovely, but probably also a little intense given her stature in the world. But where does that come from? What was sort of the formative things in her life as she was growing up?

BILL GEORGE: Well, she grew up to an unwed mother, very poor family in Mississippi. And the thing that saved her was what she called BTU, Baptist Training Union. She would go to church and as young as three and four, she was citing biblical verses and all the sisters sitting in the front row of a African-American church. And they were saying, “Oh, this girl is gifted.” And she got this idea that she was something special. And the thing that opened her life to the outside world was learning how to read and read books because she had no exposure to the world outside of poverty in Mississippi and frankly ranked discrimination in those days. It was a very rough place to grow up. And this was her refuge.

BRIAN KENNY: So she was born in 1954, is that right?

BILL GEORGE: Yes. Mm-hmm.

BRIAN KENNY: In the deep south. Post-World War II, racial prejudice was still very, very common in that part of the country in particular. She migrated back and forth. Talk a little bit about her experience moving between homes.

BILL GEORGE: Well, when she was nine, she went to follow her mother to Milwaukee. And that turned out to not be a good experience. And she was sexually abused by a relative, by an uncle, and cousins. And repeatedly so much so that she got to thinking, “Well, this is just the way life is.” That’s her statement. And a real tragedy. She wasn’t prepared for this. And then at 14, she had an unwanted child. Unfortunately, that died in childbirth, but it was just a real tragedy to go through this and be abused like that. And in those days, we didn’t recognize and make public the sexual abuse the way we are today. And I, for one, think it’s a very good thing for this to come out. I think the behaviors of many of our celebrities, political leaders and others are abominable and the treatment of women, and it’s held women back from leadership roles in many sectors of our society and something that deeply concerns me. So in part, this case gives some visibility to that too, of h