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

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 how you can deal with an incredible trauma like she did and overcome it and turn that from a crucible into what we call post-traumatic growth. So you’ve heard us post-traumatic stress syndrome. That’s the downside. Many people come back from wars and they never recover, and this is always on their mind and high level of suicide. But I think if you can turn that trauma into growth, post-traumatic growth. You can become a great person like Oprah was. And that door is open for all of us.

BRIAN KENNY: Yeah, the case mentions what sounded very much to me, like a “me too” moment. We talk about the “me too” movement, but you describe in the case where Oprah is reading the opening entry in a book, again, back to the importance of reading in her life. And this author shares her own account of sexual abuse, and that was a real eye-opening thing for Oprah.

BILL GEORGE: Yes. She was actually on the set of doing a show, and she had a woman named Truddi Chase, and Oprah was 36 at the time. I think it’s important to recognize she was not a young woman at that time. She was well into her career. But Truddi Chase is actually holding a mirror to Oprah by reciting her own experience, which were virtually identical to Oprah’s. And this got Oprah so upset. She left the set, said, “Stop the cameras, stop the cameras.” They didn’t stop. They kept rolling. And eventually, she came back. And this was the first time that she realized that she was not responsible for what had happened. But for the first time at 36, she realized that, and that changed her whole career. Up to that point in time, she’d been, I’d say muddling along doing well, but trying to be something different than she was. Earlier in her career, she tried to emulate Barbara Walters, as she said, looking nothing like her, and almost the absurdity of that. And then at 36, she said, “I can be who I am.” And her message from that time forward on her show was, “You are solely responsible for your life and you don’t have to live your life to please others.” And Oprah’s weakness, which influenced her even decades later, was that she felt she had to please people and she had to be a pleaser rather than being her own person. And when she encountered this situation with Truddi Chase, she changed and she said, “You don’t have to please people.” And that she delivered that message to women and to men through her show, and that gave a sense of real power to her and to the people who heard her show. And from then on, her career just took off-

BRIAN KENNY: Amazing.

BILL GEORGE: … and escalated very rapidly.

BRIAN KENNY: So in all of your experience meeting with leaders from all walks of life, is it fairly common to find people that have overcome odds?

BILL GEORGE: Well, no one can say they all are, but certainly many of the greatest leaders of our lifetime. Look at a Nelson Mandela, look at a Martin Luther King, look at what they overcame. Going back into history, look at what an Abraham Lincoln overcame. And I think those that have actually have a deeper experience and they become more real and they no longer feel they have to put on a mask to please the world, but they can be their own person and be accepted as an authentic person. So this way of looking at life is core to my whole thought of authentic leadership. How can you behave as an authentic leader? Be who you are and not try to emulate Jack Welch or Oprah Winfrey or anyone else. Just be yourself. And that’s good enough. You don’t have to fake it to make it.

BRIAN KENNY: Do a lot of people rise to the CEO level without kind of having figured this out? Like, they get there and they say, oh, how did I get here? What do I do now?

BILL GEORGE: They sure do. And a lot of them are scared, but they act like they have a lot of power and they fake it to make it. And they try to put on a mask to be powerful when deep inside they’re maybe a scared little boy inside that’s fearing rejection, fearing being overpowered so they overuse their power. And oftentimes they reside in having a lot of money as being a sign of success rather than how people perceive them in their own organizations, people they work with every day. And I’d say a much greater criteria is do they touch the lives of people in their own organizations every day through their actions? Do they set a standard of values and morals and commitment to a mission? And that’s what great leaders do. They don’t try to tell you how great they are. In fact, they know that they have a lot of weaknesses and vulnerabilities. And Oprah recognized her vulnerabilities, and I think that enabled her to become a great leader because in a sense, vulnerability is power. She was no longer afraid of hiding these things, and she’s been very, very public about what happened to her. And I think that’s been one of her great sources of strengths and appeal to so many people.

BRIAN KENNY: Yeah. What is she like as a business leader? I mean, we see the public face of Oprah all the time in front of the camera, and she’s remarkable in that way, but she’s leading a huge enterprise.

BILL GEORGE: She is. And I haven’t really engaged her much as a business leader. I’ve engaged her as a human being. And I think as a human being, she’s amazingly warm and personable and real. Extremely authentic. And I suspect that gets translated in her business life.

BRIAN KENNY: Yeah. You can also learn a lot from a leader when they are involved in some kind of a scandal or some kind of controversy. And Oprah’s had her share of … because she’s such a public-facing image. What would you say about the way that she’s reacted in times of controversy that involve her or her charitable activities or things like that?

BILL GEORGE: I think she’s responded very well, and I think she has every right not to kowtow to the forces that are critical of her, but she makes mistakes and she admits her own mistakes on set. And if she offends someone or says the wrong thing, she admits it. She’s very real and very authentic. So I have nothing but the highest admiration for her, and I think we need more leaders like her who are real and own their past, are open about it, share openly, and become role models for other people, that you can be authentic and become highly successful, and you don’t have to sell out to the powerful bosses and the powerful forces of money.

BRIAN KENNY: She’s also found interesting ways to bring her own personal passions and the things that she cares about into her line of work. I mean, she’s been able to be a champion for causes both in her work and also in her private life. Is this something that other leaders should try to do?

BILL GEORGE: Yes, and that’s what makes her so successful is she does champion, and you know that she’s there when she’s promoting the idea of reading. She’s been a huge promoter of reading. I think that’s a very noble thing, and I think we should all do that. There’s nothing wrong with bringing our passions and things we believe in. In fact, it’s a good thing. If you’re not passionate about your work, I think you ought to quit and go sit out on the beach. I really do. If it’s just a job, you’re giving your best years of your life away. And I think people that carry their passion through their work and emulate the values and be a role model for other people of how you can pursue your own purpose and values and be successful, and a lot of people think you can’t be successful. I find just the opposite. People that are highly successful carry those beliefs forward, and they’re reflected every day in their interactions with their customers and their employees.

BRIAN KENNY: Yeah. Have you discussed this case in class?

BILL GEORGE: Oh, sure. Of course. [inaudible 00:12:01].

BRIAN KENNY: I’m just curious, what kind of response do you get? I’m sure people are excited to talk about it.

BILL GEORGE: Yeah. I think we have to get away from Oprah the celebrity and get to Oprah the human being. And there’s a danger in a class like this that you focus on the celebrity status, not the person. And when you show videos, they’re easy to find of her, but you really focus on the human being side. And then you get down to what’s real about her and how did she deal with these things, and what can you learn from it and how can it influence you. You’re not going to be Oprah; you have to be Sarah or Charlie.

BRIAN KENNY: Bill, thanks for joining us today.

BILL GEORGE: Thank you, Brian. It’s a privilege to be here. Thanks for the great questions.

HANNAH BATES: That was Harvard Business School executive fellow Bill George – in conversation with Brian Kenny on Cold Call.

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This episode was produced by Anne Saini and me, Hannah Bates. Ian Fox is our editor. Music by Coma Media. Special thanks to Maureen Hoch, Erica Truxler, Ramsey Khabbaz, Nicole Smith, Anne Bartholomew, and you – our listener. See you next week.