Sheryl Sandberg Tells Oprah About Her 'Date' With Mark Zuckerberg, Her Marriage And Feeling Like A Fraud

Jun 06, 2013 | Updated Mar 11, 2015
Photo: Rob Howard

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Facebook's COO opens up about her boss (he's almost 15 years younger), her marriage (he does 50 percent of the housework), and how she gathered her courage to become a bold new voice for women.

By Oprah Winfrey

When Facebook COO Sheryl Sandberg invited me to the company's headquarters in Silicon Valley in 2011 for a casual chat -- yes, she interviewed me -- we discussed everything from tequila to being our authentic selves. Sheryl was so open, honest, and fun, I knew right away that I wanted to be her friend. (Would you believe she doesn't even have an office? She sits in an open workspace alongside everyone else, including her 28-year-old boss, Mark Zuckerberg.)

When she later told me she was writing a book on women and work, I knew it would be big. Sheryl is the perfect person to really take this important conversation to the next level. I was honored when she sent me some early chapters to read, and sure enough, Lean In: Women, Work, and the Will to Lead is honest and brave, like Sheryl herself. In honor of its publication, I decided it was my turn to interview her. So I flew to California to meet her at one of her favorite restaurants, the Flea Street Café -- the same place she first dined with Mr. Zuckerberg in 2008 before leaving Google to join him at the little social network he'd founded. There, over artichoke crostini and steamed garden vegetables, we talked about her high-pressure job, her insecurities (yep -- she has 'em, too!), and why she felt inspired to speak out about women and power.

Sheryl: Oprah, this is Jesse.

Oprah: Hi, Jesse!

Jesse: Sheryl comes here a lot -- she loves these biscuits.

Sheryl: I swear by the biscuits.

Oprah: You can't not have a biscuit when it's warm. [Takes one.] Mmmm, that's a good biscuit.

Sheryl: That's good, huh?

Oprah: So we're here in your neighborhood.

Sheryl: I live around the corner.

Oprah: And you came here for your very first meeting -- or should we call it date -- with Mark Zuckerberg.

Sheryl: It was date-like in the sense that I was nervous.

Oprah: It obviously went well.

Sheryl: We actually stayed so late the restaurant closed.

Oprah: That's a good date.

Sheryl: It was 10 at night, way past my bedtime. But he clearly wanted to keep talking, and he was Mark Zuckerberg. So I said, "Well, do you want to come over?" And then at midnight I had to say --

Oprah: "Time to go! My husband says, Get out!"

Sheryl: I have kids. My kids were getting up in five hours!

Oprah: So was it really like a courtship, trying to figure out whether this would work? Or did you know after that first dinner?

Sheryl: I knew immediately how warm he was, and how much he cared about Facebook. But getting to know each other was definitely a process. We spent so much time talking about the mission of Facebook, what he wanted to accomplish.

Oprah: Were you a big Facebook user then?

Sheryl: I was a Facebook user. I don't know if I was the biggest Facebook user. But it had put me in contact with people I'd lost touch with. So I understood Facebook and thought it had amazing power to change the world.

Oprah: You've been credited with turning the site into a "real business." What was your vision during that early phase?

Sheryl: I think the vision was the same one Mark has had since the beginning -- to connect the whole world. Now we just have more employees to help us do it.

Oprah: When you first started, did you feel a lot of pressure?

Sheryl: Oh, yeah, I felt a lot of pressure. I wasn't sure I could do it. And I think that is something so many women feel. Men as well, but women particularly. One of the first things Mark and I focused on was, how do we make money in a way that's good for our users? I also worried, would we get along? We needed to trust each other.

Oprah: Mmm-hmm.

Sheryl: When I was interviewing with him, we were supposed to talk one night at 9, but when I called, he was at a dinner, so he said, "I'll call you later." I said, "Well, I'm going to go to sleep in about 30 minutes, so if you're still out, we'll talk tomorrow." He called the next day and said, "Are you okay? Were you sick?" And I said, "No, I'm a mother -- I go to bed at 9:30!" So I definitely had this fear that I was going to be too old for Facebook, that I wouldn't understand what he was doing. It was scary.

Oprah: When you started, because of your background in advertising [at Google], some said you were going to ruin Facebook forever. Did you internalize any of that? As you know, women do tend to internalize.

Sheryl: Oh, yeah. Some people said terrible things. One blog took pictures of me and superimposed a gun in my hands, and wrote LIAR across my face. And everywhere I went, people would say, "Oh, don't worry," which told me they were reading this stuff.

Oprah: I've been there.

Sheryl: I lost some sleep. I cried. But Mark was hugely supportive. And there was only one answer, which was to keep my head down and make the company successful.

Oprah: So tell me, as long as we're talking about women internalizing comments about them -- is it also true that women and men can be doing the very same thing and people view it differently?

Sheryl: Oh, absolutely. I mean, look, what works for men does not always work for women, because success and likability are positively correlated for men and negatively correlated for women. That's what the research shows. As a man gets more successful, everyone is rooting for him. As a woman gets more successful, both men and women like her less. And I think part of why I wrote a book on this topic is because until about five years ago, I didn't know that. I'd experienced it, like all women do. When I was in high school, I was voted most likely to succeed.

Oprah: Of course you were.

Sheryl: But I went and told the person who was running the yearbook, a friend of mine, to get me out of that.

Oprah: And she did?

Sheryl: Yes. And the question is, why? For most of my life, I instinctively didn't talk about things that went well for me. I didn't understand why until I happened to sit next to Deb Gruenfeld, a Stanford professor [who studies leadership], at a dinner. She helped me realize that the reason I kept my success quiet was that it would have made me less likable. I don't think any of us want to judge women negatively for their success. I don't think we even know we're doing it.

Oprah: So you have now written -- I have to say, it's the new manifesto for women in the workplace. And you call it Lean In. Why?

Sheryl: Because I believe we've got to lean in to our careers -- to keep our feet on the gas pedal. And we've got to encourage girls -- as you have done with your school in South Africa -- to do the same. Women have made tons of progress. But we still have a small percentage of the top jobs in any industry, in any nation in the world. I think that's partly because from a very young age, we encourage our boys to lead and we call our girls bossy.

Oprah: It reminds me of the story you tell in Lean In about not going to the prom.

Sheryl: I spent more time in high school worrying about getting a date to the prom than I spent worrying about math. And I was the smart girl! I did end up getting a date, but he canceled on me -- a week before prom -- to go to a basketball game!

Oprah: So the reason we don't want to be leaders is that we want to go to the prom.

Sheryl: That's right. No one wants to go to the prom with the smartest girl. Don't we have to change that? Your whole life, you've been telling people to be their best selves. We need to tell women that that includes leadership. And men that it includes being partners at home.

Oprah: Were you surprised by the reaction to your TED talk in 2010? Why did you decide to talk about these issues?

Sheryl: Well, as a businesswoman, you are taught -- I'm sure you were taught this -- to never mention gender.

Oprah: You never cry and you never mention gender.

Sheryl: But by the time I was invited to speak at TEDWomen, I'd been in the workforce a long time, and at every stage, I'd seen men in my office asking for new responsibilities. And the women, even when I'd say, "You really should take on this new job," would say, "I'm not sure I'm ready." Men, in general, apply for promotions when they meet 60 percent of the criteria. Women, 100 percent!

Oprah: Wow.

Sheryl: And I wanted to talk about this. So despite all the advice I'd gotten in the past, I decided to just get onstage and talk about being a woman and the challenges we face. And the talk went viral, and I started getting letters from women all over the world.

Oprah: You saw women, as a result of your TED talk, start speaking up for themselves.

Sheryl: That's right. So I decided I needed to face my own fears and write this book.

Oprah: Why were you scared to write it?

Sheryl: My first draft had all kinds of studies and nothing about me. But you told me --

Oprah: Nobody wants to read about studies. We want to know what Ms. Sheryl is doing on a day-to-day basis! How you're doing it.

Sheryl: At first I didn't even want my picture on the cover, but I heard your voice in my head. You'd said, "Don't do the book if you're not gonna put yourself in it." You and others pushed me to open up about myself and the things that have been hard for me. We all feel like we don't belong at the table.

Oprah: Sheryl, I find that so hard to believe with all you have accomplished. But in the book you say that in 2011, when you were on the Forbes "World's Most Powerful Women" list, you had trouble with that, too.

Sheryl: I was embarrassed. People kept saying, "Congratulations!" And I'd say, "Don't talk about it." Finally my assistant took me aside and said, "You are handling this terribly. You deserve to be on that list. You're showing everyone how insecure you are."

Oprah: You said that women are perceived as less likable as they become more successful. So how do we "lean in" to our careers without appearing to be arrogant? Because that's what we fear. The question I feared for years was, who does she think she is?

Sheryl: Well, short-term, we have to be what others have called "relentlessly pleasant." Men don't have to worry about smiling, or explaining why they're asking for a raise. A man can say, "I want a raise because I deserve it." A woman has to explain not just why she deserves it but why it's good for the company. "I'm so devoted to this company, I want to continue to be able to do my job .…" That's just the way it is. The long-term answer is to change the numbers and the stereotypes. If more women are in leadership roles, we'll stop assuming they shouldn't be.

Oprah: Tell me, what are the three biggest mistakes women make in the workplace?

Sheryl: First, not sitting at the table. Women, in general, sit off to the side of the room, and they don't speak up. I do it sometimes, too. We have to make sure women know their voices are important. Second, not making their partners real partners at home. And third, we leave before we leave. Over the years, I've seen this one so clearly. Women are worried about having careers and families, so they enter the workforce almost looking for the exit! They take their foot off the gas pedal. They lean back. While men get more responsibility and get promoted. I really believe that there are good reasons, when you have a child, to leave the workforce or work less or take a different job. But I encourage women and men to make that choice once they have the child. By making it years in advance, you don't get the right opportunities. You give up before you start.

Oprah: How do we get women -- and I go through this with my staff, all working mothers -- past the guilty space?

Sheryl: Oh, I don't have the answer to that.

Oprah: How did you get past it?

Sheryl: I am not past it. You know, my husband and I have two careers, we have two kids; we share responsibilities. When we're in town -- and one of us is almost always in town -- we leave the office at 5:30 to be home for dinner. But when I drop my kids off at school and see other mothers who are staying all day to volunteer, I still feel the heart pang. Would my kids be better off if I were staying, too? Meanwhile, my husband thinks we're heroes for getting home so early.

Oprah: Boy, when you said publicly that you leave the office at 5:30 -- I mean, people who know that I know you were coming up to me and saying, "The next time you see Sheryl, please tell her thank you for that." Did you recognize how powerful that admission would be for working women?

Sheryl: No! It was the craziest thing. I was just talking to a reporter about my schedule. Though to be fair, the first time I said it, in a meeting at Facebook, I was nervous. Because we've been taught as women never to admit having anything else to do.

Oprah: Yes. Yes.

Sheryl: So when I admitted it internally, I wanted to communicate to everyone else that they could also leave when they needed to. Then I took down my guard in an interview and said it again, and my friend called to say that I couldn't have gotten more headlines if I'd murdered someone with an ax!

Oprah: But you're glad you did it.

Sheryl: Oh, yeah. I got flowers from strangers saying, "Thank you!" I believe that if we can't talk about this, then how can we fix it?

Oprah: Was there ever a discussion in your house about one of you staying home?

Sheryl: No, because we both knew we wanted to work. But there were a lot of discussions to get us to 50-50 in terms of household responsibilities. One of the things I really want all women out there to know is that almost no men come fully trained. And we don't, either, for that matter.

Oprah: I love that -- fully trained!

Sheryl: The biggest decision you make in life and in your career is, are you going to have a life partner, and if so, who? I tell girls, date the crazy boys, the bad boys. Enjoy that. But do not marry them. Because what is sexy when you're 23 is not sexy when you are 43. What's sexy where I am is my husband driving my kids to school.

Oprah: Oh, that is sexy. [Laughter.] So you got married for the first time at 24, and were divorced within a year.

Sheryl: Yes.

Oprah: What did that teach you?

Sheryl: Don't do that! I didn't know myself well enough. I married a wonderful man, and we're still friends. But I wasn't ready. And for the longest time after that, no matter what I accomplished professionally, I felt like I had this scarlet letter D on my chest. I even passed up a job at one point because I didn't want to move back to the city where he lived. In hindsight, I was leaning back.

Oprah: So how did you learn to lean in?

Sheryl: Well, I still have to remind myself to lean in all the time. When I was in college, I heard a speech about feeling like a fraud. I thought it was the best speech I'd ever heard. This impostor syndrome, as they call it, is common among women. When a man is successful, he believes it's because of what he did, his skills. A woman will attribute her success to luck, help from others, and to working hard. And even if you're confident enough to own your success, the world will attribute it, for most of us, to luck.

Oprah: Oh my gosh, you are preaching to the choir. Years ago an executive at my company, Harpo, turned to me -- I can't even remember what had happened -- and said, "Maybe it isn't all luck with you." [Laughter.]

Sheryl: We do it to ourselves, and the world does it to us.

Oprah: You say that Gloria Steinem, who marched in the streets to fight for the opportunities so many of us now take for granted, quoted Susan B. Anthony saying, "Our job is not to make young women grateful. It is to make them ungrateful so they keep going."

Sheryl: I think that's important. We need to be grateful for what we have. I have so many more opportunities than my grandmother had. But we also need to be a little dissatisfied. We're not using the full talents of our population. If we do -- if we draw on the full talents of women in the workforce, and men at home -- our companies will be more efficient and more effective, and our kids better off because they have involved fathers in happier marriages. This is good for everyone.

Oprah: Sheryl, thank you for this time. I'd love a copy of Lean In to send to each of the girls at my school.

Sheryl: Of course!

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