Sallie Krawcheck Says: You Need a Personal Board of Directors

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Sallie Krawcheck. Photo: Bloomberg/Bloomberg/Getty Images

This week, the Cut is talking advice — the good, the bad, the weird, and the pieces of it you really wish you would have taken. Here, former Merrill Lynch and Smith Barney executive (and current chair of the women's networking group Ellevate) Sallie Krawcheck on assembling a sounding board to help with life's tough decisions.

I’ve started to tell people that being an entrepreneur is harder than running Merrill Lynch, because everyone thinks being an entrepreneur is super-sexy these days, right? It's all about the office with the exposed-brick wall and the Foosball table, and you spend about six minutes in that office before you graduate to the personalized massages and becoming a billionaire. But in fact, when one makes the leap, it's hard. I never lost sleep when I ran Merrill Lynch. I didn’t. I slept like a baby. I lose sleep over being an entrepreneur. You can make lots of mistakes when you’re in corporate America, and you can blame the mistakes on other people, but now it's your personal responsibility. And the amount of cash is close to nothing. The combination of that makes it the most exhilarating, energizing, unbelievable experience you may have. You’re awake every second. It's about being fully engaged, and some people are ready for that. But a lot of people think they're ready for that, and they aren't. It takes personal introspection, real thinking about who you are.

I took a [business] personality test probably about four years ago. I was off the charts on leadership, and I was off the charts the other way on rule-following. I looked at this, and I thought, No wonder sometimes I was maybe a little ... different at big companies. Sometimes, we're not able to admit to ourselves what we're really good at, and what we're not. I think it's a thing, specifically for women, because we typically don’t receive nearly as much feedback on our work as men do. There is research to back this up, because men are still predominantly in the situations of power, and they are more comfortable giving other men the really tough feedback. So you've got to ask for feedback all the time. And then be very honest with yourself about it.

You need people around you who know you. I call it your personal board of directors. They may not know that's what they are. I mean, if you called them and said, "Did you know you're on Sallie's personal board of directors?" they would say, "She's never used that term with me, but yes, she takes me for a cup of coffee when she's trying to think through an issue that she might be too close to." People talk a lot in business about having a mentor, or having a sponsor, but this is the gold standard of that. It changes over time. Someone who was able to be very helpful to you when you were at X job may not be able to be helpful to you in Y job. And it's a two-way street, always. Just as they're helping me think through issues, I hope I'm helping them.

When I was invited to leave Bank of America, I got several offers from large institutions. I went to my personal board of directors, and I said, "What do you think? Should I go back to that? What would you do if you were me?" And then you can get this perspective: "Sallie, why would you want to run one of those one more time? Don't you want to do something else?" You have to strip away a lot of the defensiveness about this stuff, or you can't receive it. But that's one of the great things about getting fired on the front page of The Wall Street Journal.

You want people who've worked with you directly and people who are in totally different industries who bring another perspective to it. It's not 100 people. It's not ten people. It's probably five or six closest advisers. I've only crystallized the concept in the past nine months. I wouldn't have known what to call it before. But over time, I began to recognize that when I have things I'm thinking through, there is a group of individuals, without fail, whom I call. And whose advice is, without fail, additive to what I'm thinking.

But you don't put it to a vote. It's more, "Hey, I'm thinking about this. What do you think?" One would say, "Sallie, do you remember how miserable you were in all those kinds of meetings with Bank of America? Tell me, why do you want to do that again?" Or, "You started working with start-ups, and you really seem to light up when you talk about that. Doesn't this feel like a reversal for you?" And a third would say, "Sallie, are there family or other reasons for why you would do that?" It's almost like a triangulation. 

One other secret: Think about life/career-altering questions either at the beginning of the day, or at night. In the morning, in your PJs, before you get the kids up, when it's just you and the cat. At night, over a glass of wine. It's all part of the same thing — how do I strip away the day-to-day to ask myself an important question? It's just you and the cat, and the cat loves or dislikes you, no matter what.