But lately, I have had to wonder: Will she?
As a culture, we are still wrestling with who can be a CEO. When Mary Winston, CEO of Bed Bath & Beyond, became the 33rd female CEO in the Fortune 500 last May, and an interim CEO at that, she made headlines. Fortune just asked “Wall Street Has Never Had a Woman CEO. Why Not?” The article flew through the Twittersphere, doubly so because it followed Forbes’s “America’s 100 Most Innovative Leaders” list containing 99 men and one woman. Recently, the pregnant CEO of the Wing, Audrey Gelman, is staring out from the cover of Inc. magazine. Her pose is being hailed as groundbreaking. Really?
Something is shifting in me as I observe all of this. I am not thinking about how we push progress for working women. I am focusing on how we raise our girls. I think it’s time to play the long game.
I was a girl who aspired to be a cake baker or a hairdresser. Those are the workshops I picked at the career fair. I attended Stanford business school in my 20s, but that was too late to internalize messages about who deserves to have power. I had already counted myself out.
Raising a generation of girls who expect to be CEOs would be revolutionary. No amended-leave policy or plugging of a “leaky pipeline” (the phenomenon of women falling out at each step toward the top) is going to fix the fact that girls rarely consider themselves leaders. Girls curb themselves from being directive — they don’t want to be deemed bossy. About one-quarter of middle school girls say they will never achieve their dream career. In 30 out of 30 countries studied, females underestimated their IQ while males overestimated theirs.
Over the past 18 months, I have had the opportunity to interview more than 40 female CEOs as research for a collection of 31 profiles aimed at teen girls. (In rare cases where I couldn’t talk to them, I wrote about them after deep research.) At times I have felt like a scientist studying centenarians or the dwarfs of Ecuador who have extraordinarily low rates of cancer, examining a super species to understand the drivers of a desirable but unlikely trajectory. These women are my gold mine for unearthing nuggets about launching powerful girls.
Several characteristics have jumped from their narratives. Brazen behavior is everywhere. At the start of Rent the Runway, CEO Jenn Hyman was driving from Boston to New York for a much-anticipated meeting with Diane von Furstenberg. Entering Manhattan, the designer’s assistant reached Hyman in the car. She was canceling. “What?? What?? … I can’t hear,” Hyman shouted into her phone, pretending the signal was cutting out. She then just showed up. Audacity is rare in girls and women. Instead, girls are taught that it’s cute to be timid. Hyman countered fear by asking herself what’s the worst thing that could happen? Deploying that question is a good trick.
Immodesty is the real virtue. Humility keeps women stuck (even Forbes recognizes that). Research by Women of Influence and Reuters finds self-promotion to be the second most difficult thing for women in business to do. Mariam Naficy, CEO of Minted, is so certain of this she started her #shebrag campaign. In other words: Girls need to be encouraged to flaunt their stuff. I need to remember this when my daughter chirps POTUS when I ask what she wants to be when she grows up. Same thing when she shows up in the kitchen for the Friday-night dance in a belly-baring tube top.
Moxie derives from risk-taking and ditching perfectionism. Here’s what I mean: In 2000, Spanx founder Sara Blakely walked into Neiman Marcus, the first store to carry her shapewear, and found them shelved in a dusty back corner. Her reaction: She hustled to Target, bought a display rack and snuck it back inside in her coat. She then quickly arranged her red boxes front-and-center by the register on her rack, pretending they (and she) belonged there. She did not ask permission or follow the rules: Before she was a self-made billionaire, she sold fax machines door-to-door after bombing her LSATs.
Two aspects of her upbringing nurtured her resilience, as Blakely sees it. Her dad normalized failure. Nightly at dinner, he asked, “What did you fail at today?” Her answer always elicited a high-five. She also had a dad “who didn’t care what anybody thought of him.” That sent a powerful message about defying comparison and conformity. All of this freed her to go after wild ideas, be pioneering, listen to herself, fall down and bounce back up.
Indeed, these women have a unique relationship with the word “no.” They treat “no” as a word, not an edict. “No” is a necessary and expected step on the way to “yes.” Naficy went almost a month without a single sale after launching her stationery business Minted in 2017. “It was crickets,” she said.
So she pushed to make her concept more compelling. Working nights with an engineer she hired on rentacoder.com, she developed a platform to enable any designer the opportunity to have their work produced and sold on Minted. Her unique concept of contests now has her selling millions of dollars worth of cards, wall art and home decor. Facing rejection and working to make something more compelling is actually her trait. When Naficy was rejected from Stanford business school on her first try, she asked the admissions officer what she would need to do to become a better candidate — another smart tactic.
These female CEOs are not rocket scientists. Rather, they are relentlessly resourceful, which can trump specialized training and endless enrichment.
How did Hyman get in touch with dress designer Diane von Furstenberg? She tried every permutation of her name in email until one didn’t bounce back. Embrace Innovations CEO Jane Chen needed a material that, with heating, could maintain 98.6 degrees for a sustained period. This way her low-tech baby incubator for use in developing countries could be warmed with hot water and maintain body temperature. How did she find that material? She googled. Really. Christina Stembel of Farmgirl Flowers learned to make her trademark bouquets watching YouTube.
Doing less for girls is actually doing more. That is the message of Esther Wojcicki, who raised the current CEOs of 23andMe and YouTube. In her new book, “How to Raise Successful People,” she preaches independence for girls. For example, her daughters had a clothing allowance and made all the decisions; they did some of the household shopping.
Encouraging downtime is one trick we seem to have forgotten. Lisa Sugar, founder of Popsugar, feels indebted to her parents for letting her watch unlimited late-night talk shows with her favorite hosts. Her pop culture fire was lit there, and she now has 30 million daily viewers. Blakely, the Spanx founder, needs time being a couch potato to create. Before kids, she would regularly lie on her sofa, daydreaming for three or four hours. “That’s where I did my best inventing,” she says. “The key is spending time alone.” Much of this is just honoring true passions and nature rather than imposing some ideal — even when that involves screens.
So encourage your daughter to boast. Let her bike to the store and blow her money on candy and binge on how-to makeup videos. Avoid filling every minute with enrichment. Instead, push loafing. Let her fail miserably. Most of all, applaud her when she’s difficult and imperfect. These are tried-and-true tricks. Forty CEOs will tell you that. They told me.
Diana Kapp is a business journalist with an MBA from Stanford University and lives in San Francisco. She is the author of “Girls Who Run the World: 31 CEOs Who Mean Business.”
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