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Uncomfortable Truth: Women Are Allowed to Be Mean Bosses, Too

Building a successful company actually requires you to run your business like one. So why are we so hard on female CEOs who do just that?

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Morgan McMullenShutterstock

My new novel, THE HERD, is a thriller set in an all-female coworking space—when Eleanor, the workspace’s enigmatic founder, mysteriously disappears the night of a high-profile event, her equally bright and accomplished female friends are forced to risk everything to uncover the truth. It’s a dark and twisty mystery, but one of my favorite passages is a bit of satire that ran on Eleanor’s lifestyle blog. The idea: After a New Yorker profile deemed the young CEO “Steve Jobs if Steve were Eve—young, pretty, and obsessed with makeup” (the kind of sexist comparison the media has most certainly made outside of fiction), Eleanor’s team poked fun at the comment by imagining “Eve Jobs” behaving exactly as Steve did—with quite different outcomes.

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In 1985, Eve, our plucky ladyboss, insisted her new retail spaces line their stores with expensive sandstone from a particular Italian quarry. “Due to her frivolity and poor financial instincts, she was promptly removed from the company.” When, in 2005, our fearless HBIC was caught reaming out an elderly Whole Foods employee for messing up her smoothie order, “she was promptly removed from the company [due to her nasty, entitled disposition].” In 2008, our fictional “she-E-O” called a town hall to scream at her staff for messing up the rollout of Apple’s much-anticipated MobileMe system. “With shrillness, an ugly shade of lipstick, and tremendous hate in her heart, she publicly berated the team for more than 30 minutes.” To reiterate: Hallowed Steve Jobs actually did all of these things. Our fictional “fempreneur,” on the other hand, was promptly removed from the company.

THE HERD centers on a group of high-achieving women trapped by the perfection society demands of them—they need to be superhuman (and warm and funny and approachable and humble) to succeed, and they’re quietly terrified of what’ll happen if their flawless facades crack.

When I read about disgraced or fallen female CEOs, such as Miki Agrawal from Thinx and Steph Korey of Away, I can’t help but think that they, too, were lambasted for not being perfect. Forget the glass ceiling; these days, we’re smashing ambitious women into uncomfortable glass boxes—and then freaking out when they don’t remain inside, smiling beatifically, looking beautiful, and making everyone (employees, customers, investors, society at large) comfortable with their ladylike aura and good manners.

Case in point: Last week, the New York Times Magazine ran a feature entitled, "The Wing Is a Woman's Utopia. Unless You Work There." The article meticulously walks readers through employees’ complaints that the company, led by CEO Audrey Gelman, hired a Liberian-American who uses the pronoun "they" only for the optics, that staffers hired to man the front desk found themselves washing dishes and scrubbing toilets, and that the $16.50-an-hour starting salary (10 percent above minimum wage) was not, in fact, livable. Said Raichelle Carter, a chef who worked in the Flatiron location: “It’s just like any other company that wants to make their money.” Well...right, that's how capitalism works. Can you imagine a male CEO being lambasted for trying to turn a profit?

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Miki Agrawal, co-founder and former CEO of THINX

A similar trend appears when you examine other female-led companies. At Away, Korey “was infamous for tearing into people on Slack,” according to an article on The Verge, and often made employees burst into tears. Former employees criticized executives for expecting long hours, limiting PTO, and reprimanding workers for not answering messages ASAP, even on nights and weekends.

Over at Thinx, Miki Agrawal was chastized for peddling a feminist product but offering a reality rife with “dysfunction and hypocrisy, with clashes between Agrawal and key members of her team, employment policies that seem to fly in the face of the company’s women-first messaging, and an increasingly volatile work environment,” according to a Vox article published shortly after her resignation. The maternity leave policy sucked; employees claimed Agrawal could be erratic and mean and prioritized marketing and personal acclaim over creating a warm workplace environment. (I think we can all agree that Thinx’s branding, at least initially, was brilliant.) Employees were frustrated that the cheapest healthcare option cost $200 a month; while annual raises were based on performance and revenue, the amount was non-negotiable and wouldn’t accompany a midyear increase in responsibilities; in 2016, vacation days were cut from 21 to 14.

I’ve spent years at toxic workplaces and had emotionally abusive bosses, and it sucks. I don’t wish any of it on any employee, male or female. But some would describe Gelman, Korey, and Agrawal’s behavior as simply an intense or demanding way of doing business; had a male CEO done the same, we might never have heard about it. As anyone who’s ever worked at a startup will tell you, having a young, hotheaded male founder at the helm making people’s lives occasionally hellish is...kind of the norm. That’s nothing to be proud of, but if you run these stories through a gender-swapping filter, it’s hard to imagine that a male CEO expecting you to answer a work email on the weekend or refusing to give raises outside of an annual review would make the news, right?

I see why the women’s actions seem egregious when you consider that they billed their company culture as fun and inclusive and forward-thinking without the strict (read: boring, mean) parameters of traditional corporate America. With the Wing and Thinx, there’s the additional irony of feminism and female support being baked into the companies’ branding. But the dream of a bunch of women friends showing up at work and drinking champagne and taking breaks for group manicures and somehow making tons of money in the meantime is just that—a fantasy, a farce (as the women of the Herd discover). Building a successful company actually requires you to, well, run your business like one.

There are decades of research showing that society views the very same behavior as powerful in men and bitchy in women. One example: A study in the journal Social Psychology Quarterly found that when men get angry at work, they come across as authoritative. Angry women, on the other hand, are perceived as having a serious personality flaw or even seeming “sociopathic.”

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Steph Korey, co-founder and co-CEO of Away

Female leaders are punished for dishing out criticism, regardless of how it’s worded. In one study, published in the Institute of Labor Economics, contractors signed on for some online transcription work; midway through, they received some generically worded feedback (“I’m disappointed by your effort,” “your lack of attention to detail will harm the quality of our services,” etc.) from a faceless “manager” with a clearly male or female name. Workers were much more offended by negative feedback from a woman than a man. In fact, criticism from a woman led to a 70 percent bigger reduction in job satisfaction than (identical!) notes from a dude. Shocker.

Women who are successful in male-dominated companies are deemed unlikable, hostile, and undesirable as bosses, according to research in the Journal of Applied Psychology. Oh, but there is one thing a female leader can do to ameliorate this bias! If she demonstrates her “communality,” i.e., she’s a total team player who makes everyone feel super loved and important, employees (both male and female) ease up on hating her so much. Because she’s back in that glass box: She’s kind, she makes us feel good, she’s just so sweet and friendly and nice.

And hey, I like nice people, too. I want to see female leaders mentoring young women and helping them rise through the ranks. None of America’s gross gender bias makes it okay for women like Gelman, Agrawal, and Korey to pull the ladder up behind them. But that’s internalized misogyny for you—we’re awash in norms that teach women that success is a zero-sum game. That’s why for all the research I just cited, it wasn’t just men who felt offended by female leaders who broke the rules or violated the “shoulds” of our modern-day gender stereotypes; women are uncomfortable with bossy women, too.

A recent Wall Street Journal article observed, "Women earn the majority of college degrees and make up roughly half the U.S. workforce. So why are less than 6 percent of chief executives women?" With the C-suite still 94 percent male, it’s not hard to imagine that the women who do claw their way there are going to make us feel a little squirmy, like they’re where they don’t belong.

Face, Hair, White, Black, Eyebrow, Head, Nose, Black-and-white, Beauty, Hairstyle,
Audrey Gelman, co-founder and CEO of The Wing

But that has to change. Last year was a record one for female-founded companies, in terms of both number of deals and the total value of venture capitalist investment: 2019 saw 2,184 deals, up from 429 in 2009, worth a total of $183 billion, up from $2 billion a decade earlier, according to an industry report from Pitchbook. For those keeping track, that is a 9,150 percent increase in investment in female founders.

That means that in the coming decade, we’ll see a huge influx of fresh-faced non-male founders heading up companies across sectors. Some of those womxn will be sweet and funny and likable; others might be narcissistic or shady or not forthcoming (some might say: Zuckerberg-esque). Others may even be mercurial or cruel, flipping out at the elderly employee working at a smoothie bar. Are you ready to accept all types of non-male CEOs?

Feminism is supposed to be about choices: No one else gets to tell us whether to have kids or wear makeup or get Botox or vote in the Democratic primary or smile, baby, you’d be so much prettier if you smiled. Thinking that any woman in a leadership role needs to greet you with a grin and hold your hand and sing kumbaya to be a true feminist icon is...well, actually pretty sexist.

We don’t have to like ruthless female managers. We certainly don’t have to condone their behavior (or seek it out or stay in a terrible job just because there’s a woman at the top). But we do have to acknowledge that when our expectations for female (but not male) bosses are so sky-high—be kind and humble and charming and approachable in addition to being (deep breath) brilliant and visionary and risk-taking and savvy—we’re setting ourselves up to conclude that the best man for the job is anyone other than a woman. And that’s the kind of lie that keeps women out of C-suites. And distracts us from the systemic forces keeping all women down.


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