10 Women on Their Female Bosses

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(Photo: Hill Street Studios/Getty Images)

By Meaghan Winter

In too many fields, female role models are a luxury young women can’t take for granted. A woman boss can help you figure out who you want to be — whether that means showing you how to navigate workplace sexism, or serving as a cautionary example. (And, of course, as Ann Friedman has written, being a female boss comes with its own set of challenges.)

What changes when women are in charge? The Cut asked ten women about how female leadership has shaped their goals, self-image, and careers.

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She doesn’t sugarcoat.

“Sometimes after I give my opinion, I think, ‘Maybe I shouldn’t have said that,’” says Ali, 28, who works for an insurance company. “I told my boss, ‘I think I’m too outspoken.’ She said, ‘Would you think that if you were a man? Don’t second-guess yourself. Don’t change yourself!’”

Ali says that her boss, who’s British, has a refreshing directness: “She doesn’t sugarcoat.” When their team is nervous before presenting at a meeting, her boss will say, “Chin up, tits out, go get it!” Ali laughs, “Maybe using the word ‘tits’ isn’t the most appropriate, but she’s saying, ‘Hold your head up high.’”

At a previous job, Ali was the only woman on her team, and very young. “I changed my demeanor, came to every conversation over-prepared, and I never said something was my idea — I’d say, ‘Based on the data … ‘” Now that she’s supervised by a woman at a company with a more open culture, she says, “I’m more trusting that my work is valued and my ideas are taken seriously.”

She was incredibly insecure.

Rachel thought she’d landed her dream job, until her boss, a successful editor, made work difficult if not nightmarish. “She embodied every female stereotype,” Rachel, now 34, says. “The yelling, the stomping, the slamming the office door and crying. She was incredibly insecure. She’d lurk outside her boss’s office and offer to make coffee — it was like watching an insecure seventh-grader suck up to a cooler seventh-grader.” When evaluating Rachel, her boss worried that Rachel wasn’t fitting in socially.

“My response to her being so anxious was to be soothing, positive, and controlled,” Rachel says. “She wanted a minion who would freak out with her. I think she needed someone younger and eager to please. I was fired without cause.” Now Rachel has climbed the ranks at another job, where a man supervises her. The experience with her former boss has instructed her: “If I ever get frustrated at work and show my hand at all, I feel intense shame. It’s not good to get emotional in any professional circumstance, but in terms of how people perceive you, it’s riskier as a woman.”

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She’s ambivalent.

“The probability’s higher that a woman will be a good boss, but just being a woman isn’t enough — look at Margaret Thatcher!” says Stephanie, 30. “I don’t want the end game of feminism to be women rising to power to exploit other women.”

Stephanie works freelance as a producer in the film industry, where generally men direct and women produce. As producers, “women tend to take care of the loose ends, making sure everything’s ready for men to create.”

Female supervisors like those were “so competent, so good at their jobs that they couldn’t be unconfident. Over the years I’ve learned so much from female bosses — to always have things in writing, for example, and how to command respect without alienating anybody.” Her female supervisors have been better at “facilitating an open line of dialogue and communicating respect to everyone, whether they were at the top or the bottom.” But Stephanie says she’s ambivalent about staying in an industry where so much of women’s grunt work — however effective — goes largely unrecognized.

She avoided conflict.

“Being liked was extremely important to her,” Marcia, 32, says of her boss in an administrative position at a university. “At first her friendliness came across as real kindness, and that made me like the job.” But after a few months, Marcia’s perception shifted. “She carried herself like a girl and didn’t accept her authority. I saw her repeatedly avoid conflict — like firing people over email, pretending disagreements weren’t happening — and I lost respect for her. She wanted the staff to be a group of friends. It was like with parents who drink with their teenagers’ friends. You can’t be an effective authority figure if you can’t handle people not liking you for five minutes.”

Marcia is bothered by her judgments of her boss’s “nicey-niceness”: “I also avoid conflict. I hate it when I think someone doesn’t like me. I know girls are rewarded for a certain kind of smiley passive-aggressive behavior more than boys. But I know I can say something that needs to be said. Working for her was a big reminder that I need to work on my own conflict avoidance if I want to be respected as a professional.”

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She didn’t have the luxury of being nice.

Jennifer, 33, is an assistant district attorney and says that men dominate her workplace. “A woman in my office was fed up and voiced her opinion. The boss didn’t agree so he called her husband,” says Jennifer. The male lawyers are paid more even when their female counterparts have years more experience and win more trials. “They think they can say anything to you,” she says. Recently a white male co-worker walked into Jennifer’s office and said, “What you doin’, bitch?” She replied, “Working on a brief, bitch!”

Her mentor isn’t her supervisor but a senior female lawyer with a 98 percent conviction rate who took Jennifer under her wing. “If a white man had her record, they’d be calling him Atticus Finch, Lawyer of the Year. But she gets labeled as an angry black woman,” Jennifer says. She recognizes that when her mentor started out, a generation ago, “her work ethic had to be better than everybody else’s and she didn’t have the luxury of being nice.”

“She’s been invaluable,” Jennifer says. “She said, ‘I want you to be better than I thought I was.’” She immediately had Jennifer assist on a trial and gave her “a baptism by fire,” divvying evenly their witnesses to interview and jurors to select. “She said I blew it out of the park,” Jennifer laughs. Her mentor also dispenses advice: “Pinch your thigh. Tears are blood in the water … Don’t bring a problem to a boss unless you have a solution or he’ll think you’re whiny … Don’t take work home. Leave the vicarious trauma in the driveway … Keep being nice. If someone steps on your toes, say something.”

She showed me I could have a work-life balance.

“The sciences require intrinsic self-motivation — if you don’t like it and don’t work hard at it you’re not going to succeed, no matter whom you’re working for,” says Catherine, 34. A female scientist hired her to do mathematical modeling right out of college. Her new boss was the only woman in the country to have received a particular government grant, and Catherine “got the impression it was important to her to bring women into the sciences” because three of the five researchers she hired were women. Twelve years later, Catherine still works at the lab.

“I never would’ve noticed that I was the only woman in my classes unless it was pointed out, which I guess means I wasn’t intimidated by the males,” Catherine says of studying math. Her next female boss allowed her to attend daytime classes toward her Ph.D. as long as she got her lab work done. “Would a male boss have been just as supportive? Maybe. I really don’t know,” Catherine says. “I think it has to do with personalities.” Her male boss, meanwhile, has been more understanding about maternity leave, but she says, “There’s definitely a culture that favors men, who won’t take time to have children.” “Having a female boss didn’t propel me to stay in science,” Catherine says. “I was going to do that anyway. But she showed me that I could stay in science and have a family and a work-life balance and still be successful.”

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She wishes there were more women.

“I was wearing pink and I had to get buy-in from four senior men. I was so upset — I don’t know if it matters, but I never want to take that chance,” says Saroja, 28, who works at a male-run tech company. “If I worked for women, I probably wouldn’t have been worrying about seeming docile or feminine. You can’t think about building yourself professionally when you’re worrying about how you’re going to be perceived.”

In the tech industry, the “inexperience valued as fearlessness” usually translates as male. She wishes “there were more women in the decision-making positions.” When Saroja wanted to go to business school, the women in her life encouraged her. Her male bosses said an M.B.A. was a waste — they’d each climbed the corporate ladder without one. Their faith in her ascent is a compliment, but she wonders whether it’s particularly white and male to assume that smarts and drive inevitably deliver success. She speculates that women universally supported her M.B.A. idea “because there’s this good-girl thing about going to school, getting accolades.”

She’s really, really accomplished.

Carla, 33, an untenured professor, is mentored by the department’s first-ever female chair. “At meetings, it’s cool to see her sitting in the front of the room,” Carla says, because the default academic is “still a man with a wife at home.”

Her mentor also takes on female mentees from other departments. “I doubt they’re getting together to talk about being women,” Carla says, “but I know she’s invested in more women getting tenure.”

“With male colleagues I try to present myself as genderless, sexless. As a woman you risk undermining yourself if you bring up family concerns, but for academics the family thing is really hard.” Academics need to publish at the age when women have kids. When Carla was negotiating her salary, her now-mentor brought up maternity leave: “Now that she’s really, really accomplished I can see that she wants to bring it up for younger women, who can’t.”

Her mentor “directly calls out” the sexism she encounters. Carla, though, wonders about the best way to address its effects: “How do you acknowledge a problem without taking on its burden, entrenching it?” She avoids committees on women in academia, considering them distractions from her work, but teaches her female students to claim their ideas and avoid disclaimers like “I don’t know, maybe …”

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She rotated through each of us.

Soon after graduation from college, April, now 27, worked at a social-services agency. April’s middle-aged boss had just taken a leave from an order of nuns and “was coming to terms with what seemed like a painful decision to leave the sisterhood.” In hindsight, April believes her boss must have been “grappling with regret about her own life,” which colored her “intense, stormy, personal reactions” to even small workplace decisions.

“She was moody, unpredictable. At first I was her darling. Then a few months later she gave me dirty looks and seemed angry — but we never had a conversation about why. She’d openly gush about her favorite staff person at meetings. Then that person suddenly fell from her favor. She rotated though each of us. She bought her next favorite a book of poems. When she criticized or praised me, it would be for a personality attribute, not an actual accomplishment or work mistake. There were a million concrete mistakes she could’ve pointed out,” April laughs. “Now, I see that she personalized everything.”

She just gets shit done.

“I was G-chatting all day, so bored, until my new boss came,” says Lizzie, 32, who works at a tech start-up where some 80 percent of the staff are men. “She got me a pay raise and said, ‘You’re worth more than your raise, more than your title.’ She started delegating to me.”

Her boss relayed a story that stuck with Lizzie: Her father, a Marine, told her never to get coffee for a man or she’d always be the girl who got coffee. Sure enough, when she started a new job, a man asked her to get coffee. She nervously said no. She climbed up the ranks. Lizzie says, “I’m staying at this company specifically so I can learn from her — she’s confident and humble at the same time. She delegates. She trusts. She talks to the janitor the same way she talks to the CEO. She gives our whole team credit for work … She doesn’t trample on anybody — she just gets shit done. That’s how she gets her power.”

Lizzie says, “I want to do well for her. I’m getting a little SWF with my boss. I want to dress like her. I saw an engagement ring like hers and I want it. But mostly I’m feeling really good about my career. She’s made such a difference. I want to be a director now.”


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