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Women increasingly occupy leadership roles, but gender-based challenges don't necessarily disappear with progress. What forces buffet advancement—and what happens when women take the reins?

When Marna Borgstrom started out in healthcare administration 40 years ago, there were few women at the top of the field. She was regularly accused of being too soft-spoken, and the criticism wasn't unfair. "If I didn't have something close to brilliant to say, I wouldn't put it out there," she says. "At that time, the medical school department chairs were all men. They looked at me like, 'Pat her on the head—she won't be here when she starts having children.'"

Now the CEO of Yale New Haven Health, a $4.4 billion healthcare system, Borgstrom considers her role managing five hospitals and 25,000 employees as akin to that of an orchestra conductor. She rose in the ranks by learning from those above her, holding fast to her belief in quality healthcare for all, and making some personal sacrifices, such as going back to work mere weeks after giving birth. Still, getting to where she is now was more a byproduct of her purposefulness than the end-all goal. "I was never that audacious—I never said, 'I want to be the CEO.'"

Left to Right: Mariko Silver, Marna Borgstrom, Magdalena Yesil, Claire Hughes Johnson
Photos by Michael McGregor and Jonathan Sprague

And yet, like more and more of her gender, that's what she became. Women have made impressive strides as leaders over the past generation, starting businesses, helming companies, and being elected to public office at unprecedented rates. Their progress has been helped along by a dramatic increase in awareness of the barriers women face, including a lack of adequate family leave, exclusion from "boys' club" networks that still grease the paths to power, and their own socially conditioned tendency to avoid nominating themselves for prominent roles. Statistics confirm their advancement: In 2016, there were 104 women in the U.S. Congress, a number that's nearly quadrupled since 1992. One in six board members of Fortune 500 companies was female in 2013, almost double what it was 20 years earlier.

Progress, however, is certainly not parity. In most fields, the glass ceiling is firmly intact. Nor does advancement mean it's easier for women who do make it to the summit. Perhaps at no time in modern history have the challenges of female leadership been more apparent than in the campaign of Hillary Clinton. Reams have been written about why Clinton lost, but in analyzing both the blistering campaign and her 30-year career in general, commentators point to the complicated role that gender played in how she was perceived. To many of her detractors, she was too cold, rigid, canned, authoritarian, and, that biggest political stinger, unlikable. To her supporters, she perfectly illustrated the old saying about Ginger Rogers—that she had to do everything Fred Astaire did except backwards and in high heels—which is to say, not only flawlessly, but while contending with unique challenges. And still, Clinton lost.

To many female leaders and other women who aspire to their ranks, the election reflected facets of their own experiences. They've juggled, balanced, mentored, negotiated, organized, managed, delegated, decided, listened up, and leaned in only to realize that leading while female is different from leading while male. As the linguist Deborah Tannen once wrote, "The road to authority is tough for women, and once they get there, it's a bed of thorns." Social scientists who study female leadership are carefully parsing the nature of those thorns and discovering how women pluck—or navigate around—them.

Bias at Work

After giving a talk to about 400 people, Mariko Silver, the 39-year-old president of Bennington College, was pulled aside by a respected male colleague. He praised her, then offered what he thought was a helpful suggestion: Her tone should be less conversational in the future, he said, and she should use her body language and voice to convey more authority. "I appreciated that he was trying to help me," says Silver, who previously served in the Obama administration and was a policy advisor to Arizona governor Janet Napolitano. "But banging my hand on the podium doesn't feel right. Is there any other way I can express authority? I want to be a leader in a way that is authentic to me. "

Female leaders have to contend with many such implicit assumptions. When most people imagine an executive, they picture a strong, assertive man. When they think of ideal qualities in a woman, they picture warmth, sociability, and compassion. Such entrenched and often subconscious biases are hard to reconcile in the mind, creating a fundamental incongruence that affects how female leaders are perceived. If they can't contort themselves to match both images at once, they risk being overlooked, disliked, or disrespected.

Actively trying to counter stereotypes isn't always an effective strategy either: A female CEO or president has likely learned to speak up in meetings, but that doesn't mean she will get to finish her sentences. "Data show that women get interrupted more, even on boards of very educated people," says Alice Eagly, a psychologist at Northwestern University and one of the foremost researchers of gender and leadership. And if they do get a word in edgewise, they'd better not misspeak. "Women have to be competent and very well prepared. That's critical, because they can't slide by as well as men who make mistakes can. They may be held to a higher standard."

Context matters, too. For a female leader in a male-dominated environment, her "femaleness" is especially salient and incites excessive cognitive dissonance between the stereotype of a woman and that of a leader. Rosabeth M. Kanter, a professor at Harvard Business School and the author of Confidence, has found that the consequences are increased scrutiny, the exaggeration of differences compared with majority group members, and exclusion from informal workplace interactions.

Indicating that she covets power can be risky for a woman in a way that it isn't for men. Ekaterina Netchaeva of Bocconi University in Milan found (while looking at American subjects) that men are less receptive to female bosses when they're seen as self-promoting and power-seeking. Another study, by Tyler Okimoto of the University of Queensland and Victoria Brescoll of the Yale School of Management, suggests that voters prefer female political candidates who don't have actual or perceived power-seeking intentions and that they expect women to show feelings of communality instead.

The possible—though not universal—outcome of facing gender bias, Stanford sociologist Marianne Cooper wrote in 2013 in the Harvard Business Review, is that "high-achieving women experience social backlash because their very success—specifically the behaviors that create that success—violates our expectations about how women are supposed to behave. Women are expected to be nice, warm, friendly, and nurturing. If a woman acts assertively or competitively, if she pushes her team to perform, if she exhibits decisive and forceful leadership, she is deviating from the social script that dictates how she 'should' behave."

The Credibility Trap

Even when a woman does manage to get to a ladder's top rung, her grasp of it may be more tenuous than a man's. Andrea C. Vial, a Yale University researcher, and colleagues have described a "cycle of illegitimacy," whereby a female leader has a harder time earning her subordinates' admiration and respect, which in turn makes her seem less legitimate. Unless she surmounts that sense of illegitimacy, subordinates can become more negative and less cooperative, which can make their boss react negatively in turn and feel that her position is precarious. Her negative behaviors may confirm the subordinates' expectations—thus reinforcing the cycle.

Researchers Joan C. Williams and Rachel Dempsey report similar findings in their book, What Works for Women at Work, which pinpoints a key dilemma faced by female leaders, and ambitious women in general: They have to prove their abilities over and over again. The authors note that while women at lower levels can be perceived as doing good work, their efforts may be systematically devalued as they move up.

As if these challenges weren't enough, women may be more likely than men to be selected to head up organizations in turmoil—and are more likely to be blamed if they can't turn companies around, a phenomenon that's been dubbed "the glass cliff." Research confirms that a threat to an organization signals a need for change, and since male leaders are thought of as the status quo, women may be seen as the fresh choice for a new direction. That might sound like a rare female advantage, but as University of Kansas psychologist Nyla Branscombe explained in The Wall Street Journal, if a woman fails to revive an ailing firm, people are apt to forget the difficulty of the situation she stepped into and instead think, Well, women just can't do it.

Media treatment of female leaders also pushes them toward the glass cliff. A recent Rockefeller Foundation study examined news coverage of male and female CEOs and found that if a woman was leading a company in crisis, 80 percent of the stories cited her as a source of the problem, whereas a man in the same position was blamed in only 31 percent of the articles. A case in point: Marissa Mayer is often criticized for her leadership of Yahoo, even though the company was struggling for years before she took it over and managed to sell it to Verizon. Tim Armstrong was heralded for selling an ailing AOL to Verizon under similar circumstances.

The Other Women

Another determinant of a woman's success in a leadership role isn't tied to the woman herself, but the gender makeup of her organization. Working with a critical mass of women can ease or even abolish the stereotypes that harm female leaders. Samantha Paustian-Underdahl, a management professor at Florida International University, has found that if half of those evaluating a female leader are women, gender is less salient, and stereotypes that associate men with leadership weaken dramatically. In other words, the more women there are in a group, the less the one at the top sticks out and has to absorb the burden of gender bias.

That doesn't mean that sisterhood rules in a competitive work environment—Williams and Dempsey assert that one way women cope with gender discrimination is by stereotyping and criticizing each other. Studies have shown that female subordinates don't necessarily yearn for a leader of their own gender and might even be turned off by the possibility. A 2014 Pew Research Survey asked respondents whether they would prefer a male or female boss when taking a new job. Female respondents favored a male to a female boss 39 to 25 percent. The good news for women in charge, though, is that employees who currently have a female boss are more likely to prefer another one in the future. Meanwhile, Canadian researchers looked at psychological and physical markers of stress in workers and found that women working under a female supervisor reported more symptoms than those working under a male supervisor. Men's level of distress remained constant whatever their boss's gender.

One antidote to this implied friction is female leaders actively mentoring and sticking up for promising women further down the ladder, which inspires loyalty from those women and provokes the kind of honest feedback that can help a boss, in turn, become even stronger. Claire Hughes Johnson, the chief operating officer of Stripe, a software platform that enables entrepreneurs to build and run an Internet business, was formerly a vice president at Google, where she had a famous boss—Sheryl Sandberg, then the company's head of Online Global Sales and Operations, subsequently the author of Lean In, and a champion of go-getting women everywhere. "She actively included me in meetings and discussions," Johnson says. "And she wouldn't just debrief me on my performance afterwards—she would want my input as well, which was mutually beneficial."

Sandberg, Johnson recalls, was also particularly sensitive to the challenges of being a working mother and welcomed conversation about it. "When I returned to work after having my daughter, she took me out to lunch and said, 'I know coming back is really hard, but you can do it.' She asked how she could help make the transition smoother, and I told her, 'It's hard for me when I get an email from you late at night and I can't respond.' It was something she was doing that she had no idea was having an impact. If we hadn't had our close relationship, I wouldn't have been able to give her that feedback. Now if I send an email to an employee at night, I write, 'Don't respond until tomorrow.'"

Her current roles as an executive as well as a member of Hallmark's board of directors, Johnson is attuned to the importance of gender composition. "Having more women involved in a project allows for individuality to come through," she says. "If you're the only woman, you feel as though you have the responsibility of representing all women. If there hadn't already been another woman on Hallmark's board, it would have been hard for me to join." Forty percent of Stripe's managers are women, she notes, adding that she's shooting for 50 percent.

A Boss Is a Boss

Is there any real qualitative difference in how women lead? Perhaps. Organizational psychology research identifies three general leadership styles: the transformational, which is a collaborative approach where managers and subordinates seek to improve each other, develop as individuals, and meet higher goals; transactional, a traditional style focused on supervision, organization, rewards, and punishments; and laissez-faire, wherein the boss steps back and lets workers complete work as they see fit. A key study Eagly did in 2003 found that women are slightly more likely than men to be transformational leaders who serve as role models and motivate employees' creativity and dedication.

Eagly also found that women are more likely than men to reward positive behavior, which is an aspect of transactional leadership. Doling out positive rewards along with the transformational approach in general has been shown to be more effective than other styles, and some argue that it might be especially effective now, as organizations become less hierarchical and more global.

"While appropriate in certain moments, the model of leadership in which authoritative, smart people tell you what to do is outdated," Johnson says. "Allowing for different work styles and modes of thought is important. The more that we can bring all of who we are to work, and feel safe doing so, the more powerfully we can connect. Not only does it reduce stress for employees, but I've found that people produce better work that way."

In 2014, Paustian-Underdahl built on Eagly's work by conducting a meta-analysis to see whether women are indeed better leaders and, if so, in what contexts. All in all, she found that men and women do not differ in self-perceived leadership effectiveness. However, when bosses were assessed by others, as opposed to themselves, women were rated a little higher. Men bring swagger to their self-evaluations.

Paustian-Underdahl says that while people are inclined to look for essential differences between male and female leaders, "in reality, there is more variance within men and within women than there is between the two groups. Also, different situations call for different leadership styles."

Her findings underscore what leaders themselves contend—that while there are certainly cultural and social forces that affect how they act and are seen in leadership roles, women are first and foremost individuals with deeply idiosyncratic styles. "I'm uncomfortable talking about 'typically female' and 'typically male' traits," Johnson says. "Authority is not just for men, and emotional intelligence is not just for women."

Silver, of Bennington College, agrees, adding that "I think there are a lot more ways to be a female leader or a male leader than we've allowed for. Empathy and listening are not necessarily gendered traits." Silver bristles at how leadership is reduced to a "textbook" list of stable characteristics that leave out the nuance and full spectrum of qualities that are useful, like knowing when to step back. "I'm not saying leadership doesn't require special skills," she says, "but we have a fairly limited and myopic conception of what it is. Part of that narrative comes from overvaluing a stereotypically male, aggressive way of being a leader."

The Androgyny Act

Some of the qualities that Borgstrom, of Yale New Haven Health, credits for her success are by no means exclusive to women, but are more often associated with them. "You have to have emotional intelligence to appeal to a variety of people and to bring the community along," she says. "Vulnerability is also a really good attribute in a leader, and I think women are more likely to display it. The key is to be vulnerable without devaluing yourself."

Joanna Barsh, the author of How Remarkable Women Lead and the head of the Centered Leadership Project at McKinsey & Co., stresses that, in most ways, the habits of effective female leaders are those of effective leaders in general: If they derive meaning and a sense of purpose from their work, they experience greater job satisfaction, higher productivity, lower turnover, and increased loyalty from employees. Successful female leaders surround themselves with smart people who think differently than they do. Those who cultivate a sense of optimism and resilience take more risks and have more energy for their job as well as for their personal lives. "Structural bias and family problems are not necessarily going to go away," Barsh says. "But these women feel excitement about challenges, not bitterness about them."

Still, female leaders often have to factor in bias. They need to be viewed as assertive and independent, and they also need to be seen as authentic. One can fake some behaviors, but it's hard to fake being genuine. Wielding the social skills necessary to assess situations and individuals, while projecting both warmth and competence, is vital to women's success.

A key way female leaders manage this tall order is by balancing stereotypically masculine and feminine traits—either intuitively or via impression management, wherein they observe their impact on others and tweak accordingly. The way they dress is one path: By wearing clothes that are too feminine, a woman risks being judged as professionally incompetent, but by choosing masculine garb, she might be seen as failing at being a woman. Criticisms of Clinton's pantsuits and headbands are evidence of this tightrope act.

Deborah Gruenfeld, a social psychologist at the Stanford School of Business, found that while women who show verbal displays of dominance are disliked, those who show physical displays of high status, such as taking up more space, smiling less, and looking intently into another person's eyes, can assert power while staying likeable.

Eagly has also found that an androgynous physical presence and speech style can help female leaders. Successful leaders, she says, encompass the best parts of both the masculine and feminine stereotypes—tough and compassionate, aggressive and emotionally responsive, decisive and creative. She doubts that most female bosses spend a lot of time consciously crafting a unisex persona, though. "People are not necessarily self-reflective," Eagly says. "A lot of people aren't aware when they're being dominant. They're not socially sensitive. But they learn from subtle cues and feedback, whether they know it or not."

Magdalena Yesil, a longtime Silicon Valley investor, a founding board member of Salesforce, and the founder of the venture capital group Broadway Angels, credits having thrived in her male-dominated field to grit, talent, and pragmatism. "In engineering school, there were only two of us women," she recalls. "Being a 'token' woman was the reality of my chosen career. I was held to a higher standard, but I accepted that. I just assumed I had to work three times as hard as the men."

Part of that meant consciously acting like one of the guys. "I was on 12 boards at the height of my career, and I was usually the only woman," she says. "Whenever I became conscious of it, I would choose to blend in as much as possible. Guys would be talking about sports; I would do some homework so that I would have a few comments to make." She jokes that she only recently "came out as a woman."

As an Armenian Christian who grew up in Turkey, Yesil knew what it was to be a member of a reviled group. Being mocked as a child gave her a thick skin and also explains her preferred coping mechanism of fitting in to survive. "In my career, I just did what I needed to do to be successful. If someone thought I was too tough, it didn't really catch my attention. All those labels are manipulations. I had a goal to meet, a job to do, and I would do it regardless of people calling me names."

While there still hasn't been a woman in the White House, Kanter points out that highly competent women are at the top in nearly every sector. And as more and more women ascend, it has a normalizing effect that makes it easier for other women to become leaders, and to do so while being themselves, forming a virtuous circle.

"Parity hasn't been achieved yet, but we could be on the cusp of significant change," Kanter says. "There are many younger women emerging as leaders, and with these growing numbers, they believe that they can do nearly anything because someone, somewhere, is in fact already doing it. Confidence is an expectation that success is possible, which then motivates people to put in the effort to make the self-fulfilling prophecy come true." n

Carlin Flora is the author of Friendfluence: The Surprising Ways Friends Make Us Who We Are.

Mariko Silver Photo by Michael McGregor

Mariko Silver

President of Bennington College

Leadership Style: Silver sees her main role as gathering information from students and faculty and formulating ideas that take their voices into consideration. "In academia, part of how we teach and learn is by subjecting ideas to inquiry. It's not a sign of success as a leader to put out an idea you think is bulletproof and then shield it from criticism. Let others shine a light on it. You will learn that way. Of course, sometimes not everyone is satisfied, and it's your job to say, 'We're moving forward.'"

Success: When I worked for Janet Napolitano, I once referred to myself as lucky. She stopped me, saying that I'd worked for what I had. That's true. I also think that most moments of good leadership are the result of a convergence of organization and individual."

Having An Impact: "If you're the president, more people will take your calls and want you to opine. I don't enjoy being a leader every single minute, but I do enjoy being in a position to help shift conversations that go beyond the campus. Whether the topic is structural racism or the millennial generation, I can help move the needle."

Marna Borgstrom Photo by Michael McGregor

Marna Borgstrom

President and CEO of Yale New Haven Health

Leadership Style: "I'm pretty self-sufficient, so the hardest thing for me was to figure out how to step back and let other people do what they're great at, in their own style. My role is to ask a lot of questions and integrate things other people are doing with our overall strategy." In a life-or-death environment, like the hospital business, a sense of humor is essential. "I make fun of myself a lot, and people seem to like that."

Femininity: "I wear bright colors because I like them. And my assistant knows that when I have an appointment to color and cut my hair, I won't move it for anything—not even a meeting with the governor."

Feedback: Her ability to handle critiques (or, at least those that pass her "gut check") was perhaps a gift from her father, a doctor: "He was very warm and loving when I was a child, but there were few things I did that he didn't think I could do better."

Work/Life Balance: "There is more recognition now that leaders have to be cognizant of people's personal lives. I'm the sole caregiver for my 94-year-old father, and it affects who I am and how I approach my professional role."

Claire Hughes Johnson ​Photo by Jonathan Sprague

Claire Hughes Johnson

Chief Operating Officer of Stripe

Personality: "I suppose I demonstrated glimmers of leadership from quite a young age—perhaps my role as an older sister played a part in that. I hated things that were disorganized. My parents were both teachers and intellectuals, so getting an MBA at Yale was actually a bit rebellious. Early on in my career, I was always outspoken. I took some risks, and they paid off."

The Personal and the Professional: Johnson's experience as a mother of two has influenced her perspective on shaping the behavior of her team. "As a parent, you see that it's not that they're doing what you're saying, they're watching what you're doing. I try to be aware of my actions and make sure they are in line with what I say I care about."

Moving Forward: "I pay attention to job applicants and try to analyze whether gender bias is shaping our opinions." The underlying mission of Stripe—to enable anyone, anywhere to start and run an Internet business—keeps Johnson in a positive frame of mind about the future. "As opportunities equalize, I'm hugely optimistic about the future of female leadership."

Magdalena Yesil Photo by Jonathan Sprague

Magdalena Yesil

Founder of Broadway Angels

Females and Femininity: "Women aren't immune to engaging in petty politics and turf wars. Go to a PR agency, where management are all women, and you will see what a competitive environment that is. We can't put a halo on our heads and say we're always collaborative. But in fact, I never experienced backstabbing by a woman myself. When there was another woman in the room with me, it was such a treat that we enjoyed each other."

Yesil used to downplay her femininity, minimizing it in the way she dressed and talked, and even in her expressions. "My goal was to make my teammates feel very comfortable with me and willing to open up to me. There were sacrifices along the way, but I was never bitter about it, I still am not."

Mentoring: "Nothing makes me happier than seeing that someone who worked for me 10 or 15 years ago has blossomed and is making a major contribution to industry or technology. If I were a young woman today I would be discouraged. They hear about the negatives and it sounds horrible—why would they want to be in an environment where they might get paid less and be looked over for a promotion? I prefer to focus on the positive and all the role models out there who are taking risks and doing well."

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