How specifically are things different when women lead organizations, whether those organizations are companies or entire nations?
It’s the question at the core of When Women Lead, a new book by Julia Boorstin, a senior media and tech correspondent and reporter at CNBC.
Among the attributes she identifies is “servant leadership.” That’s the management approach emphasizing humility, low ego, and close collaboration with others. It’s a potentially fraught contention: Do we really need to signal to professional women that we expect them to care a lot about serving others? Hasn’t widespread criticism of Lean In demonstrated that expecting more work by women on our own behalf didn’t adequately acknowledge the need for structural change as well?
But Boorstin convincingly makes the case that servant leadership builds authority in leaders and employee trust in organizations. She explains that when executives who practice servant leadership “prioritize and empower employees, the employees’ performance improves.” (p.67) Men also employ servant leadership, and it’s advantageous to them in the workplace, too. Yet benefits in employee performance are strongest when women leaders implement this approach, and when servant leaders guide female-populated teams.
“Anyone, male or female, can reap the benefits of the stereotypically female way of managing teams,” Boorstin writes. “Though a managerial style focused on communal leadership may be associated with women, men and women should both embrace it. And if a challenge to established practices causes a bit of discomfort, well, that means it’s working.” (p. 137)
What else is different when women lead? Boorstin cites many strengths that haven’t historically been associated with powerful leadership “for the simple reason that it is women who most often exhibit them.” (p. 16) These include bringing varied perspectives into decision making. Women are also more likely to lead with an attitude of abundance and learning agility, she writes. In addition, research finds that they are more likely to exhibit greater accuracy in assessing their own abilities; prioritize social and environmental goals in addition to profitability; and express gratitude for their access and opportunities. “One thing these women (and reams of academic research) have shown me is that it’s not that female leadership is necessarily better than male leadership,” Boorstin writes. “Rather, it’s that companies whose values and priorities are more evolved and inclusive tend to have female leaders.” (p. 232)
When Women Lead doesn’t downplay the extreme challenges that these CEOs and entrepreneurs face. At the time of publication, there were only two Black female CEOs leading Fortune 500 companies. Women are 63% more likely to be recruited into leadership roles that are already unstable (a phenomenon known as the “glass cliff”) and to be fired from their leadership roles, regardless of whether a company is doing poorly or well. Women leaders are more likely than their male counterparts to be sexually harassed, including by prospective investors, and to be trolled online.
Many of the leaders featured in the book have been praised for running capital-light organizations, sometimes against their wishes. Companies with solely female founders received less than 3% of all venture capital dollars globally between 2011 and 2020 (and even less during the pandemic), despite the number of women-owned businesses growing faster than business growth overall. (The statistics were even more dismal for Black and Latinx women CEOs, who received 0.4% of VC investment in 2020.) “When those few female entrepreneurs do successfully raise venture funding,” Boorstin writes, “they generally raise less than half as much as their male counterparts.” (p. 11)
The book is realistic about lack of representation and troublesome standards while also, thankfully, offering approaches worth trying. Among them:
- Factor in what makes founders successful beyond their proximity to funders. Consider “distance traveled”: the obstacles entrepreneurs have had to overcome, how far they’ve progressed, and the effort involved in doing so. (p. 342) Freada Kapor Klein and Mitch Kapor included these considerations in criteria for their investment decisions at Kapor Capital, a venture firm focused on funding social impact ventures and backing founders of color.
- Don’t go it alone. Boorstin notes that YPO, formerly Young Presidents’ Organization, inspired the creation of other formal networks of people attracted to the prestige and professional support they found from highly accomplished, dues-paying members. But Carolyn Childers, formerly SVP of operations at home-service platform Handy, “realized quickly that in order to achieve the YPO criteria, she would need a network like YPO’s to get her there.” (p. 299) Together with mattress company Casper’s brand VP Lindsay Kaplan, she developed the executive network Chief as an answer to what they both sought: “a simple, structured solution to their networking challenges that would give them access to useful, like-minded professionals.” (p. 298) Similar frustrations led Tiffany Dufu to create the network The Cru, after she identified that time-strapped midcareer women didn’t need more pressure to find their crew, and that her company could spare them coordination pain by grouping women across industries for coaching.
- Participate in salary transparency: When industry standards were opaque, researchers found that female MBAs suffered a salary loss of an average of 10%compared to their male counterparts, which amounts to a $1.5 million wealth gap for women by age 65—and that’s before inflation. (See the Charter salary transparency playbook for guidance on disclosing pay.)
To be sure:
- While it identifies challenges inherent in a venture capital universe that often acts as a “predictable, predominantly male founder mafia” (p. 311), When Women Lead is hugely pro-venture capital. A follow-up project about founders who bootstrap, crowdfund, and raise alternative financing could show other paths that aren’t reliant on the system that Boorstin criticizes.
- Some profiles of these founders read like marketing copy. Boorstin could be more critical of companies whose growth efforts have been flawed, such as the upscale resale market The RealReal. More sourcing beyond interviews with CEOs could have helped. What is it like to work with these leaders and for them? What do their current and former customers say?
- It would have been better for readers if Boorstin heeded the tagline of one of the book’s featured companies, luxury goods retailer Cuyana, to offer “fewer, better things.” It’s unclear why Goop, a lifestyle company that has a record of poor practices that aren’t actually in service of women’s health, is featured, other than to have Gwyneth Paltrow lead a list of founder names on the book’s cover flap.
- The book could have focused more on the importance of people development in building scalable businesses. Boorstin writes little about the teams the founders assemble and the contributions made by their staff. This furthers a stereotype about tech founders as lone wolves, which diminishes recognition for strong executive teams, boards of directors, and professional networks.
- The project is an ambitious one that could have benefited from more fact checking. Boorstin cites psychology professor David DeSteno’s research about the relationship between gratitude and willpower as coming out of Northwestern (p. 80), not Northeastern. Looker is noted as being sold to Microsoft for $2.5 billion, when it was actually purchased by Google for $2.6 billion. (p. 330)
Choice quotes and anecdotes:
- Unlike most film and TV production companies, Hello Sunshine offered equity to its employees, who benefited when it was sold to Blackstone for $900 million in 2021. CEO Sarah Harden told Boorstin: “We talk about the consequence of economic success; it’s not because we want to get rich and make money. If we don’t have financial power, we don’t have the power to determine our own destiny…It’s hard to rethink the system from within. You have to step slightly outside of it and do it, and then say ‘Fucking look over here.’ And you have to do it by economic success. Show, not tell.’”
- “Over the course of countless interviews, I was struck by a unique approach to leadership many of these women were taking,” Boorstin writes. “I saw them solving problems and creating products they wanted or needed that didn’t yet exist. They were finding opportunities in arenas that men had overlooked. For Bumble, which inverted the power dynamics of online dating, to the biotech company LanzaTech, which turns pollution into fuel, women were creating and leading some of the most disruptive and innovative businesses I covered for CNBC.” (p. 9-10)
- SaaS incident-response platform PagerDuty CEO Jennifer Tejada offers plentiful guidance on hiring: any candidate interviewing to work for one of her direct reports has to interview with her, too: “‘I can help you close them. And if they end up not going well, you and I made that mistake together.’” (p. 127) Regarding DEI considerations and identifying job candidates, Tejada said: “‘The Rooney Rule [an NFL policy requiring teams to interview an ethnic minority candidate for each coaching position] doesn’t work. If there’s one underrepresented person on the slate, we know that person is very unlikely to get hired statistically…There were times when we would wait and lose a good candidate in order to get a balanced slate, and that’s when people really understand you mean business.’” (p. 128)
- Boorstin recalls an interview with Jennifer Hyman during which the reporter asked whether recent IPO flops raised concerns about the future of Rent the Runway in public markets. Hyman’s reply was unambiguous: “Those companies’ challenges and balance sheets, she explained, were very different from hers. ‘As a female CEO, I haven’t been given the permission, or the privilege, to lose a billion every quarter.’” (p. 11)
Ultimately When Women Lead serves as a thorough reference of women founders, CEOs, and funders. It is impactful in two ways. Many of the individual stories—particularly that of Bitwise Industries founder Irma Olguin., Jr.—are memorable not only for their lessons of grit and business savvy but for their creative problem solving.
And, the book makes an important contribution to entrepreneurship and leadership literature, not least of all because so much of the established canon is written by and about men. “The images put forth by CEOs and their marketing machines create a dangerously narrow image of powerful leadership,” Boorstin writes. “In fact, research shows that there is a more and varied and counterintuitive set of leadership qualities that yield better results—for both men and women.” (p. 360) Her approach is additive: “Anyone, male or female, can reap the benefits of the stereotypically female way of managing teams.” (p. 137)
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Hear Boorstin on Hello Monday with Jessi Hempel and Marketplace with Kai Ryssdal.