Women Suck at Being Bosses Just as Much as Men

The sign that former Google and Apple executive Kim Scott’s new book, Radical Candor, is not your average business tract comes in the introduction. It’s a story Scott tells from her early days at Google: After Scott gives a presentation, Sheryl Sandberg approaches, congratulates her, and offers to hire a speech coach because Scott says “um” too much and it makes her sound dumb. It’s the paradigmatic example of what Scott means by “radical candor”—you make sure a person knows you really want them to succeed, and then you tell them a slightly impolite thing they need to know and offer a resource to help them improve.

The anecdote is also emblematic of Scott’s higher ambitions: a depiction of a female boss who is critical without being bitchy, caring without being a sap. Radical Candor flows from the observation that the best bosses both genuinely care about their employees as people (in Scott’s jargon, this becomes “Care Personally”) and actually give them negative feedback when necessary (“Challenge Directly”). By asking male and female bosses alike to care more about their employees, she is trying to build a new language for talking work that doesn’t succumb to gender stereotype.

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In the same way that Sandberg’s Lean In attempts to paint a new picture of old work assumptions, Radical Candor is a feminist-adjacent manifesto, though there are obvious limitations. Like Lean In, its target audience is the “How do I seem as professional as I can today?“ set, so it just doesn’t have the same impact on someone who is more concerned with, say, where the rent is coming from this month. But coming so soon on the heels of a few start-up workplace horror stories—Susan J. Fowler’s account of widespread tolerance for harassment at Uber, and the resignation of Miki Agrawal as CEO of THINX and subsequent reports of grave HR problems there—the picture of workplace utopia painted by Radical Candor inadvertently answers the question in many minds: “How did these places and this industry go so wrong in their treatment of women?”

With little hierarchy, institutional memory, or bureaucracy beyond ideas, start-ups begin their lives in disarray. Anybody who has seen The Social Network can tell you that, and Scott affirms this stereotype when she mentions that she was generally older than her managers at Google and Apple. She seemed to be the person you called when you needed an adult in the room, and Radical Candor is her record of the knowledge she gained trying to figure out how to turn ramshackle teams into more professional ones. The book is also soul-searching; Scott is so honest about her shortcomings and the path she took to becoming a better boss that it reads a bit like a memoir of Silicon Valley in the aughts. There are homages to all the characters we think of when we consider the tech mogul: Sandberg, Steve Jobs, Tim Cook, and Sergey Brin. But for all the hagiography she engages in, Scott explains also how they were effective and caring, even if they were a little bristly. In other parts of the book, she discusses nameless bosses who are angry, frustrated, shallow, and unchallenging—much closer to the picture of the bad tech boss we’ve been reading about.

It is surprising how little has been written about the characteristics of bad bosses. That might be because the typical person who writes a book about leadership is incorrigibly optimistic and unduly confident in his or her own skills. Besides, bosses tend to be the reverse of Tolstoy’s comments about families: All bad bosses are basically the same. Like obscenity, they resist definition—you just know one when you see one.

So while the bulk of the book advises a person on how to be a good boss, Scott spends the beginning establishing what is essentially the New York Magazine Approval Matrix for bad ones. A boss who cares but never challenges? They practice “Ruinous Empathy.” A boss who challenges but doesn’t care? They’re “Obnoxiously Aggressive.” The worst of all, in Scott’s terms, is the boss who neither cares nor challenges, and thus becomes “Manipulatively Insincere.” That all of those descriptors apply to a bad boss is obvious; that they might interact and give a heuristic for the way a good boss should act is not.

This isn’t about hugs! This is about power!

It makes a lot of sense that the person who explains a pretty universal description of a bad boss worked at two of Silicon Valley’s biggest companies; tech culture has begun to rewrite our shared assumptions of what a job should be like. Our major workplace exposés aren’t like Upton Sinclair’s 1906 novel The Jungle, exposing dangerous conditions or physical abuse; today, it’s more like The Valley. In a company that makes money despite a lack of structure, the value of an employee is totally disconnected from the way that employee treats the other people in the company. This broken system explains why a company might keep a guy on despite multiple complaints that he is a harasser; that he makes most of the women in the company uncomfortable doesn’t matter if he’s a “high performer.” It’s why you can have a founder who abuses and underpays her employees but still garners fawning attention from the press.

Despite the wisdom of her description of bosses, Scott falls victim to Silicon Valley’s myth of inevitable meritocracy in a way that limits her ability to solve any of the really pernicious problems that these companies face. She mentions that she has encountered teams who have “lost all faith” in their manager; after some investigation, she decides these managers are simply people who should not have a job as someone’s boss. She never says what she thinks disqualifies a person in this regard—in fact, other than this, Radical Candor leaves out the issue of incompetence entirely. It’s aimed at a boss who is good at their job, even if they’re just OK—or even bad—at managing their direct reports. She assumes that everyone who isn’t good at overseeing a schedule, working with others, setting priorities, and managing workflows never becomes a boss. Anyone who works in the real, mediocre world knows that is not the case. In Silicon Valley, your ability to be a founder is based entirely on your ability to have an idea, convince investors to give you money, and attract media attention. None of these qualities ensures that you will be even a passable manager.

She provides little advice—beyond an implicit “just deal with it”— for employees in extreme situations like Fowler at Uber. It seems like that behavior would be the sort of disqualifying behavior she’s thinking about in those “lost all faith” teams, but that’s not made explicit. Sexual harassment comes up only one time, dropped uncomfortably into a section about how hugging in the office is OK:

Of course, a hug or touch can go wrong. Early in my career, I had a boss who gave me a big hug when I was upset about something, and then started grinding into me in a sexual and most unwelcome way. Now I was really upset. I had relied on him as a mentor and now I would forever see him as just another sleazebag.

This story is upsetting not because it’s surprising, but because it makes me want to go back in time, find younger Kim Scott, and tell her, “This isn’t about hugs! This is about power!”

The corporate-feminist response to this situation is to work harder, keep your head down, and try to get a promotion. This meritocratic argument is seductive—each individual woman gets to overcome the emotional harm of the situation with a bigger salary and the knowledge that deep down, her talent and drive were stronger than sleazebags. But when everyone makes that decision and encourages other women to make it, too, the result is an industry that systematizes sexual harassment. It creates an industry where a man who gets results will always be more important than the women he discriminates against, and a woman in a position of power will measure other women’s worth by how well they can sweep it under the rug. Scott admits that a workplace can only succeed at implementing Radical Candor when they have a “No Assholes” hiring rule; her belief is that mutual respect between employees will pay a financial dividend. But recently I’ve read about two companies that were successful despite having more than a few assholes. Even assholes have a “No Assholes” rule.

Ever since I put the book down, I keep returning to that story about Sheryl Sandberg and the “ums.” It’s gotten to the point where I even play the scene in my mind, imagining Sandberg in a white Oxford shirt and Scott in a navy dress. Perhaps it’s because the interaction is like a second-wave feminist utopia: two female executives subtly, firmly, and kindly overcoming gender stereotypes!

But then, after a few minutes, the warmth always fades, because there’s something so exceptional about the moment it’s almost comical. The moment is extraordinary because there aren’t enough women in upper management. Because women just don’t interact with each other in that way in the workplace—especially in competitive industries, they’re often as cruel, selfish, and undermining as men can be. Even the logical constraints of the book tend to make me sad. Radical Candor can only happen when a boss makes it clear that the direct report is, as Scott puts it, “a valuable team member she was ready to invest in.” Most bosses don’t see their employees as valuable; that’s just capitalism.

If nothing else, Scott’s book explains why majority-female workplaces and industries tend not to be too feminist in practice. THINX was a place where the employees were underpaid and expected to do emotional labor for their bosses; you could say the same for publishing, for media, for nursing, for teaching, for so many female-heavy industries. In order for a boss to care about you, they have to feel confident about hiring you. In order for a boss to challenge you, they have to be able to take criticism themselves. This is a pretty rare occurrence in real life.

At first glance it seems unfair that Scott calls “Manipulative Insincerity” the worst of all traits, because it is so coded female. Women are constantly told they shouldn’t be angry, so they don’t challenge directly. Women are constantly punished for being too emotional, so they don’t care personally. If Radical Candor felt like a revelation to me, it’s because I know that Manipulative Insincerity is the gold standard of management in many work places. Even though Scott doesn’t give any suggestions for how we can change this as a society, it’s something we have to do.

Of course, this is a management book, not a work of sociology, psychology, or philosophy. The sad thing is that these problems are, at their core, social, psychological, and philosophical. You will never be able to convince a boss to care personally for his direct report when he thinks she is less capable because she is a woman. You will never be able to convince a boss who sees emotion as a weakness after decades of abuse to treat her employees with care and respect. Conscious or not, that’s just the way most bosses—men or women—see their employees.