She's Back

Want To Be A Good Boss? Be A Bitch.

Millennial women are learning the hard way that leaders can’t always be nice.

by Samhita Mukhopadhyay
Millennial bosses may have overcorrected for their Gen X predecessors.
Ariela Basson/Bustle; Stocksy, Getty Images, Phoebe Philo
Bitch Week
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It happened again. I was sitting in my office after 6 p.m., working on a project one of my employees should have finished before they left for the day. But they’d had to go — and I wasn’t going to be the demanding boss who asked them to stay after hours — so I said it was fine; I’d just finish it.

After all, it was easy for me to do: I was single and childless. I’m also from the generation that had drilled into our heads that hard work is a moral good; sacrificing for work is part of my DNA. I am also a woman, a woman of color, and born to immigrant parents — in a multitude of ways, I’m primed to put my head down and get it done. On top of all that, I also didn’t want to be the mean boss, or worse, the bitch boss who — God forbid, I know — made you finish your work when it was quitting time (even if it was your job to finish it).

The idea that women in leadership are held to untenable standards is hardly new. But it is maddeningly persistent: As of last year, only 10.4% of CEO roles in Fortune 500 companies were held by women. Again, that’s last year. When women are able to overcome the social barriers and biases (unconscious and otherwise) keeping them out of boss jobs, studies show there is no safe way to be a boss. If they are too assertive, they are considered abrasive and scheming. If they are too nice, they’re seen as incompetent, less serious, and less capable.

To avoid the latter, many baby-boomer leaders leaned hard into the former. Many women of my microgeneration — young Gen Xers and elder millennials — had a boss who calls to mind Miranda Priestly from The Devil Wears Prada, and her belief that, to make it in a “man’s world,” she had to be uncompromising, cold, and strategic. We kept our heads down in the hopes we might get a chance to get the same opportunities as our elders. In retrospect, as books like Jennifer Romolini’s Ambition Monster and Anne Helen Petersen’s Can’t Even suggest, we worked way too hard, with self-destructive faith in the system that boomer women had clawed their way into. I wrote my own book, The Myth of Making It, about what ambition did (opportunities, money, influence!) and didn’t do for me (sustain me, feed my spirit, keep me healthy).

Twentieth Century Fox

As newly promoted, well-meaning young leaders, we don’t want to inflict the same pain that was inflicted on us. And, to their credit, many of the younger workers we are now tasked with managing — with their unimpeachable boundaries and healthy sense of work-life balance — wouldn’t let us get away with it anyway. But lately I’ve found myself wondering if, in our willingness to take on more work and our reluctance to hand down harsh realities, we’re denying younger workers critical experience. They need to know what the job really entails, so they can get faster or release their perfectionism — and so they won’t wonder why they never get promoted. They deserve to experience the genuine satisfaction that comes from meeting someone’s high standards on a project you deeply care about.

Lately, I’ve heard other managers, often but not exclusively women, say they feel anxious asking their employees to do anything that might interfere with their conception of work-life balance — or even anything they don’t want to work on, whether or not it’s their job. A friend who also worked in media said, “Millennials and Gen Z have really adopted this mantra that work should not be life. And I think that can actually be a really positive intervention because it is true that we are overworked and overstressed. But I think now we’ve almost diminished the value of work to a point that has brought us to an overcorrection that has demoralized basically an entire workforce.” Most managers I talk to agree that it’s great younger members of the workforce are redefining ambition. But then we look at each other knowingly, and avoid saying the quiet part out loud. “So who is going to do all this work?”

The short answer is probably the woman managing you. I asked several women bosses in my life about this and each one of them nodded emphatically in agreement: They’ve taken on additional labor in an attempt to make up for the bigger tides in the workplace. A former colleague told me that for her, this dance shows up as “emotionally coaching,” “managing up,” and knowing there are categories of tasks she can’t rely on certain employees to do, which — and there goes the cycle — invariably “makes more work” for her. Another friend said that if a junior colleague was slacking on a group project, she found it easier to just take care of it herself, rather than have the entire group suffer because of one person “being flaky and stubborn.” It usually wasn’t worth the energy in that moment to correct them.

This is a call to middle managers everywhere to restore the strength of our spines.

Further, the loosening formality in the workplace — referring to our colleagues as “family,” working irregular (and sometimes inappropriate) hours, a level of comfort discussing aspects of one’s relationships and mental health, flexible work-from-home policies — has blurred the line between professional and personal. The truth is, you are bringing a different self to work if that self is still in pajamas off-camera in the first Zoom of the day versus if you actually took a shower, put an outfit and face on, and went into the office.

On paper, the flexibility of a new style of office culture has been great for some workers for many reasons: child care, housework, and self-care are all ostensibly easier when we don’t have to go into an office every day. But for women, research suggests it has also exacerbated the care gap and women are still responsible for more child care than their male counterparts. And when it comes to management, this flexibility has also made way for a new level of comfort in how we interact with our colleagues and, especially, with our managers.

In fact, the trend is so pervasive that there are countless TikToks on the topic. Take the one with the caption, “pov that one millennial manager that’s always going to bat for their people.” It’s a back-and-forth with an employee, during which the manager’s workload grows bigger and bigger. “Forward me the email,” the manager says, enthusiastically, assuring the employee she’ll take care of it. Another is a hypothetical millennial manager who sits down to give a performance review, asking “How is your stomach?” and then chiding the employee for responding to emails while out sick. “No I don’t expect you to work while you’re sick,” the manager says before asking if their workload is OK. If not, he says, he can just “give the work to Roger.” Is he Roger? Am I Roger? What these videos are poking fun at is that young bosses — bosses like me — can be too nice, too accommodating, and too friendly.

There are consequences to absorbing an employee’s work. Every time we suck it up and do it ourselves, we are normalizing that it’s OK not to be fully accountable and responsible for your workload. We give our own managers the impression that they need fewer workers than they really do. The reality is that the more I don’t effectively communicate directives, the more the people who work for me don’t understand what’s necessary to get the job done. The coddling is a Band-Aid that doesn’t really help anyone. Ultimately, if a bogged-down boss handles all the work, projects don’t move forward, teammates can be confused about what their role is, and one day when the boss can no longer pick up the slack — which will happen eventually — that employee will suffer the consequences on a grander scale. The truth is, some things require hard work, passion, and perseverance and no one will reap the rewards through “quiet quitting” or passing the buck.

Rarely is it the top boss, the one earning the big bucks, who suffers from this dynamic. It’s usually an employee in the middle of the org chart, perhaps a person of color, someone from a lower-income background, or someone who doesn’t have the privilege to take work less seriously. “It is always going to be the hardest working person at the office who grins and bears it and who has been conditioned their whole life to grin and bear it,” one friend said to me.

As managers, we’re wading into new territory. “It must be nice,” I scornfully say to myself when an employee draws a line with me, refusing to do something or simply logging off at the end of the workday, regardless of whether everything is done.

Looking back, I probably could have worked a few less late nights, but I don’t regret them. Through those experiences, I learned what it takes to create something excellent, and the power of working together. And even my worst bosses taught me something, too — whether it was a critical skill, or simply how to say no.

I have no delusions that I am the model to whom all employees should aspire. I have bad boundaries and I’m willing to go the extra mile just to keep peace. To be fair, my work ethic has been an effective tool in climbing the ladder. Despite the cliche that all warm women are doormats, I can say with some degree of pride that at times I am the friendly and extremely accommodating boss. But I’m also considered competent, a good manager, a creative lead, and a solid team player. I’m learning from younger generations about how to set better boundaries, but I’ve also managed to work myself to a place of respect and authority. That model is wearing thin as younger members of the workforce see that it hasn’t led to our personal or financial success. Also: I’m exhausted.

The solution, I’m coming to realize, may be to reinvent the bitch boss. I don’t mean bring back the insufferable or toxic bosses of yesteryear, exactly. I mean, let’s reimagine a boss bitch who has purpose and clarity, who’s unafraid to ask for what she needs from herself or her team. This new boss bitch would provide the clarity her team seeks without fearing that she’ll be considered unlikeable. She’d stop wasting time, cut through the bullsh*t. She’d be reasonably aggressive when the need arises, sure, but mostly just clear in thought and action.

I’m not calling for anyone to “lean in” or reproduce the same vicious cycle of crappy management that exploits an underappreciated labor force. This is a call to middle managers everywhere to restore the strength of our spines.

My most functional, satisfying work management experiences have been when I was clearest about what I needed, when I could push my team without losing my humanity. When I was the editor of Teen Vogue, I felt that power when overseeing the publishing of a big project. When I worked on political campaigns, it was when we were all aligned for launch day. When we had a shared vision of success and everyone felt they were being treated and paid fairly. Sometimes, on those days, I was a “bitch” — high standards and clear objectives. Other times, that required me to be nice and flexible while being honest and firm.

Our behavior as managers, now more than ever, can’t always be to suck it up. But we can always find ways to be righteous and — sometimes — bitchy.