terrible bosses

Why Do We Lionize Bad Bosses?

Photo: Marcus Peabody/Getty

What makes a boss truly terrible — and how should you deal with it? Cut columnist Rebecca Traister addresses our culture’s tendency to romanticize power, and what that means for those who abuse it, as part of a weeklong series about what makes a bad boss, and why we’re so tortured by them.

As long as we’re rethinking power and its abuses, perhaps it’s also time we rethought bosses. Especially the bad ones. What does it mean, right now — or what might it mean in our near future — to sit atop a company or division or department, to wield power, to hire and fire and direct a group of workers to do your bidding, and to be vindictive, short-tempered, and mean?

After all: From the chilling revelations of Me Too to the resurgent labor movement and socialist critique of capitalist excess embraced by a generation (of mostly young professionals), there is perhaps a greater awareness of workplace inequity, abuse, and plain-old cruelty than there has been at any other point in my adult working life. Many of us were taught — in school and on television and by a media that celebrated power and made bosses celebrities — that being in charge was an aspiration, a signal of success and a life well spent. But relatively suddenly, the notion that those on top represent some kind of infallible authority feels antiquated and wrong.

In this climate of reassessment, what of the legendarily awful boss? Not just your own specifically shitty boss, though sure: that person too. But more broadly, what about the archetypical figure, the stapler-throwing brute or witheringly mean harridan? How do we actually feel about power now, and those who wield it severely?

From Scrooge McDuck to Dabney Coleman in 9 to 5, it’s hard to imagine America — a nation whose economy and laws were built around the literal enslavement of workers, and where greed and preening ambition have been flatteringly recast as having something to do with a Protestant work ethic and Horatio Alger rags-to-riches fables about the “American Dream” — without its bad bosses. Our current commander-in-chief is, among other things, a famously bad boss, but also one who made himself famous by playing one on a television show that people enjoyed watching.

In other eras (like five years ago … ), bad bosses were the stuff of romance and imagination — great characters, as they say — even the ones, like Trump, who turned out to be alleged rapists. After all, before being publicly exposed as a sexual predator, Harvey Weinstein was written about rapturously, with acknowledgment of his explosive temper and demanding nature, as a reincarnation of Old Hollywood studio bosses — the new Louis B. Mayer (also a predatory monster!). Meanwhile, Vogue boss Anna Wintour, whose petty professional cruelties were sent up in Lauren Weisberger’s novel The Devil Wears Prada, was reclaimed as a misunderstood badass in the movie adaptation, where she was portrayed by a winningly chilly Meryl Streep. They have built an entire television empire around British chef Gordon Ramsay’s brutish-boss tendencies.

The past few years have seen a thorough fisking of a lot about workplace culture that was permitted to pass for a very long time, especially around gender bias. Weinstein is gone; Michael Bloomberg, poised to run for president, is greeted with coverage of his long history of ill-treatment of female employees, while his would-be rival for the nomination, Elizabeth Warren, takes the stage each day to “9 to 5,” the Dabney Coleman–defeating working-women’s anthem.

But while I am encouraged by the reassessment of gendered power imbalances, as well as by a reinvigorated move, via collective bargaining, for higher wages and better working conditions, I’m not sure that we can ever truly rid ourselves of the brutal hierarchies that have for so long stood in as signals for advancement.

In short: I don’t know how any of us ever really gets free of a culture of bad bosses. Put more plainly: When you take the sex out of workplace power abuses, does anyone care about them?

Back when I worked for a series of savage supervisors, I used to wonder, while complaining with my colleagues over beer, how many of us would one day become bossmen and women ourselves. Who among us would become the kind of people who take credit for the work of the next generation of peons who’d in turn go out and curse our names over weak beer at dive bars … until they too became bosses?

I certainly didn’t yearn for this kind of progression; it made my stomach turn. But I think I did assume it was just how things worked, in nature. There seemed a kind of inevitability about bossdom as the goal, because, well, what else lay at the end of these work weeks? Surely there was some magnetic force that would pull at least some of us from the cubicles into the offices with doors, and once we got behind those doors, wouldn’t we too be alchemically changed from people with little power to people with more power, and didn’t power just operate as a corrupter organically?

To unwind these assumptions would mean the dismantling of all kinds of twisted stories we’ve told ourselves forever about our fantasized meritocracy, in which those who are offered less have often been convinced that they deserve no more, in which those who are treated without dignity are made to believe they haven’t earned it, and in which those who have more authority than we must have it because they merited it where we did not. We are taught to take socially imposed power structures as a piece of nature, to believe our place within these systems as symptomatic of our strengths and shortcomings, to understand any drive to succeed and in so doing, get more power than other people, as the ultimate goal (and reward) of working life.

But power doesn’t always go to those who know best what to do with it, and for those who aren’t sure how to confidently project authority and competence when they become the bosses, being mean can feel like an easy and familiar shorthand.

Of course, plenty of bosses treat their employees with dignity; some are supportive mentors, a few are generous. Yet hierarchies creep in (and hierarchy-free workplaces aren’t necessarily the most functional or even humane). Until the robots really do take over, there’s no taking human nature out of workplaces, and some percentage of human beings tilt toward cruelty as an expression of their comparative might.

Yes, we’re probably in a moment in which it’s harder to throw a stapler and not find yourself written about … just ask Amy Klobuchar. Recent conversations about sexual harassment, following decades of civil-rights cases that have painstakingly made workplace bias officially illegal, have led us to question that kind of behavior.

But can there be a movement around it, one that doesn’t involve gendered or sexualized abuses?

It’s worth noting, as with sexual harassment, that the loudest and most specific voices of discontent have come from some of the most privileged classes in the most high-profile industries. A recent report in the Los Angeles Times about the work of Hollywood assistants to band together to speak up about the systemic abuse they suffer as overworked low-wage employees within a very wealthy industry showcased one of the more depressing realities: Even when exposing workplace indignities, it’s in our nature to look toward the flashiest and wealthiest, and not to read the stories that more rarely get written about hotel workers, service-industry employees, janitors.

Part of that gets us back to the way we romanticize the bosses, even the bad ones: We picture them as people who on some level, we want to be, which means considering them in the fields that are understood as high-paying and aspirational. Trump’s turn on The Apprentice showcased him as brittle and shallow, but somehow those qualities — in a guy whose role in the show was expressed by regularly telling people they were fired — read to viewers as muscularity and capability. Why? Because he was rich, and on television, and because we are a culture that values money and celebrity, which are read as signals of seriousness and merit.

In late 2017 and early 2018, as I heard story after story about sexualized misbehavior, I heard almost as many from people who’d had bosses fire them capriciously, sideline them for no reason, steal their ideas and pass them off as their own; but they felt like they had no recourse, because the bad behavior hadn’t been tied to their identity.

In fact, for those with power and the instinct to abuse it, the answer to not doing it along racially drawn or gendered lines will, unfortunately, be simply to be mean to everyone. Consider that some of the legal arguments made against, say, pregnancy-discrimination law have entailed the argument that if bosses treat all their employees badly, treating pregnant ones badly doesn’t count as an instance of bias, making the ill-treatment of all employees an excellent cover for the ill-treatment of some of them.

And in a period of economic precarity, there is the question of whether it’s worth it for the vulnerable to challenge the behaviors of their mighty overlords. Is it easier to speak up because the rewards of keeping quiet are less, or does a fiercer dependence on those checks create an inability to raise your voice in challenge?

But maybe this is what we need to push harder for, as long as we’re talking about big structural change. We need to reckon with the power abuses of the bad bosses not just throughout our history and not just in our Oval Office, but also in our own offices and on our own screens. Perhaps hardest, we have to root out the bad bosses, and our ingrained admiration for them, in our own heads — especially when we land the corner office, the one with all the power.

Why Do We Lionize Bad Bosses?