terrible bosses

What Makes Some People Such Bad Bosses?

Photo-Illustration: Marcus Peabody; Photo: Getty Images

What makes a boss truly terrible — and how should you deal with it? Cut writer Katie Heaney explores the science behind what makes one person an excellent boss and another person a horrible one, as part of a weeklong series about what makes a bad boss, and why we’re so tortured by them.

One need not look far in order to find horror stories about bad bosses; they are among the internet forum’s favorite topic of discussion. The massive, continued popularity of the show The Office must be owed, in part, to what we, as employees, see in Michael Scott: something of our own dorky, embarrassing, try-hard, lazy, misguided bosses. And ultimately, Michael Scott is pretty nice — certainly, he’s near the mildest end of the bad-boss spectrum. Somewhere toward the other end, perhaps, we have Meryl Streep’s Miranda Priestly in The Devil Wears Prada: cold, inscrutable, and impossible to satisfy.

What makes bad bosses so … bad at being bosses? Let’s assume almost that every person in a “boss” role at work was once another person’s underling: Shouldn’t each new generation of bosses know better? If we can recognize what we dislike in our own managers, why aren’t we able to rectify their mistakes when we become leaders ourselves? And are we really so sure that we, the employed, aren’t impossible to satisfy ourselves?

According to Robert Sutton, professor of management science at the Stanford University School of Engineering and author of The Asshole Survival Guide: How to Deal With People Who Treat You Like Dirt, says many of the people we consider bad bosses get into leadership for the wrong reasons: specifically, because they enjoy wielding power over others, and the recognition that comes with it. “Those are hallmarks of narcissism and selfishness, which I think are pretty standard characteristics of bad bosses,” says Sutton.

Indeed, in his research on workplace bullying, Alan Cavaiola, a clinical psychologist and professor of psychology at Hofstra University, finds that narcissistic personalities abound in those managers whom employees find difficult to work with — as well as people with obsessive-compulsive personalities. “Narcissists think nothing of stealing other people’s work and passing it off as their own,” says Cavaiola. “They think nothing of throwing you under the bus if something goes wrong.” Bosses with obsessive-compulsive personality traits, on the other hand, tend to micromanage. “Nothing is ever going to be good enough for them,” Cavaiola explains. Of course, at the opposite end of the micromanagement continuum is the boss who is totally hands off, and “lets you do whatever you want,” says Sutton — and most of us don’t like that either.

Another familiar managerial grievance is plain incompetence. As a professor at Stanford, working with students to advise newbie Silicon Valley CEOs, this is something he sees a lot of. “One venture capitalist called them ‘babies with loaded guns,’” he says. “You take a 24-year-old person, give them $30 million, and they’re just so fuckin’ incompetent it’s unbelievable.” Many of us grew up under the assumption — highly encouraged by our capitalist society — that people who are in charge are in charge for a good reason, and it’s only through bad boss after bad boss after bad president (etc.) that we realize that’s not necessarily the case.

If the 24-year-old with the dubious app idea is to blame, so, too, is the mind-set with which so many of us approach our jobs, says Amy Edmondson, professor of leadership and management at Harvard Business School and author of The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. “Far too many bosses have a taken-for-granted and highly outdated mental model about what it means to be a boss,” says Edmondson. “We were brought up in an industrial-era model of not only management but schooling, where we were taught to sit still, listen up, don’t make noise, write down what the teacher says, and then spit it back. That isn’t terribly useful in making great employees or great managers today.” In today’s knowledge economy, says Edmondson, getting work done requires ingenuity and collaboration more than command and control. Being a good boss is less about telling one’s employees what to do, and more about creating the space in which they can flourish.

Edmondson calls these spaces “psychologically safe” workplaces, where employees feel free to share work-related concerns, questions, and critiques without fear of retribution. Most people, she says, don’t feel that freedom at work, and it’s up to the managers to foster it. Perhaps the first step in doing so is accepting that there is always more to learn.

For his part, Sutton has noticed a few shared characteristics among better bosses. The first of these is self-awareness: getting a sense of what it’s like for your employees to work for you makes you more aware of your strengths and weaknesses, and also makes you more empathetic to your employees’ needs.

Being recognized as a better boss, of course, presents another, loftier challenge: Aren’t most of us bound and determined to find fault with the people who hold us accountable, and who are responsible for our paychecks? Isn’t there a sickly satisfying camaraderie in banding together with one’s peers in shared disdain for the Man? Most people don’t have any choice but to work, and if we have to work, we might as well find some common ground with our fellow employees. The bad boss is an easy (if often deserving) target.

Maybe, then, a bad boss is one who ignores their employees’ grumbling wholesale, while a better boss is one who seeks and sits with legitimate critique. “People who keep getting better have people in their life who tell them the truth, and they listen,” he says. “There’s an argument that that was a key role Clementine Churchill played with Winston.” In The Office, Michael finds a moral compass in Pam, and becomes a better leader (and person) for it. In The Devil Wears Prada, Miranda Priestly listens to no one, and ends up alone — if still totally at the peak of her reign. In pop culture, a bad boss who won’t listen is punished with an empty personal life, particularly if she’s a woman. In real life, a bad boss who won’t listen can be hailed as an independent, eccentric genius, particularly if he’s a man.

So here, before we return to our Reddit forums, let’s have a brief moment of sympathy for those better bosses. “If you think about what makes a good boss, it’s someone who does all this work to be in touch with people, who’s constantly fretting over how to make employees feel safe; they’re guilty, they’re listening, they’re giving, they work so hard,” says Sutton. “It’s just — ah, I just think it’s exhausting.”

What Makes Some People Such Bad Bosses?