Stuff They Don’t Tell You How do you work with a bad boss?

Cover Image - Stuff They Don’t Tell You
Margot Lecomte
WordsAlex Moshakis

Spend enough time in the working world and you’re bound to come across a bad boss of some stripe, be it a chronic oversharer, a know-it-all micromanager, or a bog-standard bully. But don’t let them run you out of a job you love. Here, writer Alex Moshakis speaks to “Jerks at Work” author Tessa West about navigating those tricky relationships.

Illustrations by Margot Lecomte.

Have you had a bad boss? I’ve had several. One got high at work. Another threw their computer to the ground at moments of high tension. Tessa West, a professor of psychology at New York University, and expert in interpersonal and intergroup relations, has had several bad bosses, too. There was “the chip-on-the-shoulder boss,” and once, while working a job in retail, West had a boss who “micromanaged people just to reassert her authority,” she says over the phone. “We see that a lot.

In her 2022 book “Jerks at Work,” West examines the ways in which coworkers, including managers, can become toxic, and what we might do about them. There are several kinds of bad bosses, West says. There are bosses who are “mediocre at their job and have no management training,” but who have been part of an organization for so long that a promotion was inevitable. There are neglectful bosses, and the top-down controlling bosses. Bosses who overpromise, and bosses who overshare. West’s favorite bad boss is the symbolic ally: “The grand gesture boss who does all the public stuff—the tweets, the newsletters, the calling-it-out—but who is secretly totally terrible.”

How do we cope with bad bosses? First, West says, we must understand the source of their misbehavior. We tend to think that managers are terrible due to personality issues, but there are often other factors at play. “Often we assume people are being bad bosses because of X, Y or Z, but we don’t really know. Nine times out of 10, they’re getting some top-down pressure that is affecting their behavior,” West explains. Many micromanagers, she adds, feel uncertain about the stability of their own job. “In an effort to control or regulate their own feelings of uncertainty in the workplace, they micromanage the people around them.”

Sometimes, bad behavior is learned—and even incentivized. “When you have someone who acts like an asshole at work, it’s often part of the norms of that workplace,” West says. “I’m doing a lot of coaching right now, and one of the main things that comes up is this: ‘I have a person who is really abrasive, he rubs people up the wrong way.’ I will say, ‘Well, who was his last boss?’ And they will say, ‘Oh, his last boss was a person who did the same thing and succeeded because of it.’ 

“Almost every person who is forced into coaching right now is there because they came from a job where [their behavior] was acceptable and encouraged by their last boss. But now they’re in a new place where those behaviors are considered inappropriate. Half of the battle is just explaining to them why those behaviors are inappropriate.”

In some instances, the hiring process can doom a workplace relationship. While interviewing people involved in hiring recently, West discovered that bosses are rarely given much say in the content of the job ads intended to find their reports, or given the opportunity to interview candidates. “It’s like getting married to someone your friends picked for you, and then being accused of being a bad spouse because you don’t align with your partner’s expectations.”

Whatever the origins of the bad boss’s behavior, finding a solution requires careful maneuvering. First, you may want to figure out how widespread your boss’ jerky behavior is, and see whether your perception is shared by others. “Often we feel like we’re being mistreated, but when you talk to other people they view the conduct differently. Getting consensus that the behavior is bad, and on how widespread it is, is important.”

But be careful how you conduct your research: “Don’t talk shit about your bad boss. Collect data first. Frame it as communication issues or goal misalignment so that if it gets back to them, it won’t hurt their feelings and it won’t piss them off.”

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And if the consensus is that the boss is truly bad? Then it’s time for a frank conversation. People are often scared of giving upward feedback, but having those high-level conversations can be critical. 

“If you want to bring up issues with your boss, you have to think about how you are going to frame them so they don’t feel super threatened, and without allowing them to flip it on you, or engage in what we call reverse blame,” West says. 

She suggests telling your boss what you like about your role or your relationship, and then focusing on aligning goals. “Ask: ‘What are your goals for me, and what are my goals in this organization?’ You have to tiptoe into these conversations. Leading with your feelings—like ‘I feel I don’t matter here’—automatically activates another person’s threat responses, so don’t focus on behaviors.”

If you don’t believe a direct conversation with your bad boss will be productive, it could be helpful to subtly seek solutions from others within the organization. “Find someone who’s been working alongside this person for 10 years. Don’t go to them and complain and make accusations. Go to them and say, ‘You’ve had experience of working with them, what’s their leadership style? What are they into?’ Suggest there might me a mismatch, or a fit issue. That’s a very politic way of bringing up your jerky boss with someone in power.”

Clearly, West doesn’t think a bad boss should spark an automatic resignation. Afterall, who can say a new boss elsewhere would be any better? “Our current bad bosses are at least bad in predictable ways, so we feel we can at least see what’s coming,” West says. Often, when considering moving jobs, we “don’t want to walk into a place where we have no idea what version of bad we’re going to get.”

But if you try all the steps above and they don’t work, West says, then “you have to have an honest conversation with yourself about whether you should stay.”