Every time you ask your boss a question, do you cringe while you wait for her exasperated eye roll and deep sigh? Does your manager throw you under the bus when he gets flack from those higher up the ladder—but is quick to steal the credit when things go well? Does it seem like they…have no interest in actually managing at all?
Welcome to Good@Work, where twice a month, journalist, author, and all-around boss babe Amy Odell—whom you may know as the former editor (AKA HBIC) of and founding blogger of New York magazine’s The Cut—is here to answer your burning career questions. (Want Amy’s intel even more often? You can also sign up for her newsletter here.) This week, she tackles the delicate dance of dealing with a difficult boss.
Q: “If you don’t like managing people, why are you managing people?”
A: I take it you ask this question because your manager is a monster. I’m sorry. No one deserves to be managed by a monster—and yet, most of us are at some point in our lives.
The good news about difficult managers (to put it politely…even though “highly functioning dumpster fires” might feel more accurate) is that their personalities and tactics don’t have anything to do with you. If they were happy, secure people, they wouldn’t show up to work and torture you. Happy, confident people don’t try to prevent you from looking good in front of executives, and don’t feel threatened by your talent. Good bosses encourage you and try to make you better at what you do. Good bosses create an environment in which you are able to do your very best rather than micromanage or act disgusted by every little thing you do. A good boss doesn’t send nasty emails just because her husband happened to load the dishwasher wrong that morning.
Good bosses create an environment in which you are able to do your very best rather than micromanage or act disgusted by every little thing you do.
Sadly, this is how a lot of people in management are. You ask why they would get into management if they don’t have the patience for it, and the answer is simple: because they get paid more to be a manager than they would otherwise. And at most companies, people don’t get sent to Management University before they are assigned a team of people to oversee. When I got into management, I had no idea what I was doing—I just knew that I would never want to be the cause of someone’s day-in, day-out misery, and I figured the rest out as I went along. But no one ever sat me down and said, “Here are some strategies for being a good boss.” I was plopped into the position and expected to deliver. I’m also pretty sure that no one was thinking about whether or not I was making anybody miserable as a boss because they were more concerned with the company’s goals than employees’ wellbeing.
So, if you get stuck with a horrible boss, what can you do? First, remind yourself that this person’s aggression or insanity or whatever it is has nothing to do with you and everything with their own (sad) lives and petty frustrations.
Second, you can take action. Try actually talking to the person about your concerns. Like, “Hey, I noticed that you were unhappy with X, Y, and Z—what can I do to ensure we’re communicating better in the future?” The last thing you want to do is lash back out at them because, as we’ve established, you could be dealing with a sociopath, and sociopaths probably won’t react well to knee-jerk outrage or tears.
No one ever sat me down and said, “Here are some strategies for being a good boss.” I was plopped into the position and expected to deliver.
After you have the conversation, send the person an email recap of what you talked about so you have the receipts. Such as, “Thanks so much for taking the time to meet today. In the future I will do X and Y and you will do X and Y.” Make sure you save the email! If you’re ever unsure of how to protect yourself at work, remember Kim Kardashian videotaping Kanye and Taylor Swift’s phone call and do the office version of that.
If your boss is really bad and your meeting fails, and you have a folder of evidence of how bad they are (emails, work chats, texts, etc.) you can try to lodge a more formal complaint with HR. If your workplace is extremely dysfunctional (and if they hire managers who torture you, this isn’t unlikely), HR might not have an interest in helping you. This is especially true if your boss is HR’s boss and they have nothing to gain from trying to manage the boss’s behavior. But if you can speak to HR, do, and do it in the same way you approached your boss: “I was hoping you could help me because I’m having a problem and I’m not sure what to do about it. My boss and I seem unable to agree on X and Y—when she asks for X and I deliver X she gets upset and says she wants Y. I have examples of the kinds of emails she sends. I’m afraid this is really interfering with our productivity.” And on and on. Remember that when you’re at work, you have to talk to people like you’re a kindergarten teacher. I find this is especially true for women because people in workplaces are made very uncomfortable by women who are direct, though they seem to value this in men, who get to be “eccentric” while women are just “crazy.” We don’t make these rules but we do have to live with them.
It’s also worth considering whether you’re legally protected from your boss’ behavior. For instance, she can’t treat you differently because of your race, gender, or if you’re pregnant. Often, it’s hard to prove that people are mistreating you because you’re a member of a protected group, but if she sends you an email that’s like, “Dammit, Rebecca, leave your pregnancy brain at home tomorrow and stop fucking up,” you could have a legal claim and you need to tell HR immediately.
Let’s say that you do everything perfectly—you file your receipts, you have rational conversations with all relevant parties—and nothing changes. Then you should quit. I know people say you should stay in a job for at least a year and generally I agree that’s a good thing to show on a resume, but I also think life satisfaction and general happiness are much more important than a line on a resume. If you handle the situation professionally, and the company does nothing, that shows you they’re never going to have your back. So what’s the point in waiting around for a raise, a promotion, or anything at all? If they can’t do you a favor when you make a reasonable request that won’t cost them anything, they’re never going to do you a favor. So start looking for another job. And remember, the happiest people are always the ones who have just quit their jobs.
Amy Odell is a journalist and author living in New York. She is the former editor of, which became one of the most popular and award-winning sites for millennial women during her tenure. She is passionate about mentoring people starting off in their careers. She is from Austin, Texas.
Have a career question for Amy? Write us at goodwork@.
Miss Amy’s first column? Check it out here. And if you’re debating asking for a raise, here’s what it’ll cost you to put it off any longer.
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