ask a boss

9 Bad Bosses, and How to Work for Them

Photo: Frank Siteman/Getty Images

Get Ask a Boss delivered every week

By submitting your email, you agree to our Terms and Privacy Policy.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Some bosses are just … terrible. Bad bosses are poor delegators and annoying micromanagers, or they’re self-indulgently obsessed with the office gossip. Others are slackers — or so busy they’re only available on Slack, where they constantly ignore your messages. And here’s something everyone should think about: the boss who asks, “Do you have children?”

The Cut’s “Ask a Boss” columnist Alison Green has answered letters from readers with irritatingly bad bosses. Here’s her best advice on how to survive working for them.

1. ‘My Boss Treats Me Like an Assistant, Which Is Not My Job.’

What’s appropriate for your boss to delegate to you, and what’s not? Especially when your boss asks you to do simple tasks — as in: very basic duties that are part of their job — they’re walking a thin line between what’s fair for you to do and what’s not. If you don’t complete the work for them, no one else will. What can you actually do?

Usually it makes sense for the more junior person to help free up a manager’s time. “It sounds like a lot of the tasks you’re wondering about are ones that it likely does make sense to delegate to you. But not all of them,” Green writes. Before you consider quitting, think about it as an opportunity, like this.

2. ‘My Boss Is Too Busy to Actually Talk to Me!’

Some bosses are so busy they’re never free to talk — maybe they’re only reachable via instant messaging or email, but rarely ever respond. How can you get more attention from your boss? “Am I expecting too much from my manager given that he’s so busy?” this reader wonders. “Should I just suck it up and learn to forever find my own answers?”

Often, this kind of boss has no idea that you need help or that they’re ignoring you, Green says. They’re just busy. “People assume that if their boss is assigning them a ton of work, there’s no point in speaking up because they must be expected to find a way to get it all done, when in fact the boss is assuming they’ll speak up if it becomes a problem. So the boss goes on thinking everything is fine while the employee is stewing and feeling overwhelmed.” Here’s how to talk to your boss about it.

Photo: Derek Hudson/Getty Images

3. ‘My Boss Is a Total Slacker!’

Ever feel like you’re babysitting your own boss, so they finally get something done? “My boss won’t do anything unless you sit in her office and wait for her to do it,” this reader writes. Some bosses are genuinely busy, but others are just … lazy. Which can affect your own productivity as their employee, because it’s so taxing to work for someone who’s unproductive.

“I get that it’s frustrating — infuriating, even — but I think you’re discounting how much this is not your problem to solve,” Green replies. “It’s her boss’s to fix.” But if your boss’s boss doesn’t talk to her about it, there’s not much you can do. Think about your options.

4. ‘My Boss Keeps Asking, ‘Do You Have Kids?’’

Ah, yes, the question you should never ask a co-worker. This reader points out why it’s an inappropriate topic: “Maybe I’m infertile. Maybe my husband is. Maybe we tried for years before giving up. Maybe someone has a genetic disorder we’re afraid to pass on.” It doesn’t matter if none of those things are true, because for someone else, they could be. But when your boss is asking the question … what can you do?

“You will be doing all of society a favor if you point this out to him,” Green writes. You can even do it cheerfully. Here’s how to bring it up.

5. ‘My Boss Is Constantly Getting Me Sick!’

This reader’s boss comes into the office sick all the time and stages a horror scene among her employees: “She coughs into her hand and touches the phone and other desk items we share, effectively spreading her germs far and wide. … As much as we arm ourselves with hand sanitizers, Clorox wipes, Lysol, flu shots, and, in the case of one colleague, rubber gloves, sometimes we catch her illnesses.” Hello: That’s disgusting.

Usually, you can’t be sure where germs are actually coming from, Green says. So do a reality-check first: Maybe your boss did get you sick, or maybe you picked up a bug on the subway. However, if it happens again and again with someone like this boss, you can’t just ask if she’s seen a doctor. That approach says “‘I’m concerned about you,’ when the message you really need to deliver is ‘I’m concerned about the rest of us,’” Green writes. Here’s something better to say.

6. ‘I Have Two Bosses, and They Hate Each Other!’

When you report to two people who despise each other and vent to you about it — and there’s no HR department — you’re in a terrible position. You’re right in the middle of them. But there are plenty of things you can do to make your life less miserable.

When one boss starts venting about the other, Green recommends telling them it’s awkward for you to listen. “Sometimes with people like this, you can get more traction if you make your request for boundaries more about you than about them,” she writes. Read more suggestions here.

Photo: Tom Kelley Archive/Getty Images

7. ‘My Boss Is a Micromanager!’

When a boss constantly corrects tiny mistakes or decides to completely redo your work behind your back, first it’s worth asking yourself why they’re being so hands-on. “For example, if your work quality hasn’t been where it should be, or if a project is very high-stakes, or even if you’re just new and still getting acclimated to the job, a good manager would get more closely involved,” Green writes.

But if none of those things ring true, then talk to your boss. “Try to (a) get a better understanding of what’s driving his behavior and (b) see if he’d be open to doing things differently.” Here’s what to say, word for word.

8. ‘My Boss Asks for My Advice and Ignores It!’

Maybe you always want to tell your manager, “I told you so.” This reader’s boss frequently asks for her opinion, disagrees, and later changes his mind when it turns out that she was right. She wants to know: How can she make him listen and agree with her the first time around?

“I can see why this is frustrating,” Green replies, “but asking for your opinion isn’t a promise to agree with your opinion or to act on it.” It’ll be less annoying if you try seeing things this way.

9. ‘My Boss Is Clingy, Even After I Quit’

After giving your four weeks’ notice, what if a boss continues to act as if you’re never leaving the company? As in: giving you more work to do, and constantly joking that you’re not actually moving on. This reader quit her job but still cares about her company. Before she leaves, she wants to take the time to help smooth the transition for her replacement — by creating a transition document, for example. But her boss doesn’t give her the time to do it.

“Typically when people leave a job, that’s it — they’re done with it,” Green writes. She advises telling a boss “what you will and won’t do after you’re gone — and what you still need to get done before you leave.” Read more.

Get Ask a Boss delivered every week

By submitting your email, you agree to our Terms and Privacy Policy.
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Got something to Ask a Boss? Send your questions to

9 Bad Bosses, and How to Work for Them