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There are bad bosses, there are nightmare bosses, and then there are bosses who are pretty great—except for that one unprofessional habit that is driving you crazy.

Correcting less-than-ideal behavior is easy to comprehend—and fairly typical—when it comes from the top down. But it becomes much more challenging when the roles are reversed—when you’re late getting something to a client because your supervisor is the one who blows through deadlines. Or when he’s constantly late to meetings. Or uses profanity. Or does something else that you could mention in an evaluation with a subordinate, but have no idea how to broach with a superior.

If you’re in that boat, read on for a few tactful ways you can handle the situation—while not overstepping your bounds.


1. The “May I Do This, Too?” Approach

I once had a boss who regularly arrived late for work. She was unhappily surprised when, on an uncharacteristically punctual morning, she walked into the office at 9 AM and was the only person there. We weren’t a bunch of rule-breakers; rather we’d noticed that if there was a night when our boss stayed an hour or two late, she typically came in closer to 9:30 AM the following morning, so we followed her lead. When she saw what was happening, she called us all together and told us we were expected to be in the office at 9 AM every day—end of story. (And it really didn’t seem appropriate to say, “But, you arrive late all the time!”)

Though she started coming in on time after experiencing the ramifications of her “Do as I say, not as I do” approach, my colleagues and I definitely could have handled the situation better. We had regular staff meetings, and it would have been much more professional for us to ask to review the office hours, and ask questions such as, “If we work very late or have a company event one evening, may we come in late the next morning?” Perhaps we even should have broached the idea of different working hours (since everyone was de-facto working 9:30 AM to 6 PM anyhow)—who knows what creative, productive solution we might have been able to brainstorm as a team.

So, if you’ve noticed that your boss has been getting more and more casual—whether in her dress or her previously rigid rules—feel free to inquire if the office is moving in a more casual direction. At your next check-in, try, “I feel like I’m seeing a shift toward more flexible and creative approaches: Is this something I should consider?”


2. The “How Should I Handle This Situation?” Approach

I recently watched an old Modern Family episode in which Manny tries to bring fighting relatives together by telling each one a different story about a pretend classmate exhibiting similar behaviors. He had hoped that—from the outside looking in—they’d see the error in their ways. (Of course, because it’s a comedy, they all tell him that she sounds like a terrible person and he should stop studying with her.)

In real life, this approach can be a lifesaver (so long as you employ a little finesse). Let’s say your boss interrupts you regularly. Obviously, asking “Matt” for ways to correct “Pat” who always talks over you isn’t going to fool anyone. Instead, think of a situation in which people cut each other off, and some people are never heard—hello, conference calls—then ask your boss for his best advice.

Let’s say that he suggests starting every call by reminding all participants to let everyone speak—a “preface” approach. Then, right before your next team meeting, pull him aside and tell him you have some ideas that you’d like to carve out some time for. Alternatively, if he advises you to insert yourself in the situation (e.g., telling one caller that you believe another participant wasn’t finished) he may respond best to a direct approach. Next time he cuts you off try, “I’m sorry, actually, I had one more point I’d like to make.”

By learning your boss’ response to a parallel situation, you’ll gain insight into how he’s most likely to receive feedback in similar circumstances.


3. The “I’m Passing This Along” Approach

Yes, having a frank discussion with your boss about an unprofessional habit is on the list of things you never want to do at work. But sometimes, it really is the only approach.

For example, let’s say that your boss is a yeller. Not only is that totally uncool and completely unprofessional, but it could very easily make other team members, partners, and even clients feel really uncomfortable. If this is hurting your work relationships, you need to pass the feedback along to your boss.

If you position yourself as criticizing your boss, he’s likely to get defensive. Instead, say that you’re sharing generalized information (even if its meant for your boss specifically). Try, “Janet mentioned to me that she felt uncomfortable in the office the other day, because she heard raised voices and profanity. I thought it was important that I share her feedback.”



It’s not easy to call your boss out on bad behavior, but sometimes it’s your only choice. At the very least, this tough conversation will prepare you for another situation—it will already get you thinking about what you do and don’t want to do when you’re the one in charge.