That’s Awkward: Alison Green of ‘Ask a Manager’ Tackles Tough Conversations

Portrait of Alison Green
Photo by Ginny Filer


If you haven’t had a cringeworthy conversation at work, count yourself among the lucky.

Alison Green has seen plenty of the worst work situations come across her desk as the author of the work advice column and book “Ask a Manager.”

She answered a few questions from The Penny Hoarder Facebook group about how to handle dreaded conversations. (Questions and answers have been edited for clarity and brevity).

Dreaded Work Conversation #1: Dress Code and Bad Hygiene

I work with a large man whose belly hangs out of his shirts and whose body odor is offensive. As a supervisor, I have to be the one to tell him. He is a very nice man, and I hate having to have that uncomfortable conversation. How do you handle conversations about personal hygiene and appropriate attire? — Barbara

These are always awkward, because it feels like you’re passing judgment on something personal, rather than the person’s work. The best thing to do is to be as matter-of-fact and straightforward as you can.

Dress code is a bit easier: “Hey, some of your shirts aren’t covering your stomach. Can you fix that to line up with our dress code?”

Hygiene is a lot more awkward, but it’s important to address because it’s probably affecting the way your employee is perceived.

Meet with the person privately, preferably at the end of the day (so he doesn’t have to sit at work for hours afterward feeling self-conscious), and say something like this: “I want to discuss something that’s awkward, and I hope I don’t offend you.

“I’ve noticed you have had a noticeable odor lately. It might just be a need to wash clothes more frequently or shower more, or it could be a medical problem.

“This is the kind of thing that people often don’t realize about themselves, so I wanted to bring it to your attention and ask you to see what you can do about it.”

Dreaded Work Conversation #2: I Quit

I’ve always had a good relationship with my bosses. So when the time came for me to give my notice, I felt like I was betraying them, even though I was doing it for the financial good of my family. How do you give your notice without creating hard feelings? — Robyn

People often feel an immense amount of guilt and anxiety about quitting, but it’s a business decision. Any decent employer will understand that. They might be disappointed, yes, and they might even think you’re making the wrong decision. But they will understand that people move on and that this is a normal part of doing business.

When you give notice, explain that you’ve enjoyed your time there and have really appreciated working for them, but that you found an opportunity that was too good to pass up and that you’ll work with them to make your transition as smooth as possible.

That’s it — really! If they’re good bosses, they’ll not only understand but will even find a way to be happy for you.

Dreaded Work Conversation #3: Way Too Personal

My supervisor’s opening question at my monthly performance meeting was, “Why don’t you date women anymore?” I was uncomfortable and fearful since I was uncertain where this would lead, and unfortunately it led to her mistreating me at work. I ended up leaving the company. How do you deal with uncomfortable personal questions? — Raven

That’s beyond an uncomfortable personal question; that’s well into sexual harassment territory, particularly given her later behavior toward you.

If your manager is sexually harassing you, ideally you’d report it — and ask your company to ensure that it protects you from retaliation as well. Not only is sexual harassment itself illegal, but it’s also illegal for a manager or employer to retaliate against you for making a good-faith report of sexual harassment.

There’s no guarantee that your company will follow the law in that regard — we’ve seen all too many examples lately of companies that didn’t — but reminding them of their obligations there can increase your chances of a good outcome.

If your company turns out to be one that handles this poorly, a lawyer can help you figure out the best way to navigate the situation. Keep in mind that talking to a lawyer doesn’t always mean “sue!” Lawyers can help negotiate transfers, severance payments and other things you might want.

Dreaded Work Conversation #4: They’re Late. Again.

As a manager, I hate having to talk to my employees about being on time. I realize to them it’s just a job and not their career choice, but you still have to show up. How do you handle discussing the importance of being on time? — Brandy

With questions of lateness, I always want to first make sure it really matters.

There are a lot of jobs where being a little late won’t impact the person’s work or their co-workers. But of course, there are also a lot of jobs where it does.

If it’s one of those, then talk to the person and lay out the expectations around timeliness, the fact that they’re currently falling short and what they need to change.

The first time you address it, it could be as simple as this: “I’ve noticed that you’ve been coming in late recently. I need you to be here reliably by 8:30 each morning when our phones start ringing. Can you make sure you’re here on time going forward?”

If it continues after that, the conversation needs to be more serious: “We’ve talked before about the need for you to be here no later than 8:30, but you’re continuing to arrive late. I want to be clear that this is a requirement of the job. Knowing that we can’t be flexible on that, are you able to make this schedule work?”

Dreaded Work Conversation #5: From Friend to Boss

I was friends with many of my coworkers, but then was promoted to a shift manager. I went from being a peer who understood their complaints to being a superior who had to reprimand them and send people home to save on hours. As a manager, how do I have work-related conversations with employees who used to be my peers? — Allie Mae

Yeah, the relationship has to change when you become your peers’ manager, and it can be really hard!

The best thing you can do is lean in to being a really good manager — meaning that you set clear expectations, give straightforward and useful feedback (both positive and constructive), hold people accountable in a fair and transparent way, and don’t make people have to guess or read your mind.

If you get those things right, it will make the hard parts of the job much easier (on both sides). That doesn’t mean that it won’t feel awkward at times to be managing people who used to be peers — it will.

It usually takes about a year for that awkwardness to go away. But meanwhile, people will take their cues from you.

If you are matter-of-fact about your new authority — as opposed to being apologetic about it or, on the other end of the spectrum, tyrannical about it — people will adjust.

Dreaded Work Conversation #6: Asking for a Mental Health Day

Asking for a day off for a vacation or because of the flu can be difficult enough. How do I ask to take a mental health day because of depression or anxiety? — Ashley

It’s absolutely legitimate to use a sick day for mental health, but you don’t need to give your boss the details.

It’s enough to simply say, “I’m under the weather today and am going to need to use a sick day.”

That’s the same advice I’d give you for other illnesses, too. You don’t need to explain to your boss that you have diarrhea, either.

It’s true that people are often more forthcoming in other circumstances — like you probably wouldn’t hesitate to say “I threw out my back” or “I have the flu” — but you don’t need to do that.

Given the stigma that unfortunately still exists for many people around mental health, there’s no reason not to go with the vaguer “under the weather.”

A good boss isn’t going to push back on that unless you’ve been chronically absent — in which case that’s a separate discussion.

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