How to Fire a Difficult, Long-Time Employee columnist Alison Green answers questions about workplace and management issues–everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

Here’s a roundup of answers to five questions from readers.

1. How to fire a difficult, long-time employee.

I work in a small office in a declining industry. Our salespeople have seen reduced commissions because they are based on sales, and the owners have taken pay cuts to avoid layoffs and cutting employee’s salaries.

One of our designers has been in the job since the company’s inception (20-plus years) and has become increasingly difficult to deal with. Among other problems, they seem to feel we owe them something for sticking around so long, and are now demanding that we pay them a high hourly freelance rate in addition to their salary: A salary that is the highest in the company aside from the owners. They’re rude and grumpy to other staff, and also seem to think that they are irreplaceable. But frankly we could hire someone with updated skills, who is easier to work with, for less money.

We are an at-will state, so we don’t need a reason to fire this person. But I’m not sure how to handle letting a long-term employee go. What do you say to someone who has become so unreasonable in their demands that you just want to part ways?

Green responds:

Would you be willing to keep the person on if they changed their behavior? If so, have a clear, direct conversation in which you lay out what you are and aren’t willing to do, and what your expectations are for their behavior. And ask them to decide if they want the job knowing that’s the reality of it.

For example: “I want to be transparent with you about what you can expect from us, so that you can make the right decisions for yourself. We aren’t going to increase your salary because of XYZ. We really appreciate the years you’ve put in here, but we also understand if the job no longer lines up with what you’re looking for. If you stay though, we need you to (insert specific behavior changes you need here, like not continuing to push on salary after being told no, not being grumpy and negative, etc.). Would you like to take a few days and think about whether this still makes sense for you, knowing that we can’t be flexible on the things we’ve asked for?”

And then if they come back and say yes, you are up-front that if they don’t change their behaviors, you will need to part ways–so that they’re not blindsided if that ends up happening.

But if the relationship is already past the point where it can be repaired, then you should have a heart-to-heart where you explain what the issues are and say, “At this point, I don’t think we can reconcile what we each want, so I’d like to talk about a transition plan.” And that plan would ideally include generous severance, in light of their 20 years there and the fact that you didn’t warn them this was coming. But do that as a last resort; it’s generally better to at least try the first route.

2. Boss posted Hawaii vacation photos right after layoffs.

Our company recently had layoffs. I was laid off, along with about 20 percent of our department. We are all friends on Facebook and less than a week after he laid us off, my ex-boss went on vacation to Hawaii and was posting all these dreamy photos of his vacation. This seems to me to be in incredibly poor taste, given that he knows that several of us are now unemployed and have families we are struggling to support. Do you agree or am I being petty?

Green responds:

Nope, it’s in poor taste. It’s fine that he’s taking a vacation and it’s fine that he wants to share photos with people he knows socially. But he should have been more thoughtful about the way the photos would be perceived by you and your laid-off coworkers. The optics of posting dream vacation photos after laying people off are just bad.

He may have simply forgotten that he’s Facebook friends with you. But if you’re going to Facebook-friend people you manage (and I’d argue that you shouldn’t), you’re obligated to remember to think about things like that.

3. My new hire sprang major time off on me after I’d already hired her.

I recently hired an employee. The day after she accepted my offer and everything was settled, she sent an email to me explaining she had two trips planned for the near future. The first one is a Wednesday-to-Monday trip where she intended to work remotely and only take off a half day on Monday for travel. This trip is one-and-a-half weeks after she starts work.

Her next trip is two weeks later and it is a two-week trip to Europe with her husband. She did acknowledge that the timing was poor, but did not mention anything about why she didn’t say anything during the lengthy interview process. She offered to postpone her start date until after all of her travel is complete, which is quite a long time for me to wait.

What are your thoughts on how to address this with her? I’d like to make sure I communicate that it is not OK to spring this on me when she had ample opportunity to tell me sooner. I feel like this is an opportunity to set the standard for the employee-manager relationship at the onset of her employment.

Green responds:

Yeah, that’s not good. She should have brought it up as part of the offer negotiations. And if for some reason she forgot to, she should have apologized, not be matter-of-fact about it.

I would say this: “Normally, I wouldn’t approve this much time off so soon after someone started. It’s going to be pretty disruptive to our training schedule. I’m willing to try to make it work, but I wish we’d known about these dates while we were still working out the offer.”

And if you don’t want her working remotely so soon after starting, address that too: “I can let you take unpaid time off for the first trip, but it won’t make sense to work remotely since you’ll still be so new.” And you should talk about what your expectations are for time off going forward.

Has she otherwise seemed professional and displayed good judgment? If anything else has happened that has given you pause, I’d be bracing for further issues. In which case, you’d want to be really hands-on during her first few months so that if there are additional issues, you’re able to spot them and address them quickly.

4. My interviewers all burst out laughing after I left the room.

Last week, I interviewed for a position that would provide me some great experience. I thought I did well in answering all the questions, and was honest about the areas in which I had some, but not a great deal of experience.

As I left the interview room and closed the door, I overheard one of the interview panel members say something I could not make out, and then heard everyone else in the room laugh. I think they thought that once the door was closed, the room was soundproof. I have no idea if the remark and laughter were directed at me, but I am wondering if this is a red flag. I am considering pulling my application as this may be an indication that these people found me ridiculous. Even if I was hired, I now feel uncomfortable with the notion of being around these people. Am I being overly sensitive? Should I let this go and see what happens?

Green responds:

Yes, you should let it go. Absent some specific reason to believe that they were laughing at you, it’s far more likely that they were laughing at something that had nothing to do with you. Someone could have commented on a funny text they just received, or pointed out that they’d accidentally worn mismatched shoes that day, or all sorts of other things.

A roomful of people isn’t likely to burst out laughing at a candidate who just left, unless the candidate did something truly outlandish (not just not interviewing well). Really, the most likely scenario is that the laugh wasn’t about you at all!

5. My coworker constantly fact-checks everyone else.

I have a coworker who has a habit of fact-checking other team members. She is not a manager. If a team member mentions information in a meeting, casually discusses a topic in the hallway, or sends an email to the team, this coworker will fact-check the information and reply-all and/or discuss her findings with the group. The fact-checking can range anywhere from verifying incoming rainstorms to confirming/denying the accuracy of information in an article that a team member shares with the group.

If she finds out information is correct, she will share that she checked/confirmed. Typically incorrect information is pointed out a few times a week. Incorrect can mean that a rainstorm will arrive at a different hour, or that she disagrees with the premise of an article, etc.

The behavior raises eyebrows and makes others uncomfortable. Any suggestions for how to approach the issue, or if it’s best to ignore?

Green responds:

She’s fact-checking trivial information from a casual hallway discussion, and emailing her findings to your whole group? Oh dear.

If you were her manager, I’d tell you to ask her to cut it out. But as a coworker, I’d just let it go and know that everyone else finds this really weird too. I’ve got to think that this kind of know-it-all-ism is a real impediment in her relationships with people.

But if it’s really annoying you, you could say, “Hey, I’m sure you don’t mean it this way, but doing all this fact-checking of other people is coming across kind of oddly. Like you don’t trust people and want to correct them, even on inconsequential details.” Or in the moment when she does it, you could just say, “I don’t think we needed that fact-checked” (especially when she’s confirming info is correct). Or, “I’m finding the follow-up on such minor stuff kind of distracting. Could we save it for things where the substance matters more?”

Want to submit a question of your own? Send it to [email protected].

The opinions expressed here by columnists are their own, not those of

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