I’m on vacation. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.

1. Coworker tags our CEO on Twitter to point out my mistakes

I’m part of an incredibly progressive, supportive team, where one of my responsibilities is my organization’s social media. In six months, I have made three errors within tweets, two of which were mixing up the dates that two very similar events were happening on, and one of which was just a formatting error.

One coworker from a different department — who does not work with social media in any capacity — replies to the errors from her personal Twitter, tagging in our CEO’s personal Twitter to shout about the mistakes. She then emails a screen grab to my entire team (the person I manage, my manager, and my grandboss) demanding that my grandboss check all of my social media communications before they are posted, which would be ridiculous.

Obviously in an ideal world I would not be making any errors on social media. But three tweets in six months does not seem like a bad hit rate (also, our social tone is playful and conversational, and usually quite informal). Should I ask my manager to ask this woman to lay off me? Or do it myself?

That’s incredibly obnoxious. Ideally your manager would have already seen this and told her to cut it out, but since that doesn’t happen, it’s reasonable for you to say, “Jane, if you spot any errors in our tweets, please bring it to my attention directly and I’ll get it fixed. Commenting about it on Twitter brings more attention to it to people outside our organization, which reflects badly on us.”

That said … while your coworker is in the wrong in how she’s handling this, three errors in tweets in six months does strike me as a lot for public communications (especially for dates of events). If your coworker is involved in marketing or events or anything else that your social media work supports, she’s right to be concerned. I’d hold off on bringing your boss into this and instead focus on figuring out a system to catch errors before anything gets posted.

– 2019

Read an update to this letter here.

2. My employee quit smoking and is being a pain

I am the general manager for a retail location. I have an employee, “Joy,” who is a lifelong smoker. She’s been smoking for longer than I’ve been alive! Joy is a member of my leadership team, and has been a great asset for the three years I’ve worked with her. Recently, she decided to quit smoking. As far as I know, this is the first time she has attempted this since I have known her. I’m really proud of her, and she’s been doing an awesome job — she quit cold turkey over two weeks ago, and hasn’t had a single cigarette since.

However, while the first week was great, this week I have noticed a sharp dip in her performance/attitude. Joy admits that this is because she is severely craving a cigarette, which has always been her main form of stress relief. While I sympathize, and am still proud of her for taking this step towards bettering her health, I am getting frustrated at her performance. She actually called out sick today, and again, told me this was directly due to the fact that she is craving a cigarette so badly. The team has noticed her change in attitude, and are getting frustrated as well. How can I approach this as her manager, while still remaining supportive?

How cranky is she being? If she’s a little cranky, cut her some slack — everyone goes through things in their personal life that impacts their demeanor at work now and then. But if it’s extreme — if she’s being rude or hostile to people — then articulate that for her and tell her she needs to rein it in. (As in, “I know this is a tough period for you and I sympathize, but you’re starting to be openly rude to people here and I need you to stay civil.”)

Same thing with performance — if she’s slipping a bit but is still doing an overall okay job, cut her some slack since you know what’s causing it and you know this is short-term. But if it’s more serious, then you need to say something like, “I know this is a tough period for you, and I don’t expect you to be at 100% right now, but you’re making some pretty serious mistakes in your work. What can we do during this period to help keep your work quality where we need it?” (And since she’s normally a good employee, you should try to find ways to accommodate her for the next week or two, like moving deadlines around if you can or giving her projects that require less mental presence if that’s possible.)

And if she wants to use sick leave to help her get through what should be a relatively short-term withdrawal period (it’s supposed to last about two weeks, right?), let her do it. As long as it’s not impacting any crucial projects which she absolutely must be there for this week, that’s a pretty great use of sick leave and it means she’s keeping the withdrawal impact out of the office.

– 2017

3. I don’t want to carpool with a coworker

I’ve carpooled with one coworker for over a year. A new coworker has come and also wants to carpool with us. The two coworkers do not have a good relationship (but can tolerate each other). The new coworker is also incredibly annoying and inconsiderate (but not a bad person). I am technically her superior at work (although not her direct manager), and on Sunday she needed to be disciplined but as I was driving her back and forth, I asked my colleague to talk with her instead.

I really would prefer to stop driving her, but I don’t want to hurt her feelings. I like carpooling with person #1, so an excuse of like “I need some time to myself” doesn’t work. I’m unsure what to do, or how to navigate this, without putting myself in an even more uncomfortable position at work.

Oooh, this is hard. It might have been easier to say no from the start, but now that you’re carpooling together, it’s harder to get out of it without dropping out of the carpool with the original coworker too.

You mentioned the other two don’t have a good relationship. If things are tense between them in the car, you could use that — “I need to be able to unwind at the end of the day and the tension in the car is too much.” Or you possibly could say that picking up/dropping off two people is too much (although then there’s a chance she’ll offer to drive herself to the driver’s house). Or there’s the chain of command — “I realized that since I sometimes manage your work and need to give you feedback, we should have good outside-of-work boundaries and not keep carpooling.” Or, if any of her inconsideration is about the carpool itself (being late, being rude in the car, etc.), you can explain that — “We need to leave on time every day so can’t keep carpooling.”

Anyone else have better ideas on this one?

– 2019

4. Keeping a file of personal items at work

I’ve seen some great videos on having a tidy workspace and I’ve shared them with my team (I like a clean, neat workspace and I try to lead by example). I wonder what others feel about personal items in your workspace. By personal items, I don’t mean a picture of your family or a box of tea. I’ve worked in two positions where one of my admins has dedicated an unlocked file cabinet drawer to organize their life – from healthcare claims, credit card bills, and mortgage information to court information on a divorce in progress. If I’ve discovered this drawer while looking for a copy of something, how many others have discovered this, and how many have been nosey enough to have a good read? Any thoughts on this?

It’s not something you should intervene in as their manager. But if I were advising the person doing it, I’d suggest that they not keep such a file at work, at least not if they want to keep the info private. It’s normal to have some of that stuff there temporarily, like bringing a bill to work because you needed to call your credit card company about it that day, or having some paperwork there while you were in the process of applying of a mortgage, because there’s often back and forth on that during business hours. But if they’re keeping a permanent “personal documents” file at work, there’s no guarantee of privacy, or even a guarantee that it won’t somehow get accidentally thrown out in some office purge that they’re not full control of. And it’s going to look a little odd if someone comes across it, as you did; it reads as “I’m managing my entire personal life from work on the regular.”

But it’s not really something for you as their boss to be dictating. I would also lay off sending the videos about clean workspaces; focus on the work.

– 2018