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my friend is dating my employee, the problem with “gentle reminders,” and more

October 5, 2023


It’s five answers to five questions. Here we go…

1. My best friend is dating my employee

I own a small cocktail bar in a small town and recently one of my oldest and best friends, who is also a regular patron, started dating one of my employees. (He gave me an opportunity to weigh in beforehand, but I told him I had no right to interfere in my employees’ relationships, so to proceed if he wanted to. Whenever a patron starts dating an employee, there is risk, but it also goes with the bar territory.)

It seems like it is going well for them, so I had a chat with my friend, clarifying that I didn’t expect our friendship to divide any loyalties or anything dramatic, or expect him to share things with me that she had told him about work, or anything like that. He said he assumed that but it was good to hear me say it.

Should I have a similar conversation with her? On the one hand, talking to an employee about her private life seems like an overreach (although she has brought up issues with past relationships before), but on the other, she might also be relieved if I spelled out that she doesn’t have to worry about me leveraging my friendship in a problematic way. And this is a friend that I regularly travel with, including his past partners, so there may be further necessary boundary conversations in the future if they become a truly serious item.

Err on the side of being clear about where you stand, so she doesn’t need to guess. Spell out that you recognize the potential landmines (which are more risky to her than anyone else) and plan to maintain a firewall with your friend, and — most importantly — if things end with him, it won’t affect her standing at work. (You have to mean that, though! If they break up and your friend tells you horrible things about her behavior as a girlfriend, you need to be committed to not letting it impact how you treat her as an employee.)

You also need to be committed to protecting her work environment if it becomes necessary. If they break up and he’s mooning around the bar making her uncomfortable, you’ve got to be willing to handle it the same way you would if he were any other customer, not your best friend. And while it might feel weird to spell that out for her while they’re happy, it’s probably worth saying … because if at some point she does want to end things with him, you don’t want her having to worry about whether it will make things weird for her at work.

2. “Gentle reminders”

Is anyone else annoyed by the phrase “gentle reminder” in emails? It seems to almost always be followed by some sort of passive/passive-aggressive statement. Why can’t we just be direct and say “reminder, X event is happening” or “reminder, please do ABC”? Is it an overreaction to people attempting to be overly polite in emails since tone is hard to convey in the written word? Am I completely neurotic for being irked by this language (and similar language)?

“Gentle reminder” is my number one email pet peeve! It’s like announcing “I think you are very delicate, and I am going to softly tiptoe up next to you and whisper in your ear because otherwise you might be offended by a routine workplace interaction” — ugh!

People are not delicate flowers and they can handle matter-of-fact work communications! Why are the “gentle reminder” people labeling that way? (In fact, why are they labeling it all? Just give the damn reminder and let your recipients decide whether they think it’s gentle, or aggressive, or routine, or whatever. Stop telling them how you want them to feel about your email.)

3. Is it illegal to reassemble a laid-off team before a year has passed?

In January, my entire team was laid off, with the official reason being that our positions had been eliminated. We were a team of four, and there were no other layoffs or positions eliminated at that time. Cutting the entire team meant there was no one left doing the kind of work we did.

I still have friends at the company. They let me know that many people were voicing concerns about my team’s function being cut. In response, they were told that legally, because our positions had been eliminated, they couldn’t resurrect that function with a new team – nor could they re-hire any of us to perform that function – for a year.

I did a quick search trying to find any laws that applied and came up empty. My best guess was that they’d been told that if they let us go by “eliminating our positions” and then soon after hired a bunch of, say, young white men to do those jobs, they’d be open to claims of discrimination. But that doesn’t account for them saying they were legally not allowed to hire the original team back.

Now, nine months later, they are in fact resurrecting our function under a different department. I hear that the first question from folks still there was, would they be re-using the materials my team had created? And again, they were told that there are legal restrictions, in this case preventing them from using those materials.

Of course, it’s not my problem if they don’t want to use our old materials, for whatever reason. But it’s such a strange excuse to give! We were salaried employees creating work-for-hire – they clearly own it and can use it any way they like, as I understand it.

This (probably) has no bearing on my current or future work life, but I’m curious – are there some laws around this that I’m unaware of? Are they in fact legally barred from rehiring any of us for the same job within a year? And/or legally barred from using the materials we created while working for them? (We’re in the U.S.)

No law prevents companies from re-filling positions that were previously cut before X amount of time has past, either with new employees or the old ones. Some companies have internal policies about it to help avoid the appearance that they laid people off for illegal reasons (which could look like the case if the new hires are all in different demographic categories than the people who were cut — for example, if you eliminate a team where everyone is over 60 and then three months later reassemble it with a bunch of 30-year-olds, that’s going to raise concerns). But that’s an internal policy, not a law. (It also doesn’t explain why they wouldn’t hire the same people back, although some companies have that policy too.)

What’s really bizarre, though, is their insistence that they couldn’t use any of the materials your team created. As you point out, they own that material and there’s no legal reason they couldn’t. Either your company is getting really odd legal advice or they had other reasons for wanting to start from scratch that they’re not sharing with your old coworkers (or something just got lost in translation as this made its way through the grapevine, which sometimes happens).

4. My boss and I have the same side hustle — can I promote his work?

My supervisor and I happen to both pursue the same creative work outside of and in a different field from our day jobs, and we both have big new projects in this outside creative field coming out this winter (think book illustration or graphic design, where it’s project-based).

My supervisor has been extremely supportive of my outside work and mentioned that he can’t wait to promote my upcoming project on his social media, brag about me to his contacts, etc. I’m so flattered that he wants to do so! However, I’m not sure how, if at all, I should reciprocate. I regularly promote my friends’ work in this creative field on my social media accounts but it feels different when it’s my boss. But at the same time, I’m also very impressed with his work and think it’s worth promoting — if he wasn’t my boss and was just a friend or a colleague, I’d be shouting about it from the rooftops. But because of the power dynamics, I’m hesitating. Am I overthinking this? If I acknowledge the relationship in my posts (“this is my boss — isn’t his work amazing?”), does that make it better or worse? And if my boss posts about my work and I stay silent about his, is that a bad look?

Since you genuinely like his work and want to promote it, go ahead and do that! I do think you should mention the relationship just for transparency’s sake (I’d frame it as “I get to work with the artist, Burt Burtlebot, in my day job” but that’s really personal preference). It would only seem weird if he were getting a disproportionate share of your focus relative to other things you post about.

But if you didn’t want to promote his work, it would be okay to stay quiet about it. If I were in your boss’s shoes and you weren’t promoting my work, I’d just assume it didn’t occur to you to or would write it off to power dynamic weirdness (because it’s inherent in our respective work roles that I will champion your work as your boss and not necessarily vice versa). But since you’re enthusiastic about it, go ahead and share that enthusiasm.

5. Gift cards from the company didn’t work

This week my customer service team received gifts of $25 prepaid credit cards from higher-ups via email. However, we work remotely in Canada, and these cards only work in the U.S. I brought the issue up to my team and said we should talk to our boss about it next week, who is currently away on vacation.

I’m hoping our company does the right thing and replaces the basically useless gifts. I’m a little disappointed/annoyed this happened and they didn’t do better oversight on the gifts. Is this a big deal? Am I overthinking it?

Sometimes mistakes like this happen, and it would be easy to occur if the person ordering the cards is based in the U.S. and hasn’t dealt with this internationally before.

Your company will almost certainly replace the cards with working ones once they’re informed of it. If they don’t, you’d be right to take issue with that (not only did they not get the gift right but they couldn’t be bothered to fix it once they knew?!) but it’s really unlikely to play out that way. I think you’re being premature in being annoyed, and are in fact borrowing trouble! Give them a chance to learn about the error and remedy it.


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