weekend open thread – April 13-14, 2024

This comment section is open for any non-work-related discussion you’d like to have with other readers, by popular demand.

Here are the rules for the weekend posts.

Book recommendation of the week: The Husbands, by Holly Gramazio. A woman discovers that the ladder to her attic produces a seemingly endless supply of husbands. I didn’t know where this was going at first, but it ended up being surprisingly engrossing.

* I make a commission if you use that Amazon link.

open thread – April 12-13, 2024

It’s the Friday open thread!

The comment section on this post is open for discussion with other readers on any work-related questions that you want to talk about (that includes school). If you want an answer from me, emailing me is still your best bet*, but this is a chance to take your questions to other readers.

* If you submitted a question to me recently, please do not repost it here, as it may be in my queue to answer.

should a successful gamer put it on their resume, “free” company gifts that aren’t free, ad more

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

1. If you’re a successful gamer, should it go on your resume?

My son is in college and needs to find a job while he’s home for the summer. He hasn’t had much luck so far, and his experience is limited to stocking shelves at a grocery store for two years, and some volunteer work. He didn’t work at all last summer — I had surgery and was out of commission for quite a few weeks, so he took care of me, the yard, the laundry, shopping, etc. (It’s just the two of us.)

This spring break, he went on a trip that I didn’t know he could afford so I asked him where the money was coming from, and he told me that he had earned it through online gaming. I knew he had done this once in the past, but I didn’t understand he was still doing it, and that it had added up to thousands of dollars. Through skill or luck, you can earn things like weapons for playing, and the ownership of them is transferable, so they can be sold. As best I can tell, it’s legal.

Should this go on his resume? Would it help him find a job, or turn people off? It’s unusual, but would maybe be looked at as entrepreneurial? If he should add it, how should he list it?

Leave it off. Most people seeing that on a resume are going to think “how is this relevant to the job you’re applying for?” and a lot of them will judge him for including it, unless he can really spell out in concrete and credible terms how the skills transfer … and even then he’d encounter a lot of skepticism.

can I put World of Warcraft leadership experience on my resume?

2. Complaining to a manager after an employee corrects you about her gender

Was my sister-in-law wrong to complain to someone’s manager?

While I was visiting my sister-in-law, she asked my opinion on a situation she recently encountered. She was calling a customer service line and the person on the phone sounded male so when they asked if they could put my SIL on hold, she responded, “Yes sir” (she’s southern) The rep responded with, “I identify as female, please address me as such,” then placed my SIL on hold.

My SIL was incensed by this and send a nasty email to the customer service manager about how the behavior was rude and the rep made my SIL feel as if she had committed a cardinal sin, but my SIL had no way of knowing their gender other than by their voice because they were on the phone.

My response was that if the rep had said “my name is X,” then you should address them as X and not use sir or ma’am. Am I missing something?

Whether to address someone by their name or by ma’am/sir or by nothing at all is deeply cultural/regional.

But if you use gendered greetings like “ma’am” and “sir” (like much of the American south does reflexively), then occasionally you might get someone’s gender wrong and you should handle a correction politely. Sending an angry email to complain was out-of-line; even if the rep sounded irritated, it didn’t warrant a complaint to the manager. Any chance your sister-in-law is responding to something other than what happened … like is she affronted by issues around gender identity more broadly?

3. Our director left while my coworker was on vacation

I have a colleague who left for a long vacation in their home country (five weeks). In the middle of her vacation, my former director announced that he would be leaving, did his two weeks, and has now left. I was previously a peer to the colleague and now I am the acting director. My colleague is a very anxious person and I think she will feel really troubled by coming back to him having left and me being in charge. My former director has an office in town near the colleagues house in a workspace/coffeeshop-type place. Do you think we should aim for her first day back to meet there so he can break the news himself?

I really want her to have a smooth transition back after such a long time away and I don’t want her to be overwhelmed by the changes. She really likes and trusts our old director and I think she would ultimately be okay with me being the acting director, but I think the whole thing will come as a shock! She is back on Monday. Any advice?

I think asking her to meet at a coffeeshop before coming in risks setting off her anxiety on its own. And it’s too much to ask your former director, who doesn’t work there anymore, to do a Monday morning meeting at his old job just to break the news to someone delicately. That’s just … a lot of handling of someone else’s feelings for them.

Just share the news with her once she’s back and figure she’ll be surprised and need some time to process, and she’ll handle that however she handles it. Otherwise I would worry about (a) signaling to her that it’s a bigger deal than it is by setting up a special off-site meeting just for her, and (b) the precedent you’d set by trying to manage her feelings to that extent about a fairly normal workplace change.

4. “Free” company gifts that aren’t free

This is a very low-stakes, probably no-stakes question that seems unlikely to come up, but I’d like to get your take.

I started a fully remote job this week. One of my orientation tasks was to pick some standard starter items (branded notebook, water bottle, etc.) from the company’s online store, which are free and will be shipped to me for free.

New employees also get a $20 credit toward anything else in the company store. It’s a very expansive store with everything from golf tees and fridge magnets to high-end jackets and camping gear, all covered in the company logo. We also “partner” with an NFL team, so there’s some pretty cool co-branded stuff too.

However, with the exception of, like, some stickers, nothing in the store is under $20. AND shipping is $8, minimum. AND you can’t bundle your “gift” with the mandatory items. So unless you’re so into free stuff that you want $12 of bland logo stickers, this “gift” is effectively a way for employees to pay to advertise for their employer.

I realize this is pretty common practice and barely even registers on the scale of corporate grossness, so my solution is to just not buy anything and forget about it. But if someone (my boss, who probably has to promote this “perk,” or the marketing department, who almost certainly has to budget for it) asks why I haven’t used my credit, is there a tactful, professional way to say “This is icky” or should I stick to some fluff about not needing another t-shirt?

Yeah, that’s poorly thought-out!

I doubt your boss will even notice, let alone ask you about it if you don’t order anything. But if it does come up, as a new employee I wouldn’t get into it; just go with, “Oh, I’m trying to have less stuff around” or something similarly bland. However, once you’ve been there longer and have accumulated more capital, feel free to point out to whoever manages this stuff that there’s no way to use the credit without dropping a bunch of cash along with it. They might be well aware of that and fine with it — who knows, maybe a bunch of employees love the company-branded hoodies and so the credit is super popular — but it’s reasonable to point out once you’ve been there longer.

someone who barely managed me put negative feedback in my annual review

A reader writes:

I just received my annual review.

I’ve been passed between four managers over the past 12 months – one of whom was fired, one who was very hands-off for the majority of their time with me, one who worked with me for three months, and one who became my manager relatively recently.

All my managers other than the fired one contributed to my annual review. Each of their comments show up separately, in one place. The majority of the feedback was positive: I am intelligent, hard-working, and thorough. The critical feedback was mostly that I should not jump to speak too quickly in meetings, be more structured in my approach to work, and ask for help more often. It was “you’re doing well, we requested a promotion for you, here are some things to focus on next year, watch out for this area for improvement.”

Except for one manager’s feedback – the person who was my manager for three months. That person wrote that I am ultra-controlling, I am condescending, I berate my colleagues, and people avoid working with me. Essentially, she took each of my flaws and exaggerated them so it appears I am a monster to work with, who is verbally abusive and alienates her colleagues. She never shared this feedback with me when I reported to her, and nobody has ever come to me with something like this before. Outspoken and candid, sure. Maybe a bit critical or visibly frustrated when things go wrong. But berating and alienating people? It feels like a really serious accusation to deliver for the first time, in writing, in an annual review.

This individual was taken off the project (possibly due to her own performance issues, but I’m not sure) and the other two managers delivered my review, not her. They didn’t agree with her statements, but didn’t explicitly disagree with them either. There was a lot of “maybe this is her perception.” Maybe I am this person in her mind! I think that’s possible. But it seems insane to put in my review without even a warning or prior conversation. She provided no concrete examples.

Our HR system requires “confirming” you received your annual review to finalize it. I do not want to “confirm” I received this feedback. I am not the way this person describes, and I want to become a manager myself – I don’t want this on my “record.” What do I do? I want to write a rebuttal of sorts, or have them taken out, but I don’t want to open a giant HR can of worms either. (We are both women, so there isn’t really a gender dynamic at play. She is significantly senior to me.)

First, talk to HR and ask to have the feedback removed. Point out that this person managed you for a very brief period, didn’t even hint at any of this feedback while you reported to her, and it’s at odds with the assessment of the other managers who contributed to your evaluation. They may or may not remove it, but it’s reasonable to ask for.

If they won’t remove it, ask to add a written response to the evaluation that will be kept in your file along with it. They’ll probably let you do that.

If you do a written response, keep it as objective and factual as possible. You’re right to be pissed off, but you don’t want an emotional response sitting in your file forever. Instead, stick to the facts: this person only managed you for three months, didn’t allude to any of this feedback previously, and provided no examples, and the feedback isn’t echoed by anyone else familiar with your work, as the rest of the review shows. Say that you dispute its accuracy and you ask that it be discounted in favor of the feedback by managers familiar with your work.

I wouldn’t get into a big battle over refusing to confirm you received the review. That really is just to acknowledge receipt; you’re not saying you agree with or accept the feedback. You’re literally just saying that the review itself was provided to you.

update: dealing with a problematic member of a board games group

Remember the letter-writer who was dealing with a problematic member of a board games group? The first update was here, and here’s the final installment.

I am the letter writer who runs a board games group and used Alison’s excellent advice about communication to deal with a problematic member of the games group and the issues their behavior was causing.

We had a twist in the tale recently when Q, the member who was asked to leave the group because their behavior was negatively impacting others, asked if they could come back.

For four weeks every year, we use a different venue as another group needs our normal venue. One one of the four weeks, I went for a walk before the session and noticed what looked like Q in the park. When the session started, Q appeared, just “passing by,” and we had a quick chat about this and that before they asked if they could come back to the group, saying they were in a better place now. They then left without ordering anything, which makes me think they dropped in just to see us.

I said I would send a message, and gave it due consideration. I also asked a friend who knows Q and used to be in the group, but has now moved, for their more objective input.

The decision was no: the group is working well as it is, with high numbers and between 11 and 20 people per session, and Q coming back would lead to awkwardness and possible animosity from a few people, some of whom would speak their mind. We would also lose a lot of members, and the group would slowly decline. For what it’s worth, one person who had some very negative interactions with Q, when they heard why Q was there ( they were round the corner), exclaimed “No!” to Q coming back, and this person is one of the nicest people you’ll meet. Similar reactions were given from others.

I sent Q a message explaining the decision, and I was as fair and kind as possible given the circumstances. Q has found another games group, albeit one that only plays light games, (not heavy games, Q’s preference), and I mentioned that and said it sounds like a nice group (which it does).

Q was perfectly pleasant when we chatted, but that was for about eight minutes, and they knew what was coming. They also said that they weren’t often doing the things I’d mentioned anymore (moving other people’s pieces, and a couple of other examples I gave), and that although their new group likes light games, they are helping some people progress up to heavier games. It wasn’t clear if the people wanted to progress (one of the issues we had was Q assuming that everyone wanted to progress).

The games group continues to do well, with enough surplus each year to give everyone free sessions every January, and we receive frequent feedback that the atmosphere is friendly and welcoming and that people feel at home and confident to bring and teach their games there. Our annual Christmas potluck dinner and session with a Secret Santa also continues. We also have a Google sheet with people’s games collections, if they want to add them, thanks to one of our members who likes spreadsheets.

For myself, Ask a Manager continues to help me out at work! I recently applied for a job which would be a step up income wise and I used Alison’s tips, and I use the communication tips in daily life as well as at work. I was actually used as a bargaining chip in recent negotiations at work over a type of meeting that needs minuting (for my minuting skills), so I will take that as a compliment!

knowledge swap! share your expertise with people here

Are you good at something and willing to share that expertise with others here? We did this six years ago and it was a great success, so we’re doing it again. Here’s how it works:

1. In the comment section below, name something you’re really good at that you’d be willing to answer questions about. It could be Excel, or running meetings, or make-up recommendations, or resolving customer service problems, or anything else that you’re awesome at and willing to take questions on.

2. Ask questions of others, and answer the questions people ask of you.

3. Feel free to leave calls for expertise too — like “how do I confine a search to a single column in Excel?” or “how do I keep people from falling asleep in my presentations?”

If all goes well, at the end of the day you will have helped other people and been helped yourself.

is the kiss emoji appropriate at work, manager wants me to find coverage after I quit, and more

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

1. Is the kiss emoji appropriate at work?

This is a low-stakes question, but I keep wondering: Is the kiss emoji 😘 ever appropriate in work communication?

Most of our team are in our thirties and forties. Our work environment is fairly informal — few emails, but lots of Slack messages, so of course emojis are everywhere. I enjoy using them, we even have silly traditions among coworkers. (Think: one of them writes that a famous llama groomer from France will be visiting next week, and instead of 👍🏼 or ✅, people will react with 🥖 and 🍷.)

It’s a lighthearted way of joking around, but for some reason, when people use the kiss emoji, it rubs me the wrong way. I helped a coworker out with something the other day and they wrote back, “Thank you so much! 😘” I like them well enough, but this felt odd. A different coworker recently put a kiss emoji underneath a Slack post in which one of our grandbosses announced a small perk (think additional parking spaces for our team in the company lot).

Obviously I would never say something, I’m not the emoji police. But just so I know whether my gut feeling is right or I‘m being overly literal: This is weird, right?

You’re taking it too literally. People aren’t using it to mean “imagine me kissing you.” They’re using it to mean “you’re awesome” or “this is great” or “I like this.” I can see why you’d be weirded out by it if you considered it in a vacuum … but you’ve got to take it in the cultural context, where it’s just a more effusive version of the thumbs-up.

To put it in much more old-fashioned terms, think of opening a letter with “dear” — you’re not really saying the stranger you are writing to is dear to you. Language, and now emojis, evolve in strange, non-literal ways.

(Only slightly related to this, I recently came across this old post and what.)

2. I misspelled the company’s name throughout my cover letter

I spent the last hour putting together a detailed cover letter and tailored resume for a job that I thought was a great fit for my skill set. Right after sending it, I realized that I’d consistently misspelled the name of the company throughout my application materials. To give myself a little credit, it is a kind of weird name, and my brain is pretty fried with applications, so somehow I didn’t notice the error in the many times I proofread my materials and checked them against the job description. Of course I noticed right after sending instead, and now I can’t stop cringing.

This is a fatal error and I should just write off the possibility I’ll ever hear from this job, right?

Well … it doesn’t look great. If it’s a job where attention to detail is important, it’s probably going to take you out of the running, or at least move you down the list. That said, it’s not going to put you on a do-not-hire list there or anything like that, and you can try again in the future without it being held against you.

3. My job wants me to find coverage after I quit

I put in my two weeks at work (food service job) because I’m going to be moving for the summer. After I did, I got an email back from my manager saying I needed to find someone to cover my shifts for the week after I quit because they’re “going to be really busy.” Are they allowed to do that? Isn’t that their responsibility?

I’m literally going to be moving and I don’t want to deal with the stress of finding someone to cover me for a whole week after I QUIT.

Haha, nice try, manager. They can propose anything they want — they can ask you to find coverage for the entire next year if they want to — but they have no way to make you comply.

I suspect what you’re worried about is less “can they make me do this?” (they can’t) and more “will I be violating some kind of professional convention if I refuse?” And the answer to that is also no. Finding coverage for after you’re gone is not your responsibility. (To be clear, if they want you to spend some of your time on-the-clock searching for shift coverage for dates after you’ll be gone, they can assign that as a work task. But it sounds like they’re expecting you to do it on your own time and … no.)

Respond with, “That’s not something I can do, but you can certainly schedule me through the 24th” (or whatever your last day is).

4. My friend applied for a job reporting to me and I don’t want to hire her

I’ve recently accepted a new job where I’ll have a small team reporting to me. I’m due to start next week. The organization is growing and this week my boss advertised a role that I’ll take over the hiring for once I start, and that will report to me.

Not knowing this role reported to me, a close friend of mine applied for it. She sent me a message saying she was applying at (company) and it was only when she told me the job I knew it was the one in my team.

The problem is, I don’t want to hire her. I’ve worked with her before — it’s actually how we know each other — and she’s a good worker. She gets stuff done, is pragmatic, and people tend to enjoy working with her. She’s also incredibly emotional, has very few boundaries, and has struggled a lot over the years with work stress, which I think is often created because of those boundary issues. While we used to share a lot of “work chat,” like sending funny memes or venting about our bosses, since we last worked together (~2 years ago) I’ve really worked on myself to have a better experience at work. I got a promotion into people leadership and had a massive perspective change about what it means to be the boss, having so much more appreciation for what my ex-bosses would have likely been struggling with. I’m excited to go into this new company with that perspective change and am actively trying to stop the cynical humor that I used to think was just a bit of a laugh, and I now see can sometimes be uncomfortable for colleagues. The old memes don’t really resonate anymore, but she sends them still. And to be honest, I don’t want someone reporting to me who complains about their job all day long. How should I handle this?

A talent acquisition team will do first round screening, and I’m concerned she’ll ask me why I didn’t tell them I want her to interview.

Even without the issues with her work style, it’s smarter not to manage a close friend. Would you be comfortable being up-front with her about that? You could say, “I know you do great work, but I don’t feel equipped to manage a close friend, and I especially don’t feel comfortable hiring a friend as one of my first moves there.”

If you don’t think she’ll get it, it could be easier to simply explain that the applicant pool was highly competitive and a lot of really qualified people didn’t get interviews. (It’s also quite reasonable that you wouldn’t want one of your first moves to be overruling the talent team to secure an interview for a friend.)

5. I’m grossed out by our potlucks

Our director has made potlucks an office tradition. The last one we had, I found multiple dishes with hair in them. I’m choosing not to participate in the next one and not consuming any dishes. I’m bringing my own lunch. Am I wrong?


I manage my sister, and she overshares about her breaks and sick time

A reader writes:

I’m hoping you can help me with this conundrum. This situation is complicated by the fact that this is a family business, and all employees are my relatives and/or their romantic partners, but we have virtual assistant team members (independent contractors or third party services) who are party to these conversations.

Background: I’m the main operator, but not the owner, of our family business, which leans more informal than most workplaces. We have some on-site operations, but significant “back office” admin occurs virtually. It’s my responsibility to set the tone and culture, and I believe I should change some things. One problem is my younger sister, Amanda, overshares about breaks and sick time in the primary team communication channel. I think it creates a problematic impression for everyone, but especially for our virtual team who aren’t family members.

For example, when taking breaks, Amanda doesn’t say, “I’m taking my 15 minute break, back soon.” She includes details like “I’m walking my dog, be back after feeding him lunch.” Or when taking personal time: “I’m taking my dog to the vet for throwing up, might have to get his stomach pumped, wish me luck it’s nothing serious.” She also has intermittent chronic illness that the family all agreed means she can be flexible with her work hours, but she overshares this to the team also. Instead of saying “taking a sick day” or “out on sick time for a few hours,” she provides excessive details like “Have a major migraine, must go lay down for a while, don’t know when I’ll be back or if I can make the weekly team meeting,” or “My stomach is really bothering me, stuck in the restroom, please don’t contact me unless it’s an emergency.” Similarly she overshares her doctors’ visits, such as “Leaving for my appointment with my gastroenterologist, if the tests they run hurt too bad I might not be back online today.”

Her role is functionally entry-level, but she’s not a recent college graduate. She’s in her early 30s.

Oversharing about her dog, doctors, and symptoms happens nearly every day. Symptom-related sick time overshares occur two to three times per week, and she has one to three doctor appointments per month. Over time, this creates a broad impression that she is constantly taking frivolous breaks or what feels like an unusual amount of sick time, both in general and compared to other employees and team members. Family members have commented as much and, although no virtual team members have explicitly said so, I suspect they also feel this way. I’m concerned about the impact on company culture and morale. She’s privately told me and other family members that previously, both corporate and mom-and-pop employers have punished her when she clocks in late or needs to take sick time due to her symptoms or have been unsupportive of her needs for medical appointments.

From an operating perspective, our solution has been to give her flexibility for start times, end times, and breaks, and not assign her projects or tasks that require specific hours. For example, she doesn’t open or close the office or answer phone calls, but she does set up and updates customers in our CRM, process submitted applications within 24 hours, create and schedule invoices, pay bills, collect and label receipts from purchases, review security footage, initially categorize expenses for our bookkeeper, etc. These tasks largely don’t have an difference if they’re completed at 9 am, noon, or 3 pm, as long as a backlog doesn’t build up. She works 35-40 hours a week, and quality of those tasks isn’t a concern.

Can you provide some guidance about how to approach this conversation? She‘s previously been upset and resistant to feedback that she perceives is critical of her chronic illness, both from family and from previous employers. Her actual taking of breaks is within the guidelines we agreed upon, but the nature of if and how she shares with the team needs to change. I don’t think she’s aware of the impression this creates. She’s also expressed interest in raises and moving up into a position of higher responsibility, and I want to be clear about what would need to change for that to happen without coming across as judgmental or unsupportive of her medical needs.

It sounds like she’s talking to you as family rather than as colleagues … because you are in fact family.

This can be a hard boundary to draw in businesses where nearly everyone is family (and especially where those who aren’t are remote).

But that doesn’t mean you can’t address it!

I’d frame it as, “When you’re out sick or for a break or an appointment, we don’t need to know any details — only that you’re out and when you expect to be back. I want you to stop including details beyond that, because it creates the impression that we expect people to justify their time away. I don’t want other people to feel pressure to provide personal details about their own time away. We’re happy with your schedule and your work, and we trust you to manage your time well. Going forward, please just announce you’ll be out for X amount of time, no reason needed.”

Also, does she need to alert you to 15-minute breaks at all? Ideally you’d tell her that she doesn’t need to alert anyone to those dog-walking breaks at all (just like you presumably wouldn’t expect people to message “I’m going to zone out for 15 minutes”). If she truly needs to keep people that updated on her availability, that’s different — but based on the work you describe her doing, she doesn’t need to. Again, you trust her to manage her own schedule and get her work done. She doesn’t need to provide a minute-by-minute narration.

If framing it as “this is sending problematic signals to others about what’s expected of them” doesn’t work, then you could say, “As the business is growing, we need to professionalize the way we operate. Nothing needs to change about your schedule. The system we came up with for breaks and time off is working well. However, I want you to move from sharing details about why you’ll be out (like taking care of your dog or the details of an illness) and just say that you’ll be out and when you’ll be back. That’s what we’d ask of non-family employees, and I want to move us in that direction now.”

You could say, “Sharing this level of detail is making people feel like you’re constantly away, whereas they wouldn’t notice it at all if you gave less info. And some of it’s an overshare that people prefer not to hear, like details about GI symptoms.” But since she’s previously been upset and resistant to feedback that she perceives as connected to her health, just go with the more business-focused reasons above. Those aren’t about her; they’re about the business and what it needs, and you’re on solid ground taking a firm stance.

mistakes at work: a round-up

Here’s a round-up of posts about mistakes at work.

what to do when you make a mistake at work

you made a mistake at work — now what?

how do I recover from a huge, fireable mistake at work?

how do I handle a serious mistake on my self-evaluation?

how big of a deal are mistakes when you’re new to a job?

how to rebuild your credibility after messing up at work

when you didn’t make a mistake, but someone thinks you did

my boss thinks I made a mistake — but I didn’t

how can I explain a mistake wasn’t mine without looking like a tattletale?

my manager doesn’t defend me from mistaken complaints

mistakes and how you feel about them

I messed up at work and I’m so ashamed

I’m so nervous at work that it’s holding me back

I’m terrified of making mistakes at my first job (and the update)

when your coworkers make mistakes

I get angry when my coworkers make mistakes

how can I tactfully point out to coworkers that a miscommunication error is theirs?

my coworker keeps missing deadlines and it impacts my work

when you keep uncovering errors made by your well-loved predecessor

how do I reply to my coworker’s apology without saying her constant mistakes are OK?

mistakes and your manager

my manager wants me to take more responsibility for my mistakes

our boss cross-examines us over minor mistakes

should I take the blame for my manager’s mistake?

what should I say to my boss when coworkers tattle on me?

can boss deduct the cost of a mistake from my paycheck?

when you’re the boss

what to do when an employee makes a serious mistake

what to do when an employee keeps making mistakes

my employee never apologizes when his mistakes cause extra work for other people

my employee blames others for her mistakes

junior employee is flippant when I correct mistakes in her work

my employees are making mistakes, but I don’t want to micromanage

a very big mistake

I accidentally sent my boss to Italy instead of Florida

my coworker doesn’t like it when I set boundaries on conversation topics

A reader writes:

I work in an artistic field, which leads to a much more casual environment amongst coworkers and a lot of time for chatting. I’m usually fine with this, but I’m having increasing issues with one coworker, Tommy.

Tommy routinely brings up topics that I’m uncomfortable discussing. He initially respected this, but has started to get very annoyed because I do it so often. The problem is I have to do it so often because his discussion points are extremely upsetting. Today alone, for example, I had to opt out of conversations on:

• he believes abuse victims who don’t leave deserve the abuse they face and are stupid for staying
• a detailed description of the gore in a horror movie
• women who dress in revealing clothes deserve to be harassed/assaulted

Tommy is not intentionally playing devil’s advocate; on days when I’ve had the bandwidth, I’ve talked to him and changed his mind. (For example, I convinced him that using people’s pronouns is a matter of politeness even if he didn’t understand why they used those pronouns.) But I’m clocking in to do my job and handle discussions about my work, maybe some chit chatting about tv shows — not long discussions having to explain why sexual assault is bad. He genuinely doesn’t view these topics as controversial or difficult to discuss, and thinks I’m fussy for not wanting to. He’s started to say he’s “pulling a (my name)” when he doesn’t want to talk about something — which of course I always respect. But he doesn’t say it like it’s a good thing, and he tends to do it while sighing dramatically.

I’m worried Tommy’s attitude will continue to get worse as I continue to set polite boundaries, to the point it might interfere with work. Or that he might start ignoring when I ask him to stop — he already pushes it with frequently bringing up horror movies because he thinks my discomfort about the very idea of most of their plots is funny. Is there a polite way I can explain to him that I simply never want to discuss serious or violent topics at work without him taking it poorly?

Escalating this to HR or management is technically possible, but would certainly make things fraught. We’re short-staffed so there’s no way he’d get fired, and if he’s reprimanded he would know I complained and he doesn’t seem the type to take that well.

Tommy is an ass.

Your best move is to decide you don’t care what he thinks about you. If this edgelord wants to believe you’re a delicate tulip who’s ill-equipped to survive in the world, so be it. He can think whatever he wants as long as he abides by your request to let you work in peace, without having to listen to his shitty misogynistic viewpoints.

Right now, it sounds like you’re looking for a way to get him to stop without him losing respect for you in the process. And that would be nice, but it’s not a necessity. We just need him to stop repeatedly violating your boundaries. (And really, since his opinions suck on a whole range of topics, it’s not surprising that his opinion about you might end up being wrong too.)

So: “I don’t want to discuss abuse, gore, harassment, or your views on women while I’m at work. Stop bringing those things up with me. This is me clearly telling you that it’s unwelcome and needs to stop.”

If he takes that poorly, that’s on him, not you. If he’s a halfway okay guy at heart, he won’t want to keep upsetting you and you’ll be doing him a favor by spelling it out so clearly. And if he’s not a halfway decent guy (spoiler: he’s not), then why worry that he won’t like you setting a boundary?

If you use the language above and he still keeps at it anyway: “Dude, I told you to stop. My next step is HR. I’d rather not, but this is a warning that I’m approaching that point.”

If he uses “pulling a (your name)” to mean avoiding a topic, roll your eyes and ignore him. He wants a reaction from you; your reaction probably makes him feel important. Ignore him.

If he makes snarky comments about how he can’t talk about topic X or topic Y around you, say in a bored tone, “Yep, thanks.”

But please don’t rule out escalating this to your manager or HR just because he would know you were the one who complained. It’s fine if he knows you complained, as long as someone with authority intervenes with him. (Plus, I wouldn’t be surprised if he’s doing this to other people too, so there might be a whole menu of people who could have reported him. In fact, that’s another reason to escalate it: at some point he’ll do this to an intern or someone else with much less power and/or who feels less comfortable than you do asserting boundaries. You’re  doing everyone who works with him a favor if you help connect him with an official “cut this out” edict from above.)