updates: humor as the boss, the apology for snapping, and more

by Alison Green on March 13, 2025

Here are three updates from past letter-writers.

1. Does using humor risk undermining me as a manager?

Thank you so much for responding to my question! In truth, I didn’t even consider the possibility that using too many self-deprecating jokes would alter my employee’s perception of me, I was mainly focused on the quantity of my jokes. After I submitted my question, I thought over my interactions with them, and came to the conclusion that I was being way too silly, that my nervousness was manifesting as non-stop joke after joke, which had a strong possibility to detract from maintaining a professional manager/employee relationship. Some of your commenters also noted that as my report they were a captive audience, in that even if they don’t find my humor funny they may feel compelled to laugh along, even if they feel uncomfortable.

Armed with this realization, I cut way back on the jokes I made, and with your advice in mind also limited the self-deprecating humor as well. This seemed to work well over time, as I was able to build a friendly yet professional relationship with my employee, while also occasionally poking fun at our system software or the weather.

Unfortunately it ultimately didn’t last; I had to terminate them for egregious misconduct towards another employee at a company event, which was fueled by alcohol. When I hire my next employee, I’ll be sure to use the lessons you and your readers shared to use humor moderately and with mindfulness towards how I may be perceived.

2. I want to apologize for snapping at my coworker, but my manager said not to (#2 at the link)

I really appreciated your advice. I struggle with anxiety, and the idea that I’d upset someone was eating at me. Despite the consensus in the comments that my outburst wasn’t all that bad, I still felt an apology to my coworker was warranted, so I practiced what I was going to say based on your suggestions. When the time came, I was on high alert for signs of chilliness, but nothing in her behavior indicated that she was still upset. A few days later, she announced that she was leaving for a different job, and that’s the last time I saw her.

Although anticlimactic, this event was illuminating for me. There was a lot of gossip in the weeks following my former coworker’s departure, through which I learned she quit in a huff after the manager tried to have a conversation with her about her chronic tardiness. Unbeknownst to me, she had a history of showing up late, disappearing for long stretches without explanation, and (oh, the horror!) taking other people’s food from the break room without asking. Several people expressed relief at not having to deal with her anymore, including the manager.

Speaking of managers … you were spot on to call his response into question. I think he was right that texting an apology wouldn’t have had the outcome I wanted, but it’s become clear to me through this incident and others that the promises he makes and advice he gives should be taken with a grain of salt. It’s a bummer, because I like him as a person, but the more I learn about good management, the more aware I am of where he falls short (for example, his refusal to address years of complaints about my former coworker).

On the bright side, I got a promotion and a raise, and am being encouraged to find projects that interest me. I know I don’t want to stay at this job longterm (aside from the management issues, there’s too much drama and a big nepo baby problem – a whole letter unto itself), but I’m learning a lot and building new skills, so I’m sticking around for now.

Thank you again, both for your wisdom, and for the wonderful community you’ve brought together.

3. After I had to fire someone, my boss asked if I still want to be a manager (#2 at the link)

As it turns out, the question from my boss was testing my desire to move up to a director role — a position that he knew was going to be vacant soon, but he wasn’t able to share that info with me at the time. (For various reasons, including a required relocation, it was not a role that interested me.)

As I predicted, it took many months for a replacement for my employee to be hired, but the new employee is a terrific skills match and much more professional. Our team has been running very well since the new year and the lack of drama has been a relief to everyone. That said, I did recently accept a role that is a lateral move within the organization. I will have only one direct report in this new role, but it is a growth area and I expect my team will have more members in the next 12 months or so. I am very grateful to you and to the commenters who assured me that firing someone never feels good in the short term, but will help the team in the long term, and that was certainly true in this case. I also dug out my old books and training materials on management skills and gave myself a refresher course, which has been quite helpful.

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{ 42 comments }

{ 42 comments… read them below or add one }

  1. about that*

    I gotta say I have some misgivings about ‘thanks to the Internet I feel good about doing exactly what my boss told me not to do’ as a takeaway from this story.

    Reply ↓
    1. Amber Rose*

      His reasons were ridiculous and his management style is poor. Sometimes you do have to do exactly what you were told not to.

      Reply ↓
    2. Saint Elmo*

      That’s a fair takeaway, but we have to remember that (for better or for worse) bosses and managers are people too. They will make mistakes, and sometimes will give bad advice. To have 100 strangers on the internet try and help with your problem and discuss the different angles of it can be very helpful.

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    3. Stipes*

      Are you talking about #2? It doesn’t even sound like LW2 ended up giving that apology — they prepared to use Allison’s advice from the column (don’t apologize proactively based on being told the coworker was upset, because that causes the problem your boss was worried about, but feel free to apologize when/if you see signs of chilliness with your own eyes). Since the chilliness never manifested, OP didn’t have the situation to apologize.

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    4. Zona the Great*

      Eh. We all have to decide what is best for us or which is the “bigger evil”. For me, I care more about how I make people feel than how well I tow the line a boss give me. However, I will say the reaction from Jane on this was over the top and I wouldn’t have felt I owed an apology.

      I once had a boss command that I email a vendor with a shitty unkind tone and just….refused to. I feel good about that.

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    5. Ellis Bell*

      I mean, we’re all here for management expertise, aren’t we? Dismissing Alison’s advice as “the internet” strikes me as rude, especially since she didn’t tell the OP to overule the boss, she told them how to abide by instructions she didn’t agree with.

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    6. Pixel*

      I don’t see that at all in the letter. OP doesn’t say they ever went against what their boss said, nor that they think they should in the future. (They even said they think their boss was right to advise against the apology text!) All they said was they’ve learned to take things their boss says “with a grain of salt.”

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    7. Leenie*

      Putting aside the fact that it sounds like her boss isn’t quite a font of overflowing wisdom, she didn’t do exactly what her boss told her not to do. He told her not to text an apology. She didn’t do that. She expected to not be scheduled with the coworker for a while, since her boss told her that was the plan. Since that changed, she had Alison’s advice in her back pocket in case it was needed, and it turned out not to be necessary.

      So I have misgivings about a comment that isn’t just weirdly harsh, it’s weirdly harsh in a way that’s pretty far off-base.

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    8. LW #2*

      Others have put it more succinctly than I could, but yeah, that wasn’t really the outcome. I didn’t do what my boss told me not to do, and like I mentioned, I have anxiety, so I definitely didn’t feel good about any of it :)

      Reply ↓
  2. Falling Diphthong*

    Re 2, I can’t decide if I’m more surprised that people decide to become known as “the coworker who steals other people’s food,” or that that decision seems to work out fine for so many of them.

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  3. Llama herder*

    “(oh, the horror!) taking other people’s food from the break room without asking.”

    I don’t understand why people make light of stealing coworkers lunches. Stealing is stealing. If you would fire someone for taking $5 cash from a coworker’s wallet, then you should fire them for stealing lunches. It shows a lack of professional judgment and bad character.

    Reply ↓
    1. hellohello*

      I didn’t read that as making light (Though I do think that’s a fair reading for anyone who did!) but rather a nod to how often that’s popped up in the examples of Ask A Manager egregious behavior before. Not sure which one LW meant, ultimately, but just to add a different possible interpretation.

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    2. A Simple Narwhal*

      I actually interpreted that as the LW being playfully sincere, acknowledging that there are soooo many people writing into AAM about people having their food stolen, and offering it as proof that their coworker was pretty awful in general.

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    3. Not on board*

      Yeah, I was wondering if the person was being sarcastic and making light of lunch-stealing or if they were referencing the large quantity of lunch-stealing stories, both on AAM and the internet in genereal.

      If it’s the former, then I think they need to re-examine how they look at lunch stealing – you’re right, if it’s not okay to steal cash from your coworker’s wallet, it’s not okay to steal a lunch.

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      1. Zona the Great*

        It wasn’t a sarcastic remark or one made in jest. LW meant it–it was a horrible thing to do.

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    4. FSU*

      This. Taking food is a big deal. Some people have medical issues and need to eat and they plan accordingly by bringing the food they need. How is it okay that someone steals it? And even if they don’t have medical issues, they still need to eat, and if they brought their own food, they clearly didn’t plan to go out and purchase lunch or make other arrangements, and it’s pretty crappy to be forced to do so due to someone else’s horrible behaviour. It’s not okay, and it shouldn’t be downplayed.

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    5. Myrin*

      From the way the whole letter is written, I assumed the OP was actually being sincere with her parenthetical (and also, if she’s a regular AAM reader, putting this as a little reference to the many times we’ve had letters and comments about exactly this scenario).

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      1. Ellis Bell*

        Yeah, it means ‘Wow, will this never stop happening?!’ not ‘Pfft, it was nothing’. If you read to the end of the letter, it says really clearly that OP was head of the line in complaining about this coworker, but the manager ignored them.

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    6. Boof*

      I was taking that to mean that even though it’s not really directly impacting the work product, it’s like, the worst feeling issue / the most egregious thing? Maybe I’m being generous but even though the tardiness is probably the big “work issue” the stealing other’s food would definitely be what I’d personally judge someone the most for XP

      Reply ↓
      1. Fish Microwaver*

        Yeah, I read it as the food stealing being the icing on the cake of a number of serious performance issues.

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    8. LW #2*

      My intention was not to make light of the food theft, but to highlight the absurdity of what a shady character she was, as if all the other issues weren’t enough.

      Reply ↓
    1. Verity Kindle*

      I love the structure of that update: a thoughtful story about how the OP took Alison’s feedback, reflected on themselves, and grew to become a better manager. Followed by an unrelated swarm of bees from stage left.

      Reply ↓
    2. Princess Sparklepony*

      I feel like there is a juicy story that needs telling there. Duck club? Piano playing at the Christmas party? Cheap ass rolls? I will confront you on Wednesday? I want to hear if the story tops those.

      Reply ↓
  5. Varthema*

    Super tangential, but I would love an update from the no-humor letter (linked in the OG letter from today’s LW1). Did they ever leave?? was it hard to reacclimate when they did? that was one of the weirder letters I’ve ever seen. Would 10000x rather have a manager with self-deprecating humor!

    Reply ↓
    1. Hlao-roo*

      There was one update on the “no-humor” letter, posted on Feb. 1, 2022 where the letter-writer said “I don’t plan to stay here more than another year. It’s grown my technical and deliverable skills a ton, but the emotional labor involved in NOT ever being emotional is so draining.”

      If the OP followed their original plan, they left the no-humor office sometime in 2023. I would also like an additional update to the letter that answers your questions about leaving and reacclimating!

      Reply ↓
  6. Emily Byrd Starr*

    #1: Maybe it’s just best to stick to puns and wordplay at the office. Speaking of which, I couldn’t help but notice that #2, which was an update to a reaction after being bitten by a dog, contains the phrases “snapped at a coworker” and “eating away at me.”
    Sometimes, working in the office can be ruff.

    Reply ↓
    1. LW #2*

      You don’t know the ‘arf of it! ;)

      (Actually unintentional on my part, but hats off to you, a bone-a fide pun spotter.)

      Reply ↓
  7. Box of Rain*

    RE #2 – One of the things It’s taken me years to really understand is that you can dislike the person but like the employee, and you can like the person but dislike the employee. Understanding those aren’t always aligned has really helped me, both as an employee and as a leader.

    Reply ↓
    1. CC*

      I agree! I think I’ve also found that separating the feelings out helps me cut people more slack – one of my old coworkers used to annoy me, his style of working was nearly the polar opposite of mine, but I realized he was still a good guy, and that made me also realize that he was also doing good work, we just had tension and disagreements about the methodologies we’d use. That framing helped me work with him much better. (We still would generally try to avoid being on the same team, but we were friendly and able to work together well when needed.)

      Reply ↓
    2. allathian*

      It’s similar to how you can really like a person as a friend but hate traveling with them or having them as a roommate.

      Reply ↓
  8. Bruce*

    LW2 I went back to read your first letter and had to laugh at the comment that started it! I’m glad your coworker seemed to be over it, they were probably in “short-timer” mode by then anyhow…

    Reply ↓

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