updates: an acquaintance blabbed when I sent him a confidential email and now I might become his boss, and more

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

There will be more posts than usual this week, so keep checking back throughout the day.

1. An acquaintance blabbed when I sent him a confidential email … and now I might become his boss

It ended not with a bang but with a whimper:

– No one ever brought up John’s strange email behavior; it is as if it never happened.
– I decided to disconnect from him in social media.
– I haven’t contacted him to try to find out what he was thinking (“closure comes from within not without”).
– Other members of the board have complained about John to me for unrelated matters; he is wearing out his welcome.
– Leadership at his workplace offered me a different executive role than the one they originally considered me for; for many reasons I didn’t take it.

He seems to irritate everyone, which at least tells me that it’s him, not me, and there’s nothing to take personally.

thank you and the community comments for counseling me to just chill. Saying and doing nothing was exactly the right move.

2. My employee keeps working long hours even after we’ve told her to stop

I ended up having to take this in a two-fold approach. First, I had a very frank (and honestly uncomfortable) conversation about insubordination. I didn’t know that anyone had ever had the conversation with her from that perspective, so it seemed like I needed to do it. It definitely seemed like a shock to her that it could be considered insubordination to “work late.” I had to clarify that the insubordination wasn’t the work hours but that she appeared to be ignoring directives from not just me, but upper leadership in terms of hours. I pointed out safety issues that many of your readers (and you yourself) mentioned because I knew she hadn’t seen it from any perspective other than her own “i’m getting work done” one.

Next, as you said (and many echoed in the comments) the why of this working late in a job that does not require late hours was important to me. We had multiple meetings that focusing on her prioritizing and time management skills. In our weekly check-ins, we now always have time to go over the various projects she’s working on and I help her establish a urgency list if she feels behind.

There is still a struggle in terms of her working hours but she is leaving at 6 nearly everyday now. Hoping that we won’t have to revisit the insubordination conversation EVER again because it was miserable and I hated it.

3. No one has acknowledged my resignation (#4 at the link)

You kindly answered my question about resigning when nobody was responding. You reminded me that telephones exist — I confess to hating them so I had literally forgotten that was an option. However, the only phone number I had was my direct boss and they were sick with covid – once again highlighting just how disorganised the company was. I chose not to phone them given that they were posting online about how bad they were feeling. I sent a second resignation email to everyone I could think of, plus the generic location@businessname.com email & finally got a reply 4 days later.

In terms of my job, I finished up all but one of my contracts easily & and have moved to my full-time job. I was anxious about having to get up early in the morning & the big adjustment to the 8-4 I’d be doing after 3 years of light part time work but while I’m tired at the end of the week, I am thoroughly enjoying it! There was talk of a permanent contract within 2 weeks of my start date and last week one of my colleagues was lightly encouraging me to apply for the job which would be a promotion that is being advertised. I’m not going to because I’m trying to take baby steps, but it’s nice to know my peers think I’m doing well!

4. My awful former boss is terminally ill — should I reach out? (#4 at the link)

I wrote in a few years ago asking whether I should reconnect with my difficult former boss who had been diagnosed with terminal cancer.

As you may have guessed, Sansa has passed away. I heard entirely through the grapevine, so I know nothing about the details. But she’s gone. You and everyone in the comment section told me not to reach out, and I followed that advice. We did not reconnect before she died. Thanks to everyone’s incredibly thoughtful and honest advice, I do not regret this. I appreciate everyone for reframing the situation for me, especially from Sansa’s perspective, and making it clear that I was doing both of us a favor by keeping my distance.

I will say, her death has made me feel a little reflective. I am just now reaching the age she was when she first hired me. I won’t excuse the way she treated me and those around her, but I do feel a little more compassion for her now that I understand her stage of life better. Plus, I think she was fighting some pretty nasty demons in terms of her mental health. (I’m also willing to admit that managing me was probably no picnic!) Granted, I’m far enough removed from the time I spent working for her that nostalgia may have clouded my memories, but I feel like I “get” her a little more now.

My relationship with her aside, Sansa’s death is a truly incalculable loss for the nonprofit we worked for and that community. I doubt I’ll ever meet another person who worked as hard as she did. She leaves behind one hell of a legacy. May she rest in peace.

{ 63 comments… read them below }

  1. learnedthehardway*

    OP#1 – on the plus side, John outted himself as someone who can’t be trusted and who has poor judgement. While you nominated him for the board role, clearly his behaviour towards yourself was just so out there that I’m sure nobody on the board holds his nomination against you. I mean, you obviously wouldn’t have nominated him if you had been aware of his lack of professional norms.

    1. Filthy Vulgar Mercenary*

      LW#1 – I’m imagining being one of the senior people or the board members in the receiving end of that email.

      I would think “LW seems like a normal person. Wtf is up with John. This has nothing to do with me. This really confirms some of my previous experiences with that passive-aggressive weirdo”

  2. Antilles*

    #4: Seems like you’ve found the proper balance here. Recognize the good she did in her life, understand some of why she was the way she was, not bitter at her…but you’re also not idealizing things by excusing the poor way she handled things either.
    Hopefully Sansa is resting in peace.

    1. Jean (just Jean)*

      Your last paragraph struck me as incredibly compassionate. If Sansa had any surviving family, they might be glad to hear this. BUT you have to do what’s best for you and if that means not contacting her family, that’s okay. They’ve probably already heard similar praise for Sansa from others in the nonprofit organization/community. May she rest in peace and may you go in peace.

      1. Momma Bear*

        Agreed – OP you seem to have come to terms with her in a productive way. I’m glad you’re no longer working for/with her but also glad that she was doing some good in the org before she passed.

        Sometimes when I have no other closure, I donate to a cause in that person’s memory.

  3. Mid*

    LW #2: I appreciate how you handled this.

    A lot of (not great) workplaces expect you to work as many hours as possible, and it can be difficult to transition to a workplace with a healthier balance.

    It sounded like she might have been fairly new to the working world, and/or someone used to a culture that rewarded 60+ hour weeks, so laying out why she couldn’t keep working those hours clearly was a kindness.

    When you’re used to the expectation being X, and you can’t logically see a reason for Y (in this case, not needing to be paid OT, so budget wasn’t a consideration, seemed to be a sticking point), having someone explain things that are sometimes unspoken is truly the best option.

    When switching from hourly retail that constantly pushed for us to work extra hours (but also did everything in their power to keep you from getting OT or full-time status), to an office job that was salaried, it took me a while to adjust to not needing to be visibly doing a ton of hours, and understanding what truly needed to be finished versus what can be left for a day or two, or even longer. I was used to a culture that meant that not-finishing a task meant that someone else was stuck with it, which was difficult to adjust to as well.

    I hope Caroline continues to improve and find a healthy work balance.

    1. WellRed*

      the original letter states several previous managers had the same issue with this employee. The lw also refers to herself as a millennial and worries that might make her seem a little soft on working hours.

      1. Mid*

        Right, and I’m guessing that no one had explained *why* she couldn’t do the extra hours. I’m not saying Caroline was in the right here, I’m saying LW explaining clearly why things are the way they are is great.

    2. Vaunakat*

      #2 is why we don’t want one size fits all workplaces. The employee should go work in an industry that is super hardcore, eg law, investment banking, consulting, advertising, tech, political campaigns, or emergency medicine. There are people who thrive in those environments!

    1. Venus*

      Did you read the AAM response? Alison put a lot of caveats in her answer, but this was one of the possible options and could have been most appropriate for the situation. You say that burnout is more than the hours worked, but that’s a big part of it and fair for the LW to address.

    2. Tedious Cat*

      I’m guessing you missed the part in the original letter where the employee had nearly been terminated in the past over insubordination. This was absolutely a conversation that needed to happen, for the employee’s sake.

      1. Gresham*

        I saw it. I don’t know if she was exempt or not at the last positions, so maybe there was a financial reason to limit her hours in those cases. Or maybe those other managers were also micromanaging an exempt employee’s hours. We have no idea.

        I trust adults to know how many hours in a week they are capable of working–and that means in either direction. I trust adults to know when they can’t work more that 40 hours as much as I trust them to know when they can work more than 40 hours. I disagree that a conversation with an exempt adult telling her to stop working when there is no reason other than ideology is a necessary conversation.

        1. Dr. Rebecca*

          “I trust adults to know how many hours in a week they are capable of working”

          I’m a professor. My students are (technically speaking) adults. I do *not* trust them to do this, based on experience. What experience? Glad you asked. The experience of many more than one telling me that they were working DURING my class. The experience of many more than one of them turning in work due at 5pm at midnight or after.

          Sometimes even adults need to be told that a deadline is a deadline, they can’t be in more than one place at once, and they need to rest, breathe, have food and drink, and be done for the day.

          I’m very glad you’re wanting to be a champion of the worker, but in this case, the boss is the boss for a reason. The LW was doing her job, and doing it correctly.

        2. Seeking Second Childhood*

          I think you are skipping over the safety issues involved. If a firebreaks out overnight when the facility is supposed to be empty, nobody will rescue her. Or if she is working in an area with a Halon fire-suppppression, it could go off because the building is programmed to be empty.

        3. Tiger Snake*

          My trust in adults is that they can recongise and tell me when we have misjudged effort and capacity. If I tell one of my staff what needs to be done and when by, they can progress it on their own andtell me as soon as they realise it would mean taking up more or less of the expected percentage of that 40hrs a week I expect them to work.

          Otherwise, how am I going to know the work is reasonable? How else am I going to build up a better understanding of how many man days a specific activity should take and make sure that I’m spreading the load fairly?
          I don’t want to have to breath down their necks after for hourly updates of how far through each action they are, but if I can’t trust that they’ll manage their loads and tell me when they’re taking more or less they’re paid for, that’s the only way I could do it.

        4. #2LW*

          LW here. It was the same job. Over and over this has happened and my boss put it onto me to finally put a pin in it- which I should’ve mentioned in the original post (I think I did, but maybe not).

          I understand what you’re going for here, but we work in academia and the building closes at 5pm. There is no security, no nothing. The original post was sparked because she stayed exceedingly late (past 7pm) and ended up getting stuck in the building because of campus-wide flooding. If she had left on time she would’ve been home and not have slept on a cold floor. I KNOW I mentioned this in the original post.

          I can see how you think I was just being overbearing and honestly mean without the backstory, but she has been in the same role for 9+ years and this has been an issue for all nine years of it- I’ve seen the performance reviews and disciplinary letters from my boss and predeccesors about inability to stick to agreed upon work hours- there were many. It sucks that it fell to me to handle this in a harsher way, but I won’t have anyone on my team (all of whom make less than $50K per year) working 60+ hours a week or sleeping on the floor, even if it means I seem rude to strangers online.

  4. Diana*

    Ugh, LW2, I have (sort of) been Caroline. Though no one ever told me to stop for good reasons [I did have a big boss who went off on one about “lone working” in front of our whole department, which I wasn’t doing – my fellow late-night worker buddy and I were very careful to abide by both common sense and any actual rules.]
    Maybe she just wants to? Maybe that’s how she just lives her life and she doesn’t need to be someone she isn’t? Though, of course it’s very different if she truly is slow and/or being unsafe. I have been burnt out, and that is a very different thing to enjoying your job and your life and doing it as your full self – I’d call it the opposite.

    1. Aisling*

      She can of course live her life as she wants to, but her boss can also let her know that how she does that doesn’t work for that particular job. The employee can decide to work elsewhere if she feels that strongly about it. The fact that the employee was talked to and nearly fired in the past for keeping those hours means that it isn’t something that’s ok at this particular job.

    2. Clobberin' Time*

      I don’t recommend telling a boss “I’ll work as many hours as I want to because that’s just how I live my life, and I don’t need to be someone I’m not.”

  5. KHB*

    I agree. I hate that OP ended up framing this as “insubordination” (and that several commenters did the same in the original post). Competent, adult workers are not “subordinates” – they should be valued, professional team members that you trust and respect. Barking out orders of the form “do this because I’m the boss and I said so” is a great way to destroy their morale really quickly.

    Alison listed several reasons why it could make sense to require employees to limit their hours worked, but for OP, it really did seem to come down to “because I’m the boss and I say so.” I’m glad OP found it uncomfortable to articulate that to her employee directly, and I hope it will prompt her to rethink her management style.

      1. with an extra pinch of salt*

        Agreed. Sometimes one has to trot out the clown hammer as a means of last resort.

        1. Dr. Rebecca*

          Look, we can be as “anti-cog-in-a-machine” as much as we please, but sometimes we DO need people to comply to rules just because. She’s the boss. Her bosses are the boss. The employee in question is NOT the boss, and does not get to make the rules about working hours. It’s not any more complicated than that; if the employee doesn’t like it she can freelance.

          1. Cmc*

            Yes! A person is hired into a position because there is a need. That need may be 10 or 40 hours a week, or 80, whatever, that is up to the person/company doing the hiring. The person/company does not need to explain why they do what they do, it’s is THEIR decision. If they hire someone to fingerpaint and erase, that’s up to them. An Employee has the right to decide not to work for them.. simple!

          2. fgcommenter*

            And if “just because” is the only justification given, then sometimes we DO need people to point out that it is merely a desire to bark and be obeyed than any attempt at being reasonable.

            1. allathian*

              Reasons are for reasonable people. Barking out orders is unnecessary when employees comply with a simple request. The employee in this letter refused to listen and did what she wanted to do until the LW told them what had to be done.

              The LW wasn’t barking out orders for kicks, but because the employee didn’t get the message when it was stated in a softer way.

              1. Dr. Rebecca*


                Plus, in these types of situations “just because” often covers a larger (and if you stop to think about it a moment, obvious) reason, like: “the business has 800 employees to keep track of, and if all of them did what they wanted whenever they wanted to, that would be impossible, so it’s not just YOU that needs to obey, here, it’s ALL of you.”

                Jobs have parameters which are tacitly accepted when people sign on for employment. As I said above, if the employee doesn’t like this one, there are jobs out there where she can maker her own hours. Tragically, this isn’t one of them, though.

                1. metadata minion*

                  My workplace has plenty of policies where no, this isn’t necessarily any better than the 5 other ways you might do the thing, but it’s not noticeably worse either, and it *is* important that we all do it the same way.

              2. fgcommenter*

                > Reasons are for reasonable people.

                Yes, and barking orders based on feelings instead of solid reasons mean that the bosses were not being reasonable people, and KHB was right to call that out.

                1. Liffu*

                  Ok but the fact remains that they are still the employers. You can call them out as much as you like, but practically speaking the only solution is to leave for another job.

          3. Vaunakat*

            This is one of those times when LW should please her boss and spend her free time building a startup, getting involved with professional organizations, networking,etc. These are all career adjacent and will build up LW’s network and stature with other companies.

    1. FashionablyEvil*

      I think the term insubordinate should be used sparingly for precisely the reasons you cite, but sometimes it’s the only shoe that fits.

      I’ve used it once in my time as a manager–our work requires us to fill out daily timesheets; it’s an audit and compliance thing. My employee refused to complete her timesheet when I told her it was required and then refused to speak with me any further and would only talk to HR. I really don’t know what else you would call that other than insubordinate.

      1. Dr. Rebecca*

        srsly. Do I *want* to do my yearly ethics and other accountability compliance trainings which I’ve done at least ten times now? Absolutely not. I could *give* these trainings. Do I do them to remain in compliance? Yes, of course, I enjoy my job and that’s a small concession to make to keep it.

        Honest to god, never did I think “stop working and go home” would be a bone of contention on this site.

        1. UKDancer*

          Yes there are parts of work (even in a good job) which are not enjoyable and you just have to do them. I don’t enjoy having to do my company’s annual mandated anti-fraud and corruption training either. There are also rules and processes for things in workplaces that are sometimes annoying and seem pointless but I don’t think it’s worth challenging all of them.

    2. tessa*


      It’s part of a manager’s job to guard against employee burnout. When nothing else works, it’s time to say “because I’m the boss and I said so.” Professional people don’t work 16 hours a day unless mandated. This isn’t that.

    3. Phryne*

      I am extremely sceptical of the word ‘insubordination’ being used outside of the armed forces or first responders. Blindly following orders without question is not the way a normal civilian working environment should or should want to operate. But I have to admit the dislike is largely semantical. In a university office, a manager can give directions, guidance, instructions or directives, but if my boss gave me an order, I’d just stare at her in disbelief. And if an employee does not follow the directions etc, that employee can be headstrong, insolent, uppsy impertinent, audacious, rude and is probably not working in their own best interest… but ‘insubordination’… nah.

      1. Mockingjay*

        Maybe that’s true in academia, but most commercial businesses have a hierarchy (which is not a bad thing, when implemented well).

        Sometimes the boss says, “Do X.” Which means you need to do X. Period. The boss is allowed – required – to set work conditions and assign tasks. Even as a senior staffer, I don’t discuss or debate everything that my supervisor or Grandboss tell me to do. It’s their role to ensure work assignments are completed according to schedule. That schedule is carefully planned to ensure OT is rare, because the program timelines are clear and we are staffed and trained sufficiently to meet those deadlines in a normal work week (40 hours). An employee who works extra hours after being told not to, on multiple occasions – I’d say that’s a textbook case of insubordination. It’s not a term restricted to military use.

        1. DrSalty*

          It’s not even true in academia. Pull a random grad student or post doc off the street and ask them if their PI gives out orders!

        2. Don't Call Me Shirley*

          It’s pretty mixed. I do engineering work, and 90% of the time even juniors are part of consensus discussions about what we are doing to solve the problem, who is doing what, and how we are prioritizing work. Sure, we have a common understanding of what we are trying to make that comes from above, but even requirements handed to me are open for discussion, correction, and clarification.

          Insubordination definitely is possible, but disagreeing with the boss has to go pretty far to qualify.

      2. Office Lobster DJ*

        I think the problem with words like insolent, impertinent, audacious, rude, etc is that they are way more subjective and loaded than a word meaning “not following the directions of a supervisor.” And someone can be politely or even cheerfully insubordinate — look no further than good old Bartleby.

      3. fgcommenter*

        Would you happen to live outside the U.S.A.? Unfortunately, the U.S.A. is far behind a lot of the European countries when it comes to basic standards for working conditions.

        Your description of your workplace makes sense for the more civilized countries, but the U.S.A. has a severe cultural problem with expecting workers to blindly follow orders without question. Just look at all the pushback in the comments against anyone who calls out that nonsense and explains why it is nonsense.

    1. stone cold chili pepper*

      I wonder this too. I have a few colleagues who are stupidly overworked & their response to being told they had to go home by X time is to work from home after hours.

      (Mind you that’s a symptom of this place not supporting certain departments, not my coworkers being insubordinate)

    2. Santiago*

      If she works in a government type role, she can actually mess up allotments by doing more than one FTE and leave the department underfunded. This was discussed in the last letter, but idk maybe she needs an admin.

    3. Myrin*

      Yes, a lot of people speculated on that in the original comment section, and Alison mentioned it in her answer as well.

  6. Shoutout to OP #4*

    One day I hope to be as compassionate as you are towards your former boss. I may never get there but I can try.

    1. Anon for this reply*

      I am feeling the same way. A client I’ve worked with for the last 20-some years has been the nastiest person on earth….always talking endlessly about herself and never asking about anyone else’s life. She flies off the handle at odd moments and often makes people in my office cry, me included. It’s to the point that our manager insisted that she be the one to work with her. This client announced a year ago that she has terminal cancer and I’m having a hard time caring. I know this is super hateful and it really isn’t me at all, but it is so hard to be anything but ambivalent about her sickness. OP #4 is helping me to rethink my position. I am going to try to only think about the good things about this client from now on.

  7. Not Overworked*

    On #2, not everyone has a good home life they are eager to get to. The year my sister died was probably the most productive of my career.
    I worked many long hours because I couldn’t bear the thought of going home to the empty house we shared. My boss frequently told me to go home and gave me EAP pamphlets. I would of been shocked if he called ignoring his directive insubordination. Similarly, I currently have an employee going through a divorce that is often at the office until 8 pm. She “needs” to be at the office not because of the workload, but because she is avoiding the husband she still lives with. I tell her to watch TV in the break room or go to the company gym, but she insists that working keeps her mind occupied.

    1. Dr. Rebecca*

      No, sorry, she needs out of her situation and into therapy. Just because something is a coping mechanism used by a person going through trauma doesn’t make it a *good* coping mechanism.

      1. Vaunakat*

        You have a lot of nerve telling someone that your way of coping with grief is the only way, and that such a person needs therapy. Getting back to work was enormously helpful to me when a parent died.

        1. Dr. Rebecca*

          And “Not Overworked” has a lot of nerve disregarding the fact that their boss wasn’t cool with them being there past normal hours. Your grief is *not* the problem of your workplace.

          Grieve however you need, bury yourself in busy, IDC, but don’t bring that to work.

        2. Evan Þ*

          Yes. The afternoon after my grandma died, I went into the office. I didn’t want to be alone with my thoughts cycling in circles; I wanted to fill my mind with something technical to distract me.

          My boss told me to take all the time I needed; I thanked her (and took time off later for the memorial) but said that work helped in the moment.

  8. Bunny Lake Is Found*

    I’m kind of confused how if she is basically leaving at 6 pm there are still issues with her working hours? Also, if she is requiring meetings to prioritize her assignments, I assume it is because she is finding it difficult to complete all of them before 6 pm? I know in the original letter the amount of work Caroline had was discussed and that LW knew she worked more slowly on tasks (which LW seemed fine with because Caroline was producing good results), so I guess I am just wondering if LW might be locked into the “leave at 6” harder than is helpful for LW, Caroline or the rest of her team because backing off on that might feel like backing off of the fact Caroline was not listening to her manager or those before LW and that it was completely unacceptable.

  9. cncx*

    I had a job once where I was constantly interrupted during the day and working overtime was the only way to get thinking work done. I get with op2 that the real issue was insubordination but there are jobs which would have normal working loads if there wasn’t a “drive by” or “talk things out” culture. I was repeatedly berated at that job for being inefficient but my manager took no steps to stop people from just coming by my desk every second of the day or help me prioritize. I was expected both to drop everything for drive-bye but also dedicate time to thinking work. No support, no understanding. Like it’s cute to say I need to learn how to prioritize, less cute when people watch me get stopped every second of every day and not be allowed to push back with “please send me an email” or “let me finish this one thing first.”

    The job I just left had constant interruptions as well, I still set a hard close (based on being told I needed to “work smarter” in the other job) and surprise, I didn’t get my thinking work done for firefighting. Like at job number one, my manager didn’t see the disconnect between what was mainly him making me drop everything all the time and me not being able to do anything that required more than five minutes (literally) of uninterrupted time.

    I get it’s totally a different situation from op2, I’m just saying sometimes long hours are a management/company culture issue and that in both of my cases I was set up to fail. If I didn’t work late, I wouldn’t meet my deadlines, if I did I was “inefficient.”

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