my employee accidentally sent a rude message about me … to me

A reader writes:

I have an employee who was my first hire as a new manager — Jane. I have built a department from the ground up through hard work and promotions, and Jane has been with me a good majority of the time. I considered her a friend. I recently inherited another employee from a different department — Mary. I received feedback that Mary felt coming to my area was a demotion, but I’ve worked hard to form what I thought was a good team environment. We have a highly visible job that’s stressful and can be tedious. We currently are working well together (I thought) and recently I have done team-building activities (which I’ve paid for out of pocket) and I also went to bat for them both to receive a bonus from our senior executive and the CEO. I’m not looking for a pat on the back, just trying to demonstrate my loyalty to them and that I strive to create a positive environment.

Today I caught Jane sending an IM to Mary making fun of me, complaining about an instruction I’d given her, and had a tone of “OMG, she’s annoying.” I know this because she accidentally sent it to me, not to Mary. I responded that I think her message was intended for Mary and not for me, to which she tried to dance around the subject.
In addition to feeling totally blindsided, I’m hurt and embarrassed. I understand managers get talked about, but how do I move forward in a professional way, and not hold a grudge? They both do good work, so I don’t want my hurt feelings to impact how I review them, which is coming up. However, I’m struggling to view them as I did before as their behavior is unacceptable. Jane didn’t seem too upset by this either. Maybe she wasn’t or maybe she was sticking to her story that her message was truly for me … it wasn’t, I’m positive.

Maybe I created an environment that was too friendly and maybe I tried to be too cool? Thanks in advance for any help.

Even the best managers get vented about sometimes. When you have power over other people, you’re sometimes going to make decisions that they disagree with, or have habits that are at least mildly annoying. Because of that, sometimes people are going to blow off steam about you, even if they like working for you overall. It’s an uncomfortable reality to live with, but it’s the nature of being a boss.

So your goal can’t be “Mary and Jane never say a critical word about me.” You’re actually better off assuming that the people you manage will have their own private critiques of you, so that you can be thoughtful about what those might be and consider whether there’s anything you should change about your style in response. There might not be anything you should change; sometimes a good manager needs to do things that will annoy people, and you can’t not do those things just because your staff doesn’t like it. But sometimes this type of reflection can nudge you into changing how you operate, or more explicitly explaining to people why you’re doing something a particular way.

That said, it’s also possible that the IM Jane sent you was a glimpse of something that goes beyond the occasional letting-off-steam and is more entrenched, more toxic, and more worrisome than typical frustrations.

One option is to just ask Jane about it during your next one-on-one conversation. You could say, “I wanted to ask you about the IM you sent me about the X project. It sounds like you were pretty frustrated by my instruction to do Y. I’d asked for Y because ___. It sounds like that wasn’t clear, and I wonder if you feel like it would be helpful to have more context when I ask you to make changes, or whether there’s something else going on that you’d like me to handle differently.”

You can have this conversation without debating whom the IM was really intended for, since that’s likely to embarrass her or put her on the defensive. Instead, skip right over that and go to “Is there something you want me to do differently?” Even if her answer to that is “No,” you’ll be communicating that you’re open to feedback and concerned about her perspective — which is helpful for her to hear. And who knows, maybe she’ll take this as an opening to bring up concerns.

In fact, you could take this even further and use it as an opportunity to solicit feedback from both Jane and Mary (individually) about how things are going overall and whether there are things they think you could do differently to make your team more effective. If you approach that conversation with sincerity — and if you’ve created an environment where they can feel comfortable giving you real answers — it’s possible that you’ll learn really useful things. You might get insight that helps you understand why Jane was sending a frustrated IM. Or you might learn that Jane and/or Mary are out of sync with how you want your staff members to approach their work, and be able to figure out whether there’s a way to correct that. Who knows what else you might learn — there are all kinds of discoveries you could make here. This is a useful conversation to have no matter what, but that IM in particular might be a sign that you need a better understanding of how they’re experiencing their work and your management, and whether there are adjustments that either side here should be making.

One other thing! I think seeing that message probably stung more because of the personal relationships here. You say you considered Jane a friend, and no one wants to see a friend talking behind their back. It hurts — it feels like a betrayal. But while you’re managing Jane, she really can’t be a friend. You can have warm, collegial, friendly relationships with the people you manage, but they can’t be true friends because the power dynamics prohibit that. You need to be able to objectively judge their work, give impartial feedback, and make decisions that could affect their livelihoods. They need to be able to trust that you’re not letting personal feelings influence how you manage them — and to vent about you sometimes too.

While it was certainly kind of you to pay for work activities with your own money, it sounds like doing that set you up to expect a certain level of gratitude in return. But for Mary and Jane it was a work engagement, even if the activity itself was fun. I think you’re all likely to be happier in the long run if you, as the boss, reset your expectations about the type of relationship you can and should have with the people you manage. Again, being warm and friendly is great. You should aim for warm! Just don’t expect your employees to go beyond being reasonably warm and doing a good job in return.

Originally published at New York Magazine.

Read an update to this letter here.

{ 180 comments… read them below }

  1. AdAgencyChick*

    Alison’s answer is so much deeper and more thoughtful than the “have a conversation with Jane about how she needs to be more careful about venting in electronic media because it can get back to the wrong person” that I would have said.

    1. Detective Amy Santiago*

      Especially on a work system!!! I had coworkers get fired for trash talking their manager in company email.

      1. Mediamaven*

        I did that. I fired an employee for her negative talk in email. Best decision I ever made. She perpetuated such a toxic environment.

        1. Data Pseudoscientist*

          Do you mean she was the sole person responsible for the toxic environment, or was she venting about the toxic environment?

          1. Candi*

            From “perpetuate”, it sounds like she was the type of personality who makes existing problems or toxicity worse, even if she doesn’t start the issue.

            I’ve worked with those types. They can take tiny anthills most people would just stomp on or ignore and make them look like the Himlayan range. With real problems, they increase the sewage output exponentially. It’s bad. And if they’re pot-stirrers or drama-creators on top of that…

            1. Wintermute*

              I sit next to one of those, and I’m so, so torn. I feel for the guy, he’s had a rough life, to hear him tell it (laid off from a few different places, etc) but on the other hand into each life some rain must fall– everyone will get a bad break or two that doesn’t mean you have to go on long diatribes about how badly they were managed 20 years later.

              Our management has had some bad decisions forced on them from outside, that’s not their fault, but he will rant and rave and mutter curses at the system under his breath, every day, and it’s been four months!

      2. Triumphant Fox*

        Yes! I remember a few months after starting at my last job, two coworkers resigned not long after one another and they were both frantically trying to figure out how to delete their conversation history on Slack. It wasn’t until one of them was gone that I realized how vocally negative she was and how much she contributed to a really toxic environment.

        Another coworker mentioned that she had inherited the previous admin’s slack account and it kept all her correspondence. It made her so uncomfortable because those messages were cruel and inappropriate (those were the only details she gave me) and gave her a terrible impression of the workplace coming in.

    2. Tealparadise*

      It was perfection. Hit every note, especially the “I paid for work activities out of my own pocket because we are friends.” Oh no honey, oh no…. Work is always work. There are a lot of assumptions by the letter writer about how things must be because she’s gone above and beyond, but as Alison said…. seek feedback to find out if these gestures and methods are actually appreciated.

      1. Snark*

        Yeah, there’s absolutely no reason to pay for stuff yourself because you have friendly relationships with your reports. I’m of the opinion that most teambuilding exercises are BS anyway, and not a worthwhile use of time or money, but even if it was great and appreciated…you’re not on the hook for business expenses like that. And if you do, you’re paying for a work event, not a fun thing that people will be grateful to you for.

      2. Hmmmmm*

        Stuff like this can backfire both ways. The boss expects a level of gratitude for things the employees didn’t even know happened and the employees might get the misunderstanding that this is a lot cushier job than it is!

        1. OP*

          Agreed — I don’t want to set a precedent. But my expectation of gratitude was also short sighted.

      3. Clisby Williams*

        Yeah, the “I paid for team-building activities” BS. Unless that involved meeting up at a nearby bar and having some drinks and mozzarella sticks for an hour or so, just can it. Team Building = torture.

        1. MK*

          I think paying for team-building activities is not the main issue. People vent, but it’s not professional or kind to do it through company resources. It makes for a toxic environment, and I could never in a million years imagine talking smack about my boss in an IM. I would confront the person in person and tell them if we are going to be an efficient and productive team, we need to be able to better communicate–both productively and professionally. And then lay out what that means. If there is an issue, then let’s discuss. Tell her you’re open to feedback. Then, make sure you draw the line and say this is inappropriate behavior that will not be tolerated in this office–but allow her to apologize and promise to correct the mistake. Then see what happens. Force her to communicate more with you and make her have weekly/bi-weekly check ins. If she is a decent person and cares about her job, she’ll change.

    3. Cajun2core*

      I once learned the hard way a lesson that my boss taught me, after I learned it the hard way:
      “Never put anything in writing that you would not want on the front page of the New York Times”.

      1. Farrah Sahara*

        Or as another boss said to me: Dance like no one is watching and email as though it will be one day read aloud in a deposition.

        Good advice that I try to follow!

        1. AKchic*

          Yes. “Everything you write is subject to federal and state audit, or could end up in court. How will you explain what you wrote?” If its on company property, or done in the company’s name, it is subject to this rule. If it is remotely anywhere *near* the realm of the company – play it safe and consider it company-related and falling under the rule.

          Or, pretend you’re a secret agent working in politics. Everything you say can and will be used in counter-espionage war games. (fun gadgets not included, but can be purchased on your own)

        2. RUKiddingMe*

          Very good advice. Way back in the dark ages when I was just a small child — the 70s — considerably pre-email, my mother told me, “never put anything in writing that you wouldn’t want read in court.” So essentially the same thing. All these years later I still operate on that premise. Also I shelled out for the really good shredder that cuts stuff up so small that it’s basically lint…just because. ¯\_(ツ)_/¯

      2. Guesty McGuest*

        My version of this is “Never put in writing what you wouldn’t want discussed in a deposition”. Because I’ve been deposed, and they tried to use anything they could find in my computer against me.

        There was one IM convo about people using their outside voices to have a conversation over myself and the person I was IM’ing because we sat between them. (Plus some of the emails I received from people I’d met at a networking event that ended up not really being business contacts because we were in different fields, but liked me socially. I’d passed out my business cards, so work email was how they invited me to happy hours and whatnot.)

    4. EddieSherbert*

      This advice is still valid too – Jane probably just doesn’t need to be told it at this point; she’s likely a bit mortified and figured it out already!

      1. Hills to Die on*

        Yes, after this talk Alison outlines, Jane should feel about this big *makes little pinching motion with fingers*

      2. AdAgencyChick*

        You would think, but the OP’s note about “Jane doesn’t seem too upset” makes me think she’s not!

        1. Where's the Le-Toose?*

          That’s what got me about the post. Sending an IM to your boss being snarky about your boss — I’d be mortified! For Jane to apparently blow it off like no big deal seems to me that there is a lot going on behind the scenes that the OP needs to address.

        2. AKchic*

          Playing it casual isn’t out of the realm of possibility either. The “I’m going to pretend this didn’t happen. I’m going to keep my head down, play it cool, and hope everything just blows over until it’s all forgotten” situation.
          Sometimes it works. Especially in bigger companies when it’s guaranteed someone else will do something. Maybe someone will discover an underground duck club. Or someone will start a copy room lunchtime ping pong league. Or a secret llama breeding operation in the basement next to the elevator service shaft.

          1. MerciMe*

            If I had a nickel for every illicit llama-breeding operation that went terribly wrong in someone’s basement… Look, some consequences are just predictable and you bring them on yourself.

  2. Malibu Stacey*

    Don’t forget that just because Mary was the intended recipient doesn’t mean that she endorses Jane’s opinion. I have received vents like that from coworkers just because they want to get it off their chests, not because they know I feel the same way.

    1. Roja*

      I thought something similar. OP is discussing the issue like it’s both a Jane and Mary issue but so far all I see is that Mary is the intended recipient and has done nothing, as far as OP knows so far. It’s very possible she wouldn’t have wanted to receive it even if it had gotten to her. I mean, it’s also quite possible she’s sending those kinds of texts too, but unless there’s info we don’t have, right now it looks to me like a Jane thing only as an innocent till proven guilty thing.

    2. Kate*

      Great point! I’ve been vented to like that even when I’ve made it clear that I *don’t* share that opinion.

      OP said, “I received feedback that Mary felt coming to my area was a demotion, but I’ve worked hard to form what I thought was a good team environment.”

      I think maybe this is coloring OP’s view of Mary. But who delivered that feedback? Did it come straight from Mary? I understand why the OP would feel hurt thinking her team is a demotion, but who knows the reasons for that? Maybe it’s just not where Mary wanted to take her career. Or maybe she doesn’t feel that way at all (again, depending on who delivered this feedback). I like Alison’s suggestion of sitting down with them individually to see how things are going just because I think managers should be open to feedback from their staff, but I think the concerns about Mary are really a separate issue from being the intended recipient of a text message.

      1. Shiara*

        It’s possible that Jane’s comment, or other aspects of Mary’s behaviour, do make it clear in context that this was a mutual venting session.

        That said, I agree that from the information given in the letter, it’s quite possible that this is entirely a Jane thing and not a Mary and Jane thing. While I’m sure the demotion thing stings a bit, there are absolutely teams that I would consider it a demotion to be moved to at my company, even if my title and compensation level remained the same. And that’s not at all a reflection on the managers of those teams! It mainly has to do with the scope and visibility of the projects involved.

    3. Mallory Janis Ian*

      I thought the same thing. I’ve had overbearing coworkers (who assume that, of course, everyone shares their stance on things) implicate me in their nonsense when I actually felt the opposite.

    4. Beatrice*

      I have used the comment, “I hope you’re not sharing this with me because you think I agree!” to shut that down before, and it worked great! It didn’t make for a warm fuzzy relationship with the coworker in question, but chilly and distant was kind of what I was going for anyway.

  3. fposte*

    OP, speaking as a fellow manager, we almost certainly *are* annoying in some ways. That doesn’t mean that our work for our staff doesn’t count, or that we don’t have a positive environment. But our employees get to be annoyed by us sometimes.

    Absolutely, as Alison suggests, consider exploring in case there’s a deeper dissatisfaction going on. But I think it’s likely that this is just a dent in your self-esteem and also a nudge away from overpersonalizing your management relationships.

    1. Detective Amy Santiago*

      And on the flip side, I’m sure that Jane and Mary do things that annoy the OP sometimes.

      I actually said in a conversation elsewhere this week that everyone gets annoyed with everyone at some point. It’s the nature of being people.

      1. Not a Real Giraffe*


        In my last job, there were three of us at the same level doing the same work. We had a great working relationship and we were friends outside the office. But we all had quirks that annoyed the others. I would vent to Coworker A about Coworker B. It had nothing to do with the great friendship I had with Coworker B or the deep respect I had for her work, and everything to do with the fact that we are all humans and other human beings can annoy us, especially when you’re together for 40+ hours a week. (That said, I assumed A and B would also vent to each other about me because again, that’s human nature.)

        1. Pollygrammer*

          As long as you don’t vent in writing, I think this is totally fine–sometimes necessary.

      2. C.*

        Yup. I always tell myself that if X number of people annoy me, then there’s probably that same amount of people who find me annoying.

      3. hermit crab*

        Yeah, I fully believe that my previous manager was the best manager (for me) humanly possible, ever, on the face of the planet. And I still totally vented about her every once in a while (not at work, though).

    2. Lora*

      Yes. And taking this a step further, I think it’s good to work on your self-awareness of the ways in which you annoy your staff. There are some things where you can stand on “I’m the boss and I do it this way and you’re gonna have to deal” but they are really few and far between, so it’s important to know what you’re asking people to tolerate on your behalf and know when you’re on thin ice with them.

      I do things which annoy my staff all. The. Time. Some of these things are small (text, WhatsApp or email, don’t call; I don’t do a lot of meetings and the type of meetings I tolerate are No PowerPoint Allowed), some are big (I rarely have time to provide as much training as I really should). But I am good about fighting for raises for them, making processes out of chaos so their jobs are orderly and predictable, sticking up for them when other departments are looking for a scapegoat, and making sure they get professional development and networking opportunities.

      It’s better to accept that you’re going to be annoying in some way to someone, possibly to many people, and either change that about yourself or make your peace with it. Even my dearest friends I’m sure do not appreciate my foodie eating habits, my loud indoor voice, or my favorite hobby (“wanna go out on [literally any day of the week]?” “I can’t, I have dance class”) all the time.

  4. Ella Minnow Pea*

    Alison’s advice is spot-on. I’m sorry, OP, I’ve been in your shoes and it can suck. As they say, it’s lonely at the top.

    If Mary wasn’t thrilled by coming to your department, is it possible she has a negative outlook that has colored Jane’s own outlook? Just a thought for why Jane seemed friendly and now seems less so. Or maybe the friendship element was always more one-sided than you imagined.

  5. Cringing 24/7*

    Don’t. Consider. Employees. Friends. Ever.
    By taking the emotion out of the relationship, you free yourself to see things more clearly and almost guarantee that you’ll overreact less than you would otherwise.

      1. Snark*

        Me too. Because, managers… the overwhelming majority of cases, they don’t consider you their friend.

        1. Ask a Manager* Post author

          Yes! I see a lot of letter-writers say they consider an employee a friend, but I almost never see a letter-writer say they consider their manager a friend.

          1. TotesMaGoats*

            I think we need to differentiate between friend=will loan you money/keep you from drinking too much at the bar and friend=we spend a lot of time together at work and have similar background/interests and generally get along (i.e. if you are out sick, I’m appropriately concerned for your well being)

            I would call my manager a friend in the second sense. She’s asked every day how my back is doing (totally wrenched it moving a toy chest). She asked about my son and how he enjoyed christmas. We both love higher ed policy. I spend 40 hours a week with her or more.

            1. Alienor*

              I think it’s useful to make that distinction with other colleagues too. I’ve felt super-close to people at work before, and then when they left the company, the friendship either evaporated in a puff of smoke, or faded over a few months.

              I read an article a while ago that said the reason people make friends more easily in college than as adults is because friendship requires proximity and repeated spontaneous interactions, which are in plentiful supply when you live in a dorm, but not so much when you live in a house on a street of other houses. Having read it, I think the reason work friendships feel more real than they are is because work sort of artificially replicates that environment–if you’re sitting next to someone for hours every week and spontaneously going out to lunch or getting coffee, pretty soon you start to feel that sense of intimacy, but like college, it doesn’t last once someone “graduates” to another job.

            2. Snark*

              I think that second sense needs a different word, because that’s really not friendship, particularly when management and evaluation enter the picture.

          2. Chiming in*

            “I almost never see a letter-writer say they consider their manager a friend.”

            Not a letter writer, but I consider my manager — and also two former managers — a friend.

            There was an article a few years ago, I forget whether in the Harvard Business Review or the McKinsey Quarterly, that argued workplaces that encourage friendships outperform those that do not.

          3. i do!*

            We’re not out of work friends, but my manager and I are definitely above average as “work friends.” I tell her things about my family and life that I wouldn’t tell other colleagues, we have really amazing open communication, and we support each other in all of our endeavors. I like her as much as I like many of my friends, and we have a really great professional and personal relationship, without crossing any inappropriate boundaries.

          4. Elizabeth H.*

            I consider my manager a friend. I mean, not primarily – she’s primarily my manager, of course. But I feel very friendly toward her and I think she feels similarly toward me, we have a good rapport and I can’t imagine not being friends after we are no longer working together. (I think we have pretty good boundaries and are not over-share-y and keep things quite professional) Once in a great while there’s something she does (inadvertently!) that’s a little bit annoying and I might mention something like that to my boyfriend on occasion, but arguably LESS than I might mention small things about my (non work) close friends to my boyfriend in the same way! Even good friends annoy us once in a while.

            For what it’s worth though, I feel like people who write in explicitly stating that they consider their employee (or manager) a friend . . and so, [x problem ensues] are using it as an example of how the friend-considering-ness (or however they think of it) has led to whatever problem they are having, so I would imagine you mostly hear about situations in which the interpersonal dynamic is problematic.

          5. AKchic*

            I have a few former bosses as friends, but I’d also been there a long time, and they weren’t my direct managers (they were above my direct supervisor) and the culture was decidedly… not “normal”.

          6. Candi*

            I’ve noticed that when the employee considers the manager a friend, confidence in them at work and in their professionalism is where it starts, if they weren’t friends before. Team building, happy hours, and such can’t replace that foundation.

            LW, Alison has some stuff on appropriate team building in her archives. :)

          7. Alienor*

            I also have a former boss who’s one of my closest friends. That said, she’s the only one out of probably 20 bosses I’ve had over the course of my career whom I view that way, and when my current boss said a few months ago that they considered me a friend, my immediate thought was that I wished they wouldn’t. I do like them and we might really be friends under other circumstances, but I’ve been burned by those relationships before and don’t want to go there again.

    1. B*

      This! An employee is an employee, not a friend. Not only is it difficult for you to see negatives and positives of the employee but also for your emotions to be skewed. However, I would also like to point out that this has a negative effect on your perception in the office. If others see you are friends, or trying to be/consider them to be, with your employee your judgement will be questioned and other colleagues/Mary/etc. will not feel comfortable speaking with you.

    2. Tuxedo Cat*

      I think that’s a good rule. I’ve had managers who try to be managers and friends with me and others, and it wasn’t good at all. They didn’t seem to get that their abilities to determine my wages, whether I remained employed meant that there was a huge power discrepancy.

    3. bridget*

      It’s a good rule, but even so, I can see why the OP would be bothered. It’s never enjoyable to hear that someone you thought you had a positive relationship with (even if it’s just a positive boss/employee professional relationship) said something unkind about you. The OP can and will try to not take it personally and get over it, but it’s really unpleasant regardless of whether you consider the person friends or not.

    4. Bea*

      I was thrilled when I quit my last job because I was able to be friends with my team. They swear they had no problem with being friends during my time as their manager, we’re within a few years of each other but I wasn’t having any of it.

      I was able to manage my partner only because we had strict “this is business” mentality on the clock.

    5. As Close As Breakfast*

      This ‘rule’ is actually why I keep a distant sort of work friendship with my coworkers as well. If my goal was to move up to positions where I might manage other people, I figured it was a good idea to keep work relationships in the friendly-but-not-exactly-friends zone. Makes it easier to transition the relationship should you find yourself their boss one day.

      1. Cringing 24/7*

        Yes! This exactly! Same! Because then you don’t have to worry about backpedaling a friendship because you’re suddenly their boss.

    6. Pollygrammer*

      I’ve seen lateral coworkers who were friends when one was promoted over the other. They tried to maintain that friendship, and it created a really toxic environment for everyone. Imagine being at a weekly meeting where, week after week, boss only smiles/encourages one out of five of you. Incredibly discouraging.

  6. Myrin*

    “Maybe she isn’t, or maybe she’s sticking to her story that she truly meant to send her message to me”
    I am so intrigued by this being the excuse she thought of, of all things! Offence is the best defence, apparently.

    1. fposte*

      Yes, that was an intriguing detail that sort of got buried. Jane, I think you made the wrong call there.

    2. anomonom*

      Yes, that part really stood out. Our core group does that occasionally on our group emails but it’s the same five people (four of us plus our supervisor) and we are very obviously joking. We’re also generally “accusing” one person of a behavior by Big Boss that drives the whole group crazy, i.e., “I’d have had time for this if Gertrude didn’t Reply All on every single email”.

    3. Pollygrammer*

      “I was joking! There was no way it could have been construed as funny, but I was definitely joking!”

    4. OP*

      I was a little thrown by this as well! And it really boils down to me believing if Jane meant to type “you” instead of “she” which I also pointed out. A few minutes passed and she changed the subject ( this was over IM as well). I do feel she was trying to hide in plain sight so to speak and act normal so I’d believe her.

    5. Marthooh*

      Ah ha ha ha, pretending to insult you to your face, ha ha. Isn’t that a funny joke, old bean. Ha well I really must be going now, goodbye.

  7. Jady*

    In my opinion, OP is personalizing this too much. People vent. Everyone I’ve ever known had some random annoying thing about them. People let off steam and make jokes and complain. That’s even more likely to happen in a high-stress environment (as OP mentions).

    If that’s the worst people say, you’re doing quite well.

    Soliciting feedback on a regular basis is a good idea in general. Take it as a jolt to do that and let it go, imo.

    1. Tuxedo Cat*

      Even my friends and I vent about other friends. Little things like Suzy is always late by a lot (like an hour). We don’t regularly vent but we do. We still love Suzy, but sometimes, people are annoying.

    2. MCMonkeyBean*

      Yeah, I like my job and my manager but I still occasionally send my husband an email to say “ugggggh I can’t believe they are making me do this” just because I’m a little annoyed in that moment, and expressing the annoyance helps it go away. It doesn’t mean Jane doesn’t like you, and it sounds like the particular complaint you saw was pretty mild!

    3. Samata*

      Yes, the message could have been “Wakeen’s a f*@king moron.” Which is what the message read when I sent it to Wakeen instead of Wallace. Damn auto-populate.

  8. strawberries and raspberries*

    A while ago I had a former coworker send a nasty meme she made about me (a manager) to her direct manager, and I saw it when her manager and I were talking at his desk and it popped up on his Gchat. The worst thing is that she made the meme apparently while the three of us were talking and sent it to him right after, and he was also mortified. (It begs the question about what else the two of them were saying unbeknownst to me, but that’s a whole other thing.) She got written up by our director. She apologized to me and I was like, “I’m less insulted than just really surprised that you’re willing to risk getting written up by acting this childish with your manager.” In return she said I could make fun of her back and started listing all these other mean things other people have said about her that I could use, and I said, “No thank you, I graduated from 5th grade a long time ago.” She resigned a little while later. Jerk.

    1. Temperance*

      A woman was actually fired from my last company because she was caught snooping on someone’s computer. She was caught because she decided to snoop because she thought people were making fun of her. (They were.) There was an email chain between her colleague and their boss making fun of this woman’s hair and clothes, like they were in high school.

      The women were reprimanded, but she was fired for going on her colleague’s computer to print off the evidence and snoop.

      1. Esme Squalor*

        Yikes. I mean, that’s super shitty of her colleague and her boss to be mocking her (especially the boss), but breaking into someone else’s computer for the purpose of accessing information you don’t have permission to access–that’s very understandably a fireable offense. The boss and coworker seem incredibly mean and unprofessional, though. Especially when you consider that the fired woman had obviously picked up on their mockery, so they probably weren’t being very discreet about it.

      2. Hello...ello...ello..ello..llo..llo..lo*

        I kind of agree with the person being fired. While definitely crappy that people were making fun of her and she knew it, not an excuse for going into someone else’s computer

        1. Lissa*

          I just….wonder what she thought would happen? That she’d show evidence she printed off and this would somehow improve the situation after these people found out she went on their computers and read their messages? I mean, maybe she didn’t care at that point and was going scorched earth…

          1. nonymous*

            Well, I’ve been around coworkers who don’t have any qualms about gaslighting others, so it may have be worth it to clutch the printouts and affirming sanity?

      3. super anon*

        Sadly, I had this same situation go the other way–an employee snooped on another employee’s computer, printed off their venting chats with other employees, and then the snoop-ee was fired (I believe there was some blackmailing as well). While I don’t think it was necessarily a terrible move to fire that person (although it was a bit harsh), I can’t understand why you would want to continue to employ someone so vindictive.

        1. Candi*

          I’ve noticed that people who are that nasty tend to be falling down in other ways as well -usually more than enough for final warning/PIP territory. Hopefully they were slapped with such.

          I can definitely understand a company -reasonably- getting all kinds of twitchy at anything that looks like a security or information compromise, which is what breaking into someone’s computer for any reason looks like. Even looking for information when the user leaves it unlocked can get a serious reprimand. (Wallpaper changes and Ctrl-Alt-Arrow key pranks depend on the company.)

      4. Mezzo*

        Yikes. Something similar to this happened to me many years ago. When I was a young boss. I managed two underperformers, and I will admit that I was less than patient with both of them after a few months of coaching and training hadn’t made any impact. Our team initially included a third, very competent and positive employee who quit after about a year.

        One of the remaining two accidentally copied me on a months-long email chain about how horrible I was. Their comments about my inept management were mostly fair, but the bulk of their venom was directed at me personally (hair, clothes, body type, etc.). Worse yet, the emails showed that they had bullied the third employee out of the company because she didn’t agree with their assessments and didn’t participate in their venting.

        I had to go to my own manager with all of this, knowing that ultimately I was responsible for the mess. She moved the two gossipers to separate departments under experienced managers, and both of them ended up getting fired for poor performance in their new jobs. I ended up quitting, and didn’t manage people again until about 10 years later, after lots of training and soul-searching.

        1. Guesty McGuest*

          Wow. I wish I had a better response, but that would definitely sting, especially as a young boss.

          I can live with my direct reports venting about me a bit, but not making it personal. Or finding out too late that they bullied someone else out of the company.

          1. Mezzo*

            Yes, it was one of the defining events of my career. The two employees were bad, but I was the one who hired them (and also hired the third, competent employee). The whole experience taught me a lot about setting the tone for people who report to me, developing a thicker skin, and knowing when to be a hands-on manager versus a more laissez-faire manager. It also helped that I was 36 rather than 26 when I took on another managerial position–the experiences in those 10 years helped me learn to better juggle my own work with manager duties, which was one of my big problems as a young manager.

            The bullied employee and I kept in touch for a few years after she left; she went on to have success at her new job. I had no contact with the other two after they were moved to other departments. Their new managers complained to me about their poor work ethic, but I tried to stay neutral. I didn’t ever hear anything more about them after they were fired.

    2. Millennial Lawyer*

      Kudos to you for not getting down in the mud and keeping your head up.

      But “started listing all these other mean things other people have said about her that I could use” … I mean *whew* this person does not know how to be professional and has numerous other issues to deal with.

      1. strawberries and raspberries*

        She most definitely does. She experimented with making fun of me both to my face and behind my back during her short time with us. The former had me just owning the attempted insult (like if I knew some weird fact she’d say derisively, “How come you know that?” and I’d be like, “I was fortunate to have an excellent education and I’m just naturally intelligent and curious!”) and the latter obviously got her penalized. It was really clear that she was an absolutely miserable person.

  9. Orphan Brown*

    OP, I say this as someone who got fired for saying things about my supervisor in a work im. Some justified, some not so much and just blowing off steam. I really regret my actions and the biggest thing that stands out to me that Alison did not address is that those kinds of messages in work chats are super unprofessional. If she’s blowing off steam and a happy hour privately that’s one thing. Work computers can be monitored and therefore employees should conduct themselves professionally on them. So I think you do need to address that behavior with her.

  10. Snark*

    One thing I encourage you to do, OP, is to stop considering things like teambuilding exercises and going to bat for people as something for which they owe you a quid pro quo. A teambuilding exercize is an investment in a positive team environment; going to bat for high perfomers’ bonuses is something one does to make sure high performance is sufficiently recognized and rewarded. Neither one is an investment in personal loyalty to you, or in nonstop good vibes about you. Neither one creates a friendship relationship with your direct reports, and such a relationship would neither be appropriate nor welcome. You’re there to manage them, not be friends with them, and occasional resentment is part and parcel of managing and being managed.

      1. Zombeyonce*

        I love Snark’s really solid, wise advice and appreciate so much that even though it was blunt, OP took it gracefully. This stuff can be really hard to hear and I’m glad OP is open to improving their management style.

    1. PlainJane*

      I agree with this in general, but I do think that doing those things warrants respect and the benefit of the doubt. Yes, it’s part of good management, but good managers should be respected and appreciated. That said, there’s nothing to gain by treating it as quid pro quo, but it’s perfectly normal to be disappointed and hurt when an employee does something like this (and the employee is demonstrating both immaturity and poor judgment). It may not be a betrayal, but it’s pretty dang disrespectful.

      1. Snark*

        You’re not wrong. At all. And I think OP is rightly a little stung; it is disrespectful and immature. But OP can’t reach into their brains and flip that switch. They can change the mindset they have about what they do for their reports and how they do it, though, and adopt a view that’s a little less personal and….transactional is maybe the word.

    2. Bea*

      This is great advice. I used to do things for my team that nobody knew about and bought things on my own dime on the down low to avoid anyone feeling like they owed me for things I view as my job and such.

    3. Nep*

      Thank you for this advice. I suddenly understand why when one of the managers talks about how they’re not appreciated even though they’ve gone to bat for their people, I inwardly cringe.

    4. Triple Anon*

      Exactly. It’s like being a parent or older relative or teacher. You can bond and have good times, but there are power dynamics that define the nature of the relationship. You can’t get around that. You have to respect it and learn how to do well at that role.

  11. DCompliance*

    “I understand managers get talked about, but how do I move forward in a professional way, and not hold a grudge? They both do good work, so I don’t want my hurt feelings to impact how I review them, which is coming up.”

    Well first of all, Mary did nothing wrong so I don’t think you should have any grudge or hurt feelings towards her. As for Jane, you give her feedback where she needs feedback and praise where she deserves praise. That’s how you move forward in a professional way.

    1. OP*

      I understand Mary did nothing wrong but I also feel you don’t just randomly send work IMs to someone about your boss that you’ve never vented to, so to me… there seemed to be an established comfort level. I could be wrong as this is my assumption.

      1. DCompliance*

        But you don’t know how Mary responds to those vents. Maybe she response with “I didn’t find her annoying”. Also, I have received vents like the one Jane sent and didn’t share the same opinion. Maybe Mary responds in a professional manner. You can certainly give her the same reminder about electronic messaging as you did Jane, but I wouldn’t make assumptions.

      2. Ten*

        At my last job people vented to me all the time, not because I also disliked whoever they chose to complain about (I typically didn’t), but just because I would listen. A person being vented to does not mean they are also complaining.

      3. ContentWrangler*

        But even that theory only proves that Jane may have sent these messages to Mary before. If my coworker sends me a venting message, if I don’t agree with it or think it’s unprofessional, I’ll probably just give a “Mmm sorry bout that” response. You have no proof Mary has contributed or escalated these things. But also, as many people have pointed out, occasionally finding your boss or your job annoying is fairly normal. So unless this was a particularly nasty IM, I think it’s important to not overreact to this.

      4. Terbz*

        OP – I generally agree that Mary and Jane probably did have a history of venting/talking about you negatively on IM, however, I think it’s important to emphasize that you should not assume that. I am including a link to another, somewhat relevant letter. I’m not sending this because I think that you are the department joke, but so you can see an example of coworkers talking negatively about a manager to you without the history being there.

      5. super anon*

        Eh, I’ve had coworkers vent to me before. I’m actually really careful about what I’ll put in print, so it makes me uncomfortable and I would never say anything like that myself, but sometimes people will assume you’re more sympathetic than you really are.

      6. Pollygrammer*

        I think I’m in the majority, but I think OP can assume that if Jane felt Mary was receptive to that sort of thing, there are things that can probably be inferred. :(

      7. Safetykats*

        OP – I don’t know what kind of environment you work in, but I work in a mostly male industry, with a lot of craft and construction workers. I would be surprised if the worst anyone in responsible for has said about me is that I’m annoying. The thing is, you’ve got to do your job regardless of whether people like you for it or not. Some of the best advice I’ve been given about management is that there will be days where you have to choose between doing the thing that makes your people like you and the thing that makes them respect you. When that happens, you would be better off to choose the thing that makes them respect you, even though that can be hard to do. Because once they don’t respect you, they won’t like you either.

        It sounds like you have probably been trying too hard to make them like you, and now you’re hurt because it seems that not only do they lot like you, they are also disrespectful. I would caution you that venting is sometimes more of a bad habit than a deep-seated disrespect, and I’m not sure you know which this is. However, I’d also advise you that in the long run, you’ll have an easier time of it if you recognize that not everyone is going to like you – and it’s not part of your job to make everyone like you. The best way to move forward professionally is probably to file it away as a data point on the person who sent the IM, and ignore it except as it might appear to actually relate to their work. (Which it might, or might not.) This will be easier if you look elsewhere, maybe at your own peer level, for your work friends.

  12. a Gen X manager*

    I’m struggling with Alison’s advice to ask, “Is there something you want me to do differently?”

    I understand that OP is a woman, but what if OP was a man? Of the male bosses I’ve had, I can’t imagine any of them ever asking a staff member this question in any situation. I understand Alison’s point that “you’ll be communicating that you’re open to feedback and concerned about her perspective”, but this wording undermines OP by giving Jane the power. There has to be a better question for OP to ask that solicits open feedback, without kowtowing to Jane, right? maybe?

    1. Snark*

      Mmm. Interesting point. Not sure if I agree or disagree or what, but that’s an interesting take. But would your male bosses not ask that because they didn’t want to cede power, or because they tend to have that dudely ego thing going?

      1. Phoenix Programmer*

        Ironically most 75% of my female bosses have not. I have had 4 female and 4 male bosses.

      2. a Gen X manager*

        Phoenix, Was is phrased this way?

        I’m stuck on this, because even though the word “want” is used, it feels like it implies that the boss will do whatever the employee replies with and/or that if the boss can’t or won’t comply then the boss would owe an explanation to the employee. It feels like there is a better way to ask this, but still open and cooperative.

        1. Phoenix Programmer*

          Yeah it is usually phrsed “Is there anything I can be doing differently” or “do you have my items I can improve on”

          1. Guesty McGuest*

            I think I’ve heard it done in a more passive voice construction, such as “What things would you like to be done differently, if it were up to you?”. “Things” vs “me” and a huge caveat at the end.

    2. LKW*

      Just because a man hasn’t yet taken that approach, doesn’t mean they shouldn’t. And I’ve had a few bosses (male and female) who’ve said “You seem a little frustrated with the work/client/lack of daylight/Tuesdays lately, is there anything I can do to help?”

      I also don’t see it as kowtowing – I see it as recognizing that no one is perfect and the LW is giving Jane an opportunity to make positive changes. Demonstrating that the LW is open to working with people and not talking behind their backs. If Jane says “nothing is wrong, you can’t do anything better” then I would expect the LW to continue as is. If Jane continues to complain, then the LW can take the next appropriate action to put Jane on notice that her advancement, if not her job, is dependent on being collaborative and professional.

    3. S-Mart*

      Eh, my better male bosses have all asked me this, or something very close to it. The lousy ones never did and I can’t picture them doing so. The context is never ‘we’ll do it your way’, but rather ‘I’m open to learning there’s another/better way to get our goals accomplished’ (but if it doesn’t work for me for then we won’t go that route).

    4. Jesmlet*

      Just because you can’t imagine a male manager doing this doesn’t mean that they shouldn’t. All bosses should be willing to make adjustments based on valid feedback from their reports. Good bosses ask and incorporate where possible, regardless of gender. Asking also isn’t a promise to adhere to whatever they request so I don’t see it as kowtowing.

    5. Mediamaven*

      I felt the same – like she’s the one at fault when they were in appropriate. I would be more inclined to say, if you aren’t happy with a directive you are more than happy to raise concerns with me, but this behavior is not acceptable.

    6. Shiara*

      My male boss asks me this pretty routinely, sometimes in a one on one, sometimes to the whole team mid-meeting. Maybe not that exact phrasing, but very similar. It’s his job to manage us, so if there’s things he could do differently that would make our jobs easier/better he genuinely wants to know. There’s nothing about asking the question that implies that Jane’s wants will be instituted as law.

    7. Turquoisecow*

      I think if your “power” as a manager is threatened by something so simple as asking your subordinates how you can help them… you might be more obsessed with power than your actual job.

      I mean, I get that a manager should have authority. But you also should be helping the people under you to do their jobs, supporting them in their professional endeavors, and making their work lives easier so that your job is easier. If your report is struggling to do her job, you’ll struggle to do yours. Why not work together, and help each other, rather than go off on power trips?

    8. Sigrid*

      I’ve gotten this exact wording from male bosses more often than from female bosses, to be honest. Percentage-wise it’s probably equal, because I’ve had a lot more male bosses than female, but I’ve certainly not heard it less often from men. And this kind of wording is very common in my field.

  13. That Would Be a Good Band Name*

    Even my last manager, who I will tell everyone was the best manager ever, could get annoying at times. I definitely vented occassionally, even though I genuinely thought she was a lovely person and manager. I’m sure I annoyed her at times as well. It just happens when you spend so much time together.

    1. hermit crab*

      Also, I mean, I love my spouse, but sometimes I vent about him! Sometimes I vent about him **to** him (on purpose though, not like Jane). Annoying other people isn’t always a sign that there’s something wrong. It can just mean that you spend enough time with a person that you notice things about them that annoy you.

  14. AK*

    I think this situation could also present an opportunity to examine how you speak to your employees when giving them tasks. I often gripe about the way my boss sends requests to me, and it isn’t at all to do with the request itself, but rather how the request is made. For example, I got this request from my boss the other day: “I would also like to the summary ASAP given a phone call I had with [X] yesterday. Can you please draft something up today for me to look at? Thanks.” We had spoken the day before about the data in question and he didn’t even hint at a call he was having about it or that he might want to see a summary soon. Secondly, it was quite a busy week already – and he knew that – and his request didn’t acknowledge that this suddenly urgent task would take away from other stuff I also needed to get done. So again – it wasn’t the task itself, but how the request was framed.

    1. OP*

      Great point. The task itself wasn’t a big deal— I got the impression the annoyance was more over things I’ve done in the past and the way I asked might have been reminiscent of those.

  15. Mediamaven*

    Usually I think Alison is spot on with her feedback, but I think she’s going to easy on these women here. I don’t think the solution is for the manager to ask what she can do different – to me that makes it her own fault that the team is talking poorly about her behind her back. Of course everyone gossips about their managers, but the deal is you don’t get caught. if you do, it’s insubordination and inappropriate and needs to be approached that way and not in an apologetic tone.

    I had a poor performing employee who had a destructive relationship like this with another poor performer who eventually quit. The one who quit left all kinds of communication behind in which those two spoke nasty of every single employee and me. I fired her. That is such an unhealthy dynamic to create in the office. Once they were gone, our office was so much healthier and happier.

    1. Ask a Manager* Post author

      Oh no — the idea isn’t to make her fault. Depending on how this conversation goes, Jane could say “I’d like you to do X” differently and the OP could say, “X is an integral part of the way we operate because of Y, but I’m glad you raised this so I was able to better explain that context to you.” Or if X is really appalling, “It sounds like we have very different perspectives on how the team should operate. I want to be clear that X isn’t going to change, so would you like to take some time to reflect on whether you can happily work on this team knowing that?”

      Plus, part of the point of this conversation is to drive home to Jane that the OP isn’t going to weakly lie down and take Jane’s snotty text but is going to treat it as a work issue that needs to be discussed, which is going to be very awkward for Jane, as it should.

      This is the OP acting from strength, not weakness. Weakness would be just trying to shut down any dissent.

  16. Phoenix Programmer*

    Op. I love my current bosses! They d do great work and are good managers!

    I still vent about them on occasion.

  17. Marnix*

    Alison hit the nail on the head about being friends with one’s employees. I think A LOT of people are friends with their reports when they should actually be friendLY. So many people miss that distinction.

    1. Jennifer Thneed*

      Yes! Another distinction that people have lost is that between “friend” and “acquaintance”.

  18. thebird*

    A coworker once accidentally sent a text to our boss that called her a “c***”… the text was actually meant for me. My coworker immediately called our boss and tried to explain that she was talking about another person who has the same common name as boss, and boss graciously let it go. I know boss already doubted coworker’s professionalism and this really didn’t help things lol.

  19. OP*

    Thank you everyone for your comments! Really insightful and really great advice. I know I need to work on clarifying how I see my role with them and my own perspective.

  20. Friday Night*

    I had a manager that I loved, was on friendly terms with and more, I considered her a mentor and my biggest advocate. She supported my career development, helped me develop management skills, and figure out how to keep multiple large projects on track simultaneously.

    And she could get on my last nerve. I’m not going to list how or why – but there were times that she seemed clueless about things and frustrating, and uncommunicative about important things. Theoretically I knew that these things were because she was seeing a different picture than me – had different assumptions and was read in on different meetings and the fact that we had (only) slightly different technical skill sets meant that when we estimated project duration we often argued because things that she thought took ‘no time’ sometimes legitimately consumed my day and things that I ‘knew’ were 20 minute jobs were often given wide windows.

    I did vent – orally over wine. For me it was never in text or e-mail, but only because I had my e-mails ‘freedom of information act’ed once as a student and am gun shy – not everyone thinks like that. I never once ended those vent sessions thinking that I was anything but lucky to be working where I was.

    We’re still on great terms. I hope you can follow Allison’s advice, because while she messed up in sending it to you, everyone needs to vent a little sometimes, both at work and not at work, even about people we really care about.

    1. Jen in Oregon*

      Oh wow. Would love to know how that lawsuit turns/turned out. My guess is it was or will be settled….

    2. Borne*

      It is curious that the employer tried to claim that she was fired for performance. Even though she had recently received a $12 000 bonus.

      How many companies give such great bonuses to poorly performing employees?

      1. Guesty McGuest*

        Some companies give bonuses on a mathematical formula, and not just individual performance. I’ve seen some that include a factor based on stock price or revenue, customer surveys, and then a small percent personal performance. So even someone having a bad year might get a bonus. Depending on their salary, $12K could be a little or a lot.

  21. SheLooksFamiliar*

    My SOP about being a manager is that my team will have opinions about me, even fleeting ones, I’d rather not see or hear or see. Managers make unpopular decisions and requests. Even when they’re nice about it, someone on the team will get torqued about it.

    So my SOP about venting is pretty simple. When you need to vent, either pour out your heart on paper, hide it for a day, then rip it to shreds, or vent with someone outside of your workspace. Complaining at work rarely builds meaningful camaraderie. Usually, it just spawns more negativity and no one needs that. Not even the complainer.

    1. nonymous*

      I find it also helps when in that circling mode to find something completely different that demands my focus. Like run hard enough to have to count breathing, or [try to] train the dog on a new trick, or cross-stitch or whatever hobby or something like that. I used to be really bad at being able to distract myself and it took working at it when I was less agitated (e.g. during yoga or other meditation moments) to be able to deliberately clear my thoughts. Now I’ve gotten to the point where I can recognize the circling, which is a huge step forward for me.

  22. Eye of Sauron*

    See the username there ^ this is what my last team of employees called me :)

    No I didn’t micromanage, but our office was not conducive to private conversations. I’d overhear a lot of conversations from my office. Normally it was background noise, but I would on occasion passively or actively listen in on problem solving sessions, every once in awhile I would shout out a suggestion if they were heading down a disastrous path.

    Here’s my thoughts on being a boss and having a boss:
    Approximately 3.2 seconds after the first boss was invented, the first employee complained about said boss. It doesn’t matter how good, bad, or indifferent they are bosses will always be a target for their employees complaints.

    As others have said you are their boss and not their friend. They don’t owe you anything but professionalism and work output (in whatever reasonable form that takes). I’m not going to say that you shouldn’t ever spend your personal funds on the team, I do, but doing so does not obligate the employees to anything, including gratitude, friendship.

    1. Snark*

      “Approximately 3.2 seconds after the first boss was invented, the first employee complained about said boss.”

      And now I’m imagining an overseer being delivered a cuneiform tablet that was intended for one of their direct reports.

    2. That's an awesome name*

      I think I would actually be impressed if I was called ‘Eye of Sauron’ by my team. It’s too cool a name to be taken as an insult :)

  23. Down By The Bay*

    I totally did this once! My boss was frustrating me so much that I texted a mini-vent to a friend. But I didn’t realize I’d accidentally texted it to my boss instead, who was the last person I’d texted.

    I was completely mortified and immediately hurried to my boss to apologize. She’d already seen it and while she wasn’t thrilled, she wasn’t as mad as I’d feared. Though I think what helped with that was that I hadn’t texted anything too mean, just was frustrated with a certain situation. I really lucked out because I had sent a lot worse texts about her to my friends; this one was mild by comparison.

    My boss never seemed to hold it against me, and I worked hard to make sure I was always the excellent team player I strived to be, even with the misplaced text.

  24. Bea*

    Every boss I’ve had with exception of Voldemort, I’ll fight for and am grateful for on multiple levels. I talk to them and care deeply for their families etc. However I’ve been pissy and annoyed multiple times for sure.

    Think about it, have you ever said “argh mom, you’re obnoxious bleh.” or gotten pissed at how a sibling did something you don’t agree with? I fight with my mom even as an adult, we’re the worst. But we’re still the best of friends and anything said that’s less than nice is simply blowing off steam. They can adore you but when frustrated they grumble.

    1. Chapeau*

      “Every boss I’ve had with exception of Voldemort, I’ll fight for and am grateful for on multiple levels.”

      Lucius Malfoy, is that you?


  25. L*

    I want to share a story about when I did something very similar to my boss, from the employee side. She was/is actually my favorite boss, but I lashed out at her over email over a stupid thing. I felt at the time she had gone back on a promise, it was a minor issue in the grand scheme. Best of all, I accidentally replied all so not only did she see it, but our shared manager and CEO did as well. She replied “….did you know you replied all here?”

    It was awful, it was easily the worst screw-up I ever made at work. I thought I had torched my relationship with her (she has been very good to me, I was just very mad in that moment) not to mention our big bosses. I (no kidding) considered jumping in the ocean, or at least never going back to that job. I quickly sent another reply all immediately apologizing. I later learned that she covered for me with the shared manager and CEO (she’s basically a saint and I am so, so dumb). Then the next day we were both at work I went to her office in person to… grovel, basically. I’m sure she was hurt by what I did, but she only focused on how we could move past this. That actually made me feel MORE contrite and grateful for her at the same time for not totally kicking my ass as I deserved. If she had gotten mad, I probably would have got defense re: broken promise and dug in. Looking back, her handling was kinda genius. I totally prostrated myself and vowed to be perfect to her forever, as she deserves. I still work for her today, we’re on our THIRD company together.

    So my advice to OP is to try a similar approach that my boss did. Your employee, if they have any sense of the gravity of their mistake, will be so grateful and contrite that she’ll feel a new level of loyalty and need to atone.

  26. alana*

    All the good advice is covered so I’ll just say I full-body cringed for Jane. Backdoor venting via written communication isn’t the most professional thing, but if you’re in a workplace where a lot of people are remote, Slack or Skype or Campfire really are the water cooler. I’ve come close to sending a “ugh, can you believe this” DM to the person I was “ugh, can you believe this”-ing about multiple times. It’s usually a good wake-up call to not write anything I wouldn’t want the person I was writing about to see.

    That said, the level of mild complaint you’re talking about probably wouldn’t even hit that bar for me. Most managers I work with are fully aware that sometimes we’re annoying and/or ridiculous to the people we’re directing.

  27. As Close As Breakfast*

    “Today I caught Jane sending an IM to Mary making fun of me, complaining about an instruction I’d given her, and had a tone of “OMG, she’s annoying.” ”

    One of my concerns is, well, tone is just SO HARD to interpret in things like IM messages. The OP obviously knows Jane, and knows the context and nuances of this whole situation, so I tend to believe that the tone probably was “OMG, she’s annoying.” But is there any chance, any chance at all, that the tone wasn’t as harsh as the IM read? That is at least a possible explanation for Jane’s seemingly cavalier attitude when questioned about it?

      1. As Close As Breakfast*

        Thanks Alison! Some things definitely don’t need ‘tone’ inferred to be understood as negative, and I feel for the OP that this was one of those instances. This just makes it even harder for me to understand Jane’s reaction to being called out on it!

    1. Elizabeth H.*

      I was going to suggest that if there is no other sign that Jane is frustrated or has criticisms of OP’s work, it’s possible that she didn’t really feel annoyed and was trying to make conversation/sympathize with or relate to Mary if Mary was experiencing frustration about something else or Mary is the type to be annoyed with her boss. Some people find it really easy to relate via complaining (I don’t think this is great strategy, just that people do do it). However if as Alison indicated it was a genuinely harsh statement, seems there isn’t need to give benefit of the doubt.

  28. True Story*

    Okay, truth time. I have been Jane-like before, but in the context of a friendship not a work relationship.

    In college, I lived with two of my best friends (lets call them Penelope and Evelyn). To make rent, we also needed a fourth roommate and Penelope suggested one of her sorority sisters (Madge).

    When Madge moved in she was HORRIBLE. The worst sort of snooty, entitled sorority girl who used people as pawns to feed her mean girl agenda – honestly, it was like a TV trope come to life. The thing about it was that she could be really nice and act like the kind of friend you had always dreamed about, until she turned around and drug your name through the mud to the next person she saw.

    Evelyn is my best friend. She will be my maid of honor later this year, which will inform this next bit.


    One day, Madge began to do her mean girl routine of badmouthing Evelyn the minute she left the house, and in a moment of weakness I vented with her. The really horrible thing about it – and the reason why I still feel ashamed about it today – is that I got that delicious little boost you feel when the mean girl brings you into her inner circle and you forget that she’s going to do the same thing to you later.

    Evelyn came back into the apartment during the B-fest with Madge and overheard us. I never knew she was there until later. She was so upset and justifiably confused as to why I would have been venting to Madge instead of bringing up my problems with her directly.

    She confronted me about it later after she had some time to calm down, which achieved a few very important things:
    1. She had the chance to check in with me and address the problems we were having.
    2. I had to reflect on why I acted that why – and resolve to be better in the future.
    3. It gave me an opportunity to explain what happened (and that this was not an ongoing thing).
    4. I was able tell her how sorry I was about the whole incident, and we were able to move past it.

    There are moments like these that can be a blip in an otherwise wonderful relationship, or a moment that changes the dynamic forever. I think it’s how you address them that matters. Evelyn was so mature and level headed about the whole thing which made it so much easier to own up to the hurtful thing I had done and apologize.

    It’s hard to say what is going on here, but is it possible that Jane got caught up in some of the toxicity emanating from Mary? Do you get the sense that there might be something more going on with Jane, or does this seem like a very out-of-character action? Your gut feeling about your relationship with Jane will have to inform your conversation here, but it might be worthwhile to approach this as a very OOC situation. You might get a more direct response from Jane about what happened if she isn’t so embarrassed about having been a jerk.

    (I know it helped me when Evelyn came at the conversation saying “I’m confused about what happened here. Can we talk about it?”)

    1. True Story*

      Of course, big caveat here: work relationships are fundamentally different from friend relationships.

      It’s possible Jane is the problem employee and you’re just now finding out. Or that there’s some other issues with your management/general workflow. Or that it’s just coworkers letting off steam.

      I still think that approaching it with a bit of sensitivity to the fact that Jane should be mortified may get you more traction here.

  29. Green Goose*

    OP, would it be possible to share what the IM said? It can be hard to read tone over messages, and depending on how well they know each other, and how many inside jokes they may have it might be impossible to decipher what they are saying and who they are saying it about.

    With past coworkers I’ve been really close with we almost had an unintentional secret code language we spoke in because we had so many inside jokes and if someone overheard us talking they could easily misinterpret what we were saying/meaning.

    1. Not Your Babysitter*

      Alison posted above that the OP shared the messages with her but doesn’t want them published. She confirmed that in her opinion the tone was indeed harsh.

  30. 2nd shift*

    You can be friendly with the people you manage but they can’t be your friends. Sooner or later most will throw you under the bus to try and get what they want.

  31. tamarack and fireweed*

    An excellent answer as usual, but I have a slightly different perspective on the “you can’t be friends with people you manage” aspect (which, admittedly, is a very minor point here). A good number of years ago, at my first tech job in a software company, I pretty much became instant friends with a team mate. We found out we came from the same town in Germany, had attended the same school (a few years apart), and were in some ways similar in outlook and misfit status (along the lines of LGBT+). Six months later, I was promoted to team lead, which meant I had day-to-day management responsibility, though was not solely in charge of performance evaluations and other line management duties, at least initially. At the time, the general manager of our office (the European office of a much larger US company) called me into his office and said “You’re going to have to manage a friend. This is possible,” and then proceeded to tell me some somewhat contrived but well-meant anecdote (about a manager who had to fire his son for performance issues or something), but more importantly gave me a few clear instructions: That I’d have to occasionally take up the phone (most of my team was in various remote locations) and say,”B, this is your boss calling – I need you to do X/talk about Z/change the way you approach Y”. And indeed, B and I took this seriously and were committed to make both professional and personal relationship work. There were some rocky moments, and I’m sure there was no guarantee that something at the job *might* have led to irreparable damage to the friendship, or vice versa (!). But there were also advantages, like when B sat me down and told me that the team really disliked how I handled a (purely formal) aspect of our weekly team meetings — something B might only have felt comfortable to do because of our personal relationship. In any event, we went on for nearly 5 years, after which first I then B were laid off in some restructuring efforts. We’re still personal friends.

    This is not to claim that it’s generally possible to be friends with someone you manage, but just that depending on the situation at work and the personalities and maturity of the people involved, it is not necessarily impossible.

    1. oldbiddy*

      I’m glad your boss did that when you got promoted. I worked at a startup company where a lot of people the same age/training started around the same time. After a few years, one of us got promoted. He was BFF’s with a couple other people in the group and they socialized constantly both at work and outside work. Everyone in the group was a nice person but it created a very toxic atmosphere for the rest of the group.

      1. tamarack and fireweed*

        This was the best boss I’ve had to date – the first really good manager I’ve encountered. He taught me a lot, and we stayed in friendly contact for a while.

  32. Diamond*

    I ADORED my last boss! He was an absolutely brilliant manager and one of the best people I know. And even so I would occasionally vent to my husband about some irritating task he’d given me or not how I wasn’t given specific enough instructions for my liking. It wasn’t actually personal to him at all, it’s just the nature of work. People won’t always love 100% of their work, and when there is something they don’t like or feel unsure about doing it kind of comes naturally to blame the person who assigns the work. But reasonable people know that bosses do have to assign annoying tasks and they don’t actually think worse of you for it.

  33. Nacho*

    Don’t take it personally OP, it’s an employee’s prerogative to complain about his or her boss, no matter how nice that boss is. I love my boss to death, but I still complain about her with my coworkers behind her back. Partially about things like how sensitive she is to complaints.

    It’s not that we dislike her, but no boss is perfect, and group complaining can be a powerful team-building activity.

    1. Triple Anon*

      Yeah. I think it’s actually indicative of a healthy team. Well, as long as it’s not excessive. I worked at one place where people did not complain about the boss. There was an, “Everyone must love Boss. Boss is great,” mentality and I found it to be really dysfunctional. You have to give people the space and freedom to say what they want to say.

  34. Lisa*

    Love my boss, really. I don’t *really* vent about my boss, but if I do, it’s to my mom, whom I talk to every night. Yep she and only she knows about my side of office gossip. I seriously do not gossip/vent at work. I learned the hard way at an internship.

  35. Nervous Accountant*

    something similar happened to me when I was brand new, the person IMed me saying “I think NA is a bitch and doesn’t help me”…. I was still new, not in a “helping” position and I had considered that person a work friend. I wish I had handled it better. I wonder what I would do now if that happened again.

    1. Nervous Accountant*

      When I say not in a helping position, I mean I was pretty new, she had more work experience, and my role wasn’t that to assist anyone—its a collaborative environment where we all help each other w what we can but I wasn’t a senior or anything like that.

    2. Triple Anon*

      I had something like that happen too. I overheard someone venting about me in an open floor plan office. I said something. In hindsight, I think I could have handled it better. But my gut feeling at the time was, “This person should know that other people can hear her. And it’s best for me to be honest about having heard her instead of pretending I didn’t.” I think that was a good instinct, but I should have been calmer and friendlier about it considering that I was very slightly more senior. It can be hard to adjust to being more senior after you’ve gotten used to being a lower ranking person.

  36. This Daydreamer*

    I work at a job that I truly love. It’s important and fulfilling and I still get plenty of down time. Everything I do there matters. And my bosses rock.

    And there are still tasks and situations that make me roll my eyes. And there’s nothing wrong with that. Every has things that annoy them at work. I’m sure my bosses have rolled their eyes at me, too. I’m okay with that.

    Just for the record, I’m pretty sure you will never again catch Jane complaining behind your back. Just think how embarrassed she is after getting caught being so unprofessional by a boss she probably really likes – unless you give her another annoying assignment. ;)

  37. Triple Anon*

    I really like Alison’s response to this letter. And I think it relates to more than just employer – employee relationships. It’s about power dynamics in general and how to handle criticism from people with less power than you. You have to learn how to take it in stride. You have to learn when to ignore it and when to say something. Because there is a line that people can cross. You shouldn’t put up with abuse, but you do have to take a normal amount of venting and criticism. And, really, you have a greater responsibility to say no to anything abusive because people look up to you and see you as an example of how to handle things. But what is out of line and what is normal criticism? It can be hard to define. But if you want people to take you seriously in any kind of leadership role, you have to learn how to handle all of these situations gracefully, focusing on the big picture and not getting your feelings hurt.

    If this were my employee, I’d do what Allison suggested. I’d also make a joke about the IM and then say something brief about remembering to be careful with digital communications because what if it had been a client, etc. I think you have to say something in a situation like that, but the idea is to make it about digital discretion, not censoring the employees’ speech. Because they do have a right to vent about you.

  38. Pachanga*

    Ok, what if this scenario were reversed and an employer accidentally sent out a negative message about an employee to that employee? Nothing really work related just nasty, and disparaging comments? What if that employer were the chief of HR for a large urban area school district? Is this a $10M mistake?

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