my boss’s constant self-deprecation and oversharing make me uncomfortable

by Alison Green on April 1, 2025

A reader writes:

I want your help in understanding what, if anything, I can/should do about the way my boss talks about herself. I like my boss, but it’s exhausting!

My organization recently went through huge layoffs, so everyone feels overworked and off-balance. As part of that I got a new boss. I get the feeling she’s nervous about doing a good job, and wants us all to like her. I do like her! But during 1-1s and team meetings, she tends to monologue — and it’s all overly personal, self-deprecating, or sad. Too-intimate details about her personal health, negative comments about her body, “funny” stories about being mistreated as a child, general self-deprecation (“stupid” “failure”). The tone is always light, but these stories are sometimes all strung together, and I find it emotionally tiring!

I’ve struggled with self-esteem in the past (I’m doing much better today) but hearing someone constantly self-deprecate themselves, especially someone who has power over me, brings me back to … less fun times. Every meeting where she does this, it takes a lot out of me. It’s as if she thinks these things are normal, or a way of putting herself lower down so that we’ll like her more — but the more it drains me, the more I’m starting to brace myself to be around her.

Approaching her directly: I think she would be horrified to know this affects me, but sometimes people react unexpectedly to things like this and get weird/cold — if she doesn’t have the emotional awareness that this is not good, could this rebound on me in some way? She might stop if I asked her, but I think she would feel really bad … and can I even ask her to stop, if it’s only me having a problem with it? What if she feels uncomfortable around me forever? Or if it affects her treatment of me? What if she tries and fails, and then is apologizing to me on top of the self-deprecation?

Talking to my skip-level is another option. But would it make my boss feel even more paranoid that an unknown “someone” doesn’t like her, as if I were leaving a negative note on her chair? My skip-level is in all these meetings and doesn’t try to correct it — he’s a bit oblivious to social cues, I think. I know my skip-level well and he’s a supportive boss who advocates for his staff and would take this seriously — both for my sake and for my boss’s — but he also has a tendency to interrupt people and publicly correct them in meetings in ways that he really shouldn’t. “You shouldn’t have made this mistake…” “We talked about you not doing that, why did you do it?” What if he starts correcting her about this in front of all of us? Horror…

But I do not dream of labor, much less emotional labor on top of labor! Should I start with her privately, then continue to my skip-level if that doesn’t work? Talking to HR is the nuclear option, so I would want to leave it for last. I think I’m overthinking all this, and possibly thinking about my boss as too fragile, but this situation is definitely bringing up old feelings / maladaptive instincts from my distant past that served me once but no longer do.

Oh, this sounds really uncomfortable. And when I imagine what it might be stemming from in your boss — ugh, it’s just bad all around.

I’m curious about whether you might get some traction by changing the responses you’re giving in the moment when it’s happening. For example, when she tells a “funny” story about being mistreated as a child, what if you said, “That’s really sad, I’m so sorry that happened”? When she calls herself “stupid” or a “failure,” could you say, “It makes me feel terrible to hear you say that”? if she makes a negative comment about her body, what if you said, “I don’t think any of us should talk about bodies that way”? Basically, let your natural reaction show. Look stricken! Respond accordingly. It might make her realize that these stories and comments aren’t landing the way she wants them to.

I’m also curious about whether your coworkers are picking up on the same things, and whether there might be room for the group of you to collaborate on how to respond when it happens.  Depending on the dynamics you have with her, you could even say, as a group, “Hey, we don’t like the way you talk about yourself, please don’t do that.”

If that doesn’t work, I do think the next step is to talk to your skip-level, especially since it sounds like you have a good rapport with him. Yes, that might mean that he corrects her publicly … but that might be what it takes to get this to stop. It would be better if he had the skill to handle it privately (and maybe it’ll turn out that he does) but I’m more concerned that your boss hears that she needs to stop doing this, even if it’s not delivered with perfect delicacy from above.

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{ 168 comments }

{ 168 comments… read them below }

  1. WellRed*

    I mean, she also shouldn’t be monloguing, especially about herself. It would be nice if skip level at least tried to keep meetings on track even without commenting on the language. I’m exhausted just reading this.

    1. ecnaseener*

      Yeah, the monologuing piece might be the place to focus. It’d probably take the edge off for LW if it was limited to brief self-deprecating comments rather than long self-deprecating monologues, and it’s also probably the easiest for the skip-level to handle. If he starts calling her out in front of people, at least it’ll be “You’ve been talking too long, wrap it up” and not “Stop bringing the mood down with your personal problems!”

    2. OP*

      OP here – my skip-level *also* monologues.

      Meetings with both of them tend to be… long.

      1. Arts Akimbo*

        OMG you and all their other employees must be exhausted! I really hope you get some relief from this.

      2. BeenThere*

        Ah, this might be how your manager became a manager under your skip, by copying the same behaviors.

        Not saying it’s right, however this might be harder to change if your skip does it as well because now “it’s part of the culture”

    3. Six Feldspar*

      Ever since I watched The Incredibles I’ve been watching out for monologuing…

      Lucius: “So now I’m in deep trouble. I mean, one more jolt of this death ray and I’m an epitaph. Somehow, I manage to find cover and what does Baron Von Ruthless do?
      Bob (laughing): “He starts monologuing.”
      Lucius: “He starts monologuing! He starts, like, this prepared speech about how *feeble* I am compared to him, how *inevitable* my defeat is, how *the world* *will soon* *be his*, yadda yadda yadda.”
      Bob: “Yammering.”
      Lucius: “Yammering! I mean, the guy has me on a platter and he won’t shut up!”

      1. Reluctant Mezzo*

        In Final Fantasy XIV, there’s a spot where a villain Just Will Not Stop Whining. Every player wants to win that section just to get past him.

        1. Six Feldspar*

          Oof, that’s rough… A proper villain monologue should at least be entertaining!

        2. DJ Abbott*

          I do reception, and yesterday took a call from someone who was so whiny, I was fed up in less than two minutes. I was so glad I could transfer him to a counselor.

          1. MigraineMonth*

            I used to work at a hobby toy store that the owner had mostly forgotten about when she got a different job; we never saw her, she never answered her phone, she never responded to voicemail or sticky notes. Unfortunately, the owner had promised to special order a doll for a customer before disappearing.

            So every few days for the entire summer I worked there, the customer called and we had at least a 15 minute conversation where she explained that she was frustrated, that she had been waiting a long time for her doll, that it was a special order for her granddaughter, that this was an expensive long-distance phone call, she didn’t want her money refunded she wanted the doll, and also she was frustrated.

            I replied that I was sorry but I didn’t think the order had been placed, I couldn’t place it, was she really sure she didn’t want a refund? No? In that case, given that this was a long-distance call, maybe she’d like to hang up? Still no? So I just kept making apologetic noises while she monologued.

  2. Athenae*

    Could it be easier just to say “if we could bring this back around to the TPS reports, I really think” and work forward from there?

    1. Not Tom, Just Petty*

      I feel that boss would save it for later. After the meeting, “I’m sorry I got off track with my story before, it was just so funny, I remember…”
      The “bean dip technique” is going to kick the problem down the road. I think this is a situation where responding might be a more effective to shut it down.

      1. OP*

        Yes, exactly – I think she’d bring it up later and apologize again – and maybe even start apologizing in front of people after she does this? I’m trying to avoid a shame spiral / apology fractal, which I think is pretty likely…

        1. Not Tom, Just Petty*

          Yes! I get the feeling she has a process. If you interrupt, she has to start over and it ends up worse, because, as you say, she feels bad about not finishing her own story.

        2. allathian*

          I’ve heard of shame spirals before, but apology fractal’s a new one. Curiously apt, too.

          I once had the misfortune to have a constant apologist as a cubicle mate. It was exhausting. First she’d apologize for something anodyne, then she’d apologize for apologizing, and a little while later she’d apologize for apologizing for apologizing, and on and on…

          Apologies in my culture aren’t necessarily an admission of guilt, they’re just as often used for commiseration, but I was on my last nerve until she transferred to another team and switched to another part of the office.

          Being around her was exhausting, especially as my natural poker face is crap and I have to expend a lot of mental energy to maintain a professional demeanor at the office. I’ve only realized how exhausting that is thanks to being able to WFH most of the time. I only need to maintain a professional demeanor when I’m on camera, and even there our requirements are a lot less strict than in many other places. For example, nobody’s policing if we’re looking at the camera and we are allowed/expected to show some emotion when discussing things at work we care about, as long as we don’t intentionally insult other people. Obviously accidentally insulting someone isn’t great either, but some people go through life looking to take offence at anything and everything, and we aren’t expected to bend over backwards to appease those.

          With that spiraling coworker it was particularly exhausting to maintain a cool and professional demeanor because if she got even a hint that her apologies were getting on other people’s nerves, she’d double down on them.

    2. MsM*

      Yeah, that would also be my suggestion. Maybe going in with an agenda and some reason you need to keep the meeting focused would also help.

      I also kind of want to push back on HR as the nuclear option. If there’s any kind of employee assistance program, you could frame your conversation with them as being concerned and thinking it might be good to make her aware of those options, rather than “I need someone to order her not to do this.”

      1. Grizzled*

        Employee assistance is a great idea! It’ll get her to realize that these are pretty serious personal problems that should be directed elsewhere.

        1. Volunteer Enforcer*

          Maybe try saying “Let’s get back to the (positive or neutral topic) (you or colleague name) was talking about.” Or, something positive that links to the moaning your boss does? Boss: “my family don’t treat me very well.” OP: “Oh I love going to see my family for my birthday.”

          2. darn*

            I think the neutral WORK topic makes sense. I don’t like responding to someone’s unprocessed childhood trauma with a comment about how great OP’s family is. It’s just not kind and also seems really unlikely to be helpful. We need to be talking about work.

      2. OP*

        OP here – I like the “agenda” idea, but the time when she does this the most is in informal settings, like a team-building meeting, where I can’t say “Let’s get back to __” (because the end of that sentence would be “hanging out casually”)

        1. SistaSista*

          For the body comments, you could try saying “I know you are just talking about your own body, but hearing you speak so negatively about yours is making me self conscious about mine. I know you would never want to body shame someone else, do you think you could extend the same compassion to yourself?”

    3. Teapot Translator*

      I think the redirection is worth trying if the compassionate statements don’t work? In social situations, compassion only gets you so far if the other person just keeps on being negative. What makes this tricky is that this a boss/employee situation so you can’t use some of the phrases you might use with a friend.
      LW, maybe thinking back at past interactions with your boss, you could try to see if there are ways to quickly redirect to work subjects?

      1. Grumpy Elder Millennial*

        Or a combo of this suggestion and Alison’s suggestion. Let your natural reaction show, let it sit for a second, then get back to business.

    4. Sloanicota*

      I think OP might need to pick her battles. Getting a boss to change how they choose to conduct their meetings is a tough one, particularly since her own boss is in these meetings and apparently doesn’t see a problem. I think focusing on the 1-on-1s is the way to go, and then try to let these team meetings roll off your back a bit more.

      1. juliebulie*

        In a one-on-one, you can say “I wish you wouldn’t talk that way about yourself, it makes me uncomfortable.” Or maybe some word other than uncomfortable, but I think that would be the most accurate word for me.

        1. OP*

          My fear about that is that she wouldn’t even know what I was talking about, if I asked her not to!

          So I’d have to enumerate –
          “when you say bad things about your body”
          “when you call yourself stupid”
          “when you tell traumatic stories”

          – the thought of which makes me writhe pre-emptively.

          1. T.N.H*

            It’s harder with your boss, no question. But asking someone not to trauma dump on you is eminently reasonable. Also, if she’s talking about herself badly, she might be accidentally talking about others as well. As in, saying she hates her hair cause it’s brown implies something to everyone else with brown hair. (obvs, I made up this example and have brown hair).

  3. AnonymousOctopus*

    When I was in undergrad, I and others in the cohort would often talk badly about ourselves or our skills. One of our professors started responding with “Hey, quit being mean to my friend” (said with a kind and compassionate tone) whenever one of us would speak negatively about ourselves. It really helped to break the habit and to realize what we were doing in the moment. We even started saying it amongst ourselves outside of classes and over time it stopped a lot of the uncomfortable self-deprecation stuff in the group.

    Obviously that wording probably isn’t the best for a professional setting where you aren’t responsible for the other person’s education/development, but I’m wondering if there’s another way to express the same sentiment.

    2. Nerf*

      If I say something down about myself, my husband says “Are you being nice to you?” It’s very sweet.

    3. Bike Walk Bake Books*

      “Hey, quit being mean to my boss” works and could be used with a friendly tone if LW feels as if they can carry that off.

      2. ReallyBadPerson*

        Came here to suggest this very thing. “Please don’t criticize my boss.” A friend used to use that “stop talking trash about my friend” line whenever I’d say something negative about myself, and it was very effective.

      4. amoeba*

        I like that one! Basically, treat it less as a correction or whatever, more as in “hey, I don’t like to hear you talk so badly about yourself”. I’d say it comes across much friendlier and hopefully might do the job!

    4. Ann O'Nemity*

      I really like this. So gentle, so inarguable. I’m not sure “friend” would play as well with a manager, but I like the general idea.

      1. JSPA*

        “Boss, if some random person were saying these things, I’d be so on their case– ‘Stop talking crap about my cool new boss, it just makes you look bad.’ But I don’t know what to say when you’re the one talking yourself down. Please just let us be happy you’re here, happy that you are you, and focus on the pleasure of getting stuff done, now that you’re here!”

    5. Slow Gin Lizz*

      I actually was thinking of something along these lines myself. Instead of AAM’s suggestion of “it makes me feel terrible to hear you say that,” maybe say “I wish you wouldn’t insult someone who I think very highly of” or something like that.

      This is so tough because I know from experience that it’s really hard to boost the confidence of someone who has very low self esteem. In grad school, one of the most talented and hard-working people I knew was always so self-deprecating and I had no idea how to help her feel better about herself. I didn’t know about “don’t insult my friend!” at the time, but I do wonder if that would have helped her at all.

      1. Calyx*

        I like these responses. As someone who struggled myself in the past, I would have hoped that someone would be kind like this first before taking it to my boss or HR. Though of course, if the boss can’t take in the soft feedback and continues being disruptive, that’s a reasonable course of action.

      2. Jay (no, the other one)*

        It helped me. I didn’t even notice how often I put myself down until a friend started saying “hey, don’t talk about my bestie like that.” She said it with a loving smile. It took a while for it to really start to sink in, and it made a big difference.

        It’s more challenging in a work setting. I have done something like that with people junior to me – never to someone higher up. Seems worth trying if OP can figure out a wording that feels right to her.

      3. Hannah Lee*

        There are 2 threads to it –

        1) LW genuinely wishes that boss wouldn’t be so self-deprecating, down on themselves.
        2) LW needs boss to stop centering herself, and talking down about herself at LW, when LW is just trying to get through her work day.

        In this case, while #1 is a nice to have, from a human being wanting the best for another human being point of view, what LW really NEEDS is #2.

        So anything LW can do that can cause Boss to realize what she’s doing, pump the brakes, think for a second and NOT launch into negative self-talk when interacting with LW is a good thing, even if it does nothing to change Boss’s self-esteem issues or internal monologue.

        Whether it’s LW trying to stick to a meeting agenda, or letting her normal reactions show, or giving a work appropriate “hey, don’t trash talk my boss” comment, if it makes Boss aware of the habit and reduces the frequency of this kind of talk, that’s a win for LW.

        1. OP / LW*

          OP here (or do people say LW here?), yes — thanks for splitting this out, this is exactly it.

          And I think my overthinking fear-brain is adding:
          3) LW needs to accomplish 2) without getting dragged into her boss’s shame spiral permanently, which would be even more stressful – and would make me feel guilty about making 1) worse

          1. Spooz*

            Shame isn’t always a negative emotion. Like all emotions, it is information that one can use to decide on actions. Shame tells us that the “tribe” disapproves of our actions. We can use it to take a clear look at our actions and decide to act differently.

            Your job is not to ensure your boss never feels ashamed of anything. Your job is to make her aware of what her actual actions are so that she can choose to do something different.

            If she does go into an endless shame spiral, you didn’t CAUSE the shame spiral just by doing something which made her feel initially ashamed.

            Don’t overextend your circle of control here.

            1. Sam I Am*

              Agreed and I also think that part of being successful at 2 would include setting boundaries with the boss so that even in she does shame spiral, LW continues to kindly but firmly hold the line and doesn’t follow her down.

          2. allathian*

            To respond to your brackets, we use both here. I tend to use LW when referring to someone who’s had their question answered by Alison. I use OP on the Friday and weekend open threads to refer to whoever posted the first post on the main thread I’m replying to. YMMV, of course.

      4. Laser99*

        The issue I have with someone “being self-deprecating” is when it is performative, in the sense that you are expected to reassure endlessly. “My hair is so gross!” “No it isn’t, you have beautiful hair!” “When I was 10, my mom told me I was worthless.” “What a mean thing to say! That’s not true!” Etc., etc.

        1. Spooz*

          Yeah, at school we used to call this fishing, as in fishing for compliments. Just like Regina and the gang do on Mean Girls: “my hairline is so weird!”

          It is beyond tiresome, and the reassurance doesn’t even work because the Fisher needs ever more in order to maintain a baseline level of functionality. Then they start arguing back, “Oh, you’re just saying that!” And it feels mean to say, “Yeah, actually, I don’t care about your hairline at all, I am just saying it.” But that’s what you end up thinking!

          It’s a really poisonous dynamic in which NO ONE wins.

          1. Slow Gin Lizz*

            I agree with both of you. And also, if the self-deprecation is real, saying things like, “No, your hair looks great” doesn’t really help them either, it just gets them to double down on how terrible they really do think their hair looks. (Or in my case above with the grad school friend, no matter how often I told her she really was a fabulous musician, she really didn’t believe me.)

    6. iglwif*

      I have a couple of friends who do this when I get too negative about myself (which is a lifelong habit I’ve been working on for a while — pinpointing the source, it turns out, is way less than half the battle) and it’s incredibly cheesy but also soooooo helpful!

      Because they’re right, I would never talk about one of my friends the way I sometimes talk about myself.

    7. AnnieMouse*

      I was going to suggest this too. Said lightly/warmly and with a smile, with a topic change ready so the conversation doesn’t devolve into arguing the merits of the self-deprecation. I’ve also had some success with “Ok, that’s your quota of ‘sorry’ for the day”.

    8. ChrissyRose*

      Yes! This is what my wife and I use. I used to be really self-deprecating, and I’ve pretty much stopped entirely. A few months ago I was really overwhelmed with a new job, making a lot of mistakes, and feeling horrible about myself. If I ever said something like “oh, of course it was that easy, I’m just stupid”, my wife would say “hey, be nice to my wife!”

    9. TeaCoziesRUs*

      Yup! I do this with my kids – “Hey! Don’t be harsh to my kid, I love her.” It’s also worked REALLY well on a friend. Help them stick up for themselves when the most negative part has a megaphone. :)

  4. UKAAM*

    Do you have quarterly or annual development meetings? These are often a good venue for feedback, especially if she’s just finished giving you feedback, since it feels equal and not out of the blue. You could frame it positively, like, “You’re such a great boss in X and Y ways, but it makes me feel so bad to hear you self-deprecate yourself! I hope you know we all love you and it makes me worry you don’t” (or something to that effect). It might make her dial it back or realise she’s doing it.

    1. Not Tom, Just Petty*

      I like this. It’s retraining her, yes. But it’s kind. Ultimately doing her good. You will force her to practice NOT saying something negative. She may never be “I’m good enough; I’m smart enough” but she will say fewer negative things to her staff and may even stop feeling the need to.

      1. Slow Gin Lizz*

        Along the same lines as how a little venting to blow off steam is okay but constant venting actually makes you feel worse, it seems like a little self-deprecation can be fine (especially if it’s meant to lighten the mood or be humorous) but constant self-deprecation is really draining and also makes everyone around you feel terrible. Asking her or training her to limit her self-deprecation might actually help her feel better about herself. Maybe not, but if she is able to do so, it’ll at least make her team meetings less exhausting.

    2. Miette*

      This is a very good suggestion, and I hope there’s an opportunity. Because this person isn’t just triggering OP, she may be undermining herself and, by extension, the entire team by acting this way.

    3. Neutral feedback*

      I wouldn’t do this. This kind of “loving” feedback puts OP in some kind of therapist position and might encourage the boss to seek validation with OP.

      1. amoeba*

        Eh, I mean, I wouldn’t go with the “love”, but I think something like “it’s really hard to hear somebody talk so badly about themselves! I value your work and I really wish you’d stop putting yourself down” could work quite well without sending her spiraling even more.

    4. Marion Ravenwood*

      On a related note to this: does your office do any kind of 360 feedback or anything like that (where you give feedback to your boss) as part of formal appraisal processes? It could be worth including this as part of that maybe if so. Something about seeing it written down could help put it into perspective for her – especially if it comes from multiple people. If it’s anonymous that might help too maybe (less easy to dismiss somehow).

      1. OP / LW*

        OP / LW here – do you think it would make my boss paranoid, though, to receive anonymous negative feedback? In that “oh no, everyone is judging me” way?

        I remember some letter about a person getting a note on their chair about something very personal (maybe body odor?) and feeling horrible because they didn’t even know who said it.

        1. Hlao-roo*

          There was the “a coworker left me an anonymous note … and a pacifier” letter from April 3, 2018.

          There was also the “I’m upset about my anonymous peer feedback results” from February 10, 2020, which shows that anonymous feedback can be presented very badly, and also discusses how it can be done well. From that answer:

          [A manager’s] job is to understand the feedback, seek out more information if it’s not clear or it might be biased or missing important context, weigh it based on what she knows of the sources and the context, and decide what’s important to present to you. She needs to do that work in order to be able to own the feedback she’s presenting (and to work with you on anything that needs work).

          Is your skip-level someone who will do the above? Or is he someone who will handle passing along the feedback poorly, like the manager from that letter?

          I’ll link to both letters in a follow-up comment.

        2. Marion Ravenwood*

          Maybe? I guess you know her better than I do in terms of how she might respond to that. I was thinking of it that anonymous feedback might be easier for her to take as a positive, because she doesn’t know who it’s from and therefore it’s less easy to dismiss you saying something like “X is a really good manager but downplays her abilities and talks negatively about herself when she doesn’t need to do so” with a response like “oh but I’m your manager so you *have* to say nice things about me!”.

          1. amoeba*

            Yeah, I feel phrasing it like that could work even in an anonymous/360 review kind of thing. At least for me, that would reach much too positive in total (while still bringing the message across) to send me into self-doubts!
            I would *not* go with “Boss is bringing the whole office down with her constant negative self-talk, it’s hard to take, please stop” or something along those lines.

    5. Yankees fans are awesome!*

      “I hope you know we all love you…”
      ——

      Mmm, “admire,” respect,” etc. But “love”? Ick.

      1. metadata minion*

        Yeah, to a certain degree that’s going to depend on company culture, language use, etc. (I would totally say “I love you so much right now!” to a coworker if they fixed the printer the next time it does something weird, and it would be understood as a hyperbolic expression of appreciation), but when you’re comparing your feelings for your boss to your boss’s own self-esteem, it gets boundary-crossing really fast.

      2. OP / LW*

        OP / LW here – yeah, part of the issue also is that she just started being my boss a few months ago! So I *like her okay*, but am only really just getting to know her.

        I’m cautious of saying something that would sound like a friend/therapist, both because it’d be disingenuous, and because it would be too personal if I don’t know her that well.

        1. Sam I Am*

          You could say something like, LW: “I respect you and I like working with you. It would really help me if we could cut down on the negative self-talk!” Framing it as a favor to you might make it feel less like a criticism of her.

          1. Sam I Am*

            Or “I respect your experience/knowledge/handling of customers,” etc. Saying you like working with her might be a white lie but it greases the wheels for change.

  5. Juicebox Hero*

    I wonder if she’s always been like this, or if this just started after the layoffs and being put in charge of LW’s team. If the former, then it’s her personality and it’s going to be impossible to get her to change her ways. If it’s something new, I’d bet on a combination of imposter syndrome (espeically if she’s a new manager) and a hamfisted attempt to be “one of the gang” (especially if the team’s old boss was a victim of the layoffs).

    1. Observer*

      If the former, then it’s her personality and it’s going to be impossible to get her to change her ways.

      Not necessarily the case. Yes, it might be a reflection of her personality. But *behaviors* can change. And that is all the LW cares about. How the boss actually feels about herself doesn’t matter to the LW.

      1. OP / LW*

        “How the boss actually feels about herself doesn’t matter to the LW” —

        Agreed, because from my perspective *it’s not my business* – I want to keep professional boundaries – but I also don’t want to make her feel *worse* about herself if possible.

        1. Spooz*

          “if possible” – what if it’s not possible? I mean this in a nice way, but you should realise that there might not be any options in which “boss stops dragging me back into my darkest childhood memories” and “boss’s mood remains the same or better” can coexist.

          To be clear, I absolutely think you should say something! Don’t set yourself on fire to keep someone else warm. But you may need to let go of trying to manage your boss’s feelings. She can go home and cry on her husband’s shoulder or complain all evening over cocktails after work with her friend or whatever. Other people have the job of “help boss with feelings”. Your job is “assist boss to be a pleasant person to work with at work”.

          You matter. You deserve not to have to deal with all this! Your boss is paid more than you in part because she has these responsibilities to be “the boss” and not let it all hang out.

  6. Smithy*

    Under the heading of gentle approaches – but certainly not one that will call out the issue directly is that when there’s a lot of self-deprecating talk is to reply with a phrase like “hey, don’t talk about my friend(supervisor) that way”.

    It’s certainly most effective when it’s done in a more light-hearted tone, but can provide another tool to call out to gently call out the practice.

    1. MicroManagered*

      I use the variation “hey now, I wouldn’t let someone ELSE talk about you that way!”

  7. XX*

    When I was like this as a teenager I didn’t even notice. Finally my music teacher stopped me in the middle of my lesson and said (paraphrasing), “Have you noticed that you say sorry basically compulsively? You don’t need to apologize for getting something wrong. You’re here to learn.”

    That comment completely changed me. She didn’t even tell me to stop (which tbh would have made me even more mortified), she just made me aware of something I didn’t even realize I was doing. Once I stopped using “sorry” as almost a filler word I got sooooooo much more confident.

    1. Not Tom, Just Petty*

      This. I see OP using Alison’s simple, “oh, I don’t think so. I know the team likes you.” or “that’s not stupid. A lot of people needed extra training on X.” And then move on. It’s not a pep talk or therapy. OP treats it like a reasonable thing for manager to say and replies with a reasonable answer, I think boss will learn to soften the hyperbolic negative statements about herself.

      1. Green T*

        I think, depending upon the LW’s judgement of the boss’s character, also treating comments as serious work discussion points can give the boss perspective on how this is landing and help redirect the meeting towards work actions. “It sounds like you’re not satisfied with your experience in x, is there something actionable you’d like me to do, or do you want me/the team to seek additional training to support you in x?” In my experience, treating a comment with a throwaway consolation can set up a cycle of reassurance/emotional labor that the LW might not be up for in a work context.

      2. Sloanicota*

        See, I would really like this to work, and I think it’s worth a try, but in my experience people like this have a *really* hard time with compliments. So the most likely outcomes in my mind are: 1. The boss argues about why that’s not true, meaning OP is even more engaged than they want to be, or 2. The boss learned that their anxiety can be soothed by getting a little reassurance/compliments and keeps doing this to keep getting that pat on the head. That said, it’s totally worth trying a few times! People are different.

        1. HR Exec Popping In*

          Or if they are uncomfortable with compliments they will stop doing this as they will learn it will result in LW raying something nice.

      3. OP / LW*

        Well, she never stops for breath – so I won’t be able to say anything in the moment unless I interrupt her. Also, she laughs at herself while she does this, like we’re sharing a great joke, not like she’s expressing visible discomfort…

        1. Spooz*

          I think the laughter will make the “take it seriously” angle land even more forcefully in a good way. It will emphasise that she’s actually NOT sharing a great joke with her pals if YOU express YOUR obvious and natural discomfort.

          “Wow, that’s really sad.” Is there anything more likely to kill a “joke” than people not laughing along?

    2. Slow Gin Lizz*

      Wow, I love this. I wish my music teachers had said that to me – I was never so self-deprecating as I was when I was a music student and a new graduate trying to make it as a musician. Words really do matter.

    3. Jay (no, the other one)*

      I have been saying this to my piano teacher! I’ve returned to piano lessons in retirement. My teacher is absolutely delightful and also 40 years younger than I am. She apologies almost every time she corrects me. I started with “no need to apologize!” and moved on to “you do realize I am paying you to correct me” and now I just kind of roll my eyes at her. She clearly doesn’t realize she’s doing it.

  8. Atalanta0jess*

    “and can I even ask her to stop, if it’s only me having a problem with it?”

    Yes. You can. You having a problem with it is a good enough reason to say it. Because you are important and worthy of care.

    1. Hlao-roo*

      This is an excellent point!

      (I was coming here to comment that it’s highly likely the letter-writer is not the only person who has a problem with it, but reading your comment I realize that point is moot.)

      1. Observer*

        Actually, I don’t think it’s a moot point.

        I think that *both* points are valid. The LW is worthy of not having to deal with this kind of additional labor all on their own. But *als0* I’d be willing to bet that the LW is by far not the only one being bothered by this.

        And I think the latter is important for two reasons. Firstly, the practical issue – If others are also bothered there is more chance of pushing back as a group. Secondly, sometimes it’s easier to push back when you know that you’re not the only one with an issue.

        I remember many years ago I was dealing with a kid doing something rather destructive that *also* was not safe. When I pushed back I got some pushback about not being kind enough (it was a complicated situation for the parent of the child). It was *much* easier to point to the fact that the kid was also doing something dangerous. Sure, it was perfectly legitimate for me to push back on my things being possibly broken. But if there is an easier way to push back, why not choose it?

        Given how much the LW is over-thinking this, I think it’s really important for them to hear BOTH things. Yes, you are worthy to ask for yourself! And Yes, I’d bet that any non-oblivious team member dealing with this is also not comfortable with this whether they are willing to speak up or not!

    2. Phlox*

      And that might be a compelling way to request the new boss adapt – I thrive best when folks aren’t hard on themselves, could you support me in that? Thinking of how much some folks can be motivated by what it means for others and the responsibilities you assume as a boss to support your staff – it makes the ask about you in a way that aligns with why it’s important to you and bonus benefit, might be as easier way for your boss to accept

  9. Sloanicota*

    I’m trying to picture how this conversation one-on-one could go and be really positive (because I agree, that’s where OP needs to start) – but *without* drawing OP into the role of therapist, which in my experience someone who is Like This will do. I think it’d be easiest in a one-on-one conversation, where she starts this song-and-dance and you’re the only audience. “Oh man, it’s really hard to hear you talk about yourself that way,” or “I know that’s intended to be funny, but to be honest it bums me out to hear you say that!” The tone would be so important here … collegial, relatively light, but earnest. Yet not rewarding the comment or the anxiety behind it. I don’t know if you can get her to cut it out in meetings, and that’s probably not your purview anyway, but you could probably achieve the goal of getting her to not do this At You while still having a good relationship with your boss.

    1. Fnordpress*

      Yeah, a lot of the advice in this thread would significantly worsen the problem because it teaches LW’s boss that the comments/stories result in emotional comfort from others.

      1. Tango*

        And it also assumes OP/LW’s boss is a safe person to give feedback to! I have a self-deprecating monologuing boss who isn’t. Through trial and error, I learned that my work life is MUCH easier when I just play along until the meeting is over, with the help of a healthy dose of psychological distance from work and my real life.

  10. Clearance Issues*

    …I once genuinely asked a manager doing this (dark humor about traumatic events, self-deprecating beyond humility) if she’d heard about the company’s EAP offerings, because it sounded like she was struggling, and I was worried about her.
    It did not land well, she doubled down that it was just “jokes” and clearly I wasn’t getting it. I was iced out and I ended up moving to a new team by my request. New team is great.
    Last I heard she still does this to the team, but no one else has pointed out that what she’s talking about isn’t funny. I genuinely hope she gets help.

    1. KitKat*

      I think this is exactly what OP is worried about and it’s worth naming that it is a real possibility.

      Personally I would take a light tough and make it about ME rather than about HER. And 1:1, not with the skip level in the room. “Hey, I know obviously you’re just joking around [or, sharing relatable stories, or whatever] but I am just really sensitive to these types of stories because of some stuff in my own life, would you mind if we keep a little closer to work topics for a while?”

      1. OP / LW*

        This is a great “serious” script I can use during our 1-1, and I am adding it to my toolbox. Thank you.

        The trick with this will be to not have her get concerned and start crossing boundaries (in good faith) to find out more about the “stuff in my own life” so that she can support me better… and I’ll need to make sure she doesn’t treat me differently. Hmm…

        1. Sam I Am*

          You can cut out the “because” and it’s still effective. “I’m sensitive to these types of stories; it’s just how I’m wired,” or leave off any explanation. Like some people won’t watch a movie where a dog dies, it’s not necessarily because they had a traumatic incident, it’s just upsetting and they don’t want to see it. That’s reason enough.

        2. AnonymousOctopus*

          You could try something like “That’s the past, so I like to leave it in the past. But for me to work most effectively, I’m letting you know that it’s a blocker for me.” It keeps it work-focused and sidesteps the whole thing.

          I had a boss once ask for more so they could “handle those topics carefully”; I just said that if something was an issue they could trust me to bring it up, and I thanked them for hearing me out about the current situation.

  11. Green T*

    This happened to me and I was completely mortified but it changed the way I talk about myself and my past! I am (objectively) terrible at a particular skill (llama grooming) and I mentioned that in the past when I was starting out I’d been ridiculed by a llama-grooming expert for making such terrible-looking llamas with my grooming (it has always been framed in my mind as a funny story, partly because I come from a family background where humor is used to allow you to make fun of someone without any repercussions) and the person I was talking to looked at me with shock and said wow, I’m sorry, that was really horrible and out of line for them to say, I wonder how many people they’ve discouraged from entering their field by being such a jerk. I felt so embarrassed in the moment but also really grateful that they said something! It has made me really turn a keen eye to the canned stories I have that I use in social situations, which I often turn to when I’m uncomfortable or nervous. To be clear, LW, it’s not your job to do this for your boss! But in my case, having someone “let their natural reaction show” was definitely a growth moment for me and I feel I’ve become a better casual coworker and acquaintance because of it!

    1. Sloanicota*

      Great example! It’s funny, I started noticing that a *lot* of my canned little stories had a weird edge to them and wondered what quirk of human nature was causing that. Humans are just such awkward turtles, I swear.

      1. Green T*

        And the adaptations that we develop to survive in one environment can be so out of place in others! I always think of decorator crabs: if you decorate yourself with shells to fit in and then get moved you’ve gotta take a look at your surroundings.

        1. OP / LW*

          Just popping in here to say, I love the decorator crab reference <3

          they are among my favorite marine invertebrates (of which there are many)

          1. NothingIsLittle*

            Might I suggest crinoids for your consideration? Feather stars swim as though they’re biblically accurate angels and it’s completely mesmerizing.

            1. Freya*

              We saw a feather star on a school trip to Kangaroo Island (South Australia) in the early to mid 90s and it was SO COOL!!!

    2. Lexi Vipond*

      Honestly, I think that depends on whether you were laughing too – when you first start out at anything you’re going to produce a lot of things which are terrible and some things which are funny, and that is absolutely fine. (It would have been much weirder if the expert had told you everything was lovely and you were doing such a amazing job, as if you were 3 years old and couldn’t be expected to tell good from bad in your own work.)

      If someone had said that to me I wouldn’t have been grateful, I would have been furious that they thought they could tell me how I was allowed to feel about my own abilities.

      1. allathian*

        Nobody can tell you how you’re allowed to feel about your own abilities. But too much self-deprecation can really land wrong with other people. It’s not a fun little quirk, it’s an embarrassing annoyance that often requires emotional labor from your coworkers, as this letter shows, and as a coworker, you basically have zero right to expect anyone to do *any* emotional labor on your behalf. That’s what friends and family are for.

        Joking at work is also a risk because you can never trust that people are laughing because they think your joke’s funny rather than because it’s politically expedient to laugh, and the higher up in the org chart you are, the more this is true.

  12. Delta Delta*

    So – I know I can’t change other people but I can change me. I once worked with someone who frequently did things like this boss, and I knew I probably couldn’t change her. So, one Monday I declared my desk a “no complaint zone” and said that I was working hard on changing my own outlook on things. If someone wanted to complain that week, they’d have to do it with someone else. If someone complained, I’d say something like, “hey, remember – no complaint zone!” and keep it very light. They’d correct themselves or they’d go find someone else. Then, if this works, keep it up for another week with the explanation that you really enjoyed having a positive outlook, and you aren’t entertaining more complaints/negative talk.

    Manipulative? Maybe. Did it work for me? Also maybe.

    1. Silver Robin*

      Not manipulative, it is a boundary and you enforced it without singling the person out. Glad it worked for you!

    2. OP / LW*

      I can see that working well with a coworker, but the power dynamic in this situation gives me pause about adopting that kind of brisk boundary… especially if it’s more difficult to describe than complaining. I’d basically have to say “No traumatic childhood stories, self-deprecation, medical complaints, comments about your body, or anything unrelated to work while we are conversing, please!” — otherwise, like a hydra, one topic of conversation might get cut off but the others would pop up.

  13. LinesInTheSand*

    Hey OP, I think you’re probably taking on much more responsibility for the outcome of this situation than you really should. You can’t control how your boss reacts, you can’t control how your skip level boss chooses to address this. It sounds like you really want things to be emotionally “ok” and in this situation you have neither the standing nor the authority nor the responsibility to make sure that happens.

    I think you can try to stop it in the moment and say something like, “I’m sorry, I’m really not comfortable hearing about this.” Or, you could use humor: “That asshole used to live in my head too. I kicked him out.” Or, if you think you can nail it: “Do you think those thoughts about all your directs as well? I’m worried I’m not living up to your expectations, which seem like they’re probably really high.” Sometimes people need to be reminded that they shouldn’t treat themselves worse than they would allow themselves to be treated by other people.

    And if that doesn’t work, go to your skip level and let the chips fall where they may.

    1. Sloanicota*

      It’s definitely possible to be overly-empathetic … you’re currently uncomfortable *right now* which is more important than the potential discomfort you imagine and are assigning to someone else. Plus, is it possible you’re not giving this boss enough credit to receive feedback gracefully? I tend to do this thing where I assume I know what’s going on for someone else and should manage it independently on their behalf and it’s … not great.

      1. Slow Gin Lizz*

        Both of these are excellent points. OP, you are not a therapist (I realize I’m assuming here) and even if you were, you are not your boss’ therapist. You can’t control how your boss thinks about herself nor how she’ll react to you asking her to be less self-deprecating, but if you think more about what you want the outcome of any discussion with her to be, that might help you figure out better what to do here. Ultimately what you want is for meetings to be more concise and to-the-point. Do you have standing to ask her to do this? Might you be able to talk to her about how your schedule is so jam-packed and meetings are taking up a lot of time and it sure would be great if they could stick to an agenda and be shorter?

        This isn’t solving the problem of her self-deprecation, of course, but ultimately that’s not yours to solve.

        1. OP / LW*

          Hmm, asking her to be more to-the-point is a good possibility. I’ll put it in my toolbox for later.

          Maybe something I didn’t adequately express in my letter is not just that I’m *concerned about her reaction*, I’m *stressed in advance about her reaction*.

          Right now, I do get triggered into bad memories / body tension by her acting this way, but I know my internal stress level would be way worse if she kept shame-spiraling in front of me with no way to stop. So, it’s not just for her benefit that I hesitate – it’s for mine, because what if I kick the hornet’s nest and this problem gets so much worse – and my skip level doesn’t understand – and HR doesn’t help? (Overthinking again…)

          1. Spooz*

            You can avoid the shame spiral with no stopping!

            “I’m sorry, it looks like you need a minute to compose yourself. I’ll be at my desk when you’re ready.”

            GET UP. WALK AWAY, EVEN IF SHE IS STILL TALKING.

            You can do this! And please, please send in an update. You seem like a really thoughtful person for whom this is taking on an outsize role in your head. I look forward to reading, “I was so worried about X, but it never happened!” in your update!

          2. Slow Gin Lizz*

            I know what you mean, OP. I have a hard time having difficult conversations, and especially initiating them myself, and part of the difficulty is wondering whether I’m going to ruin the relationship if the person is offended and disagrees with me. Maybe thinking of it more as a work problem that you need her help solving instead of basically asking her to fix herself would be helpful for you? I guess my recommendation would be to approach it in a very detached and professional manner and if she does take it personally, ask your skip-level or HR for help in dealing with her. If neither of them help you either, then that’s a sign that you work for a lousy company and if you can you should try to move on to work elsewhere. (I absolutely know that this is way easier said than done, but at least knowing the company is lousy might help you realize that if it goes south it’s not your fault that that happened.)

            And in answer to the question you asked elsewhere, we do tend to use both OP and LW interchangeably here, but I realize I use OP a lot more because it’s slightly quicker to type. :-)

  14. Grizzled*

    I almost always agree with Alison’s advice, but in this case I don’t! Responses like “That’s really sad, I’m so sorry that happened” or even “I don’t think any of us should talk about bodies that way” probably won’t stop her emotional dumping on you, it might actual encourage her more! I’ve come across quite a few people that like to trauma dump on me (I dunno, maybe I have a face that just invites people to verbal diarrhea all over me?), and when it gets really bad I stay completely silent, or just respond with “huh”, then continually redirect the conversation to something neutral. In a work situation it’s a lot easier because you can redirect the conversation to work. Just interrupt them and change the subject. They probably won’t notice the interruption, or they might even be relieved because I think some people have trouble turning off the trauma-hose and are grateful when their captive audience does it for them.

    1. CM*

      I think the fact that the boss is laughing while saying terrible things about herself says a lot. It doesn’t sound like she’s looking for emotional support. Laughing along can reinforce this behavior — ha ha, let’s all joke about how terrible I am! But showing genuine sympathy shows that you’re not accepting it as lighthearted conversation, and I think it might stop the boss in her tracks.

      I vividly remember a doctor’s appointment for a really embarrassing problem where I kept making awkward jokes about my pain and humiliation. The doctor did not laugh or even smile. She just said, “I understand. It’s difficult.” I appreciated that so much. Until she said that, I didn’t realize how much I was trying to play off my own discomfort by making unfunny jokes.

    2. OP / LW*

      “when it gets really bad I stay completely silent, or just respond with “huh”, then continually redirect the conversation to something neutral”

      Nod nod, that’s what I’ve been doing so far. As for interrupting her, though, she’s always trying to perceive minute signals from us (of displeasure or approval I think) and I think there’s a good chance that a brisk redirect would plunge us straight into Weird Vibes Land.

      1. Green T*

        I remember listening to someone once talk about how whenever they were faced with the situation where they’d become a de facto therapist or listening to someone’s inappropriately personal stories put on a puzzled face and ask “what do you mean?” until the other person stopped and asked them what THEY meant by that and they said “I’m trying to figure out what you’d like me to do/ I’m not sure how this relates to my work on x/ I’m not sure how you’d like me to respond.” That might work for you if she’s trying to pick up facial expressions.

        I had a boss like this who would share really personal information and sometimes I would just preempt it by saying “I’m sure you don’t intend to imply that everyone who makes x mistake are idiots” or “I’m sure you’re not hoping to give the impression that everyone who wears/eats/does x is y” and my boss would always reply oh no no of course not and then move on. She was always FAR more receptive to the idea that other people would assume she was talking badly about them.

        1. Bird names*

          I do like the approach in your second paragraph. Great way to side-step a long-winded discussion and get back on topic.

      2. Grizzled*

        She sounds insufferable. Maybe Weird Vibes Land is somehow a better place than where things are at now? She is the one creating the awkward situation – not you! So you can return that back to her, rather than feeling awkward yourself. I suppose it is difficult given that she’s your manager and there’s power coming into play.

      3. Tango*

        Ugh I’m so sorry for you. My boss is like this too, and I can tell when she notices she’s overshared because it goes into Weird Vibes Zone and then she’s weird with me and subtly punitive. My work life became a lot easier when I gave up, worked on some psychological distance from her and work in general, and decided to play along. I accepted that I didn’t like her, that what she was doing is unfair, and that people pleasing her is one of my job tasks.

  15. A person*

    My boss overshares with me like that too… and I’ve done the genuine responses and that seems like it’s had the opposite effect. He shares more now. It’s very awkward.

    1. Green T*

      Oh no! Can you re-direct him towards work and get something you want in the process? Like “I’m sorry to hear your x is experiencing y, so should I take over z responsibility (preferably something you’d like to do) for you while you handle that and delegate (current responsibility you don’t enjoy) m responsibility to Josepbeth?”

      At the very least he might start to wonder if it’s making him seem incompetent…

      1. A person*

        Yeah. I’ve been trying to experiment with ways to redirect with minimal tears.

        I do experience the oversharing from a lot of people… not just him. Apparently I’m a very disarming person and people just tell me stuff… Haha! Normally I don’t mind but it is more awkward when it’s your manager.

    2. RagingADHD*

      Time to move on to the more transparently genuine response of “please stop telling me so much personal information. It puts me in a very uncomfortable position.”

      1. OP / LW*

        Thank you for this script – it sets a firm boundary, doesn’t disclose too much about my mental health, doesn’t set me up as friend/therapist, and is short / to the point.

        Adding this to my toolbox of potential replies!

    3. Sloanicota*

      Yikes :( Maybe it’s time to try Grizzled’s suggestion, above. I don’t actually think there’s One Way to deal with people like this, so you have to try a couple different tweaks and see if any of them get the impact you want.

  16. Just a Pile of Oranges*

    At some point in time, people decided that the best way to show modesty, a valued trait, was to actively put themselves down. And that habit once formed is super hard to break. First of all, you have to recognize that it’s a bad habit, which many people won’t. They cling to the idea that they are simply being modest. Then you combine that with what mistreatment and/or abuse does to a person, and you’ve created the perfect recipe for people like your boss.

    I’m kind of extrapolating here, obviously, but LW even if your boss recognizes that this is a problem, it’s not one that’ll likely be solved quickly. So I’d encourage you to find some strategies for personal self care.

    1. OP / LW*

      “At some point in time, people decided that the best way to show modesty, a valued trait, was to actively put themselves down.”

      How did you know what I was like as a teenager?? (I’m being playful but this is so true, of me and others)

      Yes, I’m definitely not trying to fix her – I just need to set the boundary *enough* that the behavior will change, without setting off the room-full-of-lasers, aka neverending shame spiral from an authority figure.

      1. Lizzie (with the deaf cat)*

        The church used to be highly influential in valuing modesty. Especially for women, surprise surprise. I am old enough to remember being called ‘clever’ as a child, when that was an unpleasant insult which implied that one was showing off, thought they were better than other people, and was therefore unlikeable.
        Basically, LW, you are just one person amongst hundreds in your boss’s life and personal history- you can only change your own responses, and keep up your own barriers so she doesn’t drain the life out of you. I have sometimes imagined myself as a wet dog having a good shake after spending time with people like this- it has helped!

        1. NothingIsLittle*

          I am in no way joking or exaggerating when I say my first parent teacher conference in kindergarten was that I was highly inquisitive, self-motivated, and independent… and that this was a bad thing. The teacher literally told my mother, “those are great traits, but not in a kindergartener.”

          There’s a lot of cultural baggage around humility, intellect, and competency, and somehow women always end up with the short end of the stick in my experience…

  17. Generic Name*

    Oh, man I really feel you. My boss does stuff like this. In her case, it’s more angry venting/ranting. So inappropriate and awkward. I only call her if I’m in a headspace where I feel like I can deal with that. It’s better because she’s in a different office from me, so it’s easier to disconnect from her emotion. But I shouldn’t have to basically manage my boss’ emotions.

  18. thiswasme*

    I had a boss like this once, and the thing that helped the most was her peers reacting in this way vs direct reports, which she didn’t always listen to. Good luck!

  19. Keymaster of Gozer (she/her)*

    The best response I ever had (and yes I used to do this a LOT) was my coworker telling me ‘I’m not the right audience for this’.

    Like a cold dash of water it really stopped me in my tracks. And it’s such a versitile phrase too!

    1. Bird names*

      That one is really useful. I have used it successfully at work myself, usually said in a very mild tone, like I’m just reminding them of something innocuous.

    2. OP / LW*

      Oh wow. I’m not sure if I’ll use it on my boss, but I’m adding it to my toolbox.

      I have needed something like this script in the past, but have never found the right words. Thank you.

  20. H.Regalis*

    Ugh, the “funny” stories. I’ve done that, my best friend has done that, and I had to talk to a third friend about not doing that in a group setting because it was sucking all the air out of the room.

    Sometimes people genuinely don’t realize how fucked up their stories are because their perspective is a mess, and sometimes they just want validation. Either way, not an appropriate thing for your boss to use you as a sounding board for.

  21. Box of Rain*

    I had this boss… but I DIDN’T like her. At all. It was miserable.

    All I was able to do was outlast her. Which I did but not until a decent amount of damage was done. You have my sympathies. :(

  22. bamcheeks*

    LW, one thing I do in a situation where someone is oversharing or being more intimate/confessional than I’m comfortable with is the direct opposite of what I would do if I was doing active listening:

    active listening says lean forward, make eye contact, look concerned but relaxed –> I sit back, look at my fingernails or stare aimlessly around the room, and fidget.
    active listening says ask open questions and confirm/reflect emotions –> I say, “Oh gosh! Well, goodness, fancy that. Anyway, [change of topic].”
    active listening says don’t deflect –> I say, “Something similar once happened to me! [talks about situation which has a superficial similarity, eg. it also happened at school / on holiday / there was a puppy, but a totally different emotional heft– your story is sad, mine is funny; your story showed you being vulnerable, mine was triumphant]

    I mean, I wouldn’t necessarily call it “channelling my inner Sister Michael”, but — that’s not necessarily a bad thing.

    This usually works one of two ways: in some cases where the person is stuck on the track and knows they ought to get off it, it just snaps them out of it, and they are able to pick up a new thread and re-orient themselves. If they are actively seeking connection and sympathy, it just makes you a deeply frustrating person to have this kind of conversation with, because you’re not giving them any “continue, I am listening and empathising” emotional cues.

  23. Neither Here Nor There*

    Honestly, the fact you’re spending all this time talking about her feelings and past and personal life would bug me almost as much as the negativity—this is work! Everyone’s boundaries are different, I don’t want to hear about childhood trauma from my coworkers. That’s “close friends only” territory. I’d feel incredibly uncomfortable if someone turned a weekly meeting into a discussion about their self-image.

    Can you set an agenda? Say “I want to make sure we get to everything important today. Let’s start with (ITEM #1).” Then stay on the agenda the whole time. If she gets distracted, say “I really want to get to this next item…” and loop back to the agenda. When you’re done, close with “That’s all I have. Is there anything else that came up this week?” and if the answer is “No,” go “Great! Thanks so much. I’ll do (X, Y, and Z) and get back to you.” Then try to end the meeting.

    This might feel chilly to someone who wants to chitchat about themselves, because now you only want to talk about work. But is that a problem? I would feel bad if someone decided that wanting to focus on work meant I hated them, and if they withdrew or were chilly to me in response, I’d feel sad about it… But honestly, if they stopped talking to me about how much they hated their bodies? I’d probably be relieved.

    1. OP / LW*

      Thank you – yes, I think this is a good idea. Maybe I can start out framing our 1-1 meeting as “I wanna get a lot of stuff done” and then when she overshares, a redirect of “Anyway, back to X” and then if she doesn’t stop, throw in one of the blunter one-liners people are sharing in this thread…

      1. Bird names*

        Certainly worth a try and it’s never a bad idea to be able to ramp your response up a bit instead of starting off with the strongest one.

  24. ErgoBun*

    Letter Writer, I used to be a lot like your boss and I didn’t realize how I was portraying myself. One of my reports said this to me, and it changed my entire perspective:

    “I have never heard anyone criticize your work except you.”

    I don’t know if that will work, but I can say it shook me to my core and started a much needed process of changing how I spoke at work.

    1. SansaStark*

      Wow. What a succinct and poignant sentence that hit me like a ton of bricks. I’m putting that in my arsenal for sure.

    2. iglwif*

      I heard something similarly earth-shaking, in a totally different context, from the therapist who responded to “I’m not really sure what my friends see in me” with “Well, what do you see in them?”

      And then when I talked about how my friends were kind, generous, really smart, funny, good listeners, knowers of interesting things, and so on, said something like “So don’t you think maybe they see those same qualities in you?”

      This sounds ridiculous but that had legitimately not occurred to me before. (THANKS, CHILDHOOD BULLYING.)

  25. RagingADHD*

    LW, I don’t think your boss is exhausting only to you, because of your individual background.

    She sounds exhausting, period.

  26. raised by broadcasters*

    Man, when I worked with teens regularly, I had the Negative-Self-Talk Spray Bottle. It was a plant mister filled with water and I told my teenagers that if I heard them saying something mean about themselves I would spray them like a naughty cat. It worked so, so well. They even got to spritz me once or twice. I wish I could tell you to do the same, LW, but spritzing teenagers with water when they say, “ugh, I’m so dumb,” is a very different beast than spritzing one’s boss.

      1. Bike Walk Bake Books*

        Oh, if she would find this funny, then could you create a virtual one? Before she goes there with the negative topics, in some meeting say, “Hey, I heard this great story about the Negative-Self-Talk Spray Bottle” and explain it.

        Then say, “Fair warning, negative self-talk from you doesn’t really inspire me to dig into this long to-do list we need to get through. Would you mind if I squirted you if that comes up in our meeting?” If she starts you interrupt to say, “Hey, I have my spray bottle here” and pretend you’re holding up the bottle, make the psh-psh noise, set down the bottle, say “And now, back to our regularly scheduled programming” and pick up the agenda item as if neither of you had said or done anything of the kind. Spiral stopped, back on track.

        You could even be looking forward to having the chance to do this so maybe that would help with the advance tension (which my mom would have labeled “borrowing trouble”). Going into a meeting wondering, “Is this going to be the right time to bring out the spray bottle?” could actually be fun.

        1. Lizzie (with the deaf cat)*

          I saw a jokey comment somewhere, where the speaker said that they were sitting on their kitchen counter when their cat walked into the room, and they felt obligated to squirt the water bottle on themself to show the cat that the rules applied to everybody!

  27. Neutral feedback*

    I have read some comments of OP that say the boss is laughing along. I could imagine to say something like: “I find it hard to share/join jokes that are about self-debrecation”

  28. Raida*

    I concur.

    When she jokes about being whipped across the back of the legs with the power lead of the toaster as a child, say “what an awful, awful thing to do to a child. Nobody should have to go through that”
    When she says she’s stupid, say “Well who told you that?”

    I would think that since she’s not joking about herself but rather repeating “you are a stupid ugly child” that she learnt growing up, she does not realise this isn’t normal.

  29. murr*

    This might come off as mean, but one thing that worked with coworkers was saying “You know, you tend to talk about yourself a lot”. Which sends those types of people into an anxiety spiral where they immediately stop talking about themselves and their problems because they don’t want to be perceived as egoistical.

    Mean, but it solved my immediate problem of having conversations or meetings derailed with self-deprecating monologues.

    1. Mean*

      This doesn’t come off as mean, it is mean. It isn’t necessarily true in the first place (there can be self-debrecating talk even in one offhand short ), and you actively aim to trigger their anxiety.
      I am sure you could do better!

      1. allathian*

        Yeah, I agree it’s a bit mean and normally I wouldn’t recommend making a boss feel bad about talking to me.

        That said, at some point enough is enough, and the ultimate goal is not to make the boss feel better about herself as that’s way beyond a report’s remit, but to ensure that the boss stops with the self-deprecating comments because she isn’t getting the sympathetic response she wants.

      2. amoeba*

        Yes, this. I mean, I have my share of self-doubt but certainly nowhere near LW’s boss and I’m pretty sure it doesn’t come out at work at all. But that comment would send me into a shame spiral, like, instantaneously. It’s basically be one of the worst things you could potentially say to me.

        So please, don’t.

        1. allathian*

          Given that you aren’t constantly coming out with self-deprecating monologues, or any other kinds of monologues for that matter, the risk of anyone saying that to you isn’t all that great.

          But if a comment like that makes someone else’s self-deprecating monologues stop, mission accomplished. The LW isn’t responsible for making the boss feel better about herself, all she wants is to stop having to hear the self-deprecating talk.

          Obviously it can be risky to make your boss feel even worse about herself than she already is. Much less risky with an annoying self-deprecating coworker, for sure.

          I’m pretty certain that the vast majority of people have episodes of self-doubt at one point or another in their lives. I know I certainly have, but I’m lucky because at this time in my life it’s not a constant companion.

          I don’t think expressing self-doubt at work is inappropriate in all circumstances, either. I’ve certainly done it in front of close coworkers before a big presentation because they know that no matter how well I prepare public speaking makes me anxious, and I know that some pep talk will make me feel better. But I don’t do presentations often, less than once a year, so I’m not constantly demanding reassurance from my coworkers.

      3. Tango*

        I don’t agree with the advice to say this to a boss because they could retaliate, but I actually disagree that it’s mean. If someone talks about themselves so much that their audience has to ask a professional advice blog for ways to get them to stop, they DO tend to talk about themselves a lot. it’s less “anxiety” and more “appropriate guilt about negatively impacting other people”

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