updates: I work with my awful boss’s sister, afraid to give feedback, and more

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

1. My awful former boss is my new coworker’s sister

I wrote to you a while ago regarding my awful former boss, who I found out is related to my new coworker.

I wanted to thank you for publishing my letter, and thank the commenters for their advice as well. I’m sorry I didn’t get to engage in the comments, but I read them all and really appreciated the insight and support that was offered. (To address something that popped up in the comments a few times, it’s not an issue that Bob and his sister work in different companies in the same industry. My old company did, say, teapot design, and the new company does teapot manufacturing – so we’re not direct competitors and there aren’t any trade secrets being put at risk here.)

My update isn’t super dramatic but I saw your call-out for updates, so I thought I’d share. There was one occasion on which Bob asked me again about my experience with Company X, but because we were in a large group setting I didn’t feel like I could directly address the faux pas I had made with him previously so I gave a pretty neutral response. A few weeks later, though, it came out through general industry gossip (of which I had no part!) that the freelancers at Company X had been asked to work for free due to budget constraints, and while many of them left because of this request a few had stayed on and kept working ‘for experience’. Company X is a large, profitable company, so this kind of news was alarming and made the rounds fast.

One of the people who had been behind this request to the freelancers was Bob’s sister. This became common knowledge in our industry pretty quickly and Bob never asked me any questions about Company X again. For what it’s worth, both he and I have continued to be polite and friendly with each other, and I’m sure we’ll remain so for the rest of my contract with the company.

2. Am I being too self-deprecating at my new job?

I appreciated your advice and some of the commenters’. As I reflected, I know some of the actions in my initial letter were due to new job anxiety mixed with languishing (word from the NYT) through COVID and lockdown. I didn’t realize at the time how much these life changes and world issues affected how I perceived my space and myself until I went through it.

I appreciated the advice that said to say “thank you.” I have been using that a lot, professionally and personally. I also make a point to recognize others’ contributions when appropriate. I catch myself when interacting with people. Instead of saying “I have a dumb question” or something similar – I substitute the word “quick” or “clarifying” or just take out the adjectives altogether. It’s much easier in email, but I’ve been working on it in conversation. I think through my wording and phrasing to be kind to myself and conscientious of others.

Another piece that helped was due to chance. We had some turnover and new hires. I also took on additional responsibilities that put me in a position to get a lot of questions. Knowing (or finding) the answers in my space has helped remind me that I own my expertise and to not diminish it. Having people come to you for your perspective or advice is also a good reminder that you are capable. So, all and all it’s a good place to be in.

I would add that we all have something we are working on. I excel in a lot of subjects. This is just the place where I’m working to improve and it’s an ongoing process.

3. I’m afraid to give critical feedback after two employees threatened suicide

I wrote in to you about a year and some change ago about having to fire two people who then threatened to kill themselves. I got a lot of really positive feedback on that post and your readers provided such amazing resources. I ended up taking some time off for mental health and came back to that position just in time to be laid off due to covid. But I started a new job that is much more in my wheelhouse and I was able to lay someone off today and have it go according to plan. If I didn’t listen to your readers and really delve into that trauma with my therapist, I don’t know if I would have been able to tell my current boss that I could handle that conversation today.

Just thought I’d let you know that the community here is beyond professional advice and I super appreciate it.

4. Success story from a student

I’m the student who wrote to you with their success story during the early stages of the pandemic (what ultimately led to Friday Good News)! As it’s been almost exactly a year since then, I thought it was fitting to send in an update.

I started off surprisingly very stressed (like sobbing in my room stress) as I went from a nonstop pace with undergrad to what seemed like sudden brakes, leading me to feel like I wasn’t meeting expectations (spoiler: the opposite ended up true). I eventually understood that that wasn’t the case, that my own expectations for myself were too high, and though it took some time and reassurance I was able to get myself to a place where I felt good about the work I was doing. Despite that hard mentality shift, my project has been going quite well! People seem genuinely interested in what I’m doing, I’ve been able to build some good connections already, and I’m with a program that will lead to excellent opportunities down the road – I’m excited and hopeful for the future when this is finished! While it’s been slow getting data, I was able to start collecting some recently which feels great and like I’m finally starting to truly “earn” my place here. As well, just this week I’ve given my departmental seminar on my project, which is a good milestone for the first year!

The pandemic has also helped me realize how important it is to prioritize my well-being even as a student. The past summer was truly the most relaxing one I’ve had since I was 15 years old (the last summer before starting my first job) as work cut everyones shifts in half and in-person training was cancelled so I had nowhere to go but enjoy my last summer at home with most of my days free to myself – it was incredible and really made me re-prioritize what’s important to me! Now that grad school has different workloads than undergrad, I’ve made it a point to turn off the computer by 10pm (unless truly necessary) and relax the rest of the night which has been a new yet lovely feeling. I can go to bed before midnight instead of after 1am, I’ve started hobbies that I haven’t had time for since high school, I adopted a sweetie of a cat, moved in with my partner, and I’m allowing myself to have actual weekends instead of half-days off! For the last 5 years, if I wanted a night off with friends, I had to plan my week around it to make sure everything stayed on schedule but now if we want to do an impromptu zoom wine-night I can just finish for the day a bit early without feeling like I’m going to regret it – it’s so great!

All this is to say, while this past year certainly hasn’t been easy with plenty of struggles and frustrations, I’m in a better place than I have been for years and this step has genuinely felt like the best decision for me. While I don’t know if I’ll continue in academia when I finish here, regardless of what happens next I know that I’ll be moving forward with a good understanding of what I want to get out of both work and life!

So thank you for your blog, it’s something I continue to truly love reading and learning from. Maybe one day my next email to you will be my own request for advice as someone fully in the workforce!

P.S. Still haven’t had that graduation but c’est la vie, I’ll get one for this degree! :)

{ 33 comments… read them below }

  1. commonsensesometimesmakessense*

    Oh really, can the freelancers work for free!?! How nice for them! Seriously, I am beginning to see why Bob isn’t telling people that she is his sister. He should NOT have pressed you for details, but I am guessing he is not entirely unaware how bad his sister is.

    1. Dream Jobbed*

      Unfortunately some did, which is why this crap continues. Sounds like a toxic company through and through.

      1. Nanani*

        And realistically, those are the newest and least-well-compensated ones (= the most desperate) who are being burned.

        Fellow freelancers: NEVER work for free.

    2. Hey Nonnie*

      I really hope that at least the rumor mill is making it clear that most folks in the industry are appalled and disgusted by what Company X did. They deserve to suffer some reputational damage for that.

    3. Amaranth*

      What strikes me as really strange is he brought it up *again* and in a group this time.

      1. allathian*

        Yeah, well, at least now that Company X is getting a bad rap and Bob’s sister’s name is firmly entrenched in that mess, Bob’s stopped talking about his sister with the LW. I’m just sorry it took so long for this to happen and things had to get so bad before Bob stopped doing it.

      1. Grizabella the Glamour Cat*

        The name of what?

        This comment is rather cryptic, and going to Clients from Hell isn’t much help without some hints about what to look at there. ¯\_(ツ)_/¯

  2. PloverPicasso*

    LW2: This came up in a department meeting I had yesterday. We’re a team of 7, and our dept. manager followed up with someone’s presentation with “I have a dumb question…” Before she could ask it, another person on the team asked her to rephrase it, “because if you think it’s dumb and I can’t answer it, what does that say about me?” I think they were trying to be amusing but it’s stuck with me.

    1. 2 Cents*

      I’m definitely guilty of the “dumb question” and it’s truly not because I’m trying to poke fun at the presenter. I will use the “clarifying” or “quick” verbiage instead, since that’s what I really mean!

      1. Laura Petrie*

        ‘Dumb’ is also quite an ableist term. ‘Quick’ is a much better alternative to use or just ask the question with no preamble.

        1. allathian*

          My favorite is clarifying. A quick question is anything but if it’s longer than a sentence, or if it can’t be answered in one or two sentences.

          1. RebelwithMouseyHair*

            IME quick questions rarely have quick answers so I kind of brace myself when someone announces that.

  3. Flurple*

    #3: I’ve been suicidal over work things before, not that anyone around me would guess. It’s a me thing, not a workplace thing (ok once it was an evil toxic workplace thing, and I wasn’t alone in my feelings then, and that’s what probably makes it happen to me occasionally in non-toxic workplaces). I promise I’m still pretty rational and fully appreciate critical feedback, where it’s constructive and rational and progress-oriented. :)

    1. Twats*

      I’ve been suicidal due to Bipolar. I’m very lucky to have a flexible job (in spite of the stress)!

  4. Snailing*

    From OP 1’s first letter, it was a mystery what Bob’s motivations were – spying for his sister? spying against his sister? just being a busybody?

    Now it seems more clear that he knows what his sister is like and maybe just trying to verify his own feelings? Anyway OP1, good outcome for you, not so good outcome for the freelancers not being paid and I hope they get out soon.

    1. Venus*

      I realize that this is a stretch, but I have family members who are awful and yet their close family gaslights others into thinking that they are the best thing of the world. Bob may be looking for confirmation that his sister is an asshole, to confirm his own impressions.

      Whatever the reason, it isn’t the OP’s role to help Bob with family issues, so best to avoid the topic!

      1. RebelwithMouseyHair*

        I’m not sure about that because he was surprised in the first instalment.

  5. BRR*

    #1 What is Bob’s deal? He pressed you for details before and you gave them and then he asks you about it again? I have the feeling he knows you’re going to talk bad about her.

    “I didn’t feel like I could directly address the faux pas I had made with him previously,” I want to emphasize you didn’t make a faux pas (maybe you shared a bit too much the first time but I’m going to give you a pass on it). Bob made the faux pas. He should address his faux pas with you that he shouldn’t have pressed so much and should have initially brought it up as “Oh you worked at Company X, my sister Jane works there. Do you know her?”

    1. Twats*

      Precisely, return the awkward back to him. I would go further and say ‘I just found out she is your sister, is that why you are asking?’ Then just stand and stare. Most bullies back down if you can stand up to them (it is easier for them to move on to another victim).

    2. Where’s the Orchestra?*

      Yeah, OP1, he owns all the awkward. Sounds like both Bob and Sister are the types to be “superficially pleasant but all about work” people.

      He seriously brought it up again, ughhh.

      I commented on the original post about doing the right thing the wrong way was still wrong in an attempt to see the bright side of Bob – but that he brought it up again makes me think his motives weren’t pure or that he was on a Sis inspired fishing expedition both times.

    3. Ellie*

      If Bob had told her that his sister works there, then there’s no way OP would have told the truth about her experiences. It was a bit sneaky, but maybe he really did want to know how his sister was being perceived? Just because they’re related doesn’t mean he gets along with her. She might have been asking him for a job or a reference and he suspected she was bad and was looking for confirmation.

      Either way though, the fact that her freelancers are now working for free gets the OP off the hook nicely. Sis is clearly a terrible person and everyone will understand why the OP doesn’t want to get into specifics about that workplace. I’d just drop the whole thing.

      1. allathian*

        Yes, and that’s what Bob’s clearly done. Since the news broke in the industry that Bob’s sister was heavily involved in treating the freelancers like crap, he’s stopped talking about the company and his sister. Maybe he finally realized that his sister really is a horrible person.

  6. Weasel007*

    For OP #3 I’m glad you got some time away after all this. I am experiencing a slightly off kilter version of this. I have a co-worker who is in the wrong role, over worked, sick she recently received a cancer diagnosis and she is completely ignored by her management. Every time I talk to her while supporting her with her work, she tells me she is going to quit. It is putting a massive amount of stress on me and others on my team. I finally responded to her today after she said it yet again. I told her that if this job is sucking the life out of her she needs to make that decision and soon. Life is too short to be in a job that is sucking the life out of you. I suspect she says it trying to get a sympathetic ear from her teammates (“oh no…don’t do that! We need you!”) but by calling her bluff today I hope she realizes how much stress she is putting on us by making those comments. That is a lot to put on someone who has not volunteered for that role.

      1. Wisteria*

        by calling her bluff today I hope she realizes how much stress she is putting on us by making those comments.

        I don’t think it was a great approach for someone who is stressed to the point of talking about quitting, either. Rather than being indirect and hoping you get your point across, try being compassionately direct and actually get your point across.

        “Jane, it sounds like the stress is really getting to you. I have to let you know, hearing you talk about quitting puts a massive amount of stress on me. I’m sure you didn’t mean to stress me out, but will you please cut down on the quitting talk? If you really need to walk away, I get that, it’s just stressful to me to be constantly wondering if that is really going to happen and what we are going to do when it does.”

        1. Blaise*

          Agreed. I’m sure she would LOVE to just quit, but who can afford to have cancer without health insurance?!

      2. restingbutchface*

        This. Suicide isn’t even in the same ballpark as threatening to leave your job and when I read “make the decision soon” in a thread about suicidal threats, a chill went though me.

        Weasel, I think you’re mad at the wrong person here. Your coworker’s reaction to how they are being treated is normal and I would feel exactly the same. What’s wrong with needing a sympathetic ear when frankly, you’re being treated appallingly AND you have cancer? Sure, they could have more emotional intelligence and just ask for what they need, but jeez. I feel for her and I don’t even know her. Sure it’s hard for you to hear but she sounds like a person in pain. Can you encourage her to redirect these concerns instead of shutting them down? I hope things improve for you all, this sounds like a terrible situation and I feel for everyone involved but especially your coworker.

  7. ecnaseener*

    Yay for LW2, 3, and 4, y’all made great progress!!!
    (LW1, uh, yay for hopefully being done with that situation?)

  8. restingbutchface*

    OP2, I think you’re doing yourself a disservice with this line – “I would add that we all have something we are working on. I excel in a lot of subjects. This is just the place where I’m working to improve and it’s an ongoing process.”

    I would totally disagree. Everyone has something they SHOULD be working on, but not everyone has the emotional intelligence and drive to actually acknowledge it and work to improve. How many people do you know who think that they’re fine and the problem is everyone else? I know a lot. It’s admirable that you are recognising these areas and working to improve, but I don’t think it’s the standard, which makes it more admirable. I am glad you recognise your talents, I hope you spend as much time acknowledging & promoting these skills and talents than you do finding your weak spots and working to improve.

    Really happy to read your update!

  9. ellex42*

    OP2, as the person who is often being asked the “dumb” question, I wish some of my coworkers would take a cue from you: not just in avoiding the self-deprecation, but in working to make yourself a person that others come to for answers as well.

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