mentoring a very timid employee, secretary asks every day if I’ve been vaccinated yet, and more

It’s five answers to five questions. Here we go…

1. How to mentor a very timid staff member

I’d love some advice about how to help out a very timid staff member, let’s call her Hermione. Hermione and I have 1-1 weekly professional development meetings where I can offer support, mentorship, and advice. She is not my direct report in any team and we don’t work in the same department so our workflows never cross. We only meet for this weekly professional development session. My job title is nothing to do with management or HR, but our company culture is that each senior staff member (i.e. me) has regular mentoring meetings with some junior employees.

Hermione is very, very timid. She doesn’t feel like she can advocate for herself in her own team, and she doesn’t push back when she’s given unachievable deadlines. If she knows she can’t meet a deadline, she tries to anyway because she doesn’t want to say no to her team leader. This results in Capital S Stress for her, and a missed deadline for the team.

Recently, Hermione ended up crying in my office, totally overwhelmed by her workload, and feeling like she’s not able to do anything about it. I investigated with her team leader, McGonagall, who told me that Hermione always produces brilliant work, even if it’s sometimes after a deadline. Her team has nothing but positive feedback about Hermione’s work ethic, even though it seems like she often works overtime to try and meet a deadline (something else that causes her stress). All in all, it seems to me like a supportive team environment. McGonagall and I are peers, and I know for a fact that she is an incredibly supportive leader who would not react badly to Hermione speaking up at the right time.

Hermione and I have tried for months now to give her some ways to help her communicate to her team members when she’s struggling, and how/when to speak up with McGonagall when she’s given a deadline that she knows is unachievable. The problem is that Hermione is so timid that she refuses to actually carry out any of the ideas that we discuss in our meetings. She just says that she “doesn’t think she can say that to McGonagall.” Hermione’s stress levels are getting worse, and I’m at a loss with what to try next.

Well … you can try giving her specific language, role-playing it with her, and setting specific plans  that you then check back about (“you were going to say X to McGonagall at your 4 pm meeting — did you? why not? so what next?”). You can also name the pattern for Hermione — “We’ve worked on this for months but you haven’t implemented any of the ideas we’ve come up with. What do you think would really help?”

But if you’ve already tried those things, I think it’s likely that you can’t fix this. Mostly it needs to come from Hermione herself, although McGonagall is also better positioned to fix it if she wants to.

Ideally McGonagall needs to ask Hermione some probing questions about her workload and take a fresh look at it herself, check in on Hermione’s progress toward deadlines earlier in the process, and give her explicit instructions about how she wants her to handle it when something is in danger of going off-track. Is your role one where it would be appropriate to suggest those ideas to McGonagall or even set up a meeting for the three of you, or are you really just supposed to be coaching Hermione behind the scenes?

It’s also possible Hermione mostly just wants a place where she can vent. If that’s the case, it’s useful for you to know that so you aren’t racking your brain for a way to move her to action.

2. Secretary asks me every day if I’ve been vaccinated yet

Our office secretary constantly asks me if I have received the Covid vaccine yet. I mean every day. And if I leave for a doctor’s appointment (I have many due to a medical condition) and return, she asks if I went to get the vaccine. I am eligible but appointments are near impossible to get in my area. She basically admitted to lying in order to obtain a vaccine earlier than she’s eligible.

I’m frustrated with the constant nagging. I have been trying but this is out of my control. How can I politely tell her that it’s none of her business? This is the tip of the iceberg. She often nags when it comes to personal information and I would like to raise this as an example to our manager but could use some guidance on how to do that without potential retaliation on our secretary’s part. (She has gotten sulky and subtly mean towards me when I’ve raised issues in the past.)

The next time she asks, say this: “It’s gotten strange that you ask me that every day!” In fact, say that every time she asks you from now on. You don’t need to give her any answer other than that. But if you want to vary it, you could say, “Please don’t ask about people’s medical appointments — they’re private.”

When you talk to your manager, be explicit that you’re concerned about the secretary retaliating against you, and explain it’s happened in the past. Ask your manager to make it clear that that’s unacceptable. A manager who’s committed to eliminating retaliation in situations like this can do it pretty easily, with a Very Stern conversation with the person about there being zero tolerance for it, then checking in regularly to ensure it’s not happening and enforcing said zero-tolerance policy if it is … but whether your boss does that will depend on how assertive she’s comfortable being. On your side, you should be assertive about following up with her if you do see signs of retaliation coming your way.

3. How to turn down a coworker’s request for a recommendation

I am in marketing and a colleague in sales recently requested a LinkedIn recommendation for “marketing initiative.” This colleague has been a constant thorn in my side for the entire time I’ve worked at this company. I could not give him a general recommendation, but for this particular area of “expertise,” my feedback would be absolutely scathing — he doesn’t know what he’s doing, and what he does in this area, he does poorly, without consideration for long-term ongoing projects, and without budget approval.

There’s no HR policy I can point to as an excuse, and I’m at a loss for a way to turn him down that doesn’t seem to invite him to try again later, without absolutely torching my relationship with his whole sales division.

If there’s any way to ignore the request, sometimes that’s the easiest option. But if not, some options:
* “I’m sorry, I don’t think I’d be the best person to write that.”
* “I almost never write recommendations — sorry I can’t help!”
* “I’m swamped and don’t know when I could get to it — you’d be better off getting one from someone else.”

But if he knows there have been problems in your work together, is it an option to just be honest? For example “We haven’t always had the easiest time working together, so I don’t think I’m the ideal person to do it.”

4. My boss didn’t tell me she was getting my email

Let me start by saying that my manager is wonderful. She’s a self-described Type A personality, but she complements my work style because I am more easygoing and ADHD so if I miss something, she’s sure to catch it quickly and without jugment. She’s not a micromanager, though. She trusts me. We work well together and she’s the best boss I’ve ever had.

I went on maternity leave last summer and returned five months ago. While I was out, I had an auto-reply on my email telling people to contact Y staff person for Y inquiry, Z staff person for Z inquiry, and my manager for anything else. We also had incoming emails automatically forwarded to my manager.

My grandboss requested a call today to go over some questions about current projects, but also to ask me if I knew that my emails were still being auto-forwarded to my manager. I did not know that. My grandboss said she told my manager that it wasn’t appropriate for her not to say anything to me, and asked me if I knew how to turn off the auto-forward or if she should contact our IT department to have the forwarding removed. I didn’t really know what to say except that we should ask the IT department to remove the forwarding.

My grandboss remarked that she seemed more upset about the situation than I was. It’s true. Maybe it’s because I’m non-confrontational, low drama, too busy with projects to worry about something like this, or maybe I’m just still in shock — but I don’t feel strongly about the situation at all. A little annoyed but that’s it. There were no sensitive emails or any messages that would make me look bad to my boss.

Should I be more upset about this than I am? Should I say something to my manager? I don’t really want to. She’s otherwise a great boss and I think my grandboss made it very clear to her that it wasn’t okay. What do you think?

Well, if you’re not upset, you’re not upset. You like your boss and she’s the best manager you’ve ever had. So I guess … maybe … there’s some explanation that makes this less bad than it looks on the surface? Like maybe she had all your emails funneling into a separate folder that she rarely went into, so it didn’t occur to her that the forwarding was still on? But if it’s not that — if she’s been seeing all your emails every day for five months and not saying anything to you — personally, I’d be pretty taken aback and would want to know why.

But if you don’t want to, you don’t want to. You don’t have to! And it sounds like your grandboss has already handled it. However, if at some point it does start to bother you, a very low-key way of raising it (since you seem pretty low-key and I’m guessing that’s what you’d be comfortable with) would be to say something like, “I was surprised to find out my email was still forwarding to you for all these months since I’d been back — you hadn’t mentioned it” and then just see what she says.

5. How quickly should I send thank-you’s after informational interviews?

I’m a fairly new grad, currently in a PhD program. I’m fairly certain that I want to work in industry rather than in academia after I graduate, and have therefore started to network via informational interviewing. Whenever I talk to someone, I will always follow up with an emailed thank-you note, formatted as: thank you so much for your time. I learned a, b, and c from our discussion. And finally, either would you mind connecting me to so-and-so that we talked about and/or thanks again for your time and help.

These notes take a bit of time to write, and cannot really be written in advance because they directly reference the conversation I had with the interviewer. Is it okay to send these notes 1-2 days later, rather than following up same day? Given my work schedule, I don’t always have time to follow up same day, even though I do realize that would likely be better. Or should I just be writing something more generic as a template so that I can send it out same day no matter what?

No, sending them a day or two later is completely fine! In fact, I’d argue that’s better than sending them on the same day as the meeting, because same-day notes in that context tend to feel a little rushed or perfunctory. Sending your follow-up a day or two later makes it clearer that you’re still thinking about and appreciating the meeting.

{ 314 comments… read them below }

  1. Julia*

    LW1: It might be about timidity. It might also be about shame. If Hermione grew up in an environment where she was punished for lateness, or if she worked in a previous environment that dealt harshly/unproductively with missed deadlines, she may have picked up a feeling that only Bad People miss deadlines and she can’t possibly discuss it with McGonagall because that would mean acknowledging she is a Bad Worthless Slacker who Misses Deadlines.

    Not that this changes Alison’s advice. It would probably be crossing a professional boundary to start asking her if this is about shame. And in any case, shame or timidity, it’s her mountain to climb; you can only do so much. I have been a shameful self-sabotaging deadline-misser and there’s no way out of that pit except by working on it oneself.

    1. Forrest*

      Yes, I don’t think you can “solve” this without working with McGonagall and Hermione. What you need is

      – a situation where McGonagall provides a visible and obvious opportunity for Hermione to speak up
      – Hermione to be coached by you on how to do that
      – positive feedback and action from McGonagal showing that speaking up is rewarded
      – this cycle to be repeated several times until Hermione starts to believe in the positive outcomes and gains confidence.

      Organising this might be within the bounds of you mentorship, or it might be WAY overstepping! It might be more effort than you are willing to give to the relationship, or it might be exactly the point of these mentoring relationships. Only you know that. But if McGonagall and Hermione were up for it, it would enormously to the benefit of Hermione personally, McGonagal’s team and ultimately the company, so it could be worth exploring.

      1. Nesprin*

        I require all my trainees/mentees to ask 1 question per meeting, because I want them to be able to function in the environment where we work. The more timid sorts really struggle with this but also ask some of the most astute, insightful questions.

      2. HKS*

        Just wanted to chime in as a still timid (but slightly less so after YEARS) employee that this sounds like good advice. For me, practice and positive reinforcement and having a well-defined space and opportunity to speak up helps. Also, maybe her preferred way to communicate is in writing instead of speaking? Any way to accommodate alternative methods of communication? I realize a person needs to be able to communicate with their manager verbally, but sometimes having the option to begin the conversation in writing helps to get started.

    2. HR Exec Popping In*

      I would recommend the OP coach Hermione to have a proactive conversation with her manager, McGonagall. In this Hermione can tell McGonagall that she struggles to push back on deadlines when she know she can not meet them and ask McGonagall for help on how they can work together. Key asks Hermione can make are for McGonagall to ask Hermione to recommend the deadlines instead of McGonagall setting them. Or if that is not an option, for McGonagall to ask Hermione how reasonable the deadline is, what does she think will get in the way of her meeting the deadline, or what support she will need (changing other priorities, getting help from someone, etc.) to meet the deadline. This way Hermione isn’t having a conversation after a deadline is set (i.e., pushing back and feeling confrontational) but is establishing a conversation with her manager on how they can work together to effectively set deadlines going forward.

      1. TootsNYC*

        It sounds like the OP has done something like this, though.

        Hermione and I have tried for months now to give her some ways to help her communicate to her team members when she’s struggling, and how/when to speak up with McGonagall when she’s given a deadline that she knows is unachievable. The problem is that Hermione is so timid that she refuses to actually carry out any of the ideas that we discuss in our meetings. She just says that she “doesn’t think she can say that to McGonagall.”

        Well, I guess this only covers the “speak up in the moment” idea; I guess I’d just assumed that the OP had given Hermione a proactive approach.

        1. Data Bear*

          It sounds to me like Hermione isn’t just incapable of saying no to McGonagall; she can’t say no to OP, either, even when she knows she won’t carry through on the discussion items from their mentoring session.

          I think all the suggestions about roping in McGongall are good ones, but my main impression is that the one area where Hermione needs mentoring the most is learning how to do something other than just agree. If that’s the case, perhaps there are some helpful coaching exercises that OP could do around that?

          (Like, “Let’s practice. I’m going to ask you for something completely unreasonable, and I want you to refuse my request.” Start by asking her to literally go fetch the moon, and work your way down to tasks with infeasible deadlines…)

          1. Anne*

            I like all the suggestions about bringing in McGonagall & agree with the need for coaching. But from what I’m seeing, the suggestions for action on Hermione’s part are all coming from OP-Hermione’s not coming up with her own ideas for action. Until Hermione’s the one coming up with the answers, she’s going to continue to say “yes” & do “no”.

          2. cat lady*

            “the one area where Hermione needs mentoring the most is learning how to do something other than just agree”– yes.

            With students, I do this by moving past the yes/no questions (“will that deadline work?”) to questions that require a thought-out response (“what deadline would be reasonable for that amount of work?”)

    3. Dasein9*

      Yes! You don’t have to raise the issue of shame so much as recognize Hermione’s motivations. It sounds like Hermione has a tremendous sense of duty and goodwill when it comes to helping her team.

      So maybe it would help to frame this not as Hermione’s deadlines, but as information McGonagall needs.
      Presumably, if a deadline is unfeasible, the team leader needs to have that information in order to make adjustments, either by putting more resources into the project or adjusting the timelines. So I bet it would help to tell Hermione that she needs to get that information to McGonagall instead of framing it as anything “missed,” which she probably internally pronounces as “failed.” This is “crucial information conveyed,” which can also be pronounced as “success” by the inner voice.

      1. Jaydee*

        I think it’s also useful to challenge with Hermione her assumptions about what makes for a good, dutiful employee and coworker. It sounds like Hermione has some people-pleasing tendencies. And she may still be stuck in a student mindset where teachers give assignments without regard to what else the student has going on and the student just has to figure out how to get it all done.

        These are things I’ve struggled with too. It sounds like the LW has talked to Hermione about the fact that she’s allowed to push back on timelines of things based on her workload. But she’s not going to do that if she thinks that it will make the other person upset. She needs to see that this isn’t just about asserting herself but about setting realistic deadlines and expectations for the good of the work and the team.

        In the moment, it makes the other person happy when a people-pleaser says “Sure, I can have the llama grooming monthly report finished by Tuesday.” That makes the people-pleaser feel relief because they successfully people-pleased. But when Tuesday comes and goes and the llama grooming monthly report is only half done and the people-pleaser is stressed and miserable, whoever asked for the report is not happy. More unhappy than they would have been if she had said at the outset, “Hey, I’ve got a pretty full day on Monday, so I don’t think I can get the report finished by Tuesday. Would Wednesday or Thursday be okay?”

        Really highlighting for Hermione the hardship that chronically missed deadlines cause for her colleagues and the setback it can cause to projects may help her start to realize that she’s not doing anyone any favors by over promising. It’s not going to solve the problem overnight. But as long as her mental framing is “I’m sacrificing to help my boss/colleagues and that makes me a good person” she’s going to continue with her current habits.

        1. Trillian*

          Seconded the point about downstream effects of upstream missed deadlines. If Hermoine is late to her handover, the next person downstream has less time to complete their step, might have to hand over less polished work than they know they are capable of. And that isn’t even adding in the extra emotional work of dealing with Hermoine’s timidity. The managers are also not necessarily going to get honest feedback about Hermoine from people who suspect favouritism.

        2. ophelia*

          One thing my team does with projects/proposals (that perhaps McGonagall could institute) is to have a group meeting to pick apart the draft calendar. The person managing does set an initial timeline, but it’s understood that the point of the meeting is to map out people’s availability, highlight times where deadlines are unworkable, make sure the flow still works, etc. (It’s all still dependent on a client deadline, and sometimes the timelines *are* unrealistic, but in that case everyone knows it). Framing this sort of conversation as part of the overall, standard process rather than “Hermione is asking for special treatment” might help as well.

        3. TootsNYC*

          In the moment, it makes the other person happy when a people-pleaser says “Sure, I can have the llama grooming monthly report finished by Tuesday.” That makes the people-pleaser feel relief because they successfully people-pleased. But when Tuesday comes and goes and the llama grooming monthly report is only half done and the people-pleaser is stressed and miserable, whoever asked for the report is not happy. More unhappy than they would have been if she had said at the outset, “Hey, I’ve got a pretty full day on Monday, so I don’t think I can get the report finished by Tuesday. Would Wednesday or Thursday be okay?”

          I think some of this is on the manager! I have been the timing-and-process person at my job, and I find that I give a little speech to new colleagues about how I want an ACCURATE answer to “when can this be done?” It don’t mean “I want you to hurry up”; if I mean that, I’ll say it. But a too-optimistic answer actually screws me over–if the truth is “not until next week,” I will make plans on that.

          But I also pay attention to whose estimates are accurate. If Hermione is not meeting deadlines, McGonagall ought to be working more closely with her to elicit the reasons, and to look at her own deadline-setting and work-allotment practices, and her own communication style.

          Coaching Hermione on when and how to give the feedback about deadlines is McGonagall’s job.

          1. Clisby*

            Dealing with Hermione just sounds exhausting. I tend to agree, this needs to be handled by McGonagall.

        4. Rose*

          I used to be a lot like Hermione and I was also exhausted and miserable because of the stress. Coming to the realization that providing reasonable initial pushback was better than just saying yes and trying to get everything done has helped me immensely. What really helped was seeing other people in my role model the behavior, and a strong emphasis (thanks to scrum) on meeting your commitments vs. just. getting as much done as possible.

    4. TootsNYC*

      This brings up the idea that I think it’s time to suggest some outside coaching or counseling.
      Whatever its root cause, this is getting in Hermoine’s way, and an expert can help her with that.

      The OP is not a therapist, though. Time to suggest an EAP.

      If McGonagall is as supportive as the OP suggests, it might also be that the workload ISN’T too high; that the deadlines are NOT realistic. And that Hermoine isn’t capable of moving at the pace that’s appropriate, and she’s hiding from them.

      1. wee beastie*

        I agree. All the time I was reading I was thinking, this is something bigger in Hermione that’s gonna take a psychotherapist to solve.

      2. ophelia*

        I also wonder if, since it sounds like Hermione is relatively new to the role, she doesn’t yet have a good sense of how long things are “supposed” to take, on average. So there’s an element of people-pleasing, compounded with her being unsure of when to try to overcome that tendency and speak up.

      3. Your Local Password Resetter*

        I’m not sure if it’s OP’s place to reccommend therapy though. And even if Hermoine can’t produce work fast enough, that’s a separate issue for her manager to handle.

      4. Not a Shrink*

        I agree. FWIW, these are some of the most frustrating employees to deal with day to day. I’ve never had one respond to coaching. Their either come around on their own or are fired/ quit. It’s a really deep-seated problem and often reflective issues that are beyond my pay grade.

      5. Willis*

        Yeah, this whole dynamic kind of confuses me, in large part because this level of coaching, role playing, shoulder to cry on-ness, is not really what I’ve ever expected of a mentor. I also don’t understand why the OP can’t suggest to McGonagall that she check in with Hermione on her workload, especially if she’s already asking about how she’s doing. (Which really, why isn’t McGonagall doing that already if she sees Hermione working overtime when it shouldn’t be needed and missing deadlines?) It doesn’t solve the long-term problem of Hermione needing to speak up, but maybe if McGonagall initiates a conversation about the pattern and ways to avoid it, etc. Hermione will feel more comfortable saying something next time. If Hermione is too timid to talk to her a boss about normal work stuff even when approached in a supportive manner, I think this is really beyond OP’s scope of work/mentorship.

      6. Hannah Lee*

        I tend to agree with you on this. Especially since it seems it isn’t just a dynamic in Hermoine’s interactions with her manager, it’s also showing up with OP as well.

        I had a manager who was trying to mentor me on something I was struggling with.* And we’d meet and outline steps I could take and then at the next meeting discuss my progress. After a couple of rounds of ‘try a-b-c’ resulting in me trying, making a little progress but still struggling and then ‘try 1-2-3’ and still not much traction, it switched to him walking through ME defining the steps I would take, but then me still struggling. He eventually said that it was probably something more fundamental about me, my make up, the way my mind worked but that it was outside the scope of his mentoring role, ability, but that he was happy to support me if I wanted to explore other resources.

        It helped me reset my own sense of what was going on, shifted ownership for progress on that issue clearly out of the mentor-mentee relationship and back to me and allowed us to focus our discussions on things that were productive and less frustrating for both of us.

        And for me, though I didn’t actually work with an EAP, just the thought process where I considered it led me to realizations that were useful: mainly that I didn’t WANT to do the thing … which is why it wasn’t happening. Partially because it was really outside my normal woman who-is-assertive-but-not-self-aggrandizing wheelhouse, but mostly because after 5+ years, I had reached the end of my rope working at a really intense, white-sports-bro dominated winner takes all who cares about work/life balance tech company and I was D.O.N.E done! Over the next couple of months, I finished up my current projects while mentoring my direct reports to step up, finished up my MBA, polished up my resume and found a new job at a company that’s a much better fit for me in a lot of ways.

        Hermione might have a particular, more fundamental, characteristic that she needs to work on overall, or she might not be working in the best role for her, but those are things that this particular mentor-mentee relationship may not be able to tackle. And it’s best if they don’t spin their wheels any more trying to.

        Maybe Hermione’s boss can help by defining clearly that Hermione’s feedback, progress reports on tasks, timelines IS a core part of her job, in addition to actually delivering the tangible deliverable. It may be something as simple as adding “individual contributors review project timeline and provide feedback” step to the project plan, to formalize what’s expected, or it may be a postmortem on projects with Hermione getting feedback to improve by providing input on completion dates. (with maybe a ‘buy’ round where boss knows that they are going to cheerfully accept/work around Hermione’s first ‘no’ or ‘push back’ to make clear that’s acceptable)

    5. Kat*

      So I’ve actually been LW1 and have since reformed!
      Finally, setting up a code word to use with her manager is not great long term, but may get the habit at least started. Something really recognizable like “Project Llama is shenanigans”. Once she can believe that the work stress can successfully be managed in response to her code, it will help build the habit.

      But the two things I found helpful were pieces of advice I got after blowing some deadlines, but getting advice instead of getting in trouble.

      1. We need something done that’s “usable by the time we need it, not perfect after it’s too late”. If her work is “always brilliant”, she’s not learning to prioritize effort. 80/20 is the goal. She can put down a section of assumptions/simplifications/approximations/follow ups if it makes her feel better. But if the ask is “research if we should do X or Y”, you need a decision input, not a treatise on X/Y.

      2. She sounds highly conscientious, so stressing the team impact may be useful. She’s probably trying to get a “gold star” and be great at her job. Stress to her that actually, the team needs should come before her own needs for praise. The team meets something useful to keep moving.

      Those 2 pieces of formal feedback spurred me to learn to deliver something on time (and iterate if we as a team decided it needed more addressing of assumptions list, very rarely).

    6. Ping*

      While I agree that shame may be the underlying factor, there’s a lot more that could be done here. This is especially true on McGonagall’s side. She now knows about Hermiones problems and doesn’t appear to be doing anything to change it. That’s a management fail. She could certainly follow up and ask Hermione about her work load. I also see another problem. Everyone has a high view about Hermione’s work. But have they actually told her about it? Withholding praise is sometimes gender specific. Does Hermione actually know she’s a valued team member? Does Hermione know that she is actually expected to push back as part of her job duties?

      OP should absolutely do play acting with Hermione.

      OP should also have a heart to heart that this will destroy her career (and life!) if she can’t learn to advocate for herself.

      Also, maybe work through the Crucial Conversations book as an exercise?

      1. TootsNYC*

        I agree with this, that McGonagall is dropping the ball.
        The bulk of this work should be hers to do.

        1. Forrest*

          Well, it depends whether it’s actually causing a problem for McGonagall. If she’s saying, “can you have that done by next Friday?” even though it doesn’t matter whether it’s Friday or the following week, then Hermione producing the goods the following Wednesday isn’t a problem. If the “problem” is Hermione being super overwhelmed and miserable but not talking to McGonagall about that, it’s not really her job to fix that. As a manager, you can only fix what you know about.

          1. Willis*

            Yeah if these are soft deadlines to McGonagall, she may think she and Hermione are on the same page, and not know about all the stress. She should still check in on her workload, but if she does that and gets a reply that there’s no problem, everythings, great, etc. she probably doesn’t know how overwhelmed Hermione is.

        2. u know*

          Yeah my reading of this is that LW1 probably is giving *way* too much weight to whatever McGonagall is telling them, and not scrutinizing McGonagall‘s actions nearly enough to figure out why Hermione doesn’t feel comfortable talking to them directly. Timidity in an employee like this is often a result of getting burned repeatedly by a shitty, vindictive boss!

          If a seriously talented employee is struggling under a certain manager(s), it’s almost certainly a management problem.

    7. Sue*

      I would suggest therapy. She actually sounds abused as à child. Some parents are disgusting.

  2. Maeve*

    It’s not happening to me at work, but I am definitely tired of being asked if I have been vaccinated yet! No, I will not be eligible until May 1, and my state won’t have enough vaccines for everyone until June 1, and now they’re saying maybe not even that, and I would love to know how so many people asking me this question have been vaccinated (I’m not accusing them of anything, I would just really like to know because I am extremely jealous!) and the situation sucks and I am extremely bitter.

    1. Where’s the Orchestra?*

      I had an older relative in a different state that was driving me semi-buggy asking if spouse and I were vaccinated yet. Eventually I got them to understand that we would let them know when we were – but the rules are different here than there.

      But it also helped that this was a relative who was just asking because they were worried about us. That’s totally different from the coworker OP is dealing with.

      I have to say I like Alison’s, “you ask me that everyday” with a puzzled to then tired of it expression on your face. Plus, the chat with the admin’s supervisor. Unless she is supposed to be tracking for the manager from the standpoint that some assignments can only go vaccinated employees, this is a none of her business – stop now deal.

      1. Maeve*

        I keep getting asked by people in my state who know I’m 33 and don’t work in health care or education so…I don’t know.

        1. Not Karen*

          It’s getting a little old here too. I live in a massive state that is still trying to vaccinate the elderly and those with pre-existing conditions. I’m 40 (not as young as I’d use to think!) but perfectly healthy. It’s going to be a while folks!

          1. Self Employed*

            I don’t know if I look about 20 years older than my real age or what, but many of my friends who were old enough to qualify kept asking if I’d been vaccinated and even responding as though I’d said I didn’t believe in vaccination. No, I just didn’t fit our state’s criteria and I’m not going to lie or stalk clinics hoping for a spare end-of-day dose.

          2. nona*

            It’s definitely getting old. Along with all the conversations about strategies to find appointments. And people offering unsolicted tips (No, I don’t want to do a 4-hr round trip for an appt.) It’s the only common conversation topic available at the moment for small talk, it seems.

        2. TootsNYC*

          some of it is just that “I can’t think of anything else to make small talk about.”

      2. LW2 (am I vaccinated yet???)*

        I’ve communicated directly with my boss (just this week I managed to finally get an appointment!) so there is no need for our secretary to know. My boss also knows about my medical condition and that I’d rather keep it private. As a person under 30, I’m definitely not eligible unless I have a medical condition so it’s a little stressful to admit because then I’m basically outing that I qualify for that reason! Which is very private.

        1. Chilipepper*

          I’d still follow Alison’s advice, this person does not need to know you will be vaccinated soon.

          1. Seeking Second Childhood*

            I would actually recommend you continue to deflect the answer even after you have been vaccinated. Because if the secretary is not supposed to know your medical history, and she does, how did she find out? And who else will she gossip with next?

          2. Momma Bear*

            I wonder if the secretary is feeling any level of guilt for lying or is just feeling like if everyone else gets vaccinated than her lie is covered? I would be annoyed, too, in large part because I know the “can’t get a shot/on every list” scenario and it’s maddening when someone has cut the line and admits it. I would tell her nothing except to quit asking.

        2. Mina, The Company Prom Queen*

          One thing you might try is to smile and reply ‘Why do you ask?’ And then be silent. Even if she says nothing at first, let the silence go as long as she says nothing, no matter how uncomfortable that silence is. Then no matter what she says, come back with ‘Hmm…interesting.’ while still smiling. Then either let there be more uncomfortable silence or change the subject. Repeat as necessary.

          And if she tries to call you out on it, just repeat the why do you ask script.

          1. Mina, The Company Prom Queen*

            And don’t fall for her saying something like ‘Well I was just asking (or just trying to help, or just worried about you, or just whatever).’ Keep the ‘Hmm…interesting’ script or something like ‘oh, thank you so much, that is so sweet of you.’ And then change the subject.

          2. Where’s the Orchestra?*

            Or maybe combine the two: you ask me that daily, why? And then complete silence while you wait for them to answer.

            I’m glad OP was able to talk with manager, but sounds maybe like another chat about this person’s daily personal interrogation habit is in order.

        3. SomebodyElse*

          Honestly, here’s how I would respond to the secretary regardless of your vaccination status and eligibility.

          “Nosy Nora, you aware of the prioritization for vaccines in this state? Yes, good, well as I’m under 30 you can figure out when I’ll be eligible for an appointment, so there is no reason to ask me every day about it. Once I am eligible I plan to get it, however, I will not be announcing nor answering questions now or then about my status so please stop asking”

          This really does a couple of things… it kicks the can down the road a bit to give time for Nosy Nora to find something else to get fixated on, it indicates that you are waiting your turn with the general population, and it draws the boundary that you aren’t answering any questions or telling anyone when you do get it.

        4. commonsensesometimesmakessense*

          In my workplace, everyone in my department was eligible to get the vaccine early due to our work, and most of us did. We all talked about it with each other, the difficulties we encountered with scheduling, the experience and side effects. We were all pretty open. That said, no one ever dreamed of asking anyone else if they did it. We just shared our personal experiences with the group to help let them know what to expect. There is no legitimate reason for someone to expect a colleague to disclose anything about their medical situation (except the limited amount management and HR may need to know for a medical accommodation – which is not something your office secretary needs to know, unless you are deathly allergic to her – which would make sense!).

        5. Hannah Lee*

          Yes this!

          I had a co-worker who kept asking me if I’d been vaccinated like it was his business.

          Then when he overheard me talking on the phone to my brother about being vaccinated, he came around the corner and asked me again. And I told him (since I figured he must have heard me) but then he immediately jumped to ‘how’d you pull that off?’ since I’m under the age cut off.

          And I thought … ‘why no Mr. Nosy, it’s not any of your business what medical conditions I have’ so I just said something like ‘oh, my doctor’s office called and said they could schedule it’ which technically is the answer for ‘how’ question he asked without answering the ‘why’ question he intended to ask. I could see him getting ready to ask a follow up question but just then felt the need to make an emergency imaginary phone call LOL

      3. tangerineRose*

        Even when it’s being asked by someone who cares, it can be frustrating. If I’m not eligible, I’m not.

      4. Magenta*

        I’m in the UK and nearly half the adult population have had their first dose, but based on my age (39) and lack of medical conditions I am not eligible yet, but will be soon. I have had a few people at work ask, I guess it is just a general subject for small talk right now.

        The issue is I’m pregnant so won’t be getting it even when I would be eligible, I don’t want to tell people until I’ve gone through all the tests and scans and know everything is ok. Every time someone asks me about the vaccine I feel put on the spot though, I say “not yet” but it feels like a lie! I wish people would drop the subject!

    2. Mina, The Company Prom Queen*

      I like the advice to shut down people who keep asking about the vaccine. It’s difficult to get an appointment where I live too. My new manager, who lives in an entirely different area of the country, actually tried to argue with me that her mother, who lives in yet another area of the country than I do, got an appointment easily and it didn’t take her mother long at all to get the vaccine, so therefore it should be that easy where I live. I don’t know why she is so anxious for me to get the vaccine when nobody is going to be traveling in the foreseeable future anyway. Clients are all working from home and won’t want to meet in person. And there is no way I’m going to travel to our home office just for face time, until the CDC says it’s safe to travel. Our company is not clamoring for anyone to travel. This person is new and trying so hard to prove herself that it’s cringeworthy. I’m not going to risk my health or anyone else’s because of this person and her desperation to look good.

      1. LifeBeforeCorona*

        Where I live my city was used as a test run for using pharmacies to give vaccines. I qualified because of my age and got my first shot. It seemed to have worked because now most pharmacies in other regions can give out vaccines.

        1. Mina The Company Prom Queen*

          That is great! It’s definitely different in different states, cities, metro areas, etc.

    3. Dust Bunny*

      I just became eligible this week but, yeah, appointments are impossible to get and I also have a (not-COVID) cold, so there is a good chance they’d turn me a way. I’m not avoiding it, I promise! But I live in a county that includes one of the ten biggest cities in the US–there is a lot of competition for vaccines.

    4. The Ace Tomato Company*

      I feel like asking if people have been vaccinated is the new way to make small talk.

        1. PT*

          We’ve been using the Game of Thrones vaccine House flags in my social group.

          House Pfizer is winning right now.

    5. Anon this time*

      In my state the definition of high risk is pretty broad; any chronic condition seems to qualify, plus being overweight or obese. That lowers the minimum qualifying age, though it doesn’t eliminate it.

      And a few rural counties have opened it up to everyone 16+.

      1. Midwest writer*

        That’s what it’s like here, too. Next week, it opens up to anyone 18 or older. I’m in a rural area that is struggling to fill clinics — my guess is we’ll be done having health department clinics for first doses by early May, with clinics through the end of May to finish up second doses. But two hours away in urban areas, no one can get a shot through the health department or through a pharmacy. Every appointment is booked within minutes. People are driving from the state capital to rural places 2+ hours or more to get the shots. Of course, as rural state residents, they’re used to driving everywhere anyway.

        1. Cercis*

          Same in Texas. Travis Co (Austin) got 7,000 first shot vaccines this week. They open the lottery for appointments each Monday at 6:30 and they’re literally gone in a second. If you hit refresh to log in even one second late, you’re behind 8,000 other folks. People are driving 2-3 hours to rural counties for shots because they have too many. It feels very political that we’re not getting them assigned based on population size.

          We have friends in rural counties where every person in their family is fully vaccinated because there were so many extra doses. Meanwhile, my husband and I just got our first shots this week and we’ll wait in the lottery for our kids on Monday (they both work during the time appointment slots are released). It’s really hard to not be bitter when I hear about younger, healthier people being vaccinated and being able to travel and go to bars, etc. I’m trying to be happy that they’re vaccinated so now the activities they’ve been doing all along as less risk to others, but still, ugh!

    6. JKateM*

      It not only depends on state but also regions within states in some cases. In my county, anyone over 16 can sign up for a vaccine and there seem to be plenty available (it might be a week or 2 to get an appointment). In a large metropolitan area about an hour away, they are having a lot of trouble getting the vaccines even for group 1 eligible individuals (our employees are considered long term care workers). It’s very frustrating.

    7. Malarkey01*

      Maeve- I lived in a state that is now open 16+ even though we were told September, then June, then May, then suddenly everyone. Just in case it helps, the “state” doesn’t have enough supply here and still do some triaging, but the grocery stores and pharmacies do have supply and don’t sort supply/need. The appointments for a lot of them tend to drop at midnight or 1 am, and if you’re willing to drive an hour the availability shoots way up. Only adding in case this does help answer how some may be getting it (and figuring out how to get medical care was not a skill I thought I’d need)

      1. Maeve*

        My state isn’t even to frontline workers yet–it’s going to be a while! I know some people have gotten extras, some people have very specific life circumstances (like they volunteer at a prison, or are a caregiver for someone), and some people I suspect are lying to get them though of course I haven’t asked and don’t know for sure. I have been following eligibility extremely closely because when I can get vaxxed (ethically) is like 100% of what I think about.

        1. Malarkey01*

          That does stink. It was weird for me too that the state Im in had my phase marked as fall 2021, then 2 weeks ago announced they were combining the phases in front of me together and opening immediately and then announced a week ago that the doors were wide open for everyone. I think it just became too much work prioritizing, the divide between rural/urban meant some areas had everyone done and others were just starting and with the May 1st deadline approaching they thought WTH. Good luck!

    8. Percysowner*

      It’s no one’s business if you have been vaccinated. As a tip for when you are eligible. Someone tweeted that they Googled “Trump wins by landslide in Ohio”, found out the counties where he won by a landslide and got an appointment almost immediately in one of the landslide counties. So, maybe you can find one within driving distance?

      1. Bananag*

        I am in a red county in Ohio. I saw something on social media last Friday about clinics organized by my county health department. I created an account, choose a time block/location, and received an email within an hour saying that my appointment was Tuesday at 4:55. Maybe a five minute drive from my house. I had not tried to get an appointment before this. I qualified once Ohio opened it up to everyone 16+ which was Monday.

      2. EchoGirl*

        I wonder if that’s because the distribution is skewed or because that group overlaps so significantly with the anti-vax and Covid denier crowds so people in those areas aren’t signing up. Either seems possible.

    9. Nikki*

      Yes, I’m high-risk and have been extremely careful, so everyone is asking me when I’ll be vaccinated.
      At this point my entire family has been vaccinated and I’m still not eligible in my state. I’m so grateful they have the vaccine, but the situation sure is frustrating!

      People I know have actively been encouraging me to lie to get the vaccine sooner. Yikes. I want the vaccine, but not badly enough to jump the line, and TBH it does affect my opinion of people when they encourage me to lie!

      1. Happy It Isn't Always Monday*

        Same here & it is frustrating. Co-workers who are 20 years younger than me are already 2 weeks past their second dose, but I am not eligible yet!

        The main frustration is that they are getting very casual towards masking & distancing because their own risk is lower now. Our company & city has not loosened those guidelines yet.

    10. I Wrote This in the Bathroom*

      and my state won’t have enough vaccines for everyone until June 1

      My state had FEMA set up a mass vaccination site in the city where I live. I believe they provide up to 6,000 vaccines a day for eight weeks, and those vaccines do not come out of the state’s “bucket” – they are in addition to it. It helped immensely. That was where I got my first shot and will be getting my second. None of the pharmacies had anything available, or were in fact updated to include all eligible groups, but at the FEMA site, I was able to schedule an appointment in a matter of seconds. Hopefully they’ll make their way to your state too. Of course, it also helps that my state now has everyone over age 16 eligible, really saddened to hear that it isn’t the case with yours.

      1. Maeve*

        We have two mass vaccinations sites (one is two blocks from me), so I assume I’ll get to go there someday! But yeah, we’re not even to frontline workers being eligible yet.

    11. Sacred Ground*

      I’ve not seen it mentioned much anywhere, but on the subject of vaccine eligibility, the Veteran’s Administration is doing vaccinations at their clinics. My local clinic recently held a mass vaccination event giving the one-shot J+J vaccine to *all ages* of enrolled veterans.

      If you or anyone you know served and is enrolled with VA healthcare, let them know if they’ve not gotten a reminder from VA. If a veteran you know isn’t enrolled with VA healthcare, tell them to check it out.

  3. Canadian Girl*

    Lw 5- absolutely a day or 2 later is better. My industry same day works it’s pretty basic but someone in your position I think what you’re sending is great and I’d much prefer that in a day or two.

    Lw 1- I’d really just ask your mentee what she wants to get out of the meetings. If she really wants to learn to advocate for herself she will need to at least try some things but maybe she’s better at trying something small first rather then a deadline kind of thing. If she just wants to vent or isn’t really ready to stand up for herself maybe the meetings can be better used on where she wants to go with her career rather then advocating for herself. Good luck, timid employees can be frustrating to try to encourage to do things but if they do it’s such a great feeling for both of you.

    1. BethDH*

      There’s another good reason to wait a day or two if I’m the person you’re writing the note to: I sometimes think of additional things/people to add at that point.
      It’s some combination of my subconscious brain continuing to ponder your situation and the different configuration of events in my day, probably. 24-48 hours is pretty much the perfect time to jog that stuff loose, and a Monday email after a Friday interview is going to work better than one that arrives in my inbox at 5 on Friday.

    2. Snailing*

      I agree for LW 1 – if Hermione is just using the time to vent, that’s not really appropriate or useful long term for these mentee meetings and LW should either point that out or guide the conversation that way. And I say this with giving Hermione the benefit of the doubt – she may not realize she’s stuck in this pattern of stressing about it, venting about it, but then not acting on anything. If coaching her to do something about it isn’t working, then coach her to at least deal with the stress better and not pull others into the stress-web.

      1. OP#5*

        Hadn’t even thought of that, but thanks! Making me feel better about my turn-around time :)

        1. CM*

          As someone who is usually on the information-giving side of these discussions, an immediate thank-you is good, but if someone followed up a day or two later, or even a week later, with the kind of thoughtful response you describe, I’d really feel like the discussion was worth my time because they continued to think about it and engage.

          I’d say a day or two is COMPLETELY fine, but if you want even more time, you could also consider a same-day quick “Thanks, I really appreciated your time and insight,” and a followup sometime in the next few weeks. I would be thrilled if someone did that.

    3. Batgirl*

      I really like the idea of asking Hermione what she wants. I’d perhaps ask her what changes she wants in general; perhaps to be asked for a timeline instead of being given one to push back on. It’s one thing to just tell people to be more confident but it’s super helpful in supporting that goal if you behave proactively like their feelings and preferences matter.

  4. Aggretsuko*

    #1: Hermione definitely has spent a lot of time in an environment where she can’t talk to someone else if she’s having problems or else they will explode. Ask me how I recognize that one :P I’m extremely cautious at work, even though I’m not as bad as her. As my therapist would say, you have to have respect, love, and trust in order to be able to disagree with someone without having it become a giant drama bomb. McGonnagal needs to make sure that Hermione feels SAFE to have problems without it becoming a nuclear bomb in the office and needs to model that she won’t lose her shit if Hermione isn’t 100% perfect. I think it needs to start there.

    #2: I would just start yelling at the secretary, “CERSEI, STOP ASKING ME! I AM TRYING TO GET AN APPOINTMENT EVERY DAMN DAY AND I STILL HAVEN’T BEEN ABLE TO GET ONE YET! YOUR NAGGING ME EVERY GODDAMN DAY IS ONLY MAKING ME FEEL SHITTIER ABOUT NOT MANAGING TO GET ONE YET! I WILL BLOODY WELL LET YOU KNOW WHEN I MANAGE IT, OKAY?!?!!”
    …my therapist has also advocated for sometimes just having moments like that because they have managed to shut people up when she lost it :P
    But seriously, I feel like it needs to be pointed out to Cersei that it’s not easy peasy for everyone to GET an appointment and constantly nagging about it is only making things worse emotionally for you. That’s an entirely reasonable thing to point out if she is doing this daily. I’m assuming she does it to everyone and not just to you?

    1. Pennyworth*

      I’d be sorely tempted to tell the secretary that I am having trouble getting a vaccination appointment because people like her keep jumping the queue.

      1. IT project manager*

        That’s exactly what I was thinking. I just got my first shot today, became eligible yesterday. But I’ve heard people say they got their shot in my area and “no questions asked”. Yeah they weren’t asking at the site how you were eligible but you had to answer an online question to verify you were eligible to get the appointment so those people lied to get their shots.

        And since OP can’t get an appointment even though eligible but the secretary lied to get one, I want to flat out tell her because of people who lie to get an appointment I can’t get one

        1. PollyQ*

          Not necessarily lying. I got a 1st shot, for which I was legitimately eligible based on my medical conditions, without answering any health questions, either at signup or at delivery.

          1. Snailing*

            Yeah I feel like there’s a lot of low-key shaming in this thread toward people who are ineligible but still got the shot. Absolutely in LW’s secretary’s case, is she straight up lied to get it, that’s shady. But depending on your state, you may still get offered a shot while ineligible, and in that case, why turn it down if there’s a high chance it’ll go to waste anyway?

            I know plenty people in my state who are not eligible but were offered a slot through our state list or were able to get one about to expire at a pharmacy. They never lied to get it, but I don’t think it’s fair to shame them for getting it in those circumstances. People gotta protect themselves!

            1. Maeve*

              I think if you’re offered the shot (without lying about eligibility, of course) you should take it! I think it’s just kind of maddening watching so many people get vaccinated and not understand how they were able to do it–and of course the details are not my business so I just continue not knowing. I don’t think they’re wrong to get vaccinated, I just want to be vaccinated!

          2. Kippy*

            I live in a state that’s now open to anyone over the age of 16. When I got my first shot on Monday, the facility was probably only at 30% capacity. There’s daily articles in the local news about the large numbers, including frontline workers and health care workers, refusing to get a shot. Based on what I’m seeing “herd capacity” is not going to happen for a very long time. I can’t get upset about folks stretching the truth to get a shot. At least they’re doing it.

            1. I Wrote This in the Bathroom*

              An artist I follow on social media posted yesterday about getting a shot (he’s in his early 30s). Someone else from his state then commented that a lot of the people in the state are refusing to get theirs, which is why anyone who’s eligible and wants one can easily get one. Agree that this is terrifying. I’d like to visit that state again someday, but would not feel comfortable doing it if most of its residents aren’t vaccinated.

        2. Loraine*

          Could also reply with just “I’m not one to jump the queue”. Which would keep the shaming, is the truth but not reveal anything about the when or the why of the vaccination.

          1. Rusty Shackelford*

            Hee! “No, the only way I could get one at this point is to lie, and I’m not going to do that.”

          2. Exhausted Trope*

            I like this idea but I think nosy secretary would be totally unfazed by that response. If she admitted to lying to get the vaccine she won’t be shamed by this. She might even encourage LP to do the same.

        3. Jackalope*

          I’ve totally had conversations like that with people sharing my husband’s experience. He got his shot the day after he became eligible, and showed up to his appointment with eligibility letter in hand, ready to give what he assumed was needed documentation. They just ignored it and gave him a form to fill out, and then moved on. We were both surprised. You may have been referring to conversations with people bragging about getting their shots through lying, and if so I get your frustration, but not having to prove that you’re eligible doesn’t mean you’re not eligible.

      2. Mina, The Company Prom Queen*

        I think that’s a great idea! Of that secretary is rude enough to nag OP about getting the vaccine, I think it’s perfectly appropriate for OP to smile and say exactly that.

      3. tamarack and fireweed*

        Well, this sort of thing can backfire. Someone can be 100% correctly eligible and an asshole.

        We should all be meticulous about that. The LW could say “I would have to jump the queue,” but that would only be a good answer for a day. What they want is to shut down the secretary for good, or at least for a while, and for that Alison’s advice is better. Whether or not the LW is eligible/vaccinated, or the secretary is eligible/vaccinated is immaterial to that.

    2. Speaks to Dragonflies*

      I like this approach, but yelling may be over the top for OP’s environment. These are the times to go all Zinda, his face black, his eyes red, and in the lowest, deepest voice that can be dredged up tell the secretary that “When it becomes your concern, you will be notified. Untill then, drop it.” But that’s just me. If the loud approach will fly,it seems likely to work though.

      1. LW2 (am I vaccinated yet???)*

        Yelling might not fit with our very quiet office, but I enjoyed the thought of it! And, no, she doesn’t ask everyone. Just me.

        She has access to my calendar and likely knows how often I go to the doctor. She’s been trying to weasel that information out of me so I’m guessing this is another angle.

        Which, I do believe she thinks she has the best of intentions. It isn’t coming across that way.

        1. Rebecca1*

          Oh that’s a whole new angle. She is trying to figure out what your condition is by finding out if it makes you eligible for a vaccine. That’s really nosy.

        2. merope*

          If she has access to your calendar, it sounds like it is time to change any out-of-office appointment (doctor, dentist, meeting with a client, preparing for alien invasion) to the most neutral catch-all you can think of. If she needs to reach you, that is what cell phones are for. But it doesn’t seem like she needs to know what you are doing at all times.

          1. Joielle*

            Yeah, I just put “appointment” for anytime I’m out of the office for part of the day. Doctor, dentist, lunch with a friend, mid-day fitness class, letting the plumber in, it’s all an appointment. If I’m gone for a full day I put “PTO.”

        3. EPLawyer*

          The issue isn’t that she is asking that you are vaccinated. The issue is THE SECRETARY is trying to get your personal medical information when she has no need to know it. The vaccination question is the current sign of the big problem. You need to shut down the BIG problem or it will continue in some form or another. You need to tell Secretary in no uncertain terms that your private information is private and will not be shared with her. You need to inform her she is not to ask you for private information of ANY KIND, again.

          1. LW2 (am I vaccinated yet???)**

            I’ve been trying to for a year now. I have to block the time on my calendar because it shuts off availability for automated appointment slots. It took me a while to realize she was asking about doctors because of my calendar (I usually just put the doctors name and nothing else) — when she slipped up and asked why I was seeing Dr xx the (specialist) to which I asked in bewilderment “how did you know that” and she mentioned my calendar (and I have no proof but reason to suspect she googled the name). After which I made the switch to “hold – out of office” and tracking who I am going to on another private calendar.

            To which she still asks where I’m going. I’ve been trying to breezy “just out” or “I’ll be back at 2!” But my office door opens to her desk so the conversation continues unless I shut my door (which she also will knock on to get me to open to talk to her)

            I’ve brought it up to my boss before but she’s really not the best at managing the people side of things. (Great at managing work, just people…not so much).

            I’m relatively open about my medical condition with my boss and another person in the office but I don’t want the whole world to know!

            1. Dwight Schrute*

              Good lord she sounds exhausting. I think it’s time for a more firm stop asking me about this conversation since she can’t seem to take the polite hints you’ve been dropping. At some point if she continues to ask you if you’ve repeatedly asked her to stop it becomes harassing you for a medical condition and an HR problem no? Alison or commenters please correct me if I’m wrong!

              1. EPLawyer*

                This. You have not explicitly told her to stop. Because you think that would be rude. So you keep hoping when you don’t supply the information she will get the hint. She will NOT. Not giving her the informatin just means she will keep asking until you do. An explicit statement of “I will not be telling why I am leaving the office so please stop asking” needs to be said. At that point, you can tell your boss that you DID tell her stop, not just hinted at it or wished she would but actually told her. That then becomes a performance problem to be addressed.

                This is a case of use your words.

              2. AnonEMoose*

                Exhausting is a good word for it; from the description, Secretary sounds a lot like the receptionist one place I used to work. She got kind of obsessed with whoever was the newest employee in the office, and constantly want to know what that person was doing, etc.

                It got to the point that I finally said something to my boss about it, because I was so uncomfortable with Receptionist constantly asking me about Newer Employee. It was just weird…I mean, yes, she needed to know if we weren’t in the office, but not what we were doing every minute of the day!

                I eventually ended up getting fired from that job, and walked out with half my brain going “Crap, just lost my job, now what?!” and the other half going “You mean I don’t have to go back?” Even at the time, it was kind of a relief, and I’m in a much better position now.

            2. pancakes*

              That is a bold question even for a shameless busybody. It’s rude enough that I think it would’ve been appropriate to get sharp with her and say something along the lines of, “I can’t imagine why you’d think that’s any of your business.”

            3. commonsensesometimesmakessense*

              Do you have HR? Because if you do and they are remotely effective, they should shut this down quickly. It could very well lead to a case of creating a hostile work environment due to a real or even perceived disability. Also, you will want to point out that you spoke to your manager and that nothing has changed.

              That said, you need to have a conversation with the secretary telling her point blank that you do not appreciate her asking about your personal medical information, that you have no intention of disclosing it, and that you need her to stop bothering you about it. HR will definitely ask if you have told her not to do it directly and probably advise you to do that before they take steps. But it still might be worthwhile to talk to them first and say that you are willing to take that action, but you are expecting retaliation, just as a head’s up.

              If your boss is the only higher up you can go to about this, then I think you still need to address the secretary directly, but also tell your boss what you said and explain your concerns about retaliation – “I wanted to tell you so that you can be prepared. I know you would not want to be caught unaware when you surely would want to put a stop to that type of behavior right away” – in other words, not really acknowledging the option of her not addressing retaliation. Also maybe use some choice phrasing of the kind Allison likes to recommend, “I find these intrusive questions into my medical information to be invasive and at times almost harassment, since she keeps pressing. Plus, I am worried that we are opening ourselves up to some big legal issues if this type of behavior continues – as you know, the ADA prohibits harassment or discrimination over even a perceived disability, and they hold the company liable even if it’s coming from an employee and not a manager, simply for not shutting it down. We don’t want to find ourselves in an awkward position, so it is best to address this now.” – the “we” language is key here; it’s not a threat, because we are on the same team and I just want to make sure we, the company, do not experience any problems!

            4. Batgirl*

              I always bold face lie to a busybody and make sure to have a reaction, such as making an ‘ugh’ face. “Did you go to the doctor?” “No”. “Oh your calendar suggested you did..” (Make an ‘ugh’ or a ‘wow’ face) “Well I’m really careful about what I put on the calendar because I’m very private.” If you get asked: “why the face?” Just say you weren’t expecting anyone to ask you something private like that.
              I do work with one of these people and it’s not that they can’t take a hint, they just think doctors etc are not private things and that they should be asking if there’s reason to think you’re not ok or worried. It’s nosiness too absolutely, but they think it’s a socially acceptable kind. I’ve had success with “If you’re worried about my health you only have to ask how I’m feeling. I don’t go into detail about my privacy anyway”. Sometimes though, the boss just has to spell it out.

            5. tamarack and fireweed*

              Ugh, I wrote a previous comment before I saw that.

              Whether or not she’s asking about COVID vaccines, THIS needs shutting down even more! It’s none of her bloody business, and I’d really suggest becoming quite assertive about it. Maybe with HR if that’s an option – this secretary really needs a clear reminder of boundaries.

        4. Mockingjay*

          Oh hell no. Shut this down now. Set all appointments to Private/shows as Busy and put the info in the body of each item instead so only you can see the details.

          Your manager needs to make it crystal clear that nosy Hermione may not think, speculate, or know about your private medical appointments.

          1. Mockingjay*

            Should have hit Refresh. Since Manager isn’t managing, I’d address it with Hermione directly: “H, you seem very invested in my schedule and private life, including medical matters. 1) Manager is aware of and has approved my schedule. 2) Stop asking about whether I’m vaccinated. My medical details are private, please respect that.”

            If Hermione freezes you out, well, if it doesn’t directly affect your work, shrug it off. If her attitude does affect your work (doesn’t pass on messages, doesn’t do thing), plop that straight into Manager’s lap. Redirect, don’t accept.

            The Hermiones of the world can really suck energy out of jobs you like, can’t they? I’m sorry you’re dealing with her.

            1. Mockingjay*

              And I used Hermione from letter 1 instead of Secretary from Letter 2. Doh! *goes to get more coffee*

            2. LW2 (am I vaccinated yet???)**

              I’d like to make it private, and in fact did so initially. Then she complained to my boss that she couldn’t see so she couldn’t schedule things for me. Then my boss asked me to share my calendar. When I pointed out what was happening my boss just told me to change it so it wasn’t obvious why I was out. It’s part of the secretaries responsibilities to know loosely where we all are (she just takes it too far).

              I’m getting that it’s time to raise this in a more stern fashion with my boss.

              1. Where’s the Orchestra?*

                Yeah – I would definitely raise this again with boss. Like some others have said above make sure you have explicitly told he to stop with the health interrogations, and then go to boss when the next one starts and let him know she is unwilling to accept requests to stop.

                And also echoing others – she sounds exhausting to deal with. Availability knowledge, yes – why you aren’t availability, nope not always (to account for things she has booked for you).

                1. tangerineRose*

                  I think this office needs a different secretary. Maybe this secretary would fit in better at a more toxic place.

              2. Rusty Shackelford*

                I don’t know what calendar you’re using, but in Outlook I think you have a setting that simply marks appointments as “unavailable” to anyone but you.

                1. LW2 (am I vaccinated yet???)*

                  It’s Google Calendar. I’ve been trying but there isn’t a way for her to be able to “manage” my appointments while still being able to block off certain ones (I thought that was how it worked but tested it to find out that’s not the case?). Any Google Calendar Wiz have a solution? I just have stopped recording it on my work calendar and just listing it as out of office.

              3. commonsensesometimesmakessense*

                At my agency, we have a separate google calendar for the department. When we are out, we add something to that calendar, like LastName – SL, for sick leave, or LastName-AL, for annual leave. No one really asks about it, but we can all see when the other people in our department are out. We can keep our personal calendars private for our own purposes. I think that makes more sense than having to share your personal work calendar with anyone and everyone. Plus, there are a lot of things that go on my personal work calendar that not everyone needs to see. If I have a call scheduled with opposing counsel to work on a settlement, it really isn’t something that everyone needs to see cluttering up the work calendar. Plus I set myself task reminders. It just makes more sense to have your own private way of organizing your calendar and a separate calendar for the department.

                If they won’t do something like that, I would just block off time in google calendar and say “out of office” and find another calendar program to use for your real work calendar.

              4. Adultiest Adult*

                My boss switched to listing personal appointments (which are usually but not always doctor’s appointments) as just that: “personal” rather than Dr. X on her calendar because she doesn’t want her boss to know. And then usually just tells me where she’s going, not that I really need to know either. In this day and age, knowing whether someone is accessible by phone or not should be sufficient.

                Google Calendar will allow you to set certain appointments as Private when you set them, so that the details will only display publicly to you and anyone you include, but that will only work for someone who doesn’t have full, unrestricted access to your calendar, so it may not shut out nosy secretary, though I would argue you should have every right to do that. Time to push back on your boss on that and limit what she can see!

              5. kittymommy*

                If you’re on Outlook you can still share your calendar (all the way up to editor) and still classify things as private. In order to override it one actually has to log into the the system as the account holder and manually go into the settings of outlook to make the other person a delegate for privacy settings. (This is what I had to do for some people I work for.)

            3. Mina, The Company Prom Queen*

              Yeah, the secretary sounds like Self-Appointed Hall Monitor at my previous job. Don’t let her get away with it. People like that suck the life out of any office.

        5. TeapotNinja*

          If I was in your shoes, I’d overshare next time she asks about your doctor’s appointments.

          Come up with a most disgusting thing you could tell her with a straight face and then in excruciating detail tell her everything you’re going through. If that doesn’t shut her questions up, I don’t know what else will.

          I’d be tempted to tell her nosy secretaries trigger explosive diarrhea episodes.

        6. Nancy Hammond*

          Depending on the calendar app, you may be able to hide the details of your appointment, so she can see “busy” but not what you are doing. We have Outlook and my default is open calendar, but I can make specific meetings private so the details are not visible to others.

          A response I have used with people asking too-personal questions is: “I’m not going to discuss that with you.” Said matter-of-factly, not angrily, it is quite effective.

        7. Chocolate carrot*

          Does your work calendar system have a private option? I can add things in all detail and those who have access to my calendar just see a block.

          If you do have that option, Mark anything they don’t need details of as private (so anything they don’t need to manage or interpret the importance of). That way they won’t be able to pick out your medical appointments from anywhere else.

          Don’t go screaming at your secretary. They would have a legitimate complaint against you for that. I screamed because they were annoying is not an appropriate response. I wouldn’t keep on someone who screams at their admin as that creates a liability for me. I get the instinct to fantasise but it’s never a good idea for a help comment to talk about responding inappropriately in the workplace. It needs to be said that that is not ok.

          Also, don’t go accusing your secretary of anything regarding their vaccination. While it is entirely likely that the lied to get the vaccination. There’s a slim chance that they were genuinely eligible and lied to keep the reason for their eligibility secret. Ultimately it has nothing to do with you why they were vaccinated. It’s not your place as a colleague to sit in judgement here, and you’ll just cause trouble if you do. I get that it is upsetting to see this happening. Because supplies are limited so it does take from others. But this isn’t something that calls for you to make it your business why she is vaccinated.

          Focus on getting their inappropriate behaviour to stop rather than petty point scoring.

    3. MK*

      I disagree all the time with people I hardly know (and so don’t have love, respect and trust with) and it doesn’t become a drama bomb because we are all adults and professionals. I don’t know if the problem here is that the office environment is such that any disagreement escalates to drama, in which case McGonagall needs to fix that, or that Hermione is so timid she wants to avoid any and all conflict, no matter how mild. If it’s the second, frankly I wouldn’t be sorry to lose an employee who needs me to be her therapist, no matter how brilliant her work.

      1. u know*

        This approach sounds like a good way to write off a talented employee without even really trying to put them in a more supportive situation. maybe give them extra time off and try having them report to someone else and see if that fixes things. kinda sounds like OP1 has tried doing nothing and it hasn’t helped. ‍♀️

      2. Aggretsuko*

        I don’t know on Hermione’s office, but I would guess that Hermione grew up in a drama bomb environment. I absolutely want to avoid even the slightest of ruffled feathers in my life due to that.

  5. CuriousGeorge*

    Lw4 – I am wondering what sparked grandboss to bring this up. Is it possible boss saw something in LW’s email and brought it up to grandboss? Just curious about the context of why grandboss suddenly realized this was still happening and addressed it…

      1. Ask a Manager* Post author

        I don’t think it’s odd that the grandboss is so upset. I’d be awfully concerned if a manager under me had been doing this too! It’s just so shady.

        1. Nancy Hammond*

          Eh, I’m with LW on this. My business email is company property and there’s nothing in it that would be an issue if my supervisor read it. I don’t think anyone is monitoring my email because they don’t have time, that’s why they pay me to work for them. But they could, and I never forget it.

        2. JB*

          Is it? I would neither be shocked nor particularly upset in LW4’s position either. It’s work email, not personal email, I don’t have any expectations of privacy in that email inbox even when nobody is actively monitoring it. For all I know someone in IT is reading my emails for entertainment, and that wouldn’t bother me either.

          I can see being upset because it’s a bad use of the manager’s time (because either LW needs to be micromanaged and therefor needs to be coached/replaced, or LW does not need to be micromanaged and it’s all a waste of time, even just to trash the emails) but I don’t see it as shady at all. Unless the manager is actively going around gossipping about whatever she’s seeing in the emails, I don’t see a real problem.

      2. LW#4 Email Forward Queen*

        LW#4 here. My boss called me apologizing profusely and I accepted her apology. I still don’t know how my grandboss found out about the email forwarding, I assume my boss brought it up casually in conversation not realizing how bad it would look. My boss said the emails came to her inbox and she moved them manually to her trash folder without reading them. As for the “how does she have time” question – she’s a workaholic and works most evenings and weekends. I contacted IT and the forwarding has now been removed.

        1. Threeve*

          It’s hard to believe she never absolutely never read them but didn’t bother for months to stop them flooding her inbox. That excuse is a little shady.

          1. Green great dragon*

            Oh, I can see it. Every day, it’s easier to move a bunch of emails than to contact IT.

            1. TechWorker*

              Especially if they’re in one folder and deleting them all is 2 clicks or something. I’m an ‘inbox zero’ person and I have multiple folders that I mark as read without reading, every day (automated emails where I might want to go back and check something but 99.9% of the time it isn’t info I need).

          2. Mango Is Not For You*

            Eh, confession time: I did this when one of my reports went out on maternity leave. We set up the auto-forwarding and I set up a folder where all the emails were directed. When she came back, I trashed the content and archived the folder…but forgot to turn off the forwarding. I get so many emails in a day, and am on so many distro lists and vendor lists and whatnot that my inbox always says something like 14,000 unread emails. I just never noticed that I was still getting hers since they never hit my main inbox. It didn’t take us MONTHS to figure it out, but it was like 4-6 weeks.

          3. I Wrote This in the Bathroom*

            I am also guessing that she set them up to go to a separate folder, and then forgot that the folder existed.

          4. WhatNow*

            Based on what LW #4 has said, this strikes me as more of an email management issue. For those of us who obsessively manage our inboxes (inbox zero at all costs!) receiving someone else’s emails seems inconceivable! But I can imagine a scenario where someone who is not a militant email organization type person would just ignore the messages.

        2. your LGBTQ work friend*

          I affirm your original assessment: This is not a big deal. Boss was probably wondering when you’d get around to turning off the forwarding, and just deleting the messages. It’s kind of weird that people see this as somehow shady, as if the onus was somehow on your boss to turn off your email forwarding. That’s on you! Better check to make sure your auto-replies aren’t still going out too!

        3. Clisby*

          I get all that – but how did you not realize your email was being auto-forwarded? Did you not wonder why you weren’t getting any email? Or does your email program send it to you *and* auto-forward it?

          1. tamarack and fireweed*

            Auto-forwarded email isn’t typically removed from your inbox. Just like when you manually forward something it doesn’t disappear …

        4. tamarack and fireweed*

          ¯\_(ツ)_/¯ It’s unclear to me how your boss could not have been aware, but then, some single-minded people just don’t stop and think when they should. “Extra email in my inbox? In the trash folder it goes, and good is.”

          It is good that once made aware by her boss, your boss had the impulse to apologize to you. And hopefully she learned something about awareness of what’s appropriate and what is (or comes across as) sneaky.

          If you trust that’s all there is to it, there’s no problem with you not being more upset about it, and for everything to continue smoothly! (And also, for this to be between your boss and your grandboss.) Just … in most case this sort of thing means a bigger failure than what it appears to be here.

          1. Hekko*

            There’s a lot of people who copy unnecessary recipients on e-mails, and also a lot of people who never check to whom an e-mail is addressed and who is copied on it. Boss could have easily thought she was copied on these e-mails, especially if OP doesn’t get tons of e-mails every day.

    1. turquoisecow*

      I was wondering if boss was complaining to grandboss and grandboss took it upon herself to complain to OP. But that would be extremely passive aggressive of the boss, and it doesn’t sound like she’s that kind of person.

      1. Crowley*

        Pretty sure OP was still getting emails, they were just also being forwarded to their manager. I’ve never known of an auto-forward that also deleted the emails from the intended recipient or prevented than from arriving at all.

      2. Myrin*

        That’s what I wondered at first, too, but I think all of these emails arrive in OP’s inbox first, they just also get forwarded to boss’s inbox.

      3. JB*

        That’s not how auto-forwarding generally works. The original recipient still also gets the email.

    2. EPLawyer*

      GB knows Boss is a micromanager. Which is why the emails were still forwarded, so the Boss can be sure the work is getting done. GB is trying to work on Boss to be less micromanaging and is upset that the Boss did something so micromanaging (probably specifically circumventing something GB told Boss NOT to do).

      Age old question with micromanaging bosses – how do they have TIME to read OP’s emails and do their own job?

      1. Lacey*

        Yeah, that’s what I assumed a s well. And man, the OP must the most laid back person ever. I’m pretty laid back, but that would IRK me. Even though I would never write anything in an email that my manager can’t see, Even though lots of my communications with people actually are seen by a variety of other people because that’s just how the work flow is.

        1. Myrin*

          That, and it doesn’t sound like boss ever did anything with the emails (other than moving them into the trash folder, as OP reveals in a comment) like grill OP about X or berate her when Y wasn’t yet done. Can you be a micromanager without ever even mentioning the emails whose content you supposedly use to micromanage?

  6. Roci*

    #1: Does Hermione have any good relationships with any of her peers or other team members? Can she communicate with them, either to vent or to get help with work?

    It sounds like a lot of this is with Hermione herself and there is a limit to what you can do. But I think there is more that McGonagall can do to actively manage Hermione, both (1) to make her comfortable and (2) to make sure deadlines aren’t missed.

    Re: (1), you say “McGonagall and I are peers, and I know for a fact that she is an incredibly supportive leader who would not react badly to Hermione speaking up at the right time.” How does she react when it’s the wrong time–is it mortifying enough that Hermione’s takeaway is “better not to say anything”? You know McGonagall as a peer, but she is Hermione’s boss. I know many people come across as brusque or strong-minded, and you can shrug it off in a peer, but it can be terrifying when you’re trying to read and please that person. Has Hermione seen that support given to herself/others when they make a mistake? Does McGonagall pass that glowing feedback on to Hermione?

    Re: (2) if the issue causing Hermione’s stress is her workload and unreasonable deadlines, McGonagall has a responsibility to be more active in checking in throughout the process, or set longer deadlines in the first place, or otherwise restructure the process so that it’s not dependent on Hermione telling her boss “no.” Regardless of Hermione’s personal growth, the work still has to get done. Maybe have someone else set the deadlines?

    Ultimately you can’t solve either of these, but I think you could check in with McGonagall–is she aware her employee is terrified of her? What is she doing about it, and how much of that is visible to Hermione? You are in a very special position as someone who can safely speak truth to McGonagall, who Hermione actually trusts and opens up to. I think it will be easier for Hermione to speak up for herself if she sees it’s safe to do so.

    1. Greige*

      Re (2): Thanks for saying that. I wasn’t sure whether I was the only one wondering why Hermione is in this situation so often to begin with. If these deadlines are easy enough to push back, why are they presented as hard deadlines?
      I use priority levels with my team and reserve deadlines for when there is an external reason something should get done at a certain time, so maybe this is just a management style. But if Heemione is like me and assumes there is a good reason for deadlines, that might be part of her hesitancy to push back. Of course, if something is impossible, she should say so, but she might not be great at judging that all the time.

      1. twocents*

        I wonder if it’s just that Hermoine has not pushed back and stressed out to meet (most) deadlines, and being timid, internalized the stress so it’s not apparent.

        End result: since there’s no indication there’s a problem, the deadlines have now been established as perfectly reasonable.

    2. EPLawyer*

      Yeah this is more of a McGonagall problem than a Hermione problem. Hermione shouldn’t HAVE to speak up often about deadline (even the best boss can let something slip). McGonagall should be setting the deadlines while knowing what is currently on everyone’s plate. Then checking in throughout the process instead of trusting that someone will speak up if there’s a problem. People often don’t, even if they aren’t timid. The assumption of “well no one is saying anything so everything is going along fine” is so often wrong.

      1. Name Required*

        It depends on what Hermione’s job is. If she’s responsible for the work and she knows it’s not going to get done, she does have a responsibility to speak up about the deadline even if McGonagall also has a responsiblity to ensure there are enough health indicators against the work to see when it’s getting derailed. But many managers aren’t project managers for the work under them, and it’s the job of the employee to manage their own work and use their manager as a resource to remove barriers, access training, and to advocate for/report against the work of the team as a whole at a high level. That might not be a good fit for Hermione, and she might be more comfortable in a role where she does work in a queue or as-it-comes without managing projects over time. I’d also be surprised if someone as conflict-avoidant as Hermione isn’t also afraid to speak truthfully about timelines when directly asked, in fear of being punished or seen as a poor employee. McGonagall could very well be asking and repeatedly, and I’d expect she would’t get an accurate response based on the fear response from the employee.

    3. Generic Name*

      This is such a good point. I think McGonnagal could be doing more to better manage Hermione. I’ve seen a similar dynamic play out at my company. For a long time, the ceo was everyone’s boss but it was the project managers who assigned people work. The PMs would assign work to who they wanted working in their projects and it was supposed to be the workers responsibility to “push back” on the PMs when there were issues with deadlines or priorities and workloads. It was a terrible system because in practice, many PMs would just say “too bad” when you tried to push back. Prioritizing work was also a problem. It was finally solved when we formed a layer of management between the ceo and everyone else.

      It might not be too much to expect a mid- or senior level person would speak up if a deadline is unreasonable, or if they have too much on their plate, but I really think it’s inappropriate to expect a very junior (and timid to boot) employee to say no to their boss when their boss assigns work. The boss really should be sitting down with Hermione to assess her work load and figure out what can get done in a reasonable timeframe, and either extend deadlines or give her work to someone else. Then McGonnagal needs to check in frequently on status to see if anything needs adjusting. It’s hounds like she’s too hands off and is thinking no news is good news. That approach often works well with seasoned employees, but less experienced folk often need a more hands on approach.

      1. Rusty Shackelford*

        I’d like to see McGonnagal build in an opportunity to Hermione to say no, if that’s not happening already. If she’s literally saying “I need this by Friday,” she might expect Hermione to say “I can’t do that, how about Monday?” Or maybe she’s making softer requests, like “Can you do this by Friday,” but Hermione is still interpreting them as demands-posing-as-questions. I wonder if something like “Can you do this by Friday, or do you need more time?” would be helpful? Or even just asking “How long would you need to do X?”

        (Honestly, I think this is a Hermione problem, not a McGonnagal problem, assuming she’s a good manager as the LW says. But it might need to be fixed on the McGonnagal end anyway.)

        1. Batgirl*

          I’m really puzzled why McGonagall hasn’t just restarted rephrasing the deadlines. Instead of going straight to “deadline is x” why not just say “what’s a reasonable deadline for x” before setting one? I think if Hermione needs therapy to interact professionally that’s one thing, but seeing what effect simply rephrasing would have would be my first stop.

  7. staceyizme*

    On the email forward- you should decide what, if anything, you want before addressing it. An apology? An explanation? A work around to prevent recurrence? Then it would be worth addressing. Maybe your boss saw something troubling and wanted to track its development? Maybe her inner child can’t resist illicit access? Maybe it was an oversight? You’re probably in the second best position to know since you’re familiar with both the content of your email history and your boss. But it might be worth asking, as long as you’re clear on what you’re asking for.

  8. Maggie*

    I find myself mostly in awe of the comment that there was nothing personal in the email being forwarded. My first thought is, “wow, good for you, LW!” My second thought is, “This kind of nightmare is exactly why I should keep writing things like call me at # to discuss this in more detail,” because it’s just good professional judgment to not put my shit talking in writing.

    1. HiHiHi*

      The modern reality, unfortunately. I’m afraid to put anything more substantive than “call me” in an email, unless it is a blatantly transparent CYA.
      I hate modern times, sometimes.

    2. I Wrote This in the Bathroom*

      The letter and this comment reminded me of how, once at OldJob, I was given an assignment to remote into each of the training room’s computers to do a software upgrade. I thought the training room was empty, but apparently there was a training class going on in there. I remoted into a PC and was greeted by an open email on the screen, from coworker X to coworker Y, describing in detail the hot and steamy things X had done, or wanted to do, to Y. I had never closed out of a remote connection so fast. At least I didn’t know either of those people. Those were simpler times, for sure. People used to use work email for everything in the times before cell phones, messenger apps, and IM. My email (both in my work and personal accounts ) is awfully boring and businesslike these days.

    3. Chc34*

      The advice I’ve been given is “never put anything in a work email you wouldn’t want read out loud at a deposition,” lol

      1. Kippy*

        I’m a paralegal and my first job, about 15 years ago, involved me reading thousands of emails from our corporate client for responsiveness. I spent weeks reading every email including horrible (racist, sexist) memes, personal notes, and generally horribleness.

        Don’t send it via work email (or IM, text, or anything) if you don’t want it read and judged by a series of legal professionals later.

        1. Rae*

          Then there was the guy that used his work email to send pictures celebrating “National Boob Day”. That was a weird week.

  9. a tired lil' bean*

    Regarding #1: when I first started my first job out of college, I was extremely timid and reticent at work, because I thought that a good employee should always be quiet and agreeable. In reality, I was missing deadlines and failing to escalate problems to my supervisor. I didn’t shift my behavior until I realized that being timid was an actual performance problem.

    When the framing switched from “a good employee is agreeable and never encounters any problems” to “a good employee proactively communicates when they run into a problem”, I started advocating for myself + proactively communicating with my boss. It was SO much better to deal with my supervisor’s slight annoyance when I raised concerns about my capacity, rather than her sheer panic because I had dropped the ball and forgotten to complete a critical task.

    1. Audrey II*

      I came here to say something similar, but from the manager’s POV. I had a very timid employee and honestly, the thing that finally made her speak up more was when she didn’t do an important ongoing task for weeks while telling me everything was good at our check-ins. I made sure not to *explode* at her, but I had to have a very serious conversation about how this was Not Acceptable and it would have been much better to clarify things with me earlier in the process. She was quite shocked and it made her withdrawn for probably the rest of the day and the day after, but ultimately it made her more proactive with me.

      I don’t know what Hermione’s role is, but with my employee her timidity started to cause other internal and external problems over time, beyond missing deadlines (interacting with coworkers, getting pushed into things she didn’t want to do, external communcations, etc.). I can’t tell what in her development is in your purview or McGonagall’s, but in my case I wished I had started managing it earlier than I did.

  10. Not A Manager*

    LW1, if you want to and this fits into your mentoring purview, you could literally loop McGonagall into the situation and role-play some scenarios with McGonagall in a cameo role, starring herself. I would encourage Hermione to start with arms-length communications via email, rather than in-person ones. With your help, she can draft an email addressing an actual situation, or a role-play situation, and send it to McGonagall for a favorable and warm response.

    Obviously this shouldn’t continue for very long, but maybe just practicing Saying The Thing And Hitting The Send Button will help her, especially if the world doesn’t immediately end when she does it.

    1. jojo*

      My thought is has this young lady had a in person work evaluation yet? Perhaps her actual supervisor can put in writing and verbally tell her what a good job she is doing. And also tell her how her not speaking up is impacting others work. Positive reinforcement of her good work habits might give her the boost she needs to be more assertive and confident.

    2. Retired Prof*

      I was wondering if OP could facilitate a discussion between Hermione & McGonagall about the expectations that Hermione would communicate any difficulties she’s having to McGonagall while getting the reality check that her boss and team think she’s doing high-quality work. And some next steps on regular checking between Hermione and her boss. Maybe if her coach is at that first meeting Hermione will be confident enough to talk with her boss and that will scaffold the employee-boss communications that should be happening without the coach involved.

      1. Malarkey01*

        To me, when you get to the point that another person has to facilitate a conversation between someone and their manager over expectations and speaking up you really have a performance problem with that employee. I can’t effectively manage someone that can’t hold a conversation with me. Absolutely bring to my attention that there’s a problem, let me know I need a clear conversation with probing questions and room for discussion, ut if Hermoine needs someone to sit in to help her speak up I don’t think I’d find it salvageable as a manager.

        1. Qwerty*

          I do this a lot so I view it more as Hermione might not have witnessed people on the successfully pushing back. It’s just a skill the Hermione needs to be guided through without feeling alone and unsupported. If the OP isn’t comfortable facilitating that conversations, she could suggest that Hermione spec out her project timelines with a senior team member, than that team member + Hermione can talk to the boss together. Once it happens successfully a couple times, she’ll be able to build on that to have those conversations with the boss solo.

          I view this the same as how I pair program with junior team members. In fact, it’s part of my training process when I’m mentoring new hires that they see me disagree with our boss so they can also witness (1) how I do it (2) what info the boss is looking for (3) how well the boss reacts to disagreement. When I was a manager, my senior employee would typically end up doing the same for new members joining the team. It can take time to build a rapport with your boss and tons of employees have bad experiences with pushing back.

          An important thing to look at is whether the rest of McGonnagall’s team feels overworked. How often do they push back on deadlines? Is Hermione the only one getting unreasonable deadlines? If so, that needs to be probed more to figure out why (needs more training, past work of meeting deadline has set unreasonable expectations, etc)

          1. Batgirl*

            Yes it’s a skill; it’s not an inherent part of anyone’s makeup. Reformulating saying “I can’t do that” as a goal, rather than being the squeeky wheel who failed to do the thing, is something you only know when you know.
            I would make it a part of a checklist of Hermione’s goals so that she has to look for opportunities to do this. “You on average need to extend a deadline once every x, would you say? By the time we next meet I hope you will have done that y times. What would you say to Macgonnagal if that needed to happen?”

        2. Oh Snap*

          Malarkey, I was thinking the same thing. Who has time for this? Assuming Mcgonagall is a good manager like OP said, it sounds like this is a performance problem for Hermione.

        3. Green great dragon*

          I think most people agree this is a performance problem! But possibly one that can be overcome. I don’t think it’s tenable long term, but it might be worth it once to set her on the right track, since she seems a pretty good employee otherwise.

        4. u know*

          Sounds like a manager problem to me. LW1 is clearly missing or overvaluing the dynamic that MG is their buddy and they aren’t looking closely enough at MG’s actions to see why Hermione has gotten to this point. Just because MG is a good boss for some doesn’t mean she is doing the work required to help Hermione succeed.

          Some questions I’d recommend asking:

          Do Hermione’s duties overlap with MG’s in any way? Is it possible that MG is either jealous of Hermione’s talent and setting her up to fail while you’re not watching?

          Are you going back far enough in your analysis of this situation to understand the roots of the problem?

          Have you really looked closely at MG’s track record or are you assuming her management style is good for everyone?

          Also, MG is Hermione’s boss. If Hermione is capable of producing top quality work, and she is telling you she is scared to talk to her boss, her boss is quite likely just a bully.

  11. Harvey JobGetter*

    Sometimes I get access to somebody else’s mailbox at work. When I no longer need it, I have to find somebody in our IT department to deactivate it. I do this, but not always right away and usually in batches because communicating with IT about this kind of thing, well.. it this isn’t our most efficient function. So sometimes I have access to somebody else’s mailbox for months after I need it. I never look. I don’t want to look. When I get around to it, I have the access turned off.

    So, maybe boss was aware of the forwarding but just didn’t bother to have it turned off because the emails were going into a designated folder. It’s not necessary for boss to have literally forgotten for this to be totally innocent.

    1. WS*

      +1, I thought the letter was going to be about how to accept an apology from the boss when the LW is pretty laid back and doesn’t mind! I would just treat it like a weird technical error and say something like, “I got IT to stop my mail forwarding to you, sorry it went on so long!” If the boss wants something different to happen, she can address it then.

      1. Annie Moose*

        This is how I feel! Yeah, LW should look into making sure the auto-forwarding is stopped now that she knows about it, but I wouldn’t automatically assume that her manager was doing this maliciously or as part of some scheme. It was likely an oversight, one of those “oh, I’ll fix that eventually” sort of things that she never got around to. Especially if she stopped actively looking at the emails when LW came back, I can easily see her simply not realizing how long it had been and that she really needed to talk to IT about it.

        And yeah… if LW’s grandboss doesn’t like it, that’s on the grandboss and manager to sort out. IMO LW’s responsibility at this point is to talk to IT and make sure the auto-forwarding is off, and then wash her hands of it!

        1. Batgirl*

          I think most of us would have an instinctual feeling of whether we’d trust our boss’s motives in this scenario. If OP trusts her boss, then I trust OP’s instincts.

  12. Harvey JobGetter*

    Alison’s interpretation is generous to Hermione, and she may be right. I tend to think Hermione is fishing to have OP talk to McGonagall for her.

    1. ceiswyn*

      That was my first thought. Because it is exactly the sort of thing I might have done.

    2. Dust Bunny*

      Same. I was this kind of timid when I was much, much, younger, and was always hoping somebody would do the uncomfortable part for me. But it’s childish to do that and it’s time Hermione figured out how to deal with it.

      But at the very least McGonagall needs to be looped in more. It doesn’t sound like there’s been a lot of direct communication about this between McGonagall and Hermione, so they’re basically trying to solve a problem through an intermediary who isn’t directly involved with the work, which is just not efficient. McGonagall needs to be the one managing this, not the LW who is not actually in a position to address it.

      1. Green great dragon*

        It’s true to say that Hermione will be a better employee if she learns to speak up more, but “it’s time” isn’t necessarily helpful. Maybe she does need more support right now than is ideal, but better to give her that support now and work towards reducing it in the future, than to say she has to learn to deal with it immediately when that is clearly not working. It seems she’s a good employee overall.

        1. Dust Bunny*

          I didn’t say she had to fix it immediately; I said she needed to figure it out, which is a process.

  13. Fancy Owl*

    I’m curious as to why Mcgonagall doesn’t seem to have a better grasp on what’s an unreasonable deadline for Hermione’s work? I would find it stressful to continually be given deadlines I can’t meet and have to push back on them now, when I have no problem being assertive. When I was a terrified new hire that would have sent me over the edge. Seems to me that having Hermione and Mcgonagall (maybe with OP mediating) sit down and hash out how long it takes to do specific task so she can be given more realistic deadlines in the future?

    1. Myrin*

      Reading the letter, it was a bit unclear to me if these deadlines are objectively tight – as in, someone who has routinely done this work well for months/years would struggle to meet them, too – or if there’s something about Hermione’s specific working stlye – like, say, she feels like everything needs to be 110% perfect before she even thinks of handing her work in, or she is just naturally a bit slower, or she stresses so much that she makes mistakes which she later has to correct – which makes them difficult to meet.

      I also wasn’t clear if McGonagall is actually aware of this deadline-related problem that Hermione has – OP says “Her team has nothing but positive feedback about Hermione’s work ethic, even though it seems like she often works overtime to try and meet a deadline (something else that causes her stress).” but I wasn’t sure if the second part of that sentence was OP’s comment on the situation or if that’s something that McGonagall actually said to OP. I have an inkling that it’s the former but if it were the latter, it would be strange for McGonagall to be aware of this specific problem of Hermione’s and yet never approach her about it.

      Regardless, I do like the suggestion in your last sentence. I’m not usually one for hand-holding but it occurs to me that maybe having her mentor there for an initial “negotiation”/talk about the topics that give her stress might help Hermione to get into the mindset of “I can and should approach McGonagall about situations like these”.

    2. Threeve*

      It would be really easy for McGonagall, in her capacity as the boss, to say, “I want you to tell me when you think you need to work overtime.”

      It’s not on McGonagall (or really OP, although she’s being doing it) to talk about why she needs to be more assertive–they should focus on changing her behavior, not the underlying issues, and that probably needs to start small and basic. So it can’t begin with “you need to speak up about your limits” because that’s an unrealistic goal for Hermione at this point. It should be a specific “your boss is telling you that you should give her a heads up about deadlines you think might require overtime.”

    3. Washi*

      I don’t know, I’ve definitely been in jobs where my manager doesn’t necessarily have all the details to know precisely how long something should take me, and the onus was on me to speak up I thought a deadline wouldn’t be realistic. Usually this would happen when first being given the assignment, and if McGonagall really is a good manager (taking OP’s word) then speaking up at that juncture shouldn’t be a big deal. I mean, obviously it is for Hermione, but what she’s being coached to do doesn’t sound unreasonable!

    4. Spencer Hastings*

      I also wonder if McGonagall is the only person who assigns Hermione work, or if she’s getting assignments from multiple managers. If it’s the latter, then that’s all the more reason to discuss with McGonagall, because no one person will know what exactly is on Hermione’s plate, except Hermione.

      So, if Hermione is currently thinking “well, McGonagall wouldn’t have assigned me this project unless she thought I could do it by next Thursday,” it may be helpful to point that out to her. That might make her feel more empowered to say something like “The TPS report I’m writing for Snape is going to take up most of my time this week, so it’s unlikely that I could finish this new one by the deadline.”

    5. Dust Bunny*

      Because supervisors don’t always know this. Mine often ask me if I can complete a task by X day/time because I do certain tasks more than they do and have a better estimate of how long the work will take.

    6. Cat Tree*

      I get the sense that these aren’t necessarily hard deadlines. Over the course of my career, I’ve learned that it’s really important to establish timing expectations on both sides. When I request something from someone else, I’ll also request timing and express how flexible that timing is. So it could be, “I need this data within one day because of XYZ important reason. Can you do that?” or “I’d like to have this in 3 weeks so I can finish my report the week after. How does that work for you?”

      The second approach often involves some negotiation. The first one occasionally does but is a lot less flexible. Of course this is all speculation, but my guess is that the boss is suggesting timelines that Hermione is expected to evaluate and negotiate, but Hermione is interpreting these requests as much less flexible than they truly are. This would make sense if she’s just out of school and used to teachers handing down assignments with specific due dates.

      Understanding your own capacity, workload, and prioritization is a super important skill to develop, just as important as advocating for yourself. But, I get the sense that Hermione is entry level, and it’s not necessarily realistic to expect that of her yet. Having a mentor is a great first step, but it sounds like McGonagall is dropping by the ball by not recognizing the needs of a new employee and helping her develop these skills.

    7. Green great dragon*

      Managers often don’t know exactly how long a task should take. And sometimes the individual doesn’t know, until they start (I’m currently into my second month of a task we merrily thought would take a day or so, because it turns out some data doesn’t actually exist…)

    8. ThatGirl*

      I don’t know how Hermione and McGonagall’s team functions, obviously, but in my job tasks are assigned from the project manager, not my direct manager. They both can see my task lists, but they don’t know if I’m having trouble finding information, or if something is unclear, or if someone is slow to get back to me, or even what my personal pace is — so I have to tell them. And they may not be fully aware of the scope of the projects either, until I get into it and realize it will take longer than originally planned.

  14. Kate, short for Bob*

    #4 I could read an opus between the lines of this one so disclaimer – I may be completely off base… Are you so comfortable with your boss being this much in your business, because she’s manoeuvred you into a bit of a parent/child dynamic? Because this is all well and good when it’s someone picking up on dropped tasks without scolding you, but the big but is that this dynamic can turn sour in a heartbeat if the ‘child’ tries to leave home (i.e. pursue a unapproved professional direction) before the ‘parent’ is ready.

    So have you got over-comfortable in this dynamic – because it is easier when someone has your back this way – to the detriment of your future independence? On the bright side, it looks like grandboss might have your back if boss does overstep, but it could be awkward to negotiate the whole thing, so be warned.

    Re #2 and the vaccine appointment – is it possible to use the secretary’s nosiness for good? Can she spend a morning on the phone, or pressing refresh on the computer, or whatever it takes to get the appointment sorted? I’m in the UK so I don’t know the process for you, but this strikes me as one time to let the intrusion go if it gets you vaccinated quicker.

    1. LW2 (am I vaccinated yet???)**

      I actually managed to get an appointment recently (thanks to my doctor!). I’m under 30, so I’d only qualify if I had certain medical conditions (I do) which are none of her business. She’s been trying to figure those out as well and I’d rather not spread that to her because it’s none of her business!

      1. Kate, short for Bob*

        Oh right, well congratulations for the appointment – I’m now 5 weeks after my first jab and even the qualified protection is a relief! But yes, liaise with your boss and squish her nosiness down hard then. Maybe even HR if there’s medical over-stepping?

      2. commonsensesometimesmakessense*

        Yeah, she is just using this to be nosy. She knows you don’t want to tell her about your medical condition, and she is not backing off. I think you need to tell her point blank that you will not be answering questions about your personal medical information, she does not need to know that information, and that you expect her to stop asking these questions and harassing you and to instead respect your privacy and act with more professionalism. I know you worry about retaliation, but I think you need to deal with that as it comes. But whatever else you do, document every circumstance and interaction. Report her to your manager by email or after reporting her, send an email to your manager memorializing what you discussed with your manager and what you told her, how she responded, etc. Keep it friendly and end it with a “thank you for your help with this!” But keep that paper trail! Because you have as big of a manager problem here as you do a secretary problem.

    2. Batgirl*

      That’s a lot of really left field psychoanalysis of OP4! The parent will stop her leaving home?! Seriously?
      I wouldn’t care if my boss forgot to unforward my emails either. I get that it’s a big deal for many and it’s bad practice, (grandboss was totally in the right) but I too would just have a hard time summoning up any outrage. “Oh no! You saw the email about the end of month reports! Before I did! How will I express my anger completely and yet professionally?!” It doesn’t take being a child to not care. She has probably just always mentally treated company email as though it’s not private.

  15. Myrin*

    I’m having a strangely hard time fully understanding #4 so maybe someone can help me out?

    OP says “While I was out, I had an auto-reply on my email telling people to contact Y staff person for Y inquiry, Z staff person for Z inquiry, and my manager for anything else. We also had incoming emails automatically forwarded to my manager.”.

    That means that every email got forwarded to manager, right? There’s not one category of emails getting the auto-reply and another one being forwarded to manager? And now, all of OP’s emails arrive in her inbox normally but her manager also receives a copy of them, right? I don’t know if I just can’t English properly this morning but I’m having a weirdly hard time parsing these two sentences together.

    1. ActuallyAutistic*

      Yes that’s what I read it ad, and what I’ve done in thr past, just so someone was monitoring my email for emergency response needed stuff

    2. LW#4 Email Forward Queen*

      LW#4 here. Those sentences were janky, but you’re correct. All emails came to my inbox and got forwarded to my manager.

        1. Hekko*

          In the settings I’m familiar with, this kind of forwarding isn’t indicated in either inbox.

  16. Drag0nfly*

    For LW 1, Hermione makes me wonder if she raised in an abusive household, or if she was actively miseducated to believe spinelessness is a virtue. Not that I would ask her that, of course.

    What I *would* ask would be along the following:

    1 – Does she recognize that missing deadlines is a problem?

    2 – If the answer is yes, then ask why she believes it’s better to miss the deadline than to speak up. Why does she prefer to let down the team when she can inform them of the situation instead?

    This may lead to the follow up question,

    3 – What does she believe will happen to her if she speaks up?

    Likely she’ll think McGonagall will be “mad,” so you might segue into asking her what she thinks McGonagall will DO to her if she’s angry. Can she turn Hermione into a toad? No? Then stop putting priority on “appeasing” her, especially since McGonagall is a reasonable person.

    Finally,

    4 – What does she plan to do to alert McGonagall in the future when deadlines are unrealistic? If McGonagall asks if a deadline is doable, does Hermione plan to lie to her, or tell her the truth? State this question plainly, so she is forced to think about what she’s really doing.

    Hermione may be conditioned to back down from someone else’s anger, or avoid it entirely. My suggestion is to put land mines on the path of least resistance: tell Hermione that her failure to speak up will be considered a performance problem. Managers and her coworkers are making decisions with the information available, and if she actively withholds information because it’s “easier” then SHE is the problem. How does she plan to solve this problem?

    Let her know that if she’s particularly stressed, your insurance covers counselors, therapists, and so on. And if she does want to vent, maybe you can introduce her to journaling, if your role allows you to convey such an idea.

  17. Phil*

    #2 If it was me I’d be like
    “Yes.”
    “Really?”
    “No, just thought I’d change up the conversation today.”

      1. Rae*

        Just pic a vaccine and say yes or no to it.
        Tetanus? Yep.
        Japanese encephalitis? Nope.
        Cooties? It’s complicated.

    1. Clorinda*

      Or there’s this:
      Have you been vaccinated yet?
      [slow motion reaction of astonishment and revelation] You mean there’s a VACCINE? Why didn’t anyone tell me? Ohmygodohmygodohmygod, there’s a VACCINE!

    2. Sola Lingua Bona Lingua Mortua Est*

      I’d just say “yes.”

      “Yes.”
      “Really?”
      “Yes.”

      If questioned later by a third party, I’d simply tell them the truth: “‘Yes’ is what she wanted to hear and my only viable exit from the conversation. I’ll get the vaccine when I’m eligible and ready.”

    3. Captain dddd-cccc-ddWdd (ENTP)*

      Give an increasingly preposterous or silly reason for being out every time she asks. “Seeing my phrenologist”, “medical assessment for going to the moon” etc.

      1. LW2 (am I vaccinated yet???)*

        These suggestions have all made me laugh — and I needed it today!

        1. commonsensesometimesmakessense*

          yeah, come up with some really absurd fake illness – so, during my previous time in NASA and also working for the NSA, I was exposed to moon toxins and Agent Orange. I know, odd combo, but I cannot explain the circumstances because you do not have the security clearance, and, well … (lean low and whisper) they can hear us you know! They are everywhere! I can’t take that risk, not just for me, but they’d want to silence you too!

          Anyhow, just know that if I suddenly develop weird twitching or start talking to non existent people or bugs, it’s a totally normal part of my condition and nothing to worry about. If you just hide under your desk and don’t move until the episode passes, everything should be just fine!

        2. commonsensesometimesmakessense*

          Or, if you are a woman, you should just look her in the eye and say, “prostate exam.” Deadpan it. Then turn on your heel and walk on out.

  18. Tsunade*

    #4: This… kind of seems like a grandboss issue? If the grandboss wants this stopped, (and their own direct report, LW #4’s boss, is seemingly nonplussed and clearly not doing anything about it), then an email from grandboss to someone in IT should have the juice to shut it down ASAP.

  19. Mannheim Steamroller*

    #2…

    Is there a chance that Secretary is being nosy on behalf of Boss?

    1. LW2 (am I vaccinated yet???)**

      Nope! I have talked with my boss about my struggle to get an appointment. My boss also knows about my medical condition and that I don’t want it spread around the office. Secretary has access to my calendar and has often asked why I’m going to the doctor before. She consistently oversteps in areas where my boss would once already. Also! I’m under 30 so if I hadn’t already disclosed to my boss, this would be a way to get info about people’s pre-existing conditions.

      1. LW2 (am I vaccinated yet???)**

        Also, I’d wonder if that’s even legal to ask that information (especially considering I’m not considered an essential worker by my state, and without a medical condition, I wouldn’t qualify yet)?

        Perhaps Alison or someone might know the potential legal ramifications of someone trying to collect this info for their company.

          1. LW2 (am I vaccinated yet???)**

            It would be a way companies could force people to put medical status.

            Meaning: I report I’ve been vaccinated with the current eligibility group and I’m obviously not qualified due to age = I either lied to get it or I have a medical condition.

            Obviously it’ll be a wash when everyone is eligible.

            1. Lunch Ghost*

              According to the EEOC (which I found through an article someone linked here earlier), just asking if you’ve been vaccinated is okay, but not asking why or why not. (And companies may want to specifically tell their employees not to say why or why not.)

            2. Snailing*

              Depending on your state, it doesn’t necessarily mean either of those things if you got it without being eligible. My state has everyone pre-register through a state-run vaccinate site and asks you all the questions – age, essential worker, health conditions, living conditions that would qualify a person under the current eligibility requirements. I know many people who are not eligible that went ahead and pre-registered, thinking/knowing they wouldn’t get a slot until much later because they answered the questions truthfully. But then they were offered a slot anyway and it would honestly be stupid to turn that down.

        1. twocents*

          I think you’d have to be able to prove that she was actually trying to solicit this for the company vs just being a nosy Nancy.

        2. commonsensesometimesmakessense*

          It can be illegal for the company. The ADA prohibits harassment or discrimination based on a disability or a perceived disability. The secretary is asking over and over despite you making it clear that you are not ok sharing it, and she even follows you and knocks on your office door to keep asking. Granted, I advise that you tell her very clearly that you need for her to stop asking and that you find it inappropriate and even harassment. But yes, this behavior could be a liability for the company if they do not shut it down.

      2. AnonInCanada*

        Is there any way you could, instead of putting “doctor’s appointment” on your calendar, you just put, in every circumstance you need to be out of the office “OOO meeting” with no more details than that? Then Secretary Kravitz will be unaware who’s the meeting with (doctor, client, secret admirer), and if she asks about that, you can respond “exactly what the calendar says” and leave it at that.

        1. LW2 (am I vaccinated yet???)**

          I made the change once I realized my calendar was where she was getting that info (see comment above). But no matter if it’s a meeting with someone for work or not, she’s pretty nosy about what I’m doing in general. Also, by company mandate, all meetings must be via Zoom at the moment so it’s making it a little difficult to escape.

          1. Batgirl*

            If she enquires about a specific thing make a big deal about the word private. “Oh just something private” “Well, private means private” etc. If she’s asking generally (or you can make a specific enquiry general): ‘Can you put in an email exactly what needs specifying in detail on my calendar and WHY? Kthanxbye.’

        2. Mina, The Company Prom Queen*

          One of my former colleagues put ‘personal appointment’ on our shared team calendar when he had whatever appointment outside the office. (Everyone used this level of info on the shared calendar.)

          1. Mina, The Company Prom Queen*

            And if Secretary asks what that appointment is, just say ‘I have a personal appointment.’ If it drives her crazy and she pushes for more information, use the ‘Why do you ask?’ Script in my comment above. :)

        3. Anon for a minute*

          I initially thought Secretary Kravitz = Lenny, not Gladys, and that would be an awesome workplace :) But I’m sure he wouldn’t be so rude.

    2. Batgirl*

      Nah, you can smell that kind of nosiness when you’re with the direct source. No sense of shame. My bet would be she sees herself as having a finger on the pulse and speaks accordingly (gossips).

  20. Green great dragon*

    #1 – I think you’re doing all the right things for the long term, but right now, Hermione just seems overwhelmed. You’re able to talk to McGonagall, so with Hermione’s permission, please push McGonagall to check in more, and to ask Hermione questions directly (and it’s not a terrible criticism of McGonagall! Her style may be fine for 90% of staff, it’s just not enough for Hermione right now).

    If you can get Hermione into a better place with workloads, and with experience of giving honest answers to McGonagall’s questions and having those answers respected, then you can try again with the coaching to encourage her to speak up more pro-actively.

    1. Blue Eagle*

      No, don’t do this. It is NOT on you to be an intermediary, which is what your mentee seems to want. It is also NOT on you to talk to McGonagall at all.
      If I were in your shoes, I would ask H what she talks to M about outside of deadline issues. Is H afraid to say anything? Maybe have H start talking to M about pleasantries, then smaller work things, smaller work issues and as her confidence improves move up to medium work issues then larger work issues.
      My experience with employee timidity is that, unfortunately, is something that cannot be changed overnight.

      1. Green great dragon*

        OP’s not obliged of course, and it’s not ideal, but as you say H isn’t going to develop these skills overnight and she’s currently “totally overwhelmed” and bursting into tears at work. Coaching isn’t working. She’s otherwise a good employee, so it feels worthwhile OP alerting McGonagall to give extra support in the short term, alongside whatever strategies they use to build her skills in the longer term.

        1. Batgirl*

          Yeah I honestly don’t understand why McGonagall hasn’t done some really simple adjustments; since she’s a great manager I can only assume she hasn’t thought of it. I’ve worked with incredibly timid people and it doesn’t take long to actively demonstrate that you’re seeking to hear about problems.

  21. Triplestep*

    #2 I also am often asked about my vaccination status by people I know who lied to get one early. I have a clotting disorder which could easily have been exacerbated by Covid and have been isolating for a year. I have waited my turn (underlying health conditions could start signing up recently in my state) and am now half-vaxed. But I suspect anyone feeling guilty about having lied to go early will keep asking me until I am fully vaxed. This is probably what’s going on with your secretary.

    1. LW2 (am I vaccinated yet???)**

      It’s possible. But I’m under 30 and she doesn’t know about my medical condition (she knows I go to the doctor a lot) and has been trying to dig that info out. I think asking about the vaccine might be about me having a medical condition more? I’m not really sure.

    2. Nikki*

      Yes! I’m high-risk and have yet to be vaccinated (due to my state’s guidelines). People keep asking me if I’ve been vaccinated, and many have been encouraging me to lie. Some are even volunteering ways that *they* lied to get the shot sooner. It’s gross!

      I wish people would keep it to themselves. I’m not here to assuage anyone’s guilt about skipping the line, and it sure does affect my opinion of them!

  22. Washi*

    OP1, you’ve gotten some good suggestions about how you could be even more hands-on. But if this mentoring program is supposed to be more behind the scenes and you can’t do that, I would say something like “we’ve been working on assertiveness for a few months now, and my sense is that my suggestions have ultimately not been that helpful since you haven’t been comfortable implementing any of them. I’m wondering if you have a better idea of how I can be helpful to you?” I think asking her point blank why she hasn’t implemented your suggestions could just shut her down, if she really is that timid.

    If she doesn’t have any of her own suggestions of what might help her, I might ask if there are other areas of professional development we could work on together. This would partly be for my own sake, since I would probably be starting to lose patience, but also I’d be worried that these repetive meetings of her crying and saying she can’t speak up are just reinforcing that she can’t do it, and taking a break from that might be beneficial to everyone. If you can coach her in some other area and she has success with that, it might help boost her confidence all around.

    1. WellRed*

      Agreed. What is the goal of these mento rships and how long do they last? This seems to have turned into a work therapy session.

      1. Saberise*

        Agreed and I think a lot of the suggestions people are making here to help the situation really cross the line into what an actual therapist would be used for. Diving deep into what in her background makes her so hesitate etc. That really isn’t what a mentor is for and I would be about ready to throw in the towel if I had to keep hearing the same complaints and she was doing nothing herself to address it.

  23. Night Vale Seems Good by Comparison*

    Op1, as a formerly timid, now confident and high performing employee thanks to a few good bosses and mentors, thank you for trying to help Hermione!

    It is interesting that even while we are learning to accommodate people with all different learning and communication styles in the workplace, there are still many people who believe that if you ever do anything to help a timid person, you’re “enabling” them. It’s bizarre (already showing up in the comments). Obviously there is a range of timidity so possibly Hermione needs more help than is practical, but I suggest a few simple things:

    1) One on ones with her boss, if not already happening. It sounds like Hermione is still viewing her boss as a vague Authority Who Must Be Obeyed, but is opening up to you because she has gotten to know you. I can’t tell you how much it helped me to learn that my bosses were just people like me, with likes and dislikes and personalities, who also happen to give me assignments. She may need only a few such meetings to help her get to know her boss.

    2) If possible, bring her into the planning process where deadlines are set. Even if she is not yet able to set deadlines herself, seeing the process and that it involves people discussing and listening and accommodating different factors could help. But ideally, since these seem to be project targets because no one is too upset when they are missed, give her a choice! Instead of “The deadline is X, will that work?” Say “We can set the deadline at X, Y, or Z; which works for you?” Making a decision and seeing that it is listened to and accepted is a huge confidence builder.

    3) Talk about real world scenarios. At some point, she will encounter deadlines that, if missed, would result in angry clients, regulatory fines, etc. It might seem counterintuitive to tell a timid person about “scary” things that might happen, but she needs to hear that not speaking up can be worse than facing that fear. Let her know that managers WANT to hear the reality of what her capacity is, so they can do proper project planning!

    OP, please speak to McGongall again and suggest that she needs to be a bit more hands-on until Hermione gains confidence. It sounds like she is assuming all is well because Hermione’s work is good. It is not “cheating” or being a crutch to let a boss know that an employee needs a little extra help! Some might say you should check with Hermione first before speaking to her boss, but from my perspective, McGongall needs to be aware that she’s dropped the ball a bit (she should already be aware if an employee is regularly working OT, unless she manages 500 employees, and she should have met with Hermione after the second missed deadline to check in). She doesn’t sound like a bad boss, just one who isn’t aware that Hermione is struggling.

    These are things that helped me; hopefully some make sense for Hermione and her boss too.

    1. Sara without an H*

      OP#1, is it possible that Hermione is unconsciously trying to triangulate you and McGonagall? As in: “I’m too scared to talk with McGonagall myself, but here is kindly Mentor — I’ll get her to speak for me.”

      I’m not suggesting that this is a conscious strategy on her part, nor that she is consciously manipulating you. But it’s a thing anxious people sometimes do, and you need to be alert to the possibility.

      If I were in your position, I’d probably schedule a meeting with McGonagall and tell her very specifically about the pattern I’ve been seeing, i.e. Hermione won’t speak to her manager when she’s overloaded, but will vent about it to me. McGonagall needs to have more structure in place for Hermione, with regular check-ins, as well as a system for reporting progress, or slippage, with a project schedule. With a more structured reporting relationship, Hermione may eventually become less anxious about communicating with her manager.

      Or not. But in any case, I really think this is something McGonagall needs to work on directly with Hermione. Putting yourself in the middle won’t solve the problem.

      1. Reba*

        I agree with this suggestion for structure. Could there be a more fine-grained project tracking system used for a while–including more frequent, low key check-ins? It occurred to me that (not knowing Hermione’s level of experience) she may not really know how long something is going to take her to complete. More frequent check ins or progress stages could help address issues before they get to a crisis point.

        And she probably feels shame for not being able to do something by the given deadline, but that is a therapy question!

        Where coaching can help is with learning to predict what time is needed is a skill and it has to be practiced.

        My team has recently been given a huge timeline of internal deadlines and dependencies, and asked for feedback on them. I literally don’t know if they are all reasonable??? But as we get into the meat of the tasks, it should become more clear, and we have monthly times to meet and adjust the timeline.

  24. TooManyPens*

    Question related to #3: I’ve only been at my job for a few months, but a coworker asked if I could be a reference for them. I was thrown off that they’d ask a new coworker to be a reference, and they mentioned other coworkers already said they wouldn’t be comfortable being a reference, so I said yes. I really don’t know anything about if they do their work well or not, and I really don’t like them as a coworker (they interrupt me throughout the day to make small talk, they are loud, they repeat things in the same convo a lot, they nag me about doing things I’ve already told them I have no interest in, they ignore hints and direct requests to be left alone because I’m busy, etc.). If I ever actually get contacted by a company, am I just supposed to try to say they are “nice” and be honest about not knowing their work?

    1. BRR*

      I think when someone agrees to serve as a reference there is an expectation that it will be a positive reference or you let the person know it won’t be a great reference and give them the option if they want to list you or not. I’d go back to your coworker and say that you’re not familiar enough with their work to serve as a reference and it would be better for them to list someone who can speak more strongly about their work.

    2. Artemesia*

      You really need to learn to have the courage to say ‘no’ when ‘no’ needs to be said. This is a classic case of ‘well I am just a peer and we haven’t worked together much so I am not in a position to be able to do that. You find someone who knows your work.’ And of course if you follow through on this, the reference is ‘Charlene is pleasant to work with but I haven’t known her long and cannot speak to the quality of her work.’ And tell her that — I haven’t known you long or worked with you enough to be able to talk about your work and that seems important so you need to find someone who knows your work.

    3. Personal Best In Consecutive Days Lived*

      Well I think you now know why none of your other co-workers wanted to be this person’s reference.
      It’s not likely that you’re going to get called, but if you are, be truthful about what you know about this person’s work, both good and bad. Whatever you say won’t get back to your coworker.

  25. No Tribble At All*

    OP#3: this is a little LinkedIn “skill endorsement” not an actual recommendation letter, correct? The thing at the bottom of a person’s page that says “Joe Schmoe and 2 other LinkedIn Members endorse this person for Project Management.” You can safely ignore it forever. There’s no consequences to him the way ignoring a letter of recommendation for, say, grad school.

    1. Willis*

      I was thinking it was the Linkedin feature where someone writes a little blurb to recommend you that shows up on your page. If it’s that or an endorsement, I think OP could ignore, it just give a vague, “I don’t do those different LinkedIn things. They seem too gimmicky to me…” which for me would have the added bonus of being true.

      1. JustDesserts*

        Also, if it is the endorsement feature, LinkedIn sends them out automatically, they may not even know about it. I got endorsed for things I never did until I turned it off and deleted all of them.

    2. Threeve*

      They’re pretty much the equivalent of someone “inviting” every single facebook friend to “like” their business. You can absolutely ignore it.

  26. MissDisplaced*

    #4 I’m going to go the route here that you manager wasn’t intending anything snoopy or nefarious with the email. Simple explanation is she had them going to a different inbox she had to manually log in to and forgot about it or thought it would automatically turn off when you’d returned. I hope you didn’t miss anything else important since you’ve been back though.

  27. Observer*

    #1 – It might we worth looking at the broader pattern with her. Like when she says “Oh, I could never tell McGongal that!” ask her WHY? Not in a challenging way, but to understand what’s going on. If the problem is that she has really badly skewed workplace norms, such as “Your superiors at work must never be contradicted!” you can start addressing that pretty directly.

    If it’s about shame or other personal issues, it’s going to be harder, but understanding what’s going on may give you some better insight as to what might help. Also, because you are not a supervisor, nor do you have any authority over her, you could suggest – ONCE- that she consider therapy / counseling / coaching because her excessive timidity and unwillingness to speak up WILL hold her back professionally. So, a piece of advice to improve her professional prospects is to find a way to get a handle on the issue.

    1. u know*

      Or maybe McGonagall is being privately abusive to Hermione while OP1 trusts their buddy.

  28. RC Rascal*

    LW#1: I’m going to throw out another idea. It’s possibly Hermione is getting something out of being this stressed.

    I say this because my college boyfriend was this way. He used to complain endlessly about how overworked he was. He refused all offers of advice on managing the situation. He also refused to look for another job. He eventually admitted he enjoyed the job and the workload , just liked to complain.

    The latter admission came out during our heated break up fight; one of his complaints about me was that I wasn’t supportive enough of his career. Yet all he did was talk about how miserable he was at work….

    1. Sola Lingua Bona Lingua Mortua Est*

      It’s possibly Hermione is getting something out of being this stressed.

      That’s possible. I’ve gone through phases of burnout where I have had to convince myself that my job was on the line to get started on projects. (It never was, at least that I know of; I just needed that level of pressure to concentrate).

    2. JB*

      This sounds like a fascinating breakdown in communication between yourself and your boyfriend, but probably not applicable to a situation where the employee is actually failing to meet deadlines.

      It is very funny that you seem to perceive your ex’s complaints as some kind of trick, rather than a normal social interaction that most people would not interpret as ‘I hate my job’.

  29. Bananaphone*

    you might want to ask Hermione if the timidness is present in other places in her life, and suggest that she seek out the EAP or coaching for support with it.

    1. GinnyWeasley*

      I was going to comment that it seems Hermione could be struggling with anxiety, as I do and am very similar to her when it comes to approaching a situation that could lead to conflict (ie. approaching her boss about missing a deadline). There is a fear of failure as well that could be contributing to this, and it seems like Hermione may need to work this through with a therapist or counselor. I think suggesting the company’s EAP program could be a good idea, at the very least to help her cope with the stress she is feeling, but could also open the door for her to seek help if she is struggling with anxiety.

  30. Sola Lingua Bona Lingua Mortua Est*

    LW #1 – Are these deadlines real or fiat?

    In my current role, I had 80 tasks by the end of my first week, at least a dozen of them 3+ months past due. It cured me of taking deadlines seriously.

    if Hermione does brilliant work, and the deadlines are fiat, just… accept her brilliant work and be happy.

  31. Seeking Second Childhood*

    Op1, even if your industry and function are not engineering oriented, the language used in Agile development processes might be worth sharing.
    In particular, during the ‘sprint’ planning period, the team gives a confidence rating–do they think the goal is easy&reasonable or hard to impossible? They are expected to flag roadblocks and problems and request manager help to expedite solutions. And I have heard team members praised for being right that a deadline was impossible and the goal was too ambitious.
    (I have some issues with Agile and how it can be misapplied, but THIS aspect is very helpful.)

  32. bopper*

    Recommendation request:

    I would used what the Catbert Performance Review Generator would spit out:

    Mr. Generator was tasked with many assignments this year. His performance defies measurement. It would be accurate to say that he has been responsible for the changes in our work group dynamics. His work may greatly impact the company. Many wonder at the extent of his knowledge and his core values show through in his work. No one has caught Mr. Generator sleeping on the job. He handles assignments with unlooked-for creativity.

  33. Natalie*

    LW#2

    She has gotten sulky and subtly mean towards me when I’ve raised issues in the past.

    If this is the sum total of her bad reaction, I think it’s perfectly fine to just let this happen. Certainly this kind of behavior is annoying and unprofessional, and she shouldn’t do it. But your not her manager and this is fairly low-level misbehavior. I think you might find her overall easier to deal with if you can see your way to just letting her sulk, without feeling like you need to prevent it or correct it somehow.

    1. LW2 (am I vaccinated yet???)*

      I guess I saw “subtle” but in reality: she leaves me off of meetings, refuses to schedule things for me, misplaces documents. All things she blows off as minor accidents but certainly disrupt my work. I’m the youngest in the office (and around the age of her daughter) so it is almost like she’s trying to mother me and taking away my “toys” if I don’t comply.

      1. Mina, The Company Prom Queen*

        Definitely document this and report it to your manager the next time it happens.

      2. Knope Knope Knope*

        That’s a whole new ballgame. She’s harassing you about your medical status and sabatoging your work when you don’t give in. Definitely talk with your boss!

      3. Natalie*

        Ah ha, that is different. I would definitely be more inclined to bring this to the manager, and I would encourage you to be specific about what behaviors you experience and when, and leave out anything you suspect about her motivation or attitude. It may very well be true, but it’s not relevant and can easily become the focus rather than the things that have impact on your work.

      4. Keymaster of Gozer*

        Nosy AND vindictive. Definitely the second part is one you could take further up the chain because that kind of crap can and should get people into real trouble. Meaning her of course. That’s not being nosy, that’s outright insubordination.

        1. LW2 (am I vaccinated yet???)*

          I honestly hadn’t thought it was all that bad until this thread because everyone acts and accepts that behavior as normal in my office….and this is my second job (first in this specific area of work). My first job had a lot of blatant toxic energy so this seems relatively minor compared to that. It’s been really helpful to get a bit of eye opening as to what is normal in an office.

      5. commonsensesometimesmakessense*

        Yeah, that is actually behavior that is interfering with your work for the company. That does need to be elevated, even beyond your boss.

      6. Batgirl*

        It’s cute when people use high school tactics and bogus hierarchy ideas instead of actual brains. She expects you to put up with it and seek approval from her because she’s hoping your age makes you vulnerable. She really thinks she’s the power behind the throne and is dispensing favours or toys.. but alas, it’s just her actual job. Document every time she fails at her job. Raise it every time she fails at her job. Phrase it as failing at her job… The fact she’s doing it on purpose, in a toddler sulk, only makes her more foolish and inclined to fail.

  34. bopper*

    Recommendation request:

    I would used what the Catbert Performance Review Generator would spit out:

    Mr. Generator was tasked with many assignments this year. His performance defies measurement. It would be accurate to say that he has been responsible for the changes in our work group dynamics. His work may greatly impact the company. Many wonder at the extent of his knowledge and his core values show through in his work. No one has caught Mr. Generator sleeping on the job. He handles assignments with unlooked-for creativity.

    Timidity:
    Can Hermione try writing an email instead of talking in person?

  35. a clockwork lemon*

    The grandboss’s reaction to 4 is so weird to me, unless grandboss found out that LW’s manager was doing something seriously out of line with those emails somehow and they’re just…not telling LW about whatever this gross invasion of privacy was? There’s gotta be a missing piece somewhere.

    1. Captain dddd-cccc-ddWdd (ENTP)*

      It struck me as odd that grandboss wanted to catch up with OP directly about the status of projects. Wouldn’t the manager normally do that and report the status to their own boss (the person’s grandboss) typically? – that’s more like how it would have worked in most of the jobs I’ve had. This seems to add to the strangeness really.

      I wonder how grandboss found out about the emails after all this time? My guess is the boss made a mistake and replied/followed up on one of them thinking it was addressed to her. Then grandboss looked into it all more closely.

    2. Name Required*

      This letter all around made no sense to me. Why go straight to REALLY BIG DEAL instead of Minor Technical Issue That Needs to be Resolved? Who cares if your boss has your email if she’s not doing anything with them and there is no impact to your work? How did grandboss find out? Why wasn’t grandboss’s reaction “Oh, did you know you had OP’s emails still getting fowarded to you?” Why would boss make a grand apology about getting the emails?

      … what? This all seems like a really strange overreaction.

      1. pancakes*

        I might’ve been inclined to agree, but the letter writer mentioned in a comment that the boss tends to work around the clock, nights and weekends. That might very well raise the question, particularly if it’s not the norm for everyone on the team or in the department, what on earth are they doing? Are they very bad at managing their time? Gunning for someone else’s job? Up to something sketchy? Maybe not, of course, but that sort of behavior doesn’t inspire trust if there’s no apparent reason for it.

  36. CM*

    OP#1, consider formal training for Hermione. Could she take a class on something like negotiation, effective communication skills, how to assert yourself? It may help her to hear from multiple sources that pushing back is a normal and expected thing to do at work, and being in a group setting could help reassure her that everybody needs to learn and use these skills.

  37. irene adler*

    #1: can Hermione’s deadline situation be reframed?

    My take: She seems reluctant to advocate for HERSELF in regards to adjusting deadlines, and (from the narrative) does not see missing the deadline as being as important as the good work quality that goes into the task itself.

    So take out the ‘personal’ aspect of this.

    Maybe get Hermione on board with the notion that it’s her job to advocate FOR the project. And that includes things like keeping the boss apprised of deadlines that are not realistic or deadlines that are no longer ‘doable’ (i.e. something came up)-along with any other aspect of the project that needs attention. Hence, reassigning deadlines are for the benefit of the project. So is setting realistic deadlines in the first place.

  38. Observer*

    #2 – When you talk to your boss, don’t mention that the secretary lied to get her shot. I get why it irks you in a big way. But unless she’s pushing you to lie as well, it’s just not relevant to the issue at hand. The problem is that she’s harassing you, she’s poking her nose where it doesn’t belong, and she retaliates when someone brings up an issue.

    1. commonsensesometimesmakessense*

      yeah, that will distract from the issue. I agree that it is best to not bring that up. This is not about the vaccine. This is about the secretary harassing OP for her private medical information, then messing with OP in retaliation for it.

  39. TeapotNinja*

    OP1: This could also be cultural. In certain cultures women, especially young women, are really hesitant to speak up. I’ve seen this so many times, thankfully less so in recent years, but it used to be really prevalent in my line of work. It’s nearly impossible to address in any proactive way. About the only thing I’ve seen work is just really gently encourage her to share her opinions, for example if you know she has experience in something being discussed mention to the group Hermione has done a lot of good work in this area and ask her if she has anything to add. Also arrange for opportunities for her to present to the group, if that’s something you do in your line of work. Those things are going to be hard for you to do, since you’re not in her team, and even so it takes a very, very long time in my experience.

  40. Stop*

    LW#4, I’m assuming that when you say “I am more easygoing and ADHD” you don’t mean that you literally have ADHD/are neurodivergent but just that you’re, I don’t know, scattered? forgetful? If that’s the case, please stop using ADHD to describe your personality quirks. It’s highly offensive and minimizing/delegitimizing for those of us who actually have ADHD and have to work with the actual deficits caused by this condition.

    1. LW#4 Email Forward Queen*

      I have been diagnosed with ADHD by medical professionals, take Adderall to manage the condition, and see a therapist regularly for ADHD and other mental health diagnoses.

  41. tangerineRose*

    LW1, would it help to reframe the issue for Hermione as more of a “Your boss needs to know if this is likely to miss the deadline.” and “Your boss needs to know how much overtime you’ve been working to get things done.”

  42. FloralWraith*

    I have the same issue as the employee #1, but I’m working on it.
    Unfortunately, this came from my dad, who, as a South Asian man, got shot down in racist workplaces in the 80s and 90s whenever he said that “he was great” and “knew what he was talking about”. He translated this down to both his children, saying we should never say we’re good, because someone else might be better. We’ve both had to work hard to get over the mentality, because it harms us in the workplace.

    My senior colleague does this mentoring too and she tells me that I need to be able to own and be proud of my work and my skills and to brag a little (and also be able to say “NO” to tasks).

  43. Old and Tired*

    #4–This appears to be a case of 6 of 1 and a 1/2 dozen of the other. If you have Outlook, it is very well marked in your email that Auto-Reply is turned on, and it is a matter of one click to turn it off. I also think it should have been extremely easy for Boss to casually remind OP to turn off Auto-Reply. There was no conceivable reason for Grandboss to even hear about it. It’s amazing the things that become a big deal.

  44. Salt Encrusted Facsimile*

    I had a student who was very much like Hermione in a past life, and have an employee with some of those same tendencies now. Both extremely smart people; both held back by hesitance to push back or ask for help when needed.

    The student (a young adult at the time, less so now) ended up turning into an assertive person with an understanding of (and willingness to enforce) their needs and boundaries by going into retail and spending many years dealing directly with the public (and then managing others doing the same). I do think the field I practice (and taught, at the time) would be better off with them in it; it’s not an approach I’d recommend to someone who doesn’t have the resources to shift gears again later.

    The employee… is still struggling a lot more than she should. We’re doing work where there’s a huge body of knowledge that needs to be incorporated and understood — as the person who first built the thing we’re working with, I’m still actively handing off information (_why_ X is built using Y; the need to check Z if changing A, etc) to even the most senior team member, so there’s no expectation of independence; trying to make best guesses and backtrack means we end up with time spent on rework. Everyone on the team has been very supportive, so she knows she has people to reach out to.

    Honestly, I’m hoping that reading through the comments here will result in advice I can follow to help the aforementioned employee get on track. I’m not going to be at this job forever, and I’m worried that the team member best positioned to replace me might leave if I do; we need more people who understand the details and can execute effectively to make sure the product survives my departure.

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