updates: the boss who didn’t pay, the cranky retiring coworker, and more

by Alison Green on December 18, 2023

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

1. Boss hasn’t paid for his share of our group collection (#2 at the link)

I used your script almost verbatim on Tristan (thanks for that!), including my Venmo AND PayPal this time, to which he said “oh yes, I’ll do that right now!” Then nothing. A few days later in a people leader meeting we were first on the Teams call, and he said he keeps getting distracted and would do it “absolutely today.” I made sure to tell him the format of my screen name as well (no dashes!) and he said he got it and … still nothing.

This went on a few more times, mostly him initiating the conversation, outside of the last instance where I brought it up. That time we were raising money for another ill coworker, and I mentioned casually in a call with him “don’t forget send mine as well!” to which he replied “yes of course.” I gave up after that, as it was almost two months of back and forth with no payment. Somehow he was able to send cash for the other collection within a few days.

My closest coworker would ask me every couple of weeks “did he pay you yet?” and was also flabbergasted over this. Despite my pleas not to, she eventually paid me half of his portion so we could split it because she found it unfair I was out double, and I never brought it up to Tristan again. It’ll be a while before any “fundraising” circles back to me to collect, thank goodness!

2. My coworker blew up at me when I asked about documenting her job before she retired (#2 at the link)

In your answer to my question, you speculated that maybe the executive director had been more transparent with me than with my coworker about her retirement. To be honest, I don’t think that the ED ever talked to me about it directly. It was my boss who told me that at some point my coworker was probably going to retire.

What I really think was going on, upon further reflection with your answer and the comments, was that she was probably having financial problems (this is based on information I had from her) and she probably wanted to retire, but was worried about what would happen if she did retire. Moreover, there were legitimate problems with her performance (e.g., conflict with staff — which she caused — not engaging well with volunteers she wanted to recruit, not obtaining grants that the organization needed). A lot of this were things that I was able to reflect on; for example, one of the people on staff needed her to renew a line of funding that was pretty easy to renew but it was taking months to do it and this person’s job was on the line if it didn’t come through!).

I think that she overreacted because I touched a nerve because of information that I wasn’t aware of or hadn’t made the connection to with her situation yet (e.g., it’s not my fault that I wasn’t aware of her personal financial circumstances when I asked — that came to light when I was almost done the contract). Realistically, it shouldn’t have been a problem; she should have been able to calmly discuss what needed to go into my plans to support a potential transition with my role without being triggered by it, but people are notoriously terrible at regulating their emotions so, okay, fine…

I think if I was dealing with a similar situation again, I would probably be more mindful of the fact that I might not have all the information (maybe the person won’t be aware that their retirement was discussed, maybe they have personal problems I am unaware of, etc.) and I can try to be more tactful/soft about it. I am a pretty direct/blunt person and tend to be the kind of person who will just say “I know you mentioned retiring, what should I add to my plans to make the transition the easiest?” As far as I was concerned, I was just discussing facts and my work; after all, it’s not like I told her I needed to know when she was putting in her notice, and … well, I recently got diagnosed with autism, which I suppose explains my tendency to be like that and not realize that not everyone would be that direct and I tend to look at it as “I’m literally dealing with this thing, why are you making it about these other issues?!” So I would probably want to prepare a script or something on how to bring something like that up in a way that’s softer or whatever.

3. Can I ask for a raise right after returning from furlough?

I’m the letter writer who wrote in asking whether I could ask for a raise at my university job after returning from furlough in June of 2020. I didn’t participate in the comments (because I was a little bit embarrassed), but I read all of them, and completely agreed with the consensus that no, I absolutely should not do that.

It took me a while to realize it, but I was really unhappy in my job. While I worked for a large university, my job was actually healthcare/hospital-based. My program was a specialized program with patients from all over the country and world. I loved the patients I worked with and when our program manager retired, I took over all of her job duties and daily functions, but with a lower title and less pay because I didn’t have a master’s degree (a requirement for a manager title within the university). One of the benefits of working for a university is free tuition, and my boss, knowing my five-year plan was to work my way to the program manager position, enthusiastically encouraged grad school. I started a masters degree (again, my boss was thrilled because she thought this would be really beneficial to the program), and then Covid hit. In our hospital setting, we were still working in person until we were furloughed (during which my boss called me more than once to help her with things) and then immediately were brought back in person. Because our program was so understaffed and with people needing to quarantine when exposed, I was doing my program coordinator job as well as filling in at the clinic as needed; I technically could say no if I was busy, but I knew patients would miss out on their optimal therapy if I didn’t help out. And then my boss told me she “didn’t think we needed a program manager” … while I was doing all of the job duties of our program manager, plus things that were added to my job descriptions as positions changed and our department recalibrated ourselves.

I was completely drained. I had so much PTO banked but felt guilty taking any time off and just was really really unhappy. I didn’t realize how unhappy until my husband told me, “You know, you can quit your job without something else lined up for a while, we will be completely fine.” That really lit a fire under me to start job searching. I had graduated from my master’s program, and one of my professors connected me with a friend who was hiring at a local nonprofit. I now work as a grants manager, and I love my job. It’s a huge change from what I was doing and took some adjusting, but I feel like I really have found my place. I work for an organization that truly values time off and separating from work when you’re out, and they were even incredibly accommodating when I recently had my first baby (I did not hear one word from anyone, except for the congratulations card and a gift card to Jersey Mikes). I’ve also gotten two raises in the time I’ve been here, and am making more money than I ever have!

Thank you for being the kick in the butt that I needed to make some changes to my work life!

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{ 44 comments }

{ 44 comments… read them below }

  1. Pam Adams*

    for LW2, maybe making it about the documentation, not the retiring. “You know,, i just realized how much of what we do is in our heads and not documented. I’m going to start documenting- do you want to join in? We can check over each others thoughts to catch whee we aren’t clear.” (This could also come from higher levels- perhaps saying this to your boss first, so it becomes an office-wide project)

    1. ecnaseener*

      I don’t even think you need to couch it in the “I just realized…” language, since it’s explicitly been assigned to you (LW). You can just say “Boss has asked me to get all of these processes documented.”

    2. Seeking Second Childhood*

      The useful script might be for when a manager assigns a task related to someone’s personal life: “Have you already told Jane you’re asking me to do this? And is her [retirement / pregnancy / ascension to the throne of Barsoom] public knowledge?”

      1. Annie E. Mouse*

        This! LW is tying themselves in knots trying to make this about Jane’s personal finances or whatever, but the reality is that anyone would be alarmed and upset to learn that their company was making plans for their retirement when they aren’t ready to retire.

    4. Talia*

      “You know,, i just realized how much of what we do is in our heads and not documented. I’m going to start documenting- do you want to join in? We can check over each others thoughts to catch whee we aren’t clear.”

      I find it a bit terrifying to think that if people have been communicating like this to me, it would have gone completely over my head, and now I’m worried about what I’ve been missing. I know that people often don’t feel comfortable giving feedback to others (and I also stay silent when I don’t think something will be received well) but if someone does say something, I take it at face value. Now I’m also wondering if I also soften what I say in this way, and I’m pretty sure I have. BRB having an existential crisis.

    2. Cyndi*

      You didn’t get the payment? I don’t understand! I definitely sent it last week! These apps, am I right?

    4. Grey*

      Dear Tristan,

      I understand finances can be tough, especially during the holiday season. Please accept my gift in forgiving your outstanding payment. I hope this helps during your difficult time!

      Merry Christmas,
      OP #1

  3. shuu_iam*

    LW2, I actually think your coworker was right to be bothered by you bringing up retirement documentation. What you heard was “It was my boss who told me that at some point my coworker was probably going to retire.” “At some point” and “probably” aren’t the same as “imminently” and “definitely,” but instead contain a strong possibility that your coworker wouldn’t be planning to retire for several years, in which case asking her about her retirement preparations now might come across as a hint that people wanted to force her out sooner.

    If it makes it easier to understand, think of if you had a female coworker who your boss mentioned “at some point was probably going to have kids.” If you approached her and started asking if she had the documentation done for her maternity leave, she’d likely be understandably a bit aghast at the number of assumptions involved.

    It would be good for your coworker to do more documentation, absolutely. But tying it to retirement when there were no actual plans wasn’t the best choice.

    2. Saturday*

      Yeah, it doesn’t sound like there was a retirement plan at that point, so I can see why that came across strangely.

    3. Kevin Sours*

      I don’t think I fully agree. If you tell people you are thinking about retirement, it’s not outlandish for those people to start considering the impact of that. “We need to document things so when you retire it’s not a trainwreck” isn’t the same thing at treating the retirement as “imminent” or “definite”. I don’t think the analogy to the maternity leave is apt because maternity leave is a “imminent” and “definite” sort of thing.

      That said, it seems like management should have communicated things better to all and sundry. It should not have been on OP to be the one to communicate that they were putting together a transition plan, however preliminary. Nor should the coworker have been surprised by it.

      1. Saturday*

        It’s not clear to me she said she was thinking about retirement. LW says her boss said, “that at some point my coworker was probably going to retire.” That’s not a lot to go on.

        1. Kevin Sours*

          I don’t think it’s a big stretch for LW to having been hired specifically to document and improve processes for a one person team and being told that person was “probably to going to retire” to make the assumption that the two were linked.

          If the coworker had not expressed any interest in retiring and the boss was merely speculating than that’s a problem — but I wouldn’t call it LW’s problem.

      2. GythaOgden*

        It’s happened with my former colleagues. They’ve been telling everyone on site they are retiring so the customer who runs to my boss with everything has been pestering her for answers. Because my former colleagues haven’t started the formal process yet, my manager can’t do anything, there’s not enough work for a third facilities staff member on reception (because I was trying to claw my way out for two of the four post-2020 years) and I would not inflict that awful third-rail job on anyone else. When my supervisor realised it was only a matter of time before I left or quit, she did go to management to beg for help. But quite honestly I doubt even if they tried recruiting for my old position they could find anyone willing to do what I was doing. They might as well have set up a cardboard cutout for all the actual substance there was in my job.

        In my case there are a lot of internal problems going on and there are reasonable needs and bloody-minded obstinacy on both sides, but I’m glad not to be holding the baby this time, so to speak. I’m not breaking out the popcorn — these are people I care deeply about as friends and colleagues on both sides — but someone really needs to lay down the law and ask my colleagues to …poop or get off the pot. Yes, it’s crappy that we didn’t replace me. No, as I said, I would not inflict the twilight zone of my old job on anyone else — I would have quit by now if I hadn’t got this particular job, because I could do better temping closer to home and have the time and energy to study for a more meaningful job in the long run, and have the finances to cover a short period of self-study. But they have a job to do and need to do it to get any kind of credit for it and allow management to deal with it.

    4. Ellis Bell*

      I was thinking the exact same thing because the boss saying: “at some point my coworker was probably going to retire” could mean literally anything. All the softener words like “at some point” and “probably” seem to have been ignored and OP only heard the main gist of the language: “coworker is going to
      retire” and did not hear the caveats “but I am not sure if I am right and I don’t know when”. Obviously if OP had extra context which made them sure that the coworker had discussed retirement with the boss that is very different (but still, the coworker had not discussed it with them which still makes the OP look like she’d come up with the idea of of thin air on the basis of age.) In the first scenario I would just respond with “I’m sorry if I misunderstood; Boss said you had discussed retirement, that’s what I am basing this on, not your age.” If the boss was being ageist and assuming retirement, it’s their problem to explain that, not OP as Kevin Sours says.

  4. Other Alice*

    The situation in #1 sounds so infuriating and baffling at the same time! Personally I would refuse to collect the funds in the future, and if anyone asks truthfully say that last time I had so much trouble collecting everyone’s money that I don’t have the bandwidth for it. Even discounting the loss of money (and at least the coworker helped cover that!) I’m sure it caused so much grief chasing after this manager for literally weeks!

    1. WellRed*

      I really think it’s best to just spend what you’ve collected and not front anyone the cash. Some people are thoughtless or forgetful and some are cheapskates.

      1. Mints*

        +1 my office just asks for “any amount” and sends a doordash gift card. It’s organized by the person’s manager, and they probably round out an odd total, but there’s no pressure to gift any thing.

    2. MassMatt*

      I would not say you had so much trouble collecting “everyone’s money”, the problem was Tristan. And yes, he’s a boss so maybe he can’t be publicly shamed as easily as a random coworker but saying “everyone” is letting him off the hook.

  5. JaneDough(not)*

    LW1 (deadbeat boss), take this with a grain of salt, bc I don’t know anything else about your manager, but: One of my two stupendously incompetent bosses did almost the same thing, and unfortunately I didn’t understand that it was a HUGE red flag — a window into her carelessness and lousy management.

    (Within a few weeks of my start date and my colleague’s — we were Manager’s only two reports — Manager asked to borrow $20 for a cab ride home. She’d forgotten her wallet, so she didn’t have her ATM card. Obviously she should have asked a peer rather than an underling; who knows why she didn’t. Of course she never remembered to repay my colleague, who (at 25) was too afraid to ask for the money. So I split it with her bc, like your colleague, I thought it was unfair for her to be saddled with the whole debt.)

    This manager was disorganized and uncommunicative. She disappeared for hours at a time w-o letting us know she was leaving or when she’d return, which meant that we two underlings had to make some decisions we weren’t qualified to make. She didn’t support us when we made mandatory changes to documents and higher-ups took umbrage at the changes. She changed guidelines without telling us and behaved as though we were in the wrong for not magically knowing the new ones. She wasn’t prepared for meetings, and in one instance because she hadn’t looked beforehand at a piece I had QA’d — that was SOP — the meeting took almost 2 hours rather than 20 minutes. These are only a few of dozens of examples. It was one of two truly appalling workplace experiences in my then-22 years as an employee.

    With “managers” like her, one has to document everything and be proactive. I don’t know whether yours is in her category, but I’m sharing this info just in case. Good luck.

    3. SansaStark*

      Right? As a boss, I’d die of embarrassment if my staff had to pay money for me on anything! I don’t think I even make that much more than they do, but it’s the principle and optics of the thing!

  7. JaneDough(not)*

    LW2, I was struck by a couple of things in your post and I’m noting them with the goal of making your life easier.

    “I think that she overreacted because …” —–> If you can avoid thinking in these blame / shame terms, you’ll be better served throughout all parts of your life. Framing this as “She overreacted” = “She was to blame, not me” — but looking at life as “In every interaction, someone is at fault and someone is innocent” is destructive for all concerned. You can dislike the way she reacted, or be hurt / angered / taken aback by it without ascribing blame.

    “Realistically, it shouldn’t have been a problem; she should have been able to calmly discuss what needed to go into my plans to support a potential transition with my role without being triggered by it, but people are notoriously terrible at regulating their emotions so, okay, fine…” —–> This is super-judge-y, and that attitude will serve you very badly. (You wouldn’t want to be judged for responding to something shocking in a way you found appropriate.) Again, you’re saying “Her fault, not mine!” and that brings abut an impasse / makes relationships prickly rather than smooth.
    . . . . . . In addition, humans (“notoriously terrible at regulating their emotions”) evolved to have emotions for a reason; please don’t assume that neutrality should be the default 100% of the time — that assumption will harm your relationships.

    “I am a pretty direct/blunt person and tend to be the kind of person who will just say ‘I know you mentioned retiring, what should I add to my plans to make the transition the easiest?’ —–> Your idea of preparing ahead of time, with a script, is great.
    . . . . . . . I’m also encouraging you to find the blandest-yet-accurate way of stating your needs or question. For example, in your original letter, you wrote, “I was explicitly hired on a contract to document, improve, and create processes for a one-person team at a small organization.” If you had said some version of that to the woman, with no mention of her retirement, she probably would have reacted very differently. (I’m not criticizing you; I understand that you thought she knew you were there *because* she was retiring. I’m just noting that something along the lines of, “Hi, Jane. I’d like to meet with you so I can start my work, which is to document the processes for this job.” ****Note the absence of “you”**** — nothing to make her feel defensive (“I’m here to document your processes because you haven’t done that”) — as well as not mentioning her retirement.

    Good luck.

    1. RachelTW*

      I think this is excellent advice for LW2. I also picked up on the “people who do not respond like me are wrong” tone. I don’t know if that’s what LW2 meant to convey, but it’s how I read it.

  8. LizB*

    I may have missed this in the letter or comments, but is there a reason other than awkwardness/power dynamics that LW1 couldn’t have figured out Tristan’s Venmo and sent him a request? They absolutely should not HAVE to, he should take 30 seconds and send the dang money, but I think they totally could have used that function and framed it as “Oh I know life gets hectic, let me just send you the request now so you don’t have to think about it!”

  9. Despairingly unemployed*

    LW 1, Tristan sounds like my last manager who promised me a reference letter multiple times and just. Never sent one. Even after I sent them a template/draft for them to modify it. Every time I brought it up, it was all enthusiasm and willingness to help, not following up, remembering they never sent me one. And the cycle started all over again. It’s hard not to take it personally (especially when this pattern ended ghosting me out of my job) but I’m glad you had a coworker step in to help!

  10. saskia*

    I wouldn’t have been able to deal with #1… after the second time, I’d be saying, “it’s a super busy time, so let’s just do it right now! Here, scan my QR code” and make him open Venmo in front of me and pay the damn money! Such an annoying dude, blah!

    1. saskia*

      And to LW 2, from a person who’s done similar things and inspired… unexpected reactions in people, sometimes you don’t need to broach a subject in a special way. Instead of saying “I know X and Y; therefore, it’s time to do Z,” you can just say, “Hey, it’s time to do Z.” Then it becomes about the task itself, not the reason behind the task. Reading this comment back, it seems quite vague, but hopefully you understand what I mean :)

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