updates: work doesn’t interest me, bringing a sippy cup to work, and more

by Alison Green on December 12, 2024

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 four updates from past letter-writers.

There will be more posts than usual this week, so keep checking back throughout the day.

1. Work doesn’t interest me anymore

I had progressed to the end stage of that job interview process I wrote in about. But what started as feelings of non-excitement turned into the strong epiphany that this ultimately wasn’t the right job for me, so I decided to remove my candidacy from the pool. From what I gather from those on the inside, it sounded like the position would’ve gone to me, but I felt no regret whatsoever to step back. I knew I made the right decision.

About a month or so later, I applied for another position I felt glimmers of excitement for. I heard great things about the team, the culture there, I knew their work well, and the position would allow me to go from managing a small team to an individual contributor role (without taking a pay cut), which was a major bonus for me. After interviewing, I was offered the position, and it’s been pretty great ever since.

And while I enjoy my work now and collaborating with other colleagues, it’s the work-life balance and flexibility my team lead offers that makes me feel closer to the feelings of excitement that I was starting to miss. They are infinitely generous with their time and energy, and they look out for their team members in ways big and small, protecting our wellbeing and always centering our needs before anything else. They also make it a point to carve out new opportunities for all of us, looking out for our career growth and development along the way. If I could give this person a medal, I would.

Although I don’t know that I’ll ever again have the level of excitement and ambition I felt early on in my career, I’m OK with that now because I’m in a place where I can do good work and be part of a team that demonstrably implements flexibility and empathy, respecting the fact that the working world has changed, that workers and their needs have changed, and that work needn’t be someone’s full and sole identity anymore. And now that I’ve been on the team for long enough to get a better sense of the pace and rhythm, I’m looking for volunteer opportunities outside of work that more closely align with my interests so that I can continue decoupling what I do for a living from who I am as a person in the world.

I feel lucky to say that it’s been a really positive experience for me so far. I also want to note how grateful I am to you and your readers for sharing their experiences in the comments section, too—they made (and still make) me feel so much less alone or weird or deficient for feeling this way about work.

2. Assigning tasks to an assistant (#2 at the link)

Firstly, my assistant’s work load was not beyond what he could get done. In fact, he’s allowed to bill up to 25 hours and he was averaging about 15 hours a week. So that was not the reason for the constant boundary setting.

The stress caused by my assistant’s “not right now but I can do it tomorrow at 10am” or “I am doing something else right now, and I can’t get to this until Friday” or “I can’t do this right now” — boundary setting responses with every single assigned task got to me in a way that I had to finally ask him to respond specifically like this: “I’ll add it to my list.”

I made it clear several times that when I assign a task, I’m not asking that it be done at the time I’m assigning it. I just need to assign and move on, knowing it’ll be done when he can get to it.

Eventually, after having to reassert many times that “I added it to the list!” is all we need to hear, that is how he responds and all is well. If there’s something super urgent, we talk about his workload to see if we can rearrange priorities, but usually he gets everything done pretty quickly so really, the timing boundaries were never really needed and did nothing but stress me out, and make me feel overly managed by my employee.

I’ve seen tiktoks and things on social media, telling employees to force their bosses into excessive prioritization of their schedule and I think it’s just brutal on the employer. We are too busy to micromanage your schedule. And if you make a mistake or need to re-prioritize, it’s not a reflection on your work, you’re not in trouble and you don’t need to be defensive. It’s part of working with others. Don’t put all of that on your boss if you’re not being pushed or over-scheduled. It’s not helpful and can turn your boss against you.

For us, it worked out though — and the vibe at work is much more productive, and calm for both of us.

3. Is it weird to bring my toddler’s sippy cup to work with me?

I wrote in a few months ago about bringing my toddler’s sippy cup into the office to rinse it out in the sink. Was I overthinking it? 100%. But I very much appreciated the nuanced response to my question! I found myself feeling weird walking down the hall holding the cup; and the feeling was reinforced by my confused coworkers occasionally calling me out on it. But to clarify, no one was ever rude about it or reacted poorly. My coworkers are all great – I think they were just caught off-guard by seeing the unexpected item and questioned it before they even realized the logical explanation of why I was holding it. And once I explained it, it was entirely a non-issue.

I was unable to respond to the comments, but I read through all of them. I appreciated the suggestions and alternative options. And I especially appreciated the commenters who “defended” not changing up my morning routine, because yes, the struggle is real in the mornings and I refuse to negotiate with my (now) 3-year-old before I’ve had my coffee! It’s not an option to rinse the cup outside or at daycare, so at the end of the day, I took Alison’s advice and changed nothing. Not only do I have some seniority in my position at the office, but I’m also the oldest in a recent influx of pregnancies and new babies among my coworkers – so I will continue to carry the cup with pride, secure in my conviction that I’m doing a social good and hopefully helping the other moms on my team (if only a little bit)!

4. I’m missing out on work conversations because I don’t smoke (#3 at the link)

I had forgotten about the Friends episode some commenters mentioned and I am an avid watcher of the program.

John was very good at his job prior to being promoted. What I meant by being “promoted out of his competency” (a term I was introduced to on AAM) was that it is difficult for him to change his mindset and have to manage his friends, interact with those who are not his “friends,” discipline staff, and be aware of how the whole department functions rather than getting input from a select few .

The smoke breaks are social, he is not going out there to hold “a meeting” and make others uncomfortable. He is a nice guy and they like spending time with him so he would be missed if he stopped going. The breaks lead to work conversations and chit chat, particularly when he and Jane walk to and from the break. My health issues are not severe enough to warrant ADA involvement.

I did not speak to John specifically about this issue and I also realized after reading the comments that for those not in his friend group his demeanor can come across as animosity, or at least indifference, which I do not believe is intentional. I did end up speaking to him about an incident where he did not communicate specific information related to my job duty but did to others who had no involvement, and he seemed to be somewhat taken aback so I don’t think he would have been receptive to having a discussion about his smoke breaks. I do plan to speak to another director, who is also above him, about my concerns. They will be dividing up the director duties at John’s level so this is a good time to have that conversation.

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  1. Generic Name*

    I think the update to #1 is so interesting. The OP expressed deep ennui about working, and it turned out that they just weren’t into the job they had applied to (or the one they were leaving). I went through something similar around the time I left my last job. I was thinking of moving to another state while still working remotely for my last company and just figuring I could “phone it in” or drop to part time in a LCOL part of the country. I’ve since gotten a new job, and feel much more energized by work because I like my new company/coworkers/projects I’m working on. I’m definitely not someone who lives to work, but this is a good reminder that if I start hating working maybe it’s the job I hate and not working in general necessarily. I’m still looking forward to being retired, though. :)

    1. Elizabeth West*

      I would give my left pinky toe to be able to retire, RIGHT THIS MINUTE. Probably never going to happen. *insert crying emoji here* Hopefully, I’ll win the lottery (gotta start playing, lol).

    2. umami*

      True! I recently was feeling less than enamored with my job, even though I was good at it and felt valued, because … I was bored! I didn’t realize it until I got a promotion that now has me working at a significantly higher level at our central office. People kept telling me how much more intense it is working here than where I was, and asking how I’m managing. And .. the answer is great! I love being busy, I love putting out fires, I feel like my talents are being used much more, and I’m definitely not bored. I didn’t even realize that was my issue, but I’m glad to have more on my plate.

    3. Pescadero*

      Yeah, I’m the opposite.

      After working part time from 14-24, and full time (5 different jobs) from 24-50… it’s working in general I hate.

      I just hate it less than eating out of garbage cans and living in a cardboard box.

  2. I should really pick a name*

    I think #2 should look into why their assistant’s responses were stressing them out so much.

    It sounded like the assistant was trying to set expectations, not asking the LW to manage their priorities.

    1. LoraC*

      If they were trying to set expectations, then they were going about it the wrong way. Your manager doesn’t need to the know the minutia of your schedule or work priority every time they assign you a task.

      Just let them know if there’s going to be an immediate conflict or a problem, otherwise it can be saved for weekly reports or check-ins or whatever your workplace uses.

    2. Starbuck*

      Yeah, I can see how any response that has more info than you need can be annoying if you’d just rather not have to deal with it, but calling it “stressful” and “brutal” is surprising to me. The first letter sounded like a classic example of someone who was used to being overscheduled and having bosses demand things done on a variety of incompatible timelines and having to deal with fallout from that when you can’t get the whole alphabet of tasks done in a day. Isn’t it easy to just say “Sure, getting to it on Friday is fine” or what have you? You don’t need to do anything, it sounds like. But oh well, glad it worked out.

      1. not nice, don't care*

        I have a coworker who responds like OP’s employee all the time. It’s definitely an attempt to derail being managed, and to make pushing through the resistance brutal and stressful.

        1. Mango*

          yeah, I used to use a version of LW’s assistant’s terms to try to slow the inbound flow of work. I picked it up out of desperation when I was assigned 100+hours of work/week with extra constant urgent requests – but I realized it doesn’t really work and mostly makes people upset with you

      2. Nusuth*

        Yeah, I was surprised by how strong the language was in that update. I believe LW that for them it was out of step with their office communication, but in my experience it’s pretty normal to set some kind of expectation of when I’ll be able to do something when I am assigned? My response is virtually always something like “great, I’ll get started on that ASAP” or “I’ll turn to that after finishing X this afternoon” or “heads up, I won’t be able to get to that until next week unless you want me to move some stuff around.” In my mind, my boss WANTS to have some awareness of what’s on my plate and how I’m handling it.

        1. Rae*

          Agreed. Every job I’ve ever had encouraged us to respond to requests this way. Its not pushing back…its just communicating.

          1. MigraineMonth*

            Yeah, there seems to be an underlying assumption that the purpose of mentioning a timeline or relative priority *must* be somehow manipulative or intended to… punish?… the manager for the request. It’s genuinely surprising to me, since I’ve always done something similar when assigned tasks and thought it was important for clear communication (“Okay, is X my top priority now?” or “Sure, I can do X by Friday, or I could do it by Wednesday if it’s more important than Y”).

            It kind of reminds me of when I first started living with my roommate, and she thought everything I was doing had a passive-aggressive message. (Passive-aggressive is not my native language and I have trouble picking up on it; if you’re giving me the silent treatment, I need you to actually tell me first.)

      3. toolegittoresign*

        I would guess the real issue is how all these statements start with “I can’t do this right now.” If every single time you ask someone for something, they respond by assuming you’re asking for it ASAP and saying “not right now,” I can see that being really exhausting. It’s normal to say “sure, is tomorrow okay?” but it’s not normal to think your manager is always making immediate demands.

        1. AgonyAunt*

          Obviously the original poster knows their office culture best but having experienced it from the other end, I would wonder if maybe there is an expectation that everything be prioritized as ASAP, leading to that kind of response (or alternatively it’s a learned response from a previous role and assistant just needs it clearly stated that when something is requested of them, it doesn’t mean ASAP).

    3. CB212*

      I once worked with someone whose job was more or less processing contracts and licenses for the department. She was good at it – but literally every time anyone brought her any new request,.she would wrap a Mantle of Heaviness around her shoulders and tell us how difficult it would be, the calls it would require, the paperwork, etc. And I’m sure it was all true… but also it was her entire job? I don’t know why every request was met with basically a “no, oh no, mmm this is a lot…. well, I’ll see what I can do.” You don’t want one person in your office to push back at every new item! I think LW2 felt like the assistant was making every task into a discussion when they could just… Not.

    4. Nodramalama*

      It sounds like they weren’t setting expectations as much as essentially asking LW to reorganise their schedule. Which yes, on top of every other task LW has, would likely be stressful

    5. lunchtime caller*

      As an assistant in a very busy environment (which LW’s assistant is not, if he’s billing 15 hours !! with a 25 hour cap), those responses to every task would be simply unacceptable from me. My job is to make my boss’s life easier and smoother and that means when they delegate, that tasks disappears from their mind unless I really need their input. You need to read the room and if you’re stressing your boss out constantly, that’s on you as an assistant to change your ways.

    6. rebelwithmouseyhair*

      The assistant was framing negatively “I won’t be able to do that before (whenever)”, but OP wasn’t even expecting him to get it done on the day.
      Sounds like the assistant could have just learned to frame things positively and OP would have been fine.

  3. Kes*

    re: 2 – I think a big part of the problem is how negative his phrasing is. “Sure, I should be able to get to that on Friday” sounds a lot better than “I am doing something else right now, and I can’t get to this until Friday” – the latter really sounds like he isn’t accepting the work and that you’re imposing a burden on him when he’s so busy. It needs to be clear that he is accepting the work and taking ownership of his own scheduling of his work (except where there actually is a conflict between different pieces of work and the conversation needs to be had to figure it out. Even then, there’s more positive ways to raise that if needed).

    However, it sounds like they did arrive at an arrangement that works for them, so glad to hear it

    1. HannahS*

      Yeah, I agree. It doesn’t really project competence to essentially say, “I can’t do that right now” to every single task you’re assigned. I get setting expectations and talking about scheduling when you have more work than you can handle within a time period–it’s a conversation I have often with my supervisors and with the people I manage. But every single time a task is assigned? It’s way too much.

      1. toolegittoresign*

        It’s so odd that the employee just doesn’t ask “when do you need this by?” every time if they’re having difficulty determining what’s urgent and what isn’t. I always just ask that so I can prioritize, so if someone says “by Friday is fine” I can respond “great — I’ll probably have it to you on Thursday.” I have to think the employee maybe worked for someone who demanded everything get done ASAP and it created a bad habit in terms of responding to assignments.

        1. rebelwithmouseyhair*

          Yes. It’s also maybe odd that OP doesn’t even say “by Friday” herself when assigning the work. The assistant wouldn’t have responded with “I can’t do that before Thursday” if he’d been told “by the end of the week please”.

    2. Turquoisecow*

      I wonder if he used to work for someone who was more of a micromanager or insisted everything was URGENT and so he felt the need to explain why he wasn’t dropping everything to do it right then and there and also confirm with OP that it was in fact okay to do that. I’m glad they found something that worked for them so OP could communicate if something IS urgent and the assistant can speak up if he is overwhelmed with work.

      1. Trillian*

        That was what I wondered too. The fact that bad jobs and bad managers leave people with defensive habits comes up repeatedly here.

      2. rebelwithmouseyhair*

        That is more than likely! My clients at the agency always joked about how they needed something “yesterday” so I was forever fending them off and may have sounded like the assistant at some point. I did eventually learn to breezily state a deadline, implying that they’re lucky I can get it done that quick, and offer to do a rush job if they needed it sooner. Somehow, with rush job implying rush fee and possible mistakes due to the rush, they usually realised that my reasonable deadline was fine.

      3. AgonyAunt*

        I wondered as much upthread; I had an old job that was like that (I remember telling my manager at one point that if everything’s an ASAP priority, then nothing can be an ASAP priority) and it took me some time to unlearn that response at my next job.

  4. Ann O'Nemity*

    “2. Assigning tasks to an assistant” was fascinating to me, simply because I’m so used to hearing advice that employees should use language like “I can do A, B, and C but not D” or “I can’t get to this until Friday because of XYZ priorities.” But we rarely hear what it’s like to be the manager on the other side of the conversation.

    1. constant_craving*

      I think that advice is generally for when an employee is overloaded rather than when they have enough time for the assigned tasks though.

      1. Wayward Sun*

        Yeah, when you’re overloaded (which is the more usual situation) it makes sense to ask your manager, “you’ve given me three tasks and I have time to get two done before the deadline. Which one should I sacrifice?”

    2. magic*

      In this case it sounds like the timeline isn’t actually an issue, though. OP says, “Don’t put all of that on your boss if you’re not being pushed or over-scheduled.” So I think that advice is still good, just not if your boss isn’t actually trying to get you to do more/faster than possible.

      1. Coverage Associate*

        Yeah, I haven’t gone back and read the original, but it takes time for a new employee to understand a manager’s rhythm. I guess ideally the employee asks “When do you need this?” though that puts a similar burden on the manager to manage the employee’s schedule.

        I have been at my job for 13 months now and am having lots of year end conversations about timing expectations like these, because my work is varied enough that I don’t understand what timing is usual for all the things I do.

        I probably mentioned this on the original post, but as an employee, a manager sending, “Do you have time for a new assignment?” emails is tricky. Time right now? Today? This week? Mostly, I have learned to respond with when I could next get to a new assignment. It’s very, very rare that I have time that day, basically only if something significant was canceled.

        1. The Formatting Queen*

          Yes, this is exactly what I was going to mention.. when I’m assigned a new task, one of the primary questions I ask is “When do you need this by?” Only then, if it conflicts with any other priorities and I need more direction as to which gets precedence, do I talk about my timing of when I might be able to do it compared to other tasks. It does sound like the OP and their assistant have gotten into a better habit of that sort of communication now.

        2. NotAnotherManager!*

          I don’t really think that asking when someone expects something to be done is burdening the requester. I work in a deadline environment and share a department admin with five other people. The ONLY way they can manage their own tasks and prioritization is if assignments come with specific deadlines. That lets them figure out on their own that of the two assignments they just got, they should start on the one that is due by the end of the day and do the one due by the end of next week second. If they just get a bunch of tasks, unless they are very experienced or really know our organization, I’m not sure how they would know how/what to prioritize.

    3. Nodramalama*

      Yes, but that language is for when work actually has to be reprioritised. OP is saying that the assistant was not at capacity

      1. Mango*

        I feel like “lots of emergencies” can mimic the stress and mindset of “at capacity” even if the actual hours are low. the best faith interpretation is that the assistant may have been genuinely trying to set expectations about when the boss should expect the task to be done (like, maybe they had a previous boss who’d ask for a task update an hour after assigning it sans deadline or extra prioritization info)

  5. Wayward Sun*

    I remember #3. The comments discussion about what was and wasn’t reasonable to do with a used sippy cup was surprisingly contentious.

    1. Sc@rlettNZ*

      And who are the weirdos commenting on it? If I saw a colleague carrying, say, a pink flamingo around the office I would probably comment on it, but a cup, even a sippy cup. WTF?

      1. Nodramalama*

        There was a massive go around last time as well, and as LW pointed out in this follow up, it seems less like weirdos and more people who noticed something out of place and innocently said something.

        1. MigraineMonth*

          Maybe they hoped there was a small child nearby they could play with and were disappointed to learn that only the cup had come to work.

  6. Zona the Great*

    I also notice the odd advice on social media. There are two “Veronicas” on TikTok who talk about boundary setting at work. One is funny and cute (the one who did Starbucks parodies) and the other advocates a lot of what I think of as aggressive interactions with supervisors. She typically does her skits in pretend office jobs rather than customer service like the other. And while her message is not to do more than you’re paid to do and to stop agreeing to help a company who wouldn’t help you when you need it, she models it as a conflict or confrontation. In one case the skit showed a supervisor ask her to do OT on a Monday for example. Then on Tuesday supervisor says, Oh I’m sorry but we can’t pay you OT after all so I need you to leave early today to off-set those hours. And Veronica replies that no she will not leave early and you will be paying me for extra hours as you committed to doing–all with a terrible tone. Even for someone like me who advocates a take-no-shit stance, this is insane behavior.

    1. Mélusine*

      What is the correct language to use, in the 2nd Veronica’s case, when promised rewards are retracted? I’ve had a similar situation happen to me recently and I don’t think I could stand up for myself like that. I’d just be internally fuming.

      1. honeygrim*

        I’m not sure what the language would be, since the supervisor’s options may be limited. If the employee is non-exempt, and the business truly cannot pay OT for the extra hours worked, then the only option is for the employee to leave early so as not to exceed overtime hours.

        I would also be frustrated, but unless the employee knows something that changes the basic facts of the situation (e.g. that the business has paid OT for other employees in the same context, etc.), I don’t think there’s anything they could do or say to change it, other than keeping this in mind for any future requests to work late.

        1. Pescadero*

          “I’m not sure what the language would be, since the supervisor’s options may be limited.”

          It feels like not lying initially would have been a good option.

      2. lunchtime caller*

        Flexing your time the next day is actually a very normal solution in jobs where overtime pay is not really in a budget but the schedule can be flexible, I think part of it is learning more norms so that you don’t feel an injustice has been committed when a solution is just less preferable to you.

      3. Great Frogs of Literature*

        If it was a big problem for me, I’d probably go with something like, “Okay. FYI, it was inconvenient to stay late last night, and I agreed to it with the understanding that I’d get extra pay to compensate for that. I know it’s the same number of hours, but leaving early doesn’t make up the time that I missed with my spouse/kids/[whatever reason you don’t like working late]. In the future, if you tell me that I’ll get overtime for doing something, can you make sure that there’s really money to do it? Right now I’m feeling like this was a bit of a bait-and-switch.”

        There may be better specific wording, but the overall approach would be, “I know you think that this isn’t a big deal because it’s the same number of hours, but it is a big deal to me; please don’t do that again.”

      4. Rex Libris*

        In this case I’d just go with something like “It was inconvenient to stay late, and I mainly did it for the extra money. Can we make sure that’s solid if it comes up again, before I take the shift?”

        It doesn’t sound accusatory in a way that will tick your boss off, it isn’t confrontational or whiny. Personally, I’d just stick with a straightforward, but professional “It caused me a problem when x happened, can we avoid x going forward if at all possible?”

    3. Skytext*

      I LOVE the “Veronica” skits! But I’ve always thought of them as demonstrations of the principles that the workplace “should” have, not literal ways to act with your manager/supervisor. They are the same principles Alison promotes over and over: basically, don’t work for free. Don’t set yourself on fire to keep your company warm. Because for too many years we heard: go above and beyond, work unpaid OT, don’t take your vacations, don’t call in sick even when you are, prove yourself by doing the work of a promotion for months without the raise or title change, etc. etc., and your company will reward your loyalty. But they don’t! So employees need to keep their best interests in mind. I think Veronica is just demonstrating that. Of course, in real life you have to handle it WAY more diplomatically or you will find yourself out of a job.

      1. Commenter 505*

        I love them too, and I agree that it’s probably not meant as an instructional video.

        One listener’s “aggressive” is another’s “firm.” I wonder if that part is just a nice vs. kind issue. Admittedly, I haven’t seen the Monday/Tuesday OT episode from above, but the ones I have seen start with a supervisor approaching Veronica with some kind of complaint or fake-sincere expectation to work more for no pay, or to go unpaid work events outside of work hours. Supervisor does a lot of volun-telling followed by excuses when V asks for clarification: “Will I be paid to go to this after-work/weekend event? Is it mandatory? My time outside of work is for me and my family. My time here is for work.”

        I guess the supervisor *sounds* nicer, but she’s fake af. She pretends her unreasonable asks are in fact reasonable. Veronica just has boundaries and presents them in a clear-but-blunt way. She’s a real one.

    4. fine-tipped pen aficionado*

      I don’t think I would call the videos advocating. I haven’t watched her entire oeuvre but I’ve never seen her frame her skits as “here’s what you should do at work”. It’s career advice like the movie Office Space is career advice.

    5. oh my god the ads*

      “And Veronica replies that no she will not leave early and you will be paying me for extra hours as you committed to doing–all with a terrible tone.”

      Ha ha, sure Jan–if you want to get fired.

      I’ve been working since like, 1999. And in hourly (but non-retail) jobs since 2005. And in all that time, there was only one employer that actually did approve overtime pay on a routine basis*. For everyone else, you either did not ever stay past your actual hours (so if work didn’t get done during those 8 hours a day, it didn’t get done that day) or if you did stay late the one day, you left early or came in late another day.

      It’s the same setup with my current, non-exempt (aka hourly-paid) job. And the way our timesheet website is set up, it’s easy to make a mistake and accidentally not clock out until after your 8 hours. If it turns out that you did actually work overtime for real and don’t leave early/come in late at a later point in that pay period to adjust for that, so now you’re owed real OT money? Oh man, is there a huge to-do about it. HR gets on your boss’ case. Your boss gets on your case. Because there’s not really money in the budget for overtime pay right now. And if it happens often enough, you can and will be let go for it. Duh.

      *the job that regularly did pay out overtime was a poisoned chalice though. Like yeah, it’s great that if you worked 60 hours a week, you got paid time and a half for those extra 20 hours. But at a certain point, a person just wants to be home after like, 10 or 11 hours in the office, you know? Especially if their usual schedule is 8:30 to 5:30 but because of endemic workplace dysfunction, they keep having to work late so they’re routinely at work from 8:30 to 6:30, or 7:30, etc. And that’s why they’re racking up overtime so often. After a while, you’re like “I just want to walk back into my front door before dark.”

    6. Annie*

      > There are two “Veronicas” on TikTok who talk about boundary setting at work.

      You know that they’re the same person, right?

        1. Broadway Duchess*

          Veronika (with a k) posted awhile ago (couple of months? )that someone had taken her content to impersonate her.

  7. Kisa*

    on #2. okay, i seem to be an outlier here, but this sounds very icky and patornizing to me. dictating the specific words YOU want to be given information sounds so demanding. and basically practising with them what tos say. i mean youre happy with their work right? i get that some things just gets under our skin, but Come on. i cant imagine my self being so fragile that someones way of phraising things would stress me this much.

    2. Kella*

      It sounds like OP had multiple conversations with the assistant to try to set expectations for what OP is communicating when they give the assistant another task, and what they want from the assistant, and the assistant just kept responding with resistance regardless. It sounds like asking the assistant to follow the script of “I’ll add it to my list” was a shortcut to changing the behavior since trying to change the underlying understanding of the situation just wasn’t working.

      A huge purpose of *having* an assistant is to be able to hand off many tasks of multiple sizes, take information about deadlines, priorities etc, and allow them to problem solve how to fit it all into their schedule. This assistant was essentially responding to every new task with, “But in order to do that, I have to figure out how to schedule everything,” as if asking them to do their job was a hardship.

      It’s also what I call “conversation-blocking communication” where you are making it harder for the other person in the conversation to accomplish their goal, rather than using the communication to enable both your goals. Having everything someone says to you be conversation-blocking is super frustrating, like you’re running into a wall every time you talk to them. And it’s even more frustrating when it’s their *job* to streamline and make your job easier!

      1. Kisa*

        Still I disagree. I have an assistant (not a personal one). They are not AI or a robot. I speak to them like a person I am an, and expect them to speak to me like a person, like they are.

        Sometimes we irritate one another, like people do. But I wont script their speech. I would find it offensive.

        1. lunchtime caller*

          You may not script their speech but a savvy assistant (as someone who works very successfully as one) will figure out the magic words to keep you happy anyway. I’m able to do that with my bosses but a lot of people would actually find it a kindness to be told their boss’s preferred style rather than have to figure it out through trial and error and people reading skills the way most of us do.

          1. Kisa*

            okay, there is HUGE difference in how we think. :D i dont think its my assistants Job to make me happy, but do their part of the job to achieve our common goal. but yeah, i kind of see where you guys are coming from, its just very different from how my company operates. im just happy that in my place of work we can appreciate each other and every once in a while give some slack to anyone regarding status

        2. rebelwithmouseyhair*

          What if they are offensive? “Eff off man I can’t look at that before Friday”

          Others are saying that the employee sounds defensive, like they’re used to managers heaping too much on them and expecting them to drop everything for the latest emergency. So OP being more explicit with deadlines and telling the assistant it’s not urgent (which is what I and others recommended when the original letter ran) and wanting their assistant to be a bit more positive, is very helpful.

          Being pleasant is part of the job after all. Everyone has to be pleasant or work soon becomes unbearable.

    3. hbc*

      Congrats if you’re strong enough to hear someone respond like Eeyore to every minor assignment you hand them, but this assistant would have driven me up the wall. If someone has to remind me how busy they are every time an “okay” or “should have it by Friday” will do, I’m going to start reacting to the subtext.

      It also doesn’t sound like OP went in demanding the exact wording, but that the assistant kept with the “I’m so busy right now, but…” qualifiers even after the initial conversations. I highly doubt that OP is scolding him if he says “Sure, will do” rather than “I’ve added it to my list.”

    4. Rex Libris*

      As a manager, when I assign a task, I then want to move on to the next thing and know it’s handled. If I have to expend the bandwidth to track the details of an employees’ scheduling, prioritizing and process, reassure them that 10:00am next Tuesday is okay (when I obviously haven’t said I need it before that) and etc. then I might as well do it myself. I’ve had employees who do that, and it’s exhausting.

      It sounds like the manager here was giving specific wording as a last resort to shut the behavior down.

    5. magic*

      The intention isn’t scripting, it’s conveying what information she wants to be given. This is a good thing for the employee – he doesn’t need to start making excuses that aren’t necessary.

      And it’s pretty rude to call the OP’s self fragile!

    6. rebelwithmouseyhair*

      To be fair, it did sound like the employee was framing everything in a negative way “I won’t be able to fit that in before Friday” or “I don’t have time for that today, because I’m working on something else”.

      I think partly OP needed to just set a deadline for him, or ask when he can fit it in, specifying that it’s not urgent for the moment. And partly, the assistant needed to be more positive. “TPS report? Sure, I can look at that on Friday.” or “I’ll get this out of the way first then I’ll be right on it!”

  8. Moose*

    … Am I missing something? How is using a sippy cup with your toddler doing a social good? Is it because LW is using something reusable instead of disposable? Was this a reference to the comments from the original letter?

    I feel like I am missing something. That last line feels very out of left field to me.

    1. Elf*

      The final paragraph of Alison’s advice was
      ‘On the other hand, if you don’t struggle to be taken seriously, change nothing. Especially if you’re senior-level and widely respected, it can be a social good to let your own behavior be a counterweight to problematic norms.’

    2. Kalongdia*

      I believe she is referring to it as a social good because she is normalizing the behavior for other new moms in the office

  9. Lego Girl*

    On the sippy cup front – I’ve started drinking coffee out of an insulated stainless munchkin 360 cup because I was constantly spilling my regular adult cup! The only downside is that it only holds 10 ounces.

    1. Rex Libris*

      I can’t recommend the Zojirushi travel mugs enough. They’ll keep drinks hot for 5 or 6 hours, and most models have a flip-top lockable lid that doesn’t leak even if you turn it upside down (or at least mine doesn’t). They’re basically sippy cups for adults.

      1. Spreadsheet Queen*

        Oh – they keep hot drinks WAY too hot! Like make your coffee, pour in your coffee, drive to work, get comfy at your desk, try to drink it? OW! It also splashes if you try to pour from it into a normal coffee cup so you can have some at a less burny temperature.

        1. Rex Libris*

          They do keep everything super hot, but I’m one of those “likes the tea just cool enough to avoid internal injury” sorts. It’s also true that they have a very “sippy cup-esque” cap that would not work well for pouring.

          I’m just finishing a mug of tea I poured over four hours ago, and it’s very nearly as hot as when I poured it.

        2. MotherofaPickle*

          I have been known to keep my insulated drinks containers in the fridge overnight for just this reason. Cold insulation + hot coffee = warm, drinkable coffee and a happy Mother of a Pickle.

          1. rebelwithmouseyhair*

            I used to have a kitten called Ginger Pickle because he had a fair bit of ginger on him and was always getting in a pickle (falling in the toilet was just the worst).
            So yay from an adoptive “mother” of a pickle who absolutely needs to research adult sippy cups to keep my drink warm!

  10. Liz*

    I’m not an assistant but I fill requests from the sales team based on my subject matter expertise. It would be totally normal for me to tell a requestor “I can have that for you on Thursday.” Or “This is something I can do this afternoon “ so they can in turn let the customer know when to expect it.

    1. Spreadsheet Queen*

      But that is different than preceding your statements with “I can’t”. And may different in that there are external stakeholders beyond your sales team who will care about when.

      There is a whole “Yes, and” thing in business communication. Start with the positive. You start with “I can”. That assistant was starting with “I can’t”.

      I’ll bet if in the beginning that communications had been more like “I can get it to you Friday” instead of “I can’t do that today, but should be able to do it Friday” it would have landed differently. Now it’s just too late to put an ETA on the end of an “I can” because there’s a pattern that gets to OP now.

      So yeah, new language. “I’ll add it to the list”. “Got it. Will do.” As long as the assistant isn’t loaded down, and LW continues to be clear when something IS more urgent and willing to discuss timelines around THAT, that’s fine.

  11. fine-tipped pen aficionado*

    Yeah. Based on how many folks are reading that letter and coming away with such different interpretations and reactions, I think it’s clear that you have to do some explicit and clear communication about expectations, interests, and needs with these types of roles. It seems like actually talking about it fixed the problem, so it hits me as strange that LW still sounds so in their feelings, but I’m willing to chalk that up to another communication challenge.

    1. fine-tipped pen aficionado*

      Nesting fail – LW 2 isn’t the only communication challenged person today it seems

  12. AnnoyedInWonderland*

    I guess it’s because I’m not a manager myself, but I just can’t wrap my head around what LW2’s problem is. Their assistant didn’t seem to be asking *them* to prioritize the task; they were just stating where it would likely fall in their schedule. And I didn’t get the impression that the assistant wasn’t actually delivering the items. Reading through the original and the (surprisingly defensive) update, I kept thinking “can you not just say ‘okay’ and be done with it? bro chill.”

    1. Broadway Duchess*

      “…I kept thinking “can you not just say ‘okay’ and be done with it? bro chill.”

      I get the impression that’s what OP wants her assistant to say — “okay” rather than a whole negative thing about where it will fall on the list.

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