update: when my boss wants me to do something I really don’t want to do, can I just … not?

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.

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

Remember the letter-writer asking whether, when her boss wants her to do something she really doesn’t want to do, can she just … not? Here’s the update.

First of all: thank you for answering my question! Most of your points were something that really felt reaffirming in a way. I felt like you saw the actual issue behind this one rescheduling, even without all the background context, and why I was even thinking this way. That was perhaps more empowering than anything else. I think this was one of those situations where you can’t find the words to say something that feels difficult – and then you complain to a friend about it and they immediately suggest something really clear and concise. This was definitely one of those situations for me and you, Alison, were very much a friend in need! Someone in the comments said that maybe I needed more of a chance to vent than to actually ask a question, and I think they were absolutely right. I also really appreciated the commiseration and advice from other people with similar jobs!

When I wrote to you I was already tired, stressed and frustrated. Although I usually handle my hectic work days pretty okay (and most of the time even thrive on facing unexpected daily challenges and sudden changes – I think any other job would feel really boring after this one!) this time it all just felt so pointless and hit hard. I should be doing so many other important things. And for some reason, it just felt so difficult to send those couple of quick emails as usual and continue with other tasks, and instead, I got stuck. And finally wrote to you. I think it was one of those situations where you just wish you could act instinctively, say or do exactly what you think, no matter how unprofessional or just plain destructive to your professional image or personal relationships. Luckily we don’t usually act upon those urges. Well, most of us don’t – I’ve read enough of this blog to know better! I think I wasn’t really asking if I should (or could) lie to my boss by omission or otherwise, I was asking how to handle the conflicting rationales in this chaos that is my job. Sometimes my boss makes decisions that feel counterintuitive to me doing my job as well as possible, which is making her daily life go smoothly and efficiently. My being good at my job means that I know everything and am constantly up-to-date about everything, ready to brief her on all subjects and present options for her to decide upon – and more to complicate this issue I’m also expected to make judgment calls on decisions. At the same time I need to remember that I actually do NOT always know everything and that in the end, it’s her job to make all these final decisions and assume responsibility for those in front of our staff and the public. I can present my information and voice my opinions, disagree and debate, but that’s where my responsibility ends, and her decisions do not indeed reflect on me personally. Sometimes you just forget when there’s not a lot of time to step back and reflect.

As someone guessed in the comments: my job is definitely not entry-level and although a big part of my day is spent wrangling her impossible calendar, I also act as her political aide: someone she discusses and debates strategies and solutions with, someone who attends important meetings with her as an active participant and not just a note keeper, someone who researches and writes her speeches and statements as well as many, many other things. It was almost strange to read many of the comments saying that I should reconsider my suitability for this work because of this issue and that perhaps I’m not cut out to be in this job. Someone even said that a good executive assistant would not feel this way. I sort of get it: this is a part of my job that I sometimes just need to deal with. But at the same time: it’s only a part of it all. I reschedule meetings all the time without any issues. It’s the circumstances that sometimes make it more unpleasant, and this time it just was the last straw during a difficult day. The thing is: I don’t think many people have jobs where there are no unpleasant tasks or, well, even an occasional unpleasant day or two… even when they really, really love what they do and do it well.

Someone also said that our work seems to compare to civil servants with high burnout rates working in Private Office in the UK, and yep, that definitely sounds familiar, although probably with a lot smaller budget, if you can believe it :) One commenter (“Baffled”) was also pretty close in explaining the scope of my work much better than I was: it’s a lot more than calendars and emails: “At this level, assistants like LW are helping shape strategy, providing insight into employee environments, executing projects and initiatives, coordinating campaigns, planning some events, and EVERYTHING else.” Our organization deals with issues in all areas of our society and I need to be able to quickly work on issues concerning all and any of them. For example: sometimes we find out in the morning that she needs to present tomorrow on the topic of llama feeding regulations and legislations, and so I have to spend the day first researching on what DO they actually feed the llamas with and who regulates that and what are our issues with it – and then writing a 20 minute speech for her in layman terms. While she’s presenting, I’m already doing something completely different, like drafting a press statement on our work with ethical guidelines for local candlemakers while trying to wrangle six different full calendars in different time zones to schedule a meeting on how to respond to local UFO sightings – and then suddenly something incredibly important comes up and I need to both clear the calendar for the next three days and start rescheduling everything as well as start preparing for the newest thing, all the while trying to find time to take care of that UFO sighting meeting and the deadline for the ethical candles is nearing in.

We have a great staff and I have many amazing coworkers I work closely with, but my line position is still pretty unique. We are also underbudgeted and overworked and that’s completely out of our hands. My boss is not the best at remembering that although we’re pretty damn capable, we’re not machines and many of our staff are crumbling under pressure as it is. It was made clear to me right from the start that she needed me to tell her when I disagreed with her, to act as her moral backbone of sorts when she got sidelined in the middle of all this chaos. With my role in between, I need to be really careful about what to say and to whom and therefore I can’t really vent with anyone or ask anyone’s opinions on what the boss would like to do. It’s the other way around: others come to me with these questions. (Sometimes I’m able to tell them her line of thinking or how she wants things to be done. Often I either direct them to ask her or ask on their behalf. I really don’t have a habit of deciding for her unless she particularly asks me to!)

FINALLY, for the actual update on how it all went down. I want to clarify that, as usual, I definitely briefed her right from the start on all the relevant context, including how annoyed the organisers were before, as they were much more annoyed than people usually are in these situations. We are reliant on our image and co-operation with these people and every other group we deal with, even when they and a meeting with them are not as important as the thing that forces us to reschedule.

But yeah, I did what I had to do and politely emailed the organisers once again and explained the situation. They responded somewhat nicely (so I think the very polite script helped!) and suggested some alternatives on how to proceed, although none of them would be very easy to arrange for different reasons. In between I had to communicate with our own staff on our options based on their knowledge of the subject and also their schedules. After gathering all the relevant information I went back to my boss to brief her of the situation and our options and to ask how to proceed. And…. after I first reminded her again what this meeting was even about to begin with, she was surprised to hear that this was still an ongoing issue, as she had assumed that we would just meet without her. “Oh, I thought we weren’t trying to reschedule? Didn’t you say this was really difficult to schedule in the first place, or was it some other meeting we were talking about back then?”

Yeah, so. This is what I meant by saying she wouldn’t likely remember… and this is why these situations sometimes are so frustrating to deal with. I could have used this time making sense of those pesky llama feeding regulations and how on earth I should go explaining their issues to the public, and now I have a little less time left to arrange that time-critical UFO meeting. And despite all this: I really, really love my job as well as (most of the time :) ) working with my boss, whom I respect a lot. I mean, where else would I learn about all the intricacies and issues with llama feeding regulations? And who knows what the subject is tomorrow! I at least have no idea.

{ 33 comments… read them below }

  1. Thistle Pie*

    LW, I completely relate to your entire update. Trying to explain what how chaotic working in government or politics is to people outside the industry feels like an impossible task. I’ve been asked to do things that I fully think are the wrong decision, but it’s not my decision to make so I just have to move forward while fully anticipating the fallout of it. It’s exhausting to work really hard on something that you know will be rendered moot in a few weeks or months. And you’re doing it over and over at warp speed trying to keep up with everything to stay relevant.

    I see you, I see the hard work you’re doing, and I see that sometimes we just need an outside perspective to validate “yes this sucks, yes you’re put in a bad position, yes you can just pull the band aid off and do it”. And then your boss is like “oh weird, did I ask you do that? why did I do that?” and you scream the whole car ride home.

    1. LW*

      Thank you for seeing me! I joke around a lot that it’s either masochism or a serious case of Stockholm syndrome that I really love and enjoy my job! Or both. Both is good.

      Luckily my boss recognises her misgivings and mistakes most of the time (as in she trusts me and my recollection of her decisions more than her own), I don’t think I could handle this all if I didn’t feel most of the time that we’re on the same boat.

  2. KayZee*

    This sounds so much like my job, including my relationship and interactions with the boss, except I’m in academia instead of politics. And, funny that commenter Beth should mention haikus – sometimes I use them to get answers the boss needs.

    1. Ama*

      Yeah this is a lot like my career path (a decade in university admin and a decade in nonprofits that work closely with academics). I don’t think I commented on the original letter but I really really get how with these kinds of jobs, sometimes when some issue (no matter how easily handled) pops up with a project/task you thought was off your plate your brain sometimes just goes “NO, this was DONE, I’m not opening it back up again.”

      (I will say I’ve recently decided that 20 years of this is enough for me and I’m making plans to move on to something where my day to day work isn’t as affected by the sudden whims/new priorities of others.)

      1. Kelly*

        I totally agree with this Ama! Especially the part of mentally closing a particular task and reacting with NO this was DONE, I’m not opening it back up again. I’ve been there!

      2. Tangochocolate42*

        Oof! This just crystallized why I’ve been having issues with my job at the moment – I’ve got tasks boomeranging unexpectedly far too often.

    2. Vin Packer*

      Also academia, also immediately identified with the letter-writer’s dilemma: it’s not just “accepting that it’s not my call and doing something I don’t agree is the best choice,” it’s “expending tons of time and labor and doing something stupid that nobody is ever actually going to follow up on and the person who is making me do it is probably going to forget they even asked for.”

      The problem is that, every 1 or 2 times out of 10, not doing the thing will come back to bite you, and plus you want to be an ethical person, so you generally have to at least make a defensible attempt of some sort. But you also can’t even physically do every stupid thing you’re asked to do, so you do have to figure out how to protect your labor a bit from carelessly-assigned nonsense tasks.

    3. Siege*

      Yep, same, but I’m in a political role where I support teachers. LW’s description of her job resonated, and I agree – what other job could hold a candle to this?

    4. Project maniac-ger*

      Yep, I’m an EA for University Admin and boy howdy did I feel this! Why are academia and politics so alike?!

  3. Varthema*

    “It was made clear to me right from the start that she needed me to tell her when I disagreed with her, to act as her moral backbone of sorts when she got sidelined in the middle of all this chaos.”

    < If this is an elected official (sounds like it is), I want to vote for her.

    Nothing but admiration for the work you do, OP. Best of luck and hope you get to have a real vacation soon so that you can recharge for doing all that good work!

  4. Jack Russell Terrier*

    Yes I was thinking ‘Principle Private Secretary’ and that you should be taking lessons from Sir Humphry in Yes Minister!!

    This might not be helpful, or even possible but how can your knowledge of her be used to smooth your path?

    In this case, could you have sent something of a placeholder message? I’m so sorry …. etc … . I wanted to let you know immediately. I’ll be back in touch tomorrow after confirming with Boss about rescheduling or going ahead without Boss.

    Then you can go back to your boss the next day and say – I think going ahead without you because of A B &C makes sense. Do you still want to reschedule? (or just leave that last bit out?)

    Would she have had enough time to relax about it?

    1. Goldenrod*

      “I was thinking ‘Principle Private Secretary’ and that you should be taking lessons from Sir Humphry in Yes Minister!!”

      Ha ha, YES.

    2. Silver Robin*

      I think I suggested that whole series in the comments on the first post because that is exactly what this entire situation made me think of. Such a delight

  5. Goldenrod*

    I really relate to your letter/situation/update, especially this part:

    “I think it was one of those situations where you just wish you could act instinctively, say or do exactly what you think, no matter how unprofessional or just plain destructive to your professional image or personal relationships.”

    I struggle with this at times! I’m an EA who generally enjoys her job, but sometimes…it just hits differently and it can be a struggle.

    Congrats on how it all turned out!

  6. Santiago*

    I found your letter and the resulting discussion really helpful in soul-searching in my own job with respect to tasks I like, and dislike.

  7. Mo*

    I’ve had a job like this. One thing I found helpful was venting to a cousin who lives far away, and couldn’t care less about what I saw as incredibly urgent.

  8. Purely Allegorical*

    I have a lot of feelings about this one. This person sounds like a Chief of Staff or Special Assistant or scheduler type role for a member of Congress. At that level there just is no taming the chaos, you can only survive and develop little strategies for making the chaos bearable.

    LW, I think in this case, you should proceed as if you do indeed have the authority to attend a meeting in her place. When you know she’s not gonna remember (or even… care?) just do the thing that gets the job done most efficiently. If you want to have a sit-down chat with her first to align on this dynamic, I think that would be good and alleviate some guilt or give you the permission to do it.

    But your constituents and partners are not being well-served by allowing more chaos than is truly necessary.

    1. Ally McBeal*

      It sounds to me that LW should not be scheduling, not because she doesn’t like it but because she has much more important priorities. They should hire an admin to deal with the minutiae of finding mutually agreeable times so LW can focus on the rest of her work. I know they’re budget-constrained but LW says “people are crumbling under the pressure” and that’s bad, bad, bad when we’re talking about keeping a government running smoothly.

  9. Happy Pineapple*

    This was exactly the update I was hoping and expected to see. Every capable administrator has moments/days where you get so incredibly frustrated and the work seems pointless. It’s a side effect of being invested in your work and wanting to be as efficient as possible. People who thrive in EA roles also tend to love structure and control, and that can clash with the chaotic nature of the job. We want to solve all the problems, but the goalposts are constantly moving! Being able to vent or commiserate with others is a mental health lifesaver.

    It’s a tough job, but it’s never boring. You’ve got this!

  10. PoliticsIsMyGame*

    As a district chief of staff for a politician, I feel this ways you don’t understand. Folks can’t understand what we go through unless you are in politics/government. When it comes to manic schedules, I try to remind myself and my team that we work for the elected official and they work for the constituency that elected them. I’m there to listen to them, they are there to listen to the people. It seems heartless, but helps me compartmentalize my responsibilities.

    1. Also Political*

      I am an elected official in one of the most political cities in the U.S. (for example, this city had over 86% voter turnout in the 2020 election), and I always feel absolutely terrible about how ridiculous elected officials and my specific colleagues are.

      I love reading AAM to read about more mundane (even if bananapants!) scenarios that have logical, rational ways to deal with things. Unfortunately in the world specifically of elected politics in the U.S., so many norms get thrown out because it’s “for the people!” and being directly voter elected somehow absolves people of terrible behavior. I believe strongly in democracy, but it’s difficult to change any sort of workplace norms when the only accountability measure is how voters vote.

  11. BigLawEx*

    I had a friend who was a chief of staff to a high-ranking Congressman for about five years. Either people have this job for a long time or burn out pretty quickly. It never changes. My friend’s boss retired and he then ran for Congress himself (and lost).

    But he says most people do this for a short period and then move on because 1) BURNOUT and 2) it’s not high paying, but can lead to a lot of lucrative positions – especially when you learn the intricacies of UFOs or llamas *and* have knowledge of how the sausage is made. LW it can be rewarding, but keep an eye out for your own mental/physical health.

    He did really enjoy it though. I loved visiting him in DC and watching the chaos from a safe distance.

    1. Reluctant Mezzo*

      And then the UFOs start picking up the llamas, so you can have both meetings at the same time!

  12. wineforcats*

    LW – this happens to me all the time! When I have a feeling that the person asking me to reschedule might fold when realizing it’s difficult, I phrase the question to the entity I’m asking to reschedule as a preference. (Ex: Person X would like me to reach out to see if rescheduling is a posssibility, their preference is to do Y at [dates/times].) That way when Person X inevitably changes their mind, I can thank the entity for being so flexible, we see the difficulty and like to keep things as they are.

    Or, opposite, if later I get the sense Person X is 100% in, I can go harder (EX: Person X is now unavailable at the current date/time and we are confirmed looking to reschedule for [dates/times]).

  13. cuddleshark*

    OP, I’m so glad that there are people like you in the world. Just READING your letter spiked my anxiety levels and gave me a good humbling about how low-stakes my own job actually is, even when it feels stressful. Keep on being awesome, and thank you for making sure those llamas are getting proper nutrition!

    1. allathian*

      Yeah, my resting pulse hit 90 when I read it.

      I can’t deal with rescheduling very well, so I simply don’t plan my days in detail. I have a list of tasks with deadlines, some of which are less fixed than others, and whenever I can, I pad my schedule because there are often urgent tasks that come up and force me to reschedule.

      The one thing I cannot deal with at all is having a detailed schedule that’s derailed by an urgent task that forces me to drop everything else. I’d rather go with the flow and deal with the urgent tasks as they come along, the Excel file of tasks with deadlines is to ensure that less urgent tasks also get done when I happen to have the time to deal with them. But I don’t use that to schedule what I do except to ensure that I have enough time to complete my work before deadline. I do sometimes use my calendar to schedule time for deep focus, when I’m allowed to be less responsive than usual.

  14. Michelle Smith*

    I used to think political advising (like for my state legislature, who sometimes hires attorneys with my background) might be a good career pivot for me at some point in the future. Reading this update letter has completely disabused me of that delusion. I am not capable at all of doing what you do and I felt a lot of anxiety just reading about your day-to-day. I think I want to do something much, much more slowly paced haha.

    So thank you! Not only did you get the advice you wanted, but you helped at least one other reader with your question!

  15. Tinkerbell*

    I choose to believe this OP was Anthea, Mycroft Holmes’s assistant from BBC’s “Sherlock” :-D

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