my assistant doesn’t know how to prioritize

by Alison Green on December 4, 2024

A reader writes:

My team recently hired a part-time assistant, Jane, to help with my work. The problem I’m running into is that Jane either doesn’t know how to prioritize or doesn’t understand that certain things need to be prioritized even if I explicitly tell her “this task needs to be completed before you do anything else.” She continues doing tasks that she finds enjoyable without working on items that have hard deadlines. For example, I asked her four weeks in advance to pack up a big shipment by the end of month – she had plenty of time and she’s done it successfully before – and yet when I asked her what was going on a week before the shipment was due? She hadn’t gotten to it yet. She had spent three weeks working on other tasks instead, like emailing leads. With such a short amount of time left for the shipment, the rest of us had to pitch in to help complete the task, when really she could have done it by herself if she had started earlier.

I tend to be a person who prioritizes any tasks with a deadline – even if the deadline is two months later just so it’s done and dusted. I get that there are some people who function very differently, and that’s fine within reason! I don’t want to dump my work style on her by prioritizing for her, but I’m at a loss for how to better manage completion of the tasks I assign to her. Help?

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

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{ 84 comments }

{ 84 comments… read them below or add one }

  1. Beth*

    If you’re telling someone “Do this before you do anything else” and they’re doing other things instead, I feel like that’s not a question of not knowing how to prioritize. That’s a question of quietly refusing to do the task you were assigned to do.

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    1. pally*

      Agree! Especially if there’s no explanation offered. For example: something is hindering completion of the prioritized task. In which case, say something!

      Reply ↓
      1. duinath*

        Yep. TBH when I hear someone was explicitly told to do something, and just… didn’t, which meant everyone else had to pitch in to get it done before deadline… I’m not thinking how better to manage them, I’m thinking how to get them out of that position pronto.

        Reply ↓
        1. Kevin Sours*

          It can be worth sitting somebody down once and saying “no, seriously, this is important and if you don’t do it you can’t do this job”. Sometimes people hear things as suggestions when they are not and being super blunt about it can get results. Not always but if it’s not a lot of effort to save you from having to hire.

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          1. ferrina*

            Agree with this. I’ve also worked with bosses who said “do this before anything else”, then were shocked when the other things weren’t done because I was working on the top priority task. (After a while I picked up the art of saying “You want me to do Task X first, which will take 3 days. This means I will need to push back the delivery of Task Y and Task Z to next Wednesday- does this work for you?”. Then when they confirm, document the change was approved by boss as a CYA.)

            It’s also worth confirming which other tasks will be affected and updating your soft deadline for those tasks, just so the person knows that you understand the impact of prioritizing Task X. But it also depends on what the other person’s role is- where I work, it would be a big problem if this was happening with a Project Manager whose literal job it was to know these things, but a more junior assistant would not be expected to know this and would require a more dedicated walkthrough by the project lead.

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          2. FedIT*

            This is true, and it reminds me of a fellow LT back in early 2001. I’ll call him Dave. Dave rode a motorcycle, and it was raining one Sunday when he had duty. So Dave parked his motorcycle inside the battalion HQ so it wouldn’t get wet. The Battalion Commander came in after church and asked Dave whose motorcycle this was.
            Dave told the Commander it was his, and the Commander says something along the lines of “I suggest you put that outside,” then went back to his office to do whatever battalion commanders do in the office on a Sunday that can’t wait until Monday.
            20 to 30 minutes later, the Battalion Commander came back out and the motorcycle was still there. The Battalion Commander then said something like “I told you to put that outside.” Dave said something like “No sir, you suggested it.” Dave had a bad day after that. And on Monday the rest of us junior officers had a meeting with the Battalion XO where we were told what had happened, and that if the Battalion Commander suggested something to you in the future, consider it a politely phrased order.

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              1. Bast*

                I don’t know about that. The response does seem a bit smart alecky, but I can think of quite a few instances – both personal and professional — where someone has indicated “Do this” or “Can you do this” with no timeline and the person hearing the request is thinking, “Sure, no problem after I finish doing X.” (not the case for LW, but the case in this comment). It seems to come up a lot in marriage as well, (I’ve seen this complaint multiple times online, and in conversations with friends) where Spouse 1 says to Spouse 2, “Hey, can you please take out the trash” or something similar, Spouse 2 says “Sure” and 20 minutes later trash is not taken out and Spouse 1 gets mad. Spouse 2, states “Well, I am going to take the trash out, I didn’t realize you meant immediately.” Spouse 1 is upset because they think Spouse 2 blew them off, and Spouse 2 is confused and upset because they didn’t realize it required immediate action, and fully intended to do it.

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      1. epicdemiologist*

        It’s also possible Jane is doing the things she knows how to do, and isn’t doing the ones she doesn’t know how to do. In which case, Jane also needs to learn how to ask for help/training. (I’ve seen this with multiple graduate assistants, but I imagine it also happens with other early-career folks.)

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        1. Lydia*

          LW say Jane had completed said task with no issue previously. Sounds like Jane did it once or twice without problem and then decided she didn’t like to do it at all.

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    3. fidget spinner*

      Right! I struggle to prioritize (ADHD, everything feels equally pressing at all times) but if someone tells me what to prioritize, I am capable of doing that.

      Reply ↓
  2. Peanut Hamper*

    Someone originally posted in the comments that having two line managers was also part of the problem. As someone who once had four line managers, I really felt for Jane. This is confusing at best, a recipe for disaster at worst. Make sure you have a clear command structure in place to minimize these kinds of issues.

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    1. They knew and they let it happen*

      That would be a big potential factor if the two managers are giving conflicting instructions, but where do you see that there are two managers?

      Reply ↓
      1. Moose*

        It’s in the letter. Technically the LW is not Jane’s manager. She was hired to be the assistant to LW and her actual manager.

        “My team is built up of me (a coordinator), one manager, and one director. The manager and I are both at the same level, reporting up to the director. We recently hired a part-time assistant, Jane, to help with the work. While Jane technically reports to the manager, he and I both share “management” of her, given that the work she was hired to help with was falling on my plate originally so it makes sense for me to assign tasks and guide her through them.”

        Honestly it feels like there was unclear expectations of who Jane reported to and who was supposed to assign her work based on the structure.

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        1. Archi-detect*

          If there was conflicting orders, I feel like she would have mentioned that, but maybe that is part of the problem or she thinks she can solve it by getting everything done but falls short. Definitely worth solving as a group at minimum

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            1. Arrietty*

              I went to school with a girl who would make up her own homework assignments and prioritise those over the actual work we were set by the teacher, then be surprised pikachu when she got bad grades. I can see her growing up to be Jane.

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    2. Myrin*

      OP also said in the original comments that 90% of all instructions come from her and that the things Jane prioritises over actually-more-important ones are part of these 90% (i. e. they also come from OP, they’re just less important), so the second manager doesn’t actually come into play here.

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    1. duinath*

      That can happen, yeah, but we know that’s not the case here, since LW said she’s completed at least one of these tasks successfully before.

      Reply ↓
      1. ferrina*

        It could still be the case here. I’ve worked with some people that were great when they were getting settled in, but once they felt comfortable, they started noping out of parts of their job.
        Not saying that this is definitely happening with Jane- not enough info either way.

        Reply ↓
      1. Archi-detect*

        It can be embarrassing if you feel like you should know it, but that takes getting used to and overcoming (and a culture that doesn’t berate not knowing)

        Reply ↓
  4. HonorBox*

    I like the idea of of naming the problem for Jane. While to me it seems pretty explicit when you say “do this before you do anything else” it might be that showing her where she’s doing what you’re expecting will help. And maybe you could tell her to “finish this before you start on anything else” … or at least explain that you actually mean that when you say “do this…” that might help too.

    But I wouldn’t wait too long to cut her loose.

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    1. ferrina*

      Another trick is to troubleshoot with Jane so she sees how serious you are about this being the number 1 priority and you are actively clearing the path for her to prioritize this task. I like to ask “is there anything that you are working on in the next week that can’t be pushed to next week?” or “what other things are you working on that might need to be done before this?”

      That way I can get all the info on what they are working on and how they understand the priorities around each task. Occasionally it also reveals that there is a higher level priority, or something that I need to support them with so they can turn their attention to Priority 1 (like maybe I need to work on something that I can get done faster than them, just so it can be done, or maybe I need to talk to a stakeholder for a different project and let them know that my person won’t be working on their task until next week because of Priority 1).

      Reply ↓
  5. desk platypus*

    My work has a person like this at a different location than me. I learned it’s apparently a chronic problem with this employee because every time she applies to our department management has to honestly tell us how often she’s spoken to about prioritizing non-urgent tasks. After so many years (yes, years!) one would think she’d be let go, but that’s government for you. At this point we’ve even stopped interviewing her for our department even if informal company policy is to be polite and at least give internal hires a chance.

    Reply ↓
  6. Lily Potter*

    My guess is that Jane doesn’t really want to be an admin. Someone that takes joy in emailing sales leads probably has their eye on a marketing or sales role. This problem may solve itself within a matter of months when Jane gives her notice for a different job. Doesn’t mean that OP shouldn’t work on Jane’s prioritization skills though.

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    1. OrdinaryJoe*

      That was my thought as well! She got hired with the hopes/expectation of getting her foot in the door and moving up to something more fun or more to her likely. I’ve had that happen to me and seen it happen too many times.

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      1. TQB*

        Agree – hopefully Jane will realize that the skills she can master as an admin will ultimately make her better at future roles. I started off my career as an admin and, quite frankly, I sucked at it. If Jane learns nothing else, she should learn to appreciate the folks that are good at it.

        What helped me greatly was my manager sitting down, handing me a planner/notebook, and actually helping me make a to-do list. We did it together every day for a short while and god as my witness, I have made a to-do list every day (even on weekends) since. Looking back, i am floored that this EVP took the time to do that with me. What a GIFT.

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        1. Ms. Eleanous*

          I worked with a very organized woman who had a ‘tickle file’ of due dates .
          kind of an oversize Rolodex .. worked for her!

          Reply ↓
  7. dmreffitt*

    I’m struggling a bit to understand how a big shipment couldn’t be done in a week if it’s being done by an assistant, and the team would need to pitch in to get it done. Even if it would require packaging multiple boxes of marketing collateral, promotional items, computer equipment, etc. a week seems like plenty of time.

    I didn’t see anything about it in Allison’s response, but I’ve had managers in the past who give a deadline of X but in their mind it should be done by Y and so they actually want it done by Z. Based on how the LW describes their own process, I have to wonder if the deadlines being given don’t actually match the expectations and that if this letter were coming from the assistant the context and experience described would be VERY different.

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    1. Kevin Sours*

      We don’t know how many days a week Jane works as a “part-time assistant” and she may have other daily tasks that also need to get done.

      Reply ↓
    2. Msd*

      I agree. The OP even says that if a task has a deadline in 2 months they’ll prioritize and finish it well before that deadline. If I’m given a deadline in 2 months I don’t drop everything to work on it. What other priorities does Jane have? It’s also possible Jane is underestimating how much time a task will take. At the end of the day it does seem like the OP says deadline is X but wants earlier than X. That’s not really fair.

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      1. Socks*

        OP said that that’s their approach, but not what they expect from Jane. There’s a difference between expecting something to be done a week in advance and expecting it to be started a week in advance. If Jane works (say) 20 hours a week, and daily tasks take up 10 of those hours, and packing takes 20 hours total, OP doesn’t have to be being unreasonable to know that Jane can’t finish this AND do her other job duties in one week.

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        1. dulcinea47*

          Maybe Jane needs instructions like, “I need you to spend two hours a day on Priority Project until it is done.” Realistically, that’s how people meet deadlines, it’s rare for there to be a situation where it’s okay to drop everything else.

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      2. Frosty*

        This part gave me pause too. As someone that has worked as admin, a 2 month deadline is very long for the type of work that you normally do. It seems strange that she’s working on shipments that then require multiple people to pitch in for a week to get done. Maybe the tasks that she’s not doing aren’t actually “admin” and that is where the friction comes from.

        Having admin should theoretically make your job easier, but it might be worth breaking down a 2 month deadline into smaller pieces if she’s not “getting it right” at this point. A weekly or bi-weekly check in. If she’s new to the position she might not realize the volume of tasks you’re requiring for a single assignment.

        For what it’s worth – as admin if I was told to “handle a shipment” that would most likely involve: contacting the shipping company to find out about potential paperwork, coordinating to make sure there are people to move the goods… making printouts/copies of documents to be signed… maybe booking some meetings for the staff involved, making sure the paperwork is all very organized and completed

        I could probably dig in there a bit to find more tasks, but surely not 2 months of work. That might be what the issue is – a real lack of clarity on what is “admin” and what she’s actually being tasked with.

        Just a thought!

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    3. Dust Bunny*

      Without knowing what is being shipped and what is required to pack it, none of us can possibly know if a week is enough time or not.

      Jane has been told in clear words what to prioritize and isn’t doing it. That doesn’t seem like a vague-communication issue. The LW told her it needed to be done in four weeks, Jane had done it before and knew how to do it and how much time it would take, and still left it until it was too late and became other employees’ problem to fix.

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      1. A Girl Named Fred*

        Plus, in this or other cases where OP says “Do X before anything else,” that means do it before anything else, no matter when the deadline is. If you have a conflicting priority, you have to bring it up and hash it out, you don’t get to just pick one and ignore the other. (And I say this as an admin who does get ZOMG THIS MUST BE DONE NOW tasks dropped on me that definitely could wait. But if I’m told to do it now, I do it now.)

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        1. Dust Bunny*

          Same. I don’t usually have conflicting priorities but if my supervisor says she needs this ASAP, it doesn’t matter what else I’m doing or how much I’d rather not do the new thing–that new thing gets done ASAP.

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    4. Samwise*

      We’re supposed to trust that OPs know their situation and we’re supposed to believe them when they tell us things like, it needed all hands to get the shipment processed.

      Reply ↓
      1. Trust but verify*

        As comments on another letter pointed out, that trust applies unless there is evidence that OP is wrong, which as dmreffitt has pointed out, there is.

        Reply ↓
    5. Not Tom, Just Petty*

      What I got from the letter is OP said, “these large group of items ship on X date, twenty business days from now. Have all of them ready to ship on that date (by working on the project with your other work until they are all packed.” Then, Monday morning of day 15, OP discovered that Jane hadn’t started the project. So OP gave the final deadline and Jane didn’t act on it in anyway. Instead of spreading the task over 20 days, it had to be completed within five days which was too much for one person to do and still meet the deadline. OP had to call in other people to help. Other people in other departments had to step in to do some part of the packaging. It looks bad on OP, her management and her department. Plus it would annoy a lot of people, the whole “failure to plan…” situation.
      Maybe Jane has a different perspective, but not starting the project at all is the real problem. Jane wasn’t told two deadlines. Jane wasn’t told not to work on it all. Jane never got to it.
      (Although, they both should have checked in at two weeks.)

      Reply ↓
    6. Annony*

      I was wondering that too. If I were told to pack up a shipment that goes out in a month, I would probably delay that until week of too (why have a box sitting around for a month?). I wouldn’t think it would take hours to do. Maybe she didn’t actually understand the scope of the project.

      Reply ↓
      2. Snow Globe*

        You are assuming it was just one box going to one recipient. If this is a central marketing department supporting multiple offices, it could be a large shipment of, say new brochures, being sent out to 50 different branches.

        The LW says it took a number people all pitching in to get the shipment done, no reason to doubt them.

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        1. MassMatt*

          This. Many years ago I was a temp for a company that needed help putting together marketing materials for a new consumer product launch. It involved tons of collating pages, putting material into binders, adding brochures and promo items to each unit, etc. Three of us worked on it FT for about 3 weeks.

          The OP says the employee had done this before so they knew it was not a quick job.

          It’s possible there’s an issue with the complicated reporting structure, but really it sounds as though this employee is a poor fit for the job.

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    7. AngryOctopus*

      I mean…”okay the tchotchke of the month packages have to be shipped out on the 20th, so all the boxes have to be packed up and have the special paperwork in them by that day. There are 1000 of them to pack up”. It’s not that hard to picture, Jane only works part time, and if a week before the 20th she has packed no tchotchke of the month boxes, she’s not going to be able to do it herself at this point, where if she did 250 a week when given the task, she’d be on track.

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    8. Jellyfish Catcher*

      I’m struggling to understand how such a large and important shipment (so large thathad no oversight for 3 of the 4 weeks before the shipment deadline. That was missed by the OP/ manager, for the first 3 weeks.

      That caused some chaos, as a number of people, including the OP, the assistant and others to be pulled off their tasks, For A Week, due to this crisis. This suggests that there is systemic looseness in the office organization and/or that tracking in general is possibly disorganized.
      Maybe this is not all the fault of the assistant.
      I’d begin with analyzing that.

      Reply ↓
      1. Happy meal with extra happy*

        I feel like this is taking all agency/responsibility away from Jane. She was given a specific job that she has done before with a specific deadline. This shouldn’t require weekly check ins. I’m sure comments here would have been calling OP a micromanager if that was the case and that maybe Jane had her own style of working.

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    9. Antilles*

      We don’t know the specifics, but the one thing we do know is that “the rest of us had to pitch in” to finish the shipment on time. These other employees presumably have their own tasks to work with and ideally wouldn’t have had to jump in. So by definition, Jane didn’t leave herself enough time.
      As for how it couldn’t be done in a week, there’s plenty of options. Maybe it’s because Jane only works 10 hours a week and it takes longer than that to get stuff prepared. Maybe Jane has other tasks that absolutely cannot be delayed, so she can’t just buckle down for three straight days because she still needs to stop to answer the main telephone line, greet visitors, sign for FedEx deliveries, etc. Or maybe it’s because the process for producing the shipment truly is that arduous and finicky; e.g., requiring a crazy amount of hand packing or folding of paper work or something.

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    10. Alan*

      Shipping can be more than sticking something in a box. It might be arranging for a courier/trucking service, arranging someone at the other hand to handle the package when it arrives, dealing with special protocols on each end, getting approvals, etc. We’ve definitely had stuff at work that needed to be shipped and took weeks, and when you have to do it sooner it creates a mad scramble.

      Reply ↓
  8. Not Tom, Just Petty*

    I think OP is asking a question Alison gets a lot, “how do I get my employee to do work they clearly don’t like and have them like it?”

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    1. I Have RBF*

      No, they are not asking to have them like it, they are just asking how to get them to do tasks that they dislike on time.

      I tend to procrastinate on tasks I dislike, often in the (faint) hope that I won’t have to do it. I know this about myself, so I try to do them first just to get them out of the way. For me, it’s an ADD thing, and it takes some effort and deliberate self talk to overcome it. My problems shouldn’t become my employer’s problem.

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      1. Not Tom, Just Petty*

        I see your point and Dust Bunny’s point. I felt like OP saw Jane doing tasks she liked and OP is hoping to find a way to get her to like packing boxes. (The text about not forcing OP to change her prioritizing or impose on Jane.)
        But this isn’t the question OP should be asking. OP is well past asking, “how do I explain that ‘do this now’ means ‘do this now’ and get Jane to do this now?” and should be asking why is Jane still there?
        I wonder if she is.

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        1. EDIA*

          Count me as a third person who thinks you’re still focusing on the wrong/a non-issue. OP isn’t concerned about Jane’s attitude towards the work. The problem that OP brought up is that the work didn’t get done. The words about not forcing OP’s work style on Jane is about OP’s desire to not be overly controlling/a micromanager, you know, acknowledging that what works best for OP may not necessarily work for Jane.

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    2. Dust Bunny*

      No, she’s asking how do I get my employee to do work that they implicitly agreed to do because it’s part of the job?

      Nobody is asking Jane to like it. We all have parts of our jobs we don’t like but that we do, anyway, because they’re parts of our jobs.

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  9. Samwise*

    Buh bye, Jane.

    She can’t do a central function of the job, the very reason she was hired (or she won’t do it — doesn’t matter, result is the same). PIP, or even just, fire her now.

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  10. Kate from the north*

    For some reason, your employee doesn’t want to listen to your direction, she needs to be clearly told what you expect.
    But I have had a procrastinator. I ask for a task list to be kept on the corner of her desk, that I could look at to check status without interrupting her. We started with a division of three categories, then moved to four. Hot/ASAP; priority next 2 days; priority by date, whenever/time filler. We reviewed together every couple of days, then was able to review once a week. It did help that employee had to recognize any task problems they were having early on.

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  11. Kevin Sours*

    I think this shows the value of regular status updates. While Jane needs a serious sit down about expectations, I think it’s a failure of management to be surprised by the fact that nothing has been done on an urgent item for three weeks.

    Reply ↓
    1. Guacamole Bob*

      I was wondering about this, too. Is OP having regular checkins with Jane where she reviews status on things? If Jane’s work is generally good otherwise, spending more time in checkins asking about the full list of what’s on her plate, whether tasks have been started, how much time Jane expects them to take, which things are priorities, etc. could help address the time management and prioritization aspects. It might be that a period of more intense hand-holding and closer supervision could help Jane to develop these skills.

      On the other hand, for an assistant type role, there may be too many small urgent tasks moving too quickly for this approach to make sense, and someone who needs coaching in this area may not be a good fit for the role. It really depends what kind of work she’s being asked to do.

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      1. Kevin Sours*

        A simple “this is what I worked on this week and this is what I intend to work on next week” email would resolve a lot of it. You don’t necessarily need to go tediously through every outstanding task nor include the daily firefighting explicitly beyond stuff like “this week was mostly small urgent tasks” etc.

        But if there is an urgent multi week project that isn’t showing up on either list it becomes something to look into.

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      2. ferrina*

        Totally agree with this. At OldJob I managed a team that routinely had a lot of balls in the air and conflicting priorities. For each of my direct reports, we kept a living agenda with a list of all of their projects, and each week we’d discuss where each project was at. It could take just a few seconds per project, and I could ask them if I was concerned about anything.

        For one particular person who had trouble with deadlines (this person told me they had ADHD, and the time blindness hit them hard), we would set checkpoints for their tasks and look at the tasks during each checkpoint. This helped them know how much they needed to do by the deadline, and I was always aware of how much progress they made and I could step in early as needed.

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    2. carrot cake*

      When I am given a task and a time frame, I mark my calendar and schedule time to work on it, and let my boss know if I think I’m going to need more time, and why.

      It’s not complicated. Jane isn’t a child.

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      1. Kevin Sours*

        And yet OP was caught out and had to scramble because she didn’t ensure that the work was being done. A simple weekly checkin would have surfaced that while there was still time to course correct.

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    3. Tea Monk*

      Yea, even if Jane was just blowing things off, at least the manager would be prepared before all heck broke loose

      Reply ↓
      1. Slow Gin Lizz*

        Thanks for this, I was wondering how it turned out. Seems like, pretty ok, but who knows how things turned out during and after 2020….but let’s ignore that year insofar as people’s work performances, shall we?

        Reply ↓
  13. Elbe*

    Knowing what to prioritize can be a challenge for new workers, so it would make sense that Jane is struggling with this if she is very young or new to this type of work.

    But it’s concerning that she’s not working on the right tasks even when the LW outright told her what the priority is. Any chance she’s avoiding tasks that she doesn’t like, knowing that other people will step in the do that work as the deadline looms? Is she apologetic or embarrassed when other people have to do that work for her? Or does she consider it a good outcome when other people step in?

    If the work with deadlines is significantly different that the work without deadlines, it could be that she’s avoiding that type of work rather than having an issue prioritizing.

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  14. Managing Upwards*

    I’ve got one of these… but it’s my supervisor. Absolutely nothing works to make him do something he doesn’t want to do in a timely fashion.

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  15. Tradd*

    There’s a guy in our import department (I’m a customs broker) who is apparently incapable of prioritizing air freight over ocean freight. Air freight gets to the US 1-2 days after departure, depending on routing. Ocean freight takes at least 2 weeks, if not more, depending on where it’s coming from. Stuff from India takes 6-8 weeks.

    Someone prioritizing ocean freight arriving in 6 weeks over air freight that’s arriving tomorrow is just broken. It makes no sense. He’s been spoken to about it multiple times. There are many other issues so I hope he’s on his way out.

    Reply ↓
  16. Julia*

    It very well may be that Jane is selecting tasks she enjoys rather and ignoring your instructions point blank, but this also could be a communication issue rather than a prioritization issue.

    It might be worth taking a closer look at her workload. She may be receiving “urgent” requests from other members of your team. Her inbox might be flooded with ad hoc questions from clients and vendors. Or maybe she has a task that takes longer than you realized. You also might consider if your prioritization is correct. As someone who has done a lot of admin work, my non-admin supervisors don’t always understand the consequences putting off certain tasks. If either of those issues are the case, then she needs to learn to communicate those issues before you figure out the prioritization issues.

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  17. She of Many Hats*

    I agree with Alison’s advice but the wording may need to be changed when talking with your assistant. Alison uses “Can you do ….” when in many cases it needs to be “I need you to do…” or This must be done….” Using “can” in situations like this is a softening word that gives someone a loophole to avoid what is needed. It unintentionally undercuts the manager especially female or new managers.

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  19. CeeBee*

    I see Jane.
    I see Jane getting fired.

    I mean really, you told her she needed to package up the shipment and then she didn’t and you all had to pitch in? She’s supposed to ASSIST you – not do what tickles her fancy.

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  20. TQB*

    Going out on a bit of a limb… is this person new to office work or the admin role? I think it’s getting better, but when I went through school, no one talked about how to prioritize or handle workload. You were just expected to do it. When I had my first real job after college, I was clearly a mess. My manager sat me down, handed me a special notebook (one of those Red/Black ones with the plastic covers – I used these for over a decade!) and together we made a to-do list.

    I learned a lot from that manager. He didn’t have to take this time, but I’m so grateful he did. All the fancy tech and things, but I still start every morning with my paper to-do list.

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  21. commensally*

    I do wonder in this situation how much of it really was about LW and Jane having different styles around deadlines. It sounds like the shipment wasn’t a situation where LW had said “you have to do this before anything else!” – LW gave Jane a deadline, checked in with Jane a week before the deadline, saw that the job wasn’t done, and decided that meant Jane hadn’t met the deadline. LW may be right that it wouldn’t have been possible for Jane to do it by herself in a week – but if Jane had done the job successfully before, it’s also possible that she had decided based on experience that she could get it done in a week if she worked straight through, had planned out the necessary time to work on it straight through for that week, and decided that was the best way to make it work within her schedule, for any of a bunch of reasons. (She may have been wrong about being able to get it done in a week, but even that would not be a “prioritization” issue – it would be a time management issue.)

    I’ve had managers diagnose me with prioritization issues when my prioritization was fine, but either we had fundamentally different strategies for time management or they misunderstood which of my other tasks were time-sensitive. It’s very frustrating to be given a big project with a set deadline, to push ahead on all of your other time-sensitive work first so that you will be able to concentrate on just the project in time before the deadline, and then have a manager pull it out from under you because you “can’t prioritize”!

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  22. Raida*

    Worse case scenario, she’s too timid to say “I need to get X done because…”
    So ensure that you build that feedback into the prioritisation setup with her – You say “X needs to be done first.” She says “No problem, I will finish Y before starting.” or “That will mean Z is pushed to Thursday, is that right?” or “X? Sure, I’ll start that now.”

    If she’s not giving you those kinds of responses indicating she’s aware of her workload and the prioritise, maybe do some 1:1’s to lay out what is going to work for you and her to get on the same page

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