my assistant doesn’t know how to prioritize

A reader writes:

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.

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 instance, 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? 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 manager, the director, and I all had to chip in to help complete the task, when really she could have done it by herself if she had started earlier.

I tend to be the 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??

If Jane isn’t following your instructions when you explicitly tell her “do this before you do anything else,” that’s a serious problem.

Even without that, a general inability to prioritize on her own would be concerning, but when you throw in the disregarding of explicit instructions, I’d start considering that she may not work out in this role.

But we’re not there yet! The first step is to name the problem you’re seeing and tell Jane clearly what you need her to do differently. So, sit down with her and say this: “I need you to prioritize your work differently. Some of the projects you’re given will be time-sensitive and some won’t be. I need you to finish the time-sensitive work before you turn to other projects. For example, in the last week, that would mean doing X and Y before spending time on Z. And when I ask you specifically to finish something before on working on anything else, I need you to follow that instruction. You can’t do this job well if you don’t prioritize the work correctly, so it’s really important for us to be on the same page about this.”

Then, if it continues to happen, address it immediately. For example, if you give her something time-sensitive and later see her working on something low-priority, say, “It looks like you’re working on X, but Y was the highest priority for today. Is it it finished?” … and then assuming it’s not finished, “Can you switch to Y and work on it until it’s done?” Then, after the immediate need is handled, follow up with her about why the pattern is continuing: “Earlier today with Y, that was an example of what I was talking about when we talked about prioritizing. What happened there?”

Also, I get that you don’t want to impose your working style on her and order her to prioritize anything with a deadline, even if the deadline is months from now … but when you see that her own style isn’t working and is causing serious problems, it’s okay to tell her to use a different system. In general, you’re right that you should give people leeway to figure out the best way to approach their work — but only as long as that’s working! When it’s not, you can step in and say “let’s try it this way instead.”

It’s possible that if you’re clear and direct about what’s not working and what she needs to do differently, that might solve the problem. But I’d also prepare for the possibility that it won’t — that she’s just not well matched with what you need from the person in her role and you’ll need to replace her. That means you should (a) talk with the other manager about the problems you’re seeing so they’re in the loop and (b) find out what process, if any, your company requires if you need to fire someone. (For example, if they require formal warnings, it may make sense to get that in motion now so that you keep the process moving along.)

But first, lay this all out for Jane. Your job right now is to connect the dots for her about what’s not working and tell her clearly what needs to change.

Read an update to this letter here.

{ 309 comments… read them below }

  1. Hey Karma, Over here.*

    Jane knows that you want X done first, but she chooses not to do it. The result is that you, your peer and your boss jump in help do it. You would be embarrassed by this. I would be embarrassed by this. Jane is not embarrassed by this. Jane thinks that you were incorrect about the deadline, because she thought she still had a week to do it. You jumping in and doing it makes it look like you were fixing your own error. And since you didn’t explain to her that you were fixing her error, she’s not getting it.
    I would honestly start with that. Tell her that it can’t happen again. That she has to do things in the order that you need them. And if she can’t prioritize after that, you can help her…at first. And then see how much is unwillingness and how much in inability.

    1. Shamy*

      This is a really valid point about OP fixing their own error versus Jane’s error in her mind. I was originally thinking, if she wants to do it with a week remaining, let her…until I saw that because of her procrastination, other peoples’ work was impacted. That is really not ok. It sounds like OP has been explicit as possible. I don’t have much hope for this arrangement to work out.

    2. Seeking Second Childhood*

      If she admits that she simply dislikes doing the X part of her job, I’d suggest that you & she schedule a certain amount of time on the task she does like. But I suspect she is so poor at estimating how long a project will take to complete that she might have been caught unawares as well.
      Help her calculate how many hours were spent packing up the shipment — hers AND the three people who pitched in to get it done. Walk her through dividing that up by the number of hours/day that could be spent on it to see how far in advance she COULD have started to do only 4 hours/day of the disliked task.
      It is of course possible she didn’t realize it was FINISH project X by a certain date… she thought it was START project X by a certain date — but it’s more likely she didn’t have a clue how long it would take.
      For some of us this time estimation doesn’t come naturally — thus the dreaded college all-nighter. We can learn — it can take a swift kick in the pants for us to realize we can ask for help learning how to estimate.

      1. Meredith*

        Indeed, especially if it was her first time doing a project of this magnitude, it would be very easy to underestimate the time needed. Add some other tasks popping up on her list that might be high priority and well, plus a less-than-stellar ability to prioritize and here we are.

        1. valentine*

          If she admits that she simply dislikes doing the X part of her job, I’d suggest that you & she schedule a certain amount of time on the task she does like.
          She has always had this freedom, but OP/Letter Writer may have to remove it, at least until she proves she can work independently.

          Help her calculate how many hours were spent packing up the shipment — hers AND the three people who pitched in to get it done. Walk her through dividing that up by the number of hours/day that could be spent on it to see how far in advance she COULD have started to do only 4 hours/day of the disliked task.
          This is a lot of hand holding, the rushed work of the others will throw off the estimate, and she had already done a shipment. This is on Jane.

          1. Jaydee*

            It’s really not that much handholding if it’s done once or twice.^ Certainly it would get excessive if it needs to be done every single time. There are many organization and time management processes that are skills that need to be learned. They may seem to come very naturally to some people, but those people usually just learned them earlier in life or found them easier to learn. Other people are perfectly capable of doing them but need more explicit instruction or modeling of the process before they get really good at doing it.

            I’m totally a “do it all in one fell swoop right before the deadline” kinda gal, but I have always aspired to be someone who breaks projects into steps and works on them incrementally in advance of the due date. I’m just terrible at implementing it. I overestimate how much I can do in a day, forget to take into account other tasks, get distracted by new additions to the to-do list, etc. I would *love* to have someone help me plan out my projects or watch how someone else plans out their projects and schedules their days/weeks so I can learn how to do it myself.

            ^This is all appropriate in general, but I can see where it seems less worthwhile when the employee has failed to do a task she was told to prioritize above all other tasks. I still think it’s worth one additional attempt to clarify expectations and to ask this employee why she did the lower priority task first. It’s possible she had a logical, if erroneous, reason that you can address to prevent further issues.

            1. Decima Dewey*

              If something has a deadline, I make it a priority. My thought is that anything can happen if I wait too long to start. I keep the deadline in mind, work on other things, tweak the project from time or time, submit it when I feel the project is as good as I can make it.

              I don’t think OP’s subordinate has a problem prioritizing. I suspect she’s refusing to prioritize.

            2. Freya*

              If you look up ‘GTD Connect’ you can sign up for a two-week free trial and they have loads of tips, webinars etc.

            3. Mindovermoneychick*

              I second Getting Things Done, even if you just read the book. It’s very helpful

      2. Rusty Shackelford*

        But it’s hard to misunderstand “do this first,” which she apparently ignored.

      3. TootsNYC*

        I frankly wouldn’t allow a part-timer to prioritize the tasks she likes. A full-timer, maybe, but part-timers get hired for highly specific reasons, and they need to do those first.

    3. Letter Writer*

      This is a really good point! I’d love to think that my panic-induced “all hands on deck” freak out should have identified that for her, but you’re right that it might not have! Next time it needs to be a bigger conversation on “this is on you and can’t happen again”.

      1. Artemesia*

        This person should be on the path to being fired. She isn’t getting it so it needs to be explicit. That means a very clear and hard conversation that this is a big deal. One more incident and a PIP or equivalent needs to be underway so she can be fired as soon as possible if there is not dramatic change. The longer you string along with someone who is incompetent the harder it gets in most organizations to fire them. Line up your ducks now with the other manager and director. Make it clear that this is a pattern and you fear this person may not ‘work out’ and outline steps you are taking to turn it around. Be read to fire her if it doesn’t. And nothing cements bad behavior by an employee like doing their work for them.

      2. Triplestep*

        What are the chances that Manager and Director are giving her conflicting direction? You may want to chat with them to make sure the three of you have been on the same page all along. Couldn’t hurt just to verify first.

        1. 16 Pieces of Flair*

          I was thinking this. I’ve been often a resource for a project doing X. And every time each project manager thinks that I am there for only their project, which of course is the only one running and thus I am at their beck and call. While for me they are way down on the list of X’s… actually they are a very small x

          So if there are two demibosses and the big boss, there should be a clear pecking order and not just thinking your project is the priority. It might not be the case, but if it is then the management level should deal it amongst themselves first before chewing out the minion.

          1. Whatever'sClever*

            She “reports” to manager A but is actually managed by Manager B, this is silly imo. I agree that it needs to be looked at whether the two managers are landing her with work and not communicating to each other because of the weird set up here?

            Or is it just me, cos I remember being annoyed that as a manager/dept head, I had three/four line managers at any given time, as well as having had an assistant hired for me, who was then “given” to another manager without me being informed.

      3. Snark*

        I would also make it very clear that you know she’s choosing to do more fun or personally rewarding things instead of the things you’ve identified as priorities, and that that doesn’t fly.

      4. Hey Karma, Over here.*

        I think the concern you have of inflicting your style on her is a problem as well. She is interpreting your “I work this way, but if something works better for you, that’s fine” as “you do you, Jane.”

    4. Squid*

      Right. Most of us tend to underestimate how long tasks will take, so Jane may have thought it would be fine to pack the shipment in the last week. In other words, it seems like there may be multiple deadlines in play: the explicit deadline Jane was told and seems to have had in her head (four weeks out), the tacit deadline you seem to have had in your head for peace of mind (three weeks out? Earlier?), and the tacit deadline by which Jane needs to start a long task in order to finish it on time without causing problems. So you could try making some of those tacit deadlines explicit while you’re coaching her and see if it gets you on the same page. (Of course, if you’re clearly saying in so many words, “This is due in four weeks, but I need you to drop everything and complete it before you work on anything else,” and not just, “This is due in four weeks, so it’s a priority,” then this isn’t about a misunderstanding.)

      1. Daisy*

        I don’t see the ‘tacit deadline’ you’re referring to? It sounds like OP asked her a week before the deadline and was shocked that it hadn’t been *started*, not that it hadn’t been finished.

        1. lemon*

          That’s the tacit deadline right there: get started by X date, which is a couple of weeks before the final deadline.

          1. sunny-dee*

            That’s not a tacit deadline, though. If the job takes, say 3.5 weeks working 3-4 hours a day for a single person (I’m making it up, but that sounds about right), then it should have been started more or less right away. That’s just the math. That’s not some unspoken, unfair expectation –it’s literally the scope for the job.

            1. Squid*

              I don’t mean to suggest that the OP is being unfair at all, just that being over-the-top clear about when they expect to see what done might help them get better results from Jane if that’s the ultimate goal. So if the task is expected to take 3.5 weeks, they might tell Jane, “You’ll need to get started by this Friday to finish on time,” and then check in the following Monday, when there’s still time to recover if Jane is off track. Weekly progress check-ins are the approach I use with my assistants for big projects, particularly when they’re pretty new to being accountable for work deadlines.

              It’s entirely reasonable if the OP doesn’t want to do this kind of hand-holding. (I work with college students and so err on the side of oversight more than I would with more experienced folks.) But if they want to give Jane a shot before replacing her, then being very directive about what they want to see done and when (and following up on that) seems like it would be less time-consuming than having to bail her out at the end.

              1. motherofdragons*

                I agree with this approach. Being super clear about ALL of the deadlines for this project (and documenting this!) will help either get Jane in the right mindset for this work, or make it obvious that she can’t hang in this job.

              2. nonymous*

                Jane could probably benefit from having some structure to her weekly check-ins and that’s where OP can really help as a manager. Set up a standing agenda item where OP is asking about status of ongoing projects, and whether priorities need to be changed to meet deadlines. Maybe even task Jane with creating a spreadsheet to track this.

                It’s hard to tell from OP’s letter whether Jane is really bad at prioritization or really bad at communicating what she thinks her priorities are. Maybe when OP says “this task needs to be done before all others” Jane is interpreting the task as something she does before any other of OP’s tasks, but all of Director and Reporting Manager’s tasks will take priority.

                1. Letter Writer*

                  I do like the idea of a spreadsheet that I can access too with all of her running tasks and where she’s at with them. Would probably also help structure our weekly check-ins beyond her updates if she has to continually update a spreadsheet.

            2. JustMyImagination*

              I wonder if LW could try to build off of this approach. I need this done by DATE and it will take ~80 man hours to complete, please schedule your time appropriately. If she’s new and not sure of the magnitude of these projects she may have thought one week was sufficient to pack up that shipment.

              1. motherofdragons*

                This is what I was thinking, but then I re-read the “she’s done it successfully before” part and that got me wondering what the deal really is. If Jane has done it before, she should know how long it takes. How long did it take her last time? If it was roughly a week, then I don’t fault her for assuming she could put it off for 3 weeks and still make it by the deadline…but obviously that wasn’t the case, so I’m curious about what was different, if anything.

                1. Rectilinear Propagation*

                  Different shipment sizes or different type maybe?

                  Could also just be that she forgot, procrastinated, or legitimately got her priorities mixed up.

            3. lemon*

              I don’t think anyone (or least I’m not) saying that the LW had unfair, unspoken expectations for Jane. I think a more experienced employee can hear “project Y has a deadline of X date” and knows that they need to work 3.5 hours a day to get it done by that date. But a fresh grad with limited work experience, especially one who isn’t naturally good at setting priorities to begin with, won’t necessarily know that. I think the suggestion here is to try to account for Jane’s lack of experience by filling in those details that seem obvious to more experienced folks.

      2. Observer*

        Actually, there were no “soft” or “implied” deadlines here. The OP was explicit – the deadline for completion was “4 weeks”, the deadline to start in order to complete it on time was “Now”.

        The OP didn’t panic because the task was not DONE at week 3, but because it was NOT STARTED. Leaving a week to do a job that was scheduled to take 4 weeks. Jane ignored the first explicit deadline – ie the instruction to start immediately. And the job was on track for missing the hard deadline for completion.

        1. motherofdragons*

          I don’t see evidence that “the deadline to start in order to complete it on time was ‘Now'” nor that “the first explicit deadline – ie the instruction to start immediately” was given. OP says she gave Jane a heads up about the deadline 4 weeks in advance, and the only deadline actually mentioned was the one 4 weeks out. Perhaps Jane thought that one week was plenty of time to accomplish this task; clearly it was not, and I think that should be the focus of OP’s discussion with Jane, not that she missed a clear instruction to start right then and there (which she didn’t).

      3. boo bot*

        I had this same thought about tacit deadlines. Letter writer, you say “I don’t want to dump my work style on her by prioritizing for her,” but what’s happening now is, you’re getting frustrated with her work and not giving her the tool she needs to fix it: your work style, and your priorities!

        She’s there to support you and take on tasks you used to be responsible for – there’s nothing at all wrong with telling her how she needs to prioritize them.

        1. Letter Writer*

          That’s reasonable! I think I received a lot of advice here on which tools I can use to help her, which is what I was looking for!

        2. TootsNYC*

          I agree–Letter Writer, having a part-timer is going to always be more work than having a full-timer, because you need to supervise MUCH more closely.

          and Jane needs even MORE supervision.

          So you will need to break down big tasks into steps, and set interim deadlines; you will need to check with her every single time she’s in; and you will need to be explicit each day about what she should be doing.

          You will need to never have a moment that you don’t know what she’s working on. Or, at least, never have a moment that you don’t know what she has been TOLD to work on. So every morning she’s in, you give her the marching orders; halfway through the day, you check to see what she’s doing, and at the end of every day, you find out what she did.

          It’s work. But that’s what you will need to do, especially at first, until she gets it. If she doesn’t start coming through by the end of a week, then you need someone who doesn’t need so much help: No hard feelings, this is not the job for her.

      4. Emily K*

        I agree with this. I want to leave room for the possibility that since Jane has done this before, it’s reasonable for LW to expect her to be able to back into the due date based on the amount of time it will take her to get it done – but to me as a total outsider to the situation, “Do this within the month,” and then being disappointed that I hadn’t done it within 3 weeks,” feels a lot like minimum-pieces-of-flair doublespeak.

        1. sunny-dee*

          I think since Jane *had* done the work before, it was reasonable to assume she understood the scope of the work this time. Like, if I told someone I needed them to make a delivery by noon to a city three hours away, and I told them at 8am, I’m not making some kind of unfair doublespeak when I walk past them at 10am and get upset that they haven’t left yet. They don’t have until noon to start, they have until noon to arrive. She was given a job that would take roughly four weeks (which she should have known because she had done similar jobs before) and hadn’t even started with only a week left. That’s pretty much all on Jane.

          1. Name Required*

            LW can assume that Jane should have known this, or LW can explicitly say it next time and know that the expectation is clear. How does it benefits LW to continue to operate on assumptions when she isn’t getting the results that she wants? How does it hurt LW to be more explicit and know that she has eliminated the possibility that her expectations aren’t clear?

            1. sunny-dee*

              I’m not saying that for the moment, the LW shouldn’t supply a lot of detail and explanation — but that’s because of Jane’s performance, not that the LW was doing something wrong before.

              I’m very much objecting, though, to the characterization that the OP was setting some kind of covert deadline or “minimum pieces of flair doublespeak” or being upset that Jane hadn’t completed the job “before” the deadline. All of that is unfair to the OP and the situation.

            1. sunny-dee*

              I’m extrapolating, of course, but the OP told Jane to do it in 4 weeks. When it was 1 week out and hadn’t been started, it took 4 people to get it completed, which seems to indicate that 4 weeks for 1 person was about right.

              1. Kesnit*

                LW doesn’t say it took 4 people an entire week to do the project. LW says 4 people worked on it. Those 4 people could have been (likely were) doing other things as well, and it may not have taken the full week for the 4 people to work on it.

          2. Kimmybear*

            Except that there are some people that legitimately can’t figure this out. My husband cannot figure out what time he needs to leave the house to get to an event downtown at a certain time. It drove me nuts for years until I realized that he can’t figure it out and I started telling him “You need to leave at x time to arrive at y time.” If that’s the issue, Jane might not be the right person for the job or the OP may need to change what she is communicating.

        2. Ask a Manager* Post author

          She wasn’t disappointed that it wasn’t done in three weeks. The issue is that it wasn’t going to be done in four weeks — the deadline — because she didn’t start soon enough.

        3. Aquawoman*

          I think “disappointed that she hadn’t done it in 3 weeks” misconstrues the situation. If you give someone a 4 week deadline for a job that will take two weeks, then that person having not started it in 3 weeks means you have enough info to know they will miss their deadline. She wasn’t “disappointed,” she knew that it was either not going to get done or in significant danger of not getting done (and given that three higher-level folks had to help, pretty clearly would not have gotten done).

          I think the OP might want to consider interim status reports from the assistant for jobs like this in the future.

          1. Emily K*

            I think maybe I was just thrown by the idea of packing up a shipment taking so much time since it’s outside of my wheelhouse to pack up anything that would take more than a day/8 hours at most – that’s why I had said I wanted to allow for the possibility that it’s completely reasonable to expect the employee to have worked out that she needed to start earlier, and that it was just my perspective as an outsider that made the idea of starting something that early sound strange to me, so I guess I was also allowing room for the possibility that maybe different shipments take different amounts of time, and maybe a part timer who is new has completed similar work once or twice before, but still doesn’t have enough experience to estimate things accurately.

  2. Caroline*

    As someone who (like Jane) also basically has two line managers, I would encourage you to look at that structure again. It sounds like Jane definitely has major problems prioritising, and I don’t want to deny that, but for someone with that issue, having two line managers giving her different work (and probably both telling her it needs to be done urgently) will make her even more unsure of which projects to get to first.

    1. Dust Bunny*

      I was just getting on here to say this: Make sure her other manager isn’t telling her exactly the same thing, and she’s prioritizing *his* work because he (or she thinks he) outranks you. This might be a too-many-cooks problem as much as it is a Jane problem.

    2. mf*

      This is a good point–in a lot of cases where there are 2 line managers, the employee has competing projects passed down to them. That can be very confusing and frustrating and makes it doubly hard for the employee to prioritize.

    3. Sara without an H*

      Jane has two managers — is she getting conflicting or confusing signals from them? OP needs to agree on priorities with the other manager before giving Jane instructions. Yes, of course Jane should speak up when/if she gets conflicting instructions, but we all know from reading this blog that many people won’t speak up, they’ll just take their best shot at resolving the issue and hope they guess right.

      Alison’s script is fine, as far as it goes, but I really think the first step needs to be a frank talk with the other manager.

      1. Former Retail Manager*

        Came to say just this. The two managers need to be on the same page and it might be worth it for all of them to have a discussion together to ensure that everyone is clear, rather than just OP and Jane.

    4. AJK*

      I had this also. Adding to the problem, one of my managers was… very difficult for me to work with, I guess that’s the best way to say it. She expected her work to be done immediately despite the fact I had multiple other people giving me work, and I felt like I could not do anything to her satisfaction, which spiked my anxiety and made the whole situation worse. I was so terrified of First Manager that I always put her work first even when the other managers told me to prioritize their work, which of course got me in trouble with the other managers. I knew if I took too long to do First Manager’s work she’d go and complain about me to her bosses, which happened several times, even when I told her I was on a deadline for one of the others.
      I felt like I was in a classic no-win scenario! First Manager would always tell me I was doing it wrong no matter what I did. It was awful, I’ve never been so frustrated by any job as I was there. Four years and one much better job later I’m still wondering what I did wrong, or how I could have handled it better.

    5. Glitsy Gus*

      I was wondering if this was part of the problem as well. Though, if it is, a lot of Allison’s advice will still work. If you say, “I told you to complete X first thing, why isn’t that finished before you do Z?” and she replies, “but Fergus then asked me to do Z.” then you and your manager need to have a discussion. It’s really easy for lines to get crossed in this situation, I know that from experience.

      1. nonymous*

        A softer way of asking this is “What are you working on right now?” I bring up the softer approach because depending on the personalities at play (OP might be focused on project outcomes and think she is communicating urgency), the line of questioning described may make Jane think that she is being scolded, which will not encourage her to be forthright.

        I’d note that it’s slightly mysterious how much actual authority OP has over Jane. The letter says that Jane technically reports to the other manager, and who knows what direction that person has given Jane. I’ve worked in situations where my supervisor delegated projects to me which involved getting another team to do tasks. However the supervisors did not agree a priori that those tasks were necessary (or even that I was supposed to organize that project) so you can only imagine how quickly that other team completed the tasks I identified.

        1. Letter Writer*

          The other manager signs her timesheet so he’s got “official” authority while I do more of the day-to-day management. The three of us have weekly check ins to align our priorities, tasks, and make sure no one is overwhelmed, but I’m open to other suggestions!

    6. Working Mom Having It All*

      Yeah, that was my first thought here. Maybe this is a matter of a title composed by Alison but where the reality in the letter itself is more complicated, but… someone who is your manager’s assistant, but who is being trained to take tasks off your plate, is not “your assistant”. They don’t report to you, and it’s highly likely that they are getting different messaging about this stuff from their actual manager, who is not you. You are being asked to train them to do certain tasks, not to have them manage their time exactly how you would manage your time if you were still doing those same tasks.

      That said, others having to step in to help complete a task she was assigned with plenty of notice is a real problem. I’m just wondering if the issue is the assistant, or the issue is something else like lack of communication or unclear chain of command.

      Also… is it possible that the assistant just doesn’t understand how deadlines and workflows work in your industry or at your company? Because as a career admin, if someone assigned me a task with a deadline a month away, I would not be acting as if that task was my chief priority. That would definitely be a back-burner task (a high priority task would be something like a phone call that needs to be set for this afternoon, or a memo that needs to be drafted to go out tomorrow). Is it possible that the assistant didn’t realize that a deadline a month away meant crunch time? Does this person have extensive experience doing this type of work? Do they know how long a task like this will take to accomplish, and what steps are involved and how long each step will take?

      1. Letter Writer*

        Yeah, the wording in the title isn’t great. She’s a Program Assistant so really the role is designed to help all three of us, not just me! It’s just that until she was hired I was doing most of the work so even though the Manager technically signs off on her paycheck and whatnot, he doesn’t know these tasks like I do which is why I am training, delegating, and finalizing tasks.

    7. JediSquirrel*

      I feel this so much. I worked at a job where I went from having two bosses in two different buildings (which was completely manageable) to having six different bosses over three different buildings, all of whom felt free to dump work on me via email that had to be done immediately, because if I wasn’t in their building, I obviously wasn’t working. I noped out of there hard.

  3. Red5*

    It sounds like there are potentially two people giving Jane work to do, which could mean that there are two people trying to prioritize her time and tasks differently. I’d check in with the other manager first to determine if the problem is that Jane is receiving conflicting directions from the two of you.

    1. Detective Amy Santiago*

      My very first ‘grown up job’ I ran into a similar issue, though it was just my manager who would keep giving me tasks, telling me they were “top priority” and then not understanding why the first thing he gave me in the morning wasn’t done at the end of the day because I’d spent it working on the five other “top priorities” he gave me throughout the day.

      1. Zaphod Beeblebrox*

        A classic case of “do you want me to do this rush job before or after the rush job I was rushing when you rushed in?”.

      2. AKchic*

        Ugh. I had a manager at my last job who thought everything he gave me was “top priority” or an “emergency” and therefore needed to be done ASAP. I also answered to (at the time) one office manager, 6 other C-Suite suits (including the VP and the CEO), the president of our sister department/org, all of the program managers (5-6 at the time), and the board of directors (they rarely called, but they all knew me because of my longevity with the organization so I did get the occasional call). Most of his “top priority emergencies”? “Can you type this phone list for me for tomorrow’s meeting so I look organized?”
        Yeah… how he managed to stay in that position as long as he did was beyond me.

    2. Myrin*

      OP clarified in a comment below – posted after this one, though, so you obviously couldn’t have seen it – that she herself assigns about 90% of all of Jane’s tasks and the remaining 10% generally aren’t time-sensitive.

  4. JayNay*

    Excellent advice.
    I want to add to maybe see if the reporting structure needs to be clarified. LW writes “While Jane technically reports to the manager, he and I both share “management” of her”.
    This arrangement sounds… frustrating if I were Jane. Does she know you are her “manager” too? Does this maybe need to be clarified? Do you need to check in with your colleague about whether you two are aligned in the tasks you give her and the work style you expect from her? If two people are co-managing one person, it’s really helpful to be clear that that’s happening and to be on the same page about it.

    1. Letter Writer*

      Letter Writer here – That’s a good point, JayNay! The three of us do weekly check-in meetings to figure out what her tasks are, whether she’s feeling overwhelmed or has any questions, and to give her line of sight to future tasks that might be coming her way. I’d like to think that’s enough to be aligned, but open to any other thoughts or suggestions you might have!!

      1. Ask a Manager* Post author

        It’s absolutely worth looking at, but if you’re telling her “do X before anything else” and you later see her doing Y instead, and Y came from you rather than the other manager, this isn’t about conflicting instructions from the two of you.

      2. Angry with numbers*

        What is happening in these weekly check ins ? That’s the perfect time to check on long term projects. This would have come up in the check ins I do with my team. A “Where are you on the packaging” or “well you can’t work on X because packing will be taking up most of your time”, would have revealed she hadn’t started and you could redirect her then before it became an emergency.

  5. "Senior" Software engineer*

    Question from an employee perspective: If either

    A) You sense that the way that you intuitively prioritize tasks doesn’t match your organization


    B) You look at your email inbox and other sources of tasks and feel overwhelmed — you feel you don’t know how to prioritize tasks

    What should you do? Is there a good way to get prioritization-training without embarrassing yourself, revealing a skills gap that the org doesn’t know how to help you fill, or getting fired? I’ve done a search for people who teach prioritization skills, but that job doesn’t seem to exist.

    1. Falling Diphthong*

      For (A), I routinely fire off “Here’s W; I’m now going to move to X, then Y, then Z” emails, to which the person either says “Great” or occasionally “Actually prioritize Y, then Z–X should wait until we have final numbers.”

      For (B), how to prioritize tasks is going to vary so much by context. I don’t think it’s something a general expert could help you with–it’s something you need to pick up by industry, office, and job. If you aren’t doing that automatically, then by asking specific questions along the lines of my email in (A).

      1. Ariana Grande's Ponytail*

        I am seconding this. As a person who has recently had issues with prioritzation (two bosses who do not cross-coordinate but do hand me time-sensitive assignments on a regular basis), I think there are several options.

        I would do what Falling Diphthong suggests above, but also consider planning out your time in a more structured way each week, using a list, a calendar, the Notes app, etc. That way you can say “I have Tuesday afternoon scheduled to work on A, then all day Wednesday set aside to work on B, but I may need a little bit of time on Thursday morning to finish B, is that okay?”. I find that this makes me look and feel more competent as well as appropriately communicate expected timelines to those involved with each project.

      2. valentine*

        You look at your email inbox and other sources of tasks and feel overwhelmed
        Step 1 is consolidating. Jane should have a running list or a calendar with the due dates. I doubt she does, and OP/Letter Writer might ask her what her system is and wait out an answer, versus suggesting things she might say yes to because she doesn’t know what to say or doesn’t have a system.

    2. KWu*

      This seems to me less like a skill that would benefit from formal training on, because it’s very context-dependent on what the business needs and expectations are, and more an area to seek direct feedback on. For A, you can check in with your manager/team lead/peers with something like, “I had x, y, and z assigned to me and decided to start with y because ___. Does that sound like the right reasoning, or do you think I perhaps should have started with x or z instead?” For B, this is something to work with your manager/team lead on, as in, “I’m finding my inbox of tasks a little overwhelming and could use some help thinking through how to figure out which is most important.” You’re looking for the broader algorithms to learn to apply.

      1. "Senior" Software engineer*

        “I’m finding my inbox of tasks a little overwhelming and could use some help thinking through how to figure out which is most important.”

        Wait, Is that a question that I could actually ask which wouldn’t be met with a sense that I was asking to be handheld through a basic professional skill I should have learned by now?

        1. Susie*

          When I said this to my manager, they took a look in my inbox and freaked out because my workload was roughly 3x what other people in my position were dealing with. That then prompted a review of the workloads for everyone in my department and a reallocation of the work so that we were all roughly equal. If I hadn’t said anything I’d still have an unmanageable workload and management would be none the wiser.

          It could be that you need direction on what to prioritize, or it could be you prioritze just fine but there’s too much work for you to complete effectively in the time that you have.

    3. Kiwiii*

      You can sometimes find prioritization related things when you look at task management or time management or organizational-related thigns. I know Lynda has at least a half dozen options-related.

      Additionally, when given an assignment, it doesn’t hurt to let them know what else is on your plate and asking if they have a preference for where it goes in the order?

      It also might help with some of the nebulous tasks to give yourself a specific time to do them? For example, if you’re supposed to be working on following up on leads but it’s not a priority, assign yourself blocks of time to do it. For example, every day from 10AM-11AM, or maybe just Tuesday from 1PM-3PM and Friday from 9AM-Noon; you can only respond to follow up questions outside of those time frames, and only in the afternoon.

    4. Seeking Second Childhood*

      Look up the Urgent/Important matrix. Also called the Eisenhower matrix, from this quote:
      “I have two kinds of problems: the urgent and the important. The urgent are not important, and the important are never urgent.” –Dwight “Ike” Eisenhower
      Learning how to evaluate tasks by rote on this matrix was a life-saver for me. I use it at home as well — the key idea being you invest time&energy early on things that are important but not (yet) time-critical. Theory being this reduces the number of things that become fires to put out ASAP despite the cost.

      1. General von Klinkerhoffen*

        Yes, I was explicitly taught this quite early in my career – to categorise everything as urgent/non-urgent along one axis and important/unimportant along the other. Tasks that are neither urgent nor important shouldn’t even feature on your to-do list until and unless they become one or the other. Tasks which are both urgent and important go to the top of the list. Managing those tasks which are only one or the other is a matter of self-discipline!

    5. Massmatt*

      Honestly I think people need to prioritize according to what their manager needs. Things with a deadline happen first, and when the manager says “do this first” then do that. The frustrating thing is when managers can’t decide a priority (the worst is “everything is a priority”) or change their minds about what they want done. Neither sounds like the case here, it seems this employee is prioritizing based on what she prefers and largely ignoring her manager.

      OP it sounds as though you need to be firmer and clearer about what you need her to do, and that there are consequences for failing to do it. Is the other manager on board with this, is she having a similar experience? You have avoided the nightmare situation where 2 managers are pulling in opposite directions and wondering why the employee isn’t getting anywhere, but both of you need to be on the same page regarding her performance and how to correct it also.

    6. Koala dreams*

      A) I think the first step is to have a talk with your manager, and check with them if your understanding is the same as their understanding. If it isn’t, you need to find out what your manager (or your organization) prioritize. You can ask them for help to prioritize, or check in more often to see if your priorities sounds right to your manager.

      B) When I’m overwhelmed I start by doing an easy task, then try on a more difficult one. Sometimes just doing something makes the feeling go away. If I’m still overwhelmed after that, it’s time to ask for help.

    7. Pommette!*

      I used to work in an environment where prioritization was necessary (there more work to be done than could possibly be done), but difficult (multiple managers who did not communicate with one another much, and sometimes valued incompatible goals; lots of competing deadlines and lots of long-term projects). The challenge was magnified by the fact that planning doesn’t come naturally to me. It was not a good situation.

      What helped was framing the problem. Instead of emphasizing my needs/failures (“I don’t know how to plan and need training”), I treated the request as one for information about my managers’ priorities (“There is a lot going on, and I need to make sure that we are on the same page about planning and priority setting”). So every week, I’d go through the list of things that were on my plate, and break them down into categories: 1) Things that would get done thatweek; 2) things that might get worked on, with anticipated finish date of X; things that would get worked on later, with anticipated finish date of Y; things that were probably never going to happen. I’d email the priority list to the managers, and ask if it seemed reasonable. It took work on their part, but probably saved time in the long run because disagreements could be identified and discussed early on. Over time, I got better at guessing what mattered, and the check-ins got less frequent/the lists shorter.

    8. Emily K*

      I took a few organization/time management courses on Lynda (which recently changed its name to something I can’t recall right now) that helped me a lot. I have ADD so really needed the help.

    9. drpuma*

      B sounds like A + poor time management skills. Does that make sense? And there are a TON of resources about time management – I know a lot of folks who like Getting Things Done. I see you’re a software engineer; if your organization works in Agile I bet your scrum-master could make some suggestions without that lingering worry of “am I telling my boss I don’t know how to do my job.” When your time management skillset is strong, I agree with the other posters who’ve suggested more open communication to resolve A.

    10. Freya*

      I once went on a training that was literally called managing multiple priorities. So this definitely does exist!

  6. Princess Consuela Banana Hammock*

    OP, I was a person who derived a lot of satisfaction from crossing things off lists, which encouraged me to tackle easy, low-hanging, low-priority tasks over more complex or long-term tasks. I don’t know what Jane’s particular tic is, but she has a work tic that’s keeping her from being useful to your team. And it sounds like she’s flat-out not listening to your feedback. That’s either a fundamental work problem, or she is so deep into her status quo that she doesn’t recognize when she’s doing it or doesn’t know how to fix it.

    Something that helped me reprogram my work style was to change my “to do” list. My list now breaks down all projects into several subparts, and includes deadlines for every task/line, a priority ranking (1-5, 1 = highest priority), and a “progress” column for long-term tasks. This helps keep me focused on tasks that matter, even if the deadline is far away. Each week I revisit it and update the priority rankings and the “progress” column. I can identify where I didn’t make progress, which helps me reprioritize for the upcoming week.

    You may want to ask Jane to do a version of what I’ve described. That way, you can go through her list with her on a weekly basis and catch where things are failing. I don’t normally recommend this level of intensive coaching, but it sounds like she may need it until she resets. And if she continues to fail to prioritize and execute tasks the way y’all need her to, I do think a conversation about separation is in order.

    1. Princess Consuela Banana Hammock*

      Addendum: This approach may also help if she’s getting conflicting messages from OP and OP’s manager. It’s an awful experience to have multiple bosses with conflicting priorities who want all their things done when it’s functionally impossible to satisfy both.

    2. Letter Writer*

      Letter Writer here – that’s a brilliant system, and I honestly might use it for myself! But that might be a good fit for her too. Sometimes I wonder if she doesn’t realize how big a task really is and that’s why she gives herself less time to complete it, so breaking it down like that might really help identify allll the little pieces that go into each task.

      1. MissBliss*

        Some research has shown that people will underestimate how long it would take *them* to complete a task, but will more accurately estimate how long it will take *someone else* to complete the task. You might consider asking her to think how would be a reasonable amount of time for someone else to complete the task, and see if that differs from her assessment of herself.

      2. Princess Consuela Banana Hammock*

        I think lots of people have this problem! My advice is to tell someone to budget 1.3x the amount of time they think it will take them. That way, if something unforeseen happens, they have buffer room.

        Breaking big things into little tasks is so necessary for me. Otherwise, tasks feel like huge, insurmountable lifts that I want to put off. But being able to complete a finite subtask makes the big project feel less overwhelming, and it also helps me see that I can make progress without having to dedicate 100% of my attention and time for a week to get it done.

        1. Make a Comment*

          I used to have a senior, highly skilled developer who estimated his time to complete a task. I would have to budget 2-3x the time for a “typical” developer. I called it The [Wakeen] Factor.

          1. lasslisa*

            To do a thing for the first time, my factor is apparently about 3. So if I think the task “should” take a day, it’s going to take me one day to figure out how to do it, one day to do it, and one day to debug / fix it. And after that I’ll know how to do it and it’ll take about a day.

      3. R*

        One thing that might help this if she truly doesn’t know the level of effort and time. Can you assign what I call ‘Tshirt Sizing’ to tasks/projects along with priority.

        So it would look something like this.

        Pack up big mailer Priority = 1 Effort/Time XXL Due date= 8/15
        Contact vendor about X = Priority = 3 Effort/Time S Due date = Next week
        Sort paperclips Priority 2 Effort/Time: L Due date = 8/20

        Ideally you would only have to do this for awhile until she was either able to effectively estimate LOE and time needed herself or ask enough questions when given the task to figure that out or get the estimate from you.

        Honestly this way you also have some KPIs to go back to when/if it comes to more formal coaching. Giving the benefit of the doubt, it’s also something you can use in 1:1s to keep tabs on the projects.

      4. Vienetta*

        I was coming here to say this, too, LW. When I first read your description of the month-long task, it sounded to me like she had a month to do a project- packing up the shipment. If it were me, and I wasn’t clear on all the things that were involved and how long they would take, or underestimated those things, I would think, “great! I have a month to do this, that’s lots of time.” So it might be important to spend some time on that part of it, too- which PCBH’s approach would help her accomplish, as well.

      5. Alexander Graham Yell*

        Another possibility is the Eisenhower matrix – a good explanation is found here:

        This helps prioritize, and if Jane takes to it then it’d be very easy shorthand to use when assigning tasks, or in your weekly touch base to say “This is still a quadrant 2, but will move to 1 soon so it really needs to be addressed.” It could also be a way for you to check that she is prioritizing the way she needs to be.

        (Honestly, I’m not usually a fan of telling somebody else how to handle their to do list, but providing options and trying them to figure out what gets the best results might be worth it for a limited period of time, with the understanding that if nothing does, this isn’t the job for Jane.)

        1. lasslisa*

          I actually wonder if one of the mistakes Jane is making is thinking that she’s doing the right thing by deferring urgent work in order to do “important” work like bringing in new clients.

    3. Box of Kittens*

      What do you use to organize this? I fall into the “previous you” pattern sometimes, so I do a version of what you do by breaking down projects into specific tasks, but I’m not super organized about that. Do you have an Excel template or anything like that you could share?

      1. Me*

        I use the Fluxes app to do something similar to what Princess does. I’ve tried about a billion PM type applications and it’s by far my favorite because of the layers of grouping I can do like subtasks, tasks, project, project group.

        1. Princess Consuela Banana Hammock*

          I had never heard of this, but now that I’ve taken a look I like it! It’s way better than my Excel template, and I suspect easier to use as it can be accessed on your phone.

          1. applegail*

            SmartSheet might be really good for this, since you can switch between calendar/Gantt chart views pretty easily

          2. Me*

            Awesome! You can have it email you summaries of your previous days work, reminders etc as desired.

            It really helped me big time because so many of my projects are inter-related Russian nesting dolls of projects. And I like how I can add notes etc. I don’t work for them, I just really really like the product.

      2. Princess Consuela Banana Hammock*

        I use Excel. I’m happy to share the template via Alison, if it would be helpful.

        1. Box of Kittens*

          I’d love to see your template if you don’t mind sharing. I’ll have to look into Fluxes too – looks super organized. Thanks!

        2. Just wondering (pronouns: she or they)*

          Yes please! I would love to see how specifically how people organize themselves.

        3. Ask a Manager* Post author

          I’m trying to move away from an expectation that I can do this kind of thing, but maybe you could post a dropbox link or something similar!

    4. BeeGee*

      This is exactly how I was! But anything you can do to keep a project organized and have reminders the better. I like using a combination of a digital file or slack-like organization tool to keep track of the parts I am doing and or have completed, and adding reminders on your calendar for follow up tasks. For example, if you need to wait for a person inside or outside the company to complete something first before being able to continue with the project, put calendar notifications to remind yourself to get back in contact if you haven’t heard anything back. I feel like I would often drop projects because I would forget to follow up and then would forget where the project was when it got held up waiting on something.

      1. Box of Kittens*

        This is my life! I have written reminders in my planner, Outlook reminders, reminders in my personal Google calendar for some stuff if it’s really important…what a struggle.

  7. The Man, Becky Lynch*

    I have to wonder how she is with the other manager’s tasks and how they are prioritized. Have you spoken with the other manager about your issues with Jane’s prioritization? I want to know if she’s doing everyone spot on for them and then putting yours off to the side because she doesn’t know that she has two managers after all? This may be that she’s bad her job or may be her lowkey way of saying “You’re not my boss, I don’t have to do things for you.” since she’s under the impression that you’re not actually authorized to give her tasks, let alone tell her to drop her other tasks for yours.

    How does her other manager react if she doesn’t get a task done in the normal time span? It could be that she’s raked over the coals if she doesn’t get those leads out by the other person.

    I think the best thing is to get on the same page as her other manager to see how they are interacting and experiencing her work product. Then to make sure she knows you’re supposed to be giving her these tasks. Then if she’s just tossing your stuff to the side for whatever reason, that’s a performance issue that needs to be worked through.

    1. Letter Writer*

      In all honesty, I give the majority of tasks – think like a 90 to 10 split. The tasks others assign to her are often not time sensitive so they haven’t run into that problem. Because I’m giving the majority of tasks and she is coming to me with questions when she has them I get the sense that she knows I’m supposed to assign her tasks, it’s just a matter of timeliness, maybe?

      1. ChachkisGalore*

        Just a thought – is there any chance that she thinks of you more as a “senior colleague” than a “manager”? I’ve been in roles where I’ve had senior colleagues/team members giving me tasks and even handling the majority of my questions/training, but they weren’t my managers. They didn’t really have any actual authority over me. They sometimes provide feedback or if they asked me to do x instead of y I would generally follow their wishes, but if it came down to conflicting priorities or me having a reason for doing y not x, then I had the ability to push back* and then if they had an issue with that they took it to my manager.

        *The key here was that I either proactively involved my manager or at least was very clear that I could not do what they were asking/how they were asking/when they were asking.

        I’m wondering if maybe she’s seeing you as the “senior colleague” and the manager as her formal manager? Maybe not! But just agreeing that it might be a good idea to be 1000% sure that she understands the chain of command/that you are officially one of her managers.

      2. General von Klinkerhoffen*

        You said she favours certain tasks: are they within your 90% or the manager’s 10%?

        Honestly, I do identity with Jane to a certain degree, in that I put off dull-but-important tasks as long as humanly possible in favour of ANYTHING more interesting regardless of its urgency.

        I have to set myself all kinds of false interim deadlines to make sure I stay in track. Learning a little project management taught me to break large tasks into small tasks, and putting deadlines on each of those and checking them off as I go is how I manage my multiple responsibilities in a timely fashion with minimal last-minute panic.

        It might be that the “pack this up within a month” task was simply too big an elephant for Jane to eat, but “pack hardware by 8th”, “pack paperwork by 15th”, “pack housing by 22nd” etc would have been clearer and easier for her, not to mention clearer and easier for LW to monitor from a management perspective. Ideally she’d identify the bites for herself, but that could be a useful coaching springboard.

          1. General von Klinkerhoffen*

            I feared it might be. “Why is LW complaining? I’m busy with her teapot project!”

            Good luck!

      3. The Man, Becky Lynch*

        Okay that answers that question, then I wouldn’t waste any time on making sure that’s all sorted out!

        She probably needs a performance improvement plan. Sadly some people aren’t cut out for assistant roles due to this very issue. I would try to coach her first of course, with telling her that she needs to meet deadlines and by doing that, it means shifting around when necessary.

        I’ve sadly had to let people go fort his very reason.

  8. Kiwiii*

    It sounds mostly like in the example, that she maybe isn’t properly factoring in the time it takes to do larger hard-deadline assignments OR is taking those deadlines as a date to have started it by. She may need more guidance regarding larger scale projects and time management around those. It also might be useful to figure out if she had been trying to prioritize things and ended up pushing the duties back because other things came up. Or if she’s not quite sure where to start with the larger projects because of not being as familiar with them, and so they feel daunting but like she can’t ask where to start.

    I sometimes feel my day filling up with small, not particularly urgent things, because I’m better at those or already working on something related to it or it’ll only take 15 minutes.

    1. Letter Writer*

      That’s a perfectly reasonable thought, although I’ve run into this with smaller tasks too. One was to identify a list of 20 people that fall into a certain category – shouldn’t take more than a few hours really. When does she start it? The day it’s due. When she runs into problems or questions? We miss the deadline. I think some of it needs to be me doing a little more check-in and hand-holding, but you’d think someone should be able to manage these smaller tasks on their own…

      1. Sarah N.*

        Is it possible to give her soft early deadlines? Like, explicitly mapping it out and saying: “We need to have this list ready to send to our vendor on August 20. So, let’s plan a meeting to review where you are and go over any questions on August 17, and then I’d like a final draft from you to review on August 19.”

        1. Princess Consuela Banana Hammock*

          I like this approach, in part because it will make OP’s life less miserable (I hope).

        2. Kiwiii*

          Yeah, even including something like “Can you start this this week? I’d like to be able to field any questions you might run into when beginning the project.”

          1. Samwise*

            Except I would not say “can you start…” Sounds like Jane needs explicit, can’t possibly pretend that there’s any leeway directions: “Please start this week” or even “I’ll expect you to start on it this week and will check on Thursday to make sure you’ve done so.” Until Jane demonstrates she can manage her time to meet deadlines, she gets no wiggle room on high priority tasks. None.

          1. Glitsy Gus*

            I agree. Not only will this (hopefully) help with the missing deadlines it might help identify if the problem is poor planning on her part, or some kind of misunderstanding, or some other issue without you having to take significant time every day to check in on her.

        3. Just wondering (pronouns: she or they)*

          Soft early deadlines are a good start, but I’d encourage it to be framed as something to try in order to help Jane get used to doing this herself. I don’t think you want to set the expectation that you’ll be doing this forever, because then you’re giving yourself more work.

        4. Alanna of Trebond*

          Yeah, I think this is the right thing to do. I’m a little confused by this specific dilemma/example, although admittedly I’m not necessarily great at prioritization or time estimation. If my boss gave me a task that would take 2 hours, and gave me 2 weeks to do it, I’d be surprised and a little upset if he started getting annoyed with me a few days before the deadline because it wasn’t done yet. I had plenty of time to finish it!

          1. Working Mom Having It All*

            Yeah, this confuses me about every aspect of this post, to the point where I really can’t tell what the actual problem is here.

            If someone gave me a task with a deadline a month away, and it wasn’t obviously apparent that the task would occupy an entire month of my work life, I wouldn’t assume it was an urgent task. If someone gave me a task with a deadline a month away, and it seemed like it would take a few hours to do it, I too would be irritated to have people coming behind me getting annoyed that it wasn’t finished weeks in advance. Just… tell me when you actually want it done by. If it’s something that needs to be completed weeks in advance of the actual deadline you just gave me, give me the real deadline! If it’s not immediately obvious that this task needs to be done well in advance (for example booking plane tickets), give me a heads up that it’s going to take longer than I think, or that while it may not sound urgent right now, there’s a lot that goes into it and it will take the full month to complete.

            To an extent it’s OK to have unstated expectations (for example our expense reports are required to be turned in every 45 days, but in reality they need to be done much more quickly than that), but if it’s getting to the point where someone’s job is on the line, it might be time to make sure everyone is on the same page rather than assuming the person is lazy or hates you or something.

            1. Avasarala*

              I think the issue is that it SHOULD have been apparent to Jane that this was going to take a while. Like if your landlord says “you need to move out by the end of the month” and on the 25th you’re starting to look at apartments. You’re not going to make the deadline at that point and you should have known there were lots of steps in there that could take time. Not being able to estimate how long stuff like this will take is a skill in itself that it looks like Jane doesn’t have.

            2. Cherries on top*

              @ WMHIT Thank you. I think the OP might have to clarify how they want things done, and not blame Jane for not compleating a task ahead of deadline. This might not work out due to other problems with her work, but don’t blame Jane for not being like you or reading your mind.

      2. Eleanor Konik*

        This is a terrible long-term solution, but as a short-term stopgap have you considered just lying to her about when deadlines are? Treat them as absolute hard deadlines for her — and chastise her appropriately — but maybe YOU would be less stressed out when she screws up while you try to “retrain” her?

        1. Artemesia*

          it isn’t even lying. If I have a grant proposal due, I will have a hard submit deadline to internal offices that have to sign off; I need the material a couple of days before that to edit even if parts of it are assigned to others. The deadline to get something to the boss should always be X days before it had to be forwarded to meet the hard deadline. Stuff always needs to be fiddled with at the end.

          1. Cassie*

            Agreed – it’s not lying, it’s simply the date that the LW wants the task to be completed by. I used to be the kind of person who would complete tasks right away if there was a hard deadline (even if said deadline was a week away) but nowadays, I sometimes take my time if I feel like it or if other more interesting tasks come up. If the requester wants the task done by an earlier date, they should have given an earlier date.

            I also have to make sure that when I give a deadline, I don’t try to follow up before the deadline. Give the person a chance to meet (or miss) the deadline. I build in sufficient time in my deadlines that I can give a half a day leeway before I start knocking on the door.

        2. Working Mom Having It All*

          I think this can be stated better, and will have a better outcome, if instead it’s framed as if the LW would consider giving more context as to when the items are needed and what the deadlines actually mean.

          There’s a task I do regularly in my capacity as an admin where, technically, the “deadline” is a month away, but in reality there are several steps that need to happen after I’m finished with my part but before that supposed deadline. If we have an option that expires September 5, while that seems like a long way away, in reality I need to gather information about the initial deal from 2-3 people (some of whom may not be available at short notice), draft an amendment, have an attorney review that amendment, send it to the company point of contact who will also need to review it, and then that person will send my amendment to the person’s agent, who will send it to the talent for signature (and the talent, too, might not be able to do this at short notice). I typically need to shoot for it to be ready to send to the talent’s agent a week before the supposed deadline, which means I probably need to start on it 2 weeks out, not a month out. My part of the task takes about half an hour, but there’s a lot of slack time in between my work and the task itself getting completed.

          If the assistant knows this but just isn’t doing it because they suck, that’s one thing. However, if this person is new in the role, it’s entirely possible that they don’t know what the deadline actually means and how long each of those steps will take.

          1. Cherries on top*

            Yes. I have a hard time doing things “because”, but with some context there usually isn’t a problem. And having that context can also make you feel a bit more respected than just being told and build towards more self sufficiency and less need for hancholdind. (Sorry for sloppy writing. Tired.)

      3. Kiki*

        I think it sounds like her sense of how long things will take is off or doesn’t take any potential delays into account. It honestly could be that this just is not the type of job for her, but if you have the time and bandwidth to help her with it, you could actively discuss the break-down and timeframe for finishing tasks as you assign them. Giving deadlines with padding is one option that would work in the short-term, but I think over time she will recognize the deadlines are false and planning with that in mind.

      4. Angry with numbers*

        You don’t need to giver her the final deadline as her deadline. I compile monthly reports that are presented to our SVP. I do some , some by my team and some by people on other teams. Most we can just pull data from the system to complete but others need input from other groups or are dependent on other reports being done first . My deadline to the SVP is the 25th, my deadline to others getting them to me range from the 5th to the 21st. This gives me time to review everything and wiggle room if someone is late or out sick ect. I used to give people until the 24th but then I would be in the office printing and binding everything (our SVP likes real paper reports) late because people would be sending me stuff at 5 or 6 pm on the 24th. I went through the reports figured out when things could be started , how long it “should” take and some other factors and gave everyone new deadlines. Most of the reports only take a few hours so I know why people waited until the last minute because in theory it worked but in reality there is always a hitch somewhere along the way.

      5. Working Mom Having It All*

        Does she know how long it should take to do various tasks?

        As a career admin “identify a list of 20 people that fall into a certain category” sounds like something I could absolutely start the day it’s due. In fact it sounds like a task that might only take a few moments, depending on the specifics.

        Is this admin experienced in this type of work? Are you absolutely sure that she understands how long tasks like this will take and exactly what is involved in accomplishing them? Because if I was asked by my manager, “Could you send me a list of 20 projects we haven’t greenlit yet with options that expire within 6 months?” I would assume that would be a half-hour task, not a multi-day task.

    2. Kiwiii*

      and then it’s 3PM and I can’t start big-giant project because I won’t make any noticeable progress on it in the hour left .

    1. Princess Consuela Banana Hammock*

      I’m not sure that affects the advice, though. The approach remains the same, and as you note, it would be inappropriate (i.e., illegal) for OP to attempt to diagnose Jane or ask if Jane has a particular condition.

      If Jane later discloses an ADA-qualifying disability, then OP can field accommodation concerns at that point. But OP can’t move forward assuming Jane has a disorder she may not have. The bottom-line business problem is the same—Jane’s inability to properly prioritize.

      1. Sonya*

        Well, my (compulsory workplace-mandated) training says that we should always, always be considering the possibility that someone is neurodiverse. Even if they don’t tell you they are. Even though it’s rude to ask.

        And, truly, who among us has not discussed things with their friends or read an article that switched a metaphorical lightbulb on in their head that got them thinking?

        1. fposte*

          Right, everybody might be neurodiverse–Jane, her more capable colleagues, the OP, the OP’s boss, etc. And odds are high that people among them have other invisible disabilities as well. All of them should get managed kindly and fairly, with reasonable expectations, and all of them might need to be managed out or terminated if they can’t meet them.

          There’s nothing special about Jane here. You’re struck by the map of her behavior onto a disorder you know about and it’s causing you to overanchor on her situation, but it’s illustrating why armchair diagnoses derail more than they help: work isn’t there to diagnose and manage its employees’ disorders, and reasonable managers are aware that everybody might be facing a disability but that ultimately, accommodated or not, employees have be able to do the job.

            1. Sonya*

              I just don’t think Jane’s necessarily a bludger. Being focused on doing a fantastic job at the things she enjoys is not a bludger, that’s a person who wants to be good at something.

              *shrug* I think there’s more to this, and as a manager it’s an area that is really important.

              Maybe Jane’s NT, and that’s fab. Maybe she’s ND, and that’s also fab! But what about the next hire?

              It’s never too early to learn about strategies that could be implemented for managing neurodiverse employees. Hell, maybe some of those strategies could help NT employees too.

              1. fposte*

                I don’t think anybody’s saying she’s a bludger. It seems like you’re locked in this dichotomy whereby people are either blameworthy or NT/disabled, and she can be poor at this job without being a bad person even if she’s in robust physical and mental health.

                1. OhNo*

                  Good point, and well said. There’s every chance she’s just not right for this job. It sucks, but it might just not be the right position for her right now.

              2. Princess Consuela Banana Hammock*

                I’m trying to find a way to say this kindly, and I’m really struggling.

                So here’s my best effort: In your attempts to school us all on neurodiversity, you are making recommendations that literally violate U.S. employment law. Inclusivity does not mean we ignore underperformance in the workplace—it means we trust people to disclose when they may need a different set up, and we then accommodate that set up whenever doing so is reasonable (in the legal sense of that word).

                I must also say: as someone who falls in the “neurodiverse” bucket, I find it incredibly patronizing to be told that a manager should ignore underperformance or worse, assume Jane has a particular condition and treat her like she has that condition. Frankly, this falls into the “soft bigotry of low expectations” bucket for me. I’m even more offended by the idea that someone is looking at their coworkers and guessing at whether a person is NT or ND. It is possible to create a workplace that accepts and accommodates (or even celebrates) neurodiversity without mollycoddling employees.

                1. Sonya*

                  I am not saying to ignore underperformance at all. Maybe I’ve got the ADA wrong, but it protects people with disabilities, including in the workplace. Part of that is reasonable accommodations. That can mean longer deadlines or other management strategies that are tailored to that employee.

                  A company that is reactive to issues like this, instead of proactive (learning about work and management strategies for ND people) is already lagging behind other organisations, and it will pay for that, when talented employees who just perceive the world differently, go somewhere else.

                  As I said in another comment, learning about these things may also help with managing NT employees better: they might produce better work, they might work smarter, not harder, and they might share these ideas with their colleagues, who then have another way of doing things if what they currently do is purely survival. What if they could thrive? What is wrong with being forward-thinking?

                  Does it not make good business sense to get a jump start on learning about these things so that when (not if) it happens, you’re prepared for it? You can learn these strategies and share them in your workplace without asking Jane if she has a condition. Different strategies work better for different people.

                  I see an opportunity to learn from Jane: what it’s like to manage her, what’s not working, and what can change about how you manage her. Information that may help you critically evaluate how to manage another Jane down the line. It does not involve letting her coast along without improving.

                  I work in a call centre, and my manager certainly doesn’t manage everyone the same way. Our KRAs are all the same, but the strategies we each use to hit them are individualised. For instance, I don’t do side-by-side coaching because it is an enormous anxiety trigger; other employees love side-by-sides because they get immediate feedback. My manager has adapted to that, and we have an alternative strategy in place. I didn’t have to tell her I have anxiety or that I’m autistic. I just explained how I cannot deal with being observed like that. I hate work social events; I understand and accept that to some extent I can’t really advance too far. But nobody is going to fire me because I don’t want to go to happy hour. And so on. I don’t know about how she manages other employees (and nor should I!) but I can ask her if she has any suggestions on strategies that might help me do my job better that have worked for other employees she has managed.

                  I really didn’t feel like writing essays, but here you go.

                2. LSC*

                  Replying to Sonya because the thread ran out of nesting: giving longer deadlines would, in many (probably most) workplaces, not be a reasonable accomodation. It could mean running afoul of laws/regulations or simply losing business from clients who are not willing to accomodate it.

                  It almost appears as if you are working under the assumption that Jane has the right to be at this specific job no matter what, and that it is OP’s duty to find a way to make the position work for her at all costs. That is simply not the case. Without even going into the ilegallity of assuming someone has a disability and treating them differently as a result (which, even if well intentioned, is, for all intents and purposes, discrimination), there is a limit to accomodations (hence “reasonable”), which is, in general terms, that the person needs to be able to do the job for which they were hired.

                  It doesn’t appear that this job and Jane’s abilities are well suited to each other. It would probably be better for Jane in the long run to find work where she can excel.

        2. Gravity Rising*

          How does this change the advice for the OP? What does this look like in practice? What strategies are you suggesting for the OP?

          It has to be actionable to be relevant.

          1. Sonya*

            Mate, I’m not here to teach a course on it, all right? If I can access training in my organisation as a lowly peon (as well as mental health awareness, autism awareness, how to serve vulnerable customers…) I am deadset certain a manager can find this information too. A few courses wouldn’t hurt. Hell, maybe the organisation would be able to avoid hiring another Jane, particularly if she’s just a bog-standard bludger taking the piss, too.

            You learn to pick the bludgers and who genuinely cares about getting better at the job. They’ll be the ones asking for help, or finding help on their own.

            Question is: which one is Jane? Lazy Bludger or Just Doing My Best?

            1. Princess Consuela Banana Hammock*

              Gravity Rising is asking you a really fair question, and your response reads as a little… sanctimonious? defensive? (I’m trying to find a less loaded word, but having a hard time identifying one.)

              If you’re going to break the commenting rule to make armchair diagnose and make generalized statements about neurodiversity in the workplace, then you have to pair your comment with specific, actionable advice for the letter writer.

              It’s derailing to say, “I support neurodiversity in my enlightened workplace” but refuse to explain how that would play out in OP’s situation. At least in the U.S., you don’t get to suggest that workplaces change how they deal with employees based on your unvalidated perception of an employee’s neurological functioning because doing so violates that employee’s civil rights.

              1. Sonya*

                I answered the questions being asked of me by several people. Perhaps I missed one. There’s been such a pile-on that I lost track.

            2. fposte*

              “Question is: which one is Jane? Lazy Bludger or Just Doing My Best?”

              Aha, that’s where the problem is: that’s a false dichotomy, and it’s also very much not the question. The question is “Can Jane do this job with the support we can offer her?” The answer may be yes even if she’s a lazy bludger, and it may be no even if she’s ND. That’s where the job differs from therapy.

            3. Gravity Rising*

              You seem to have some really oddly rigid, defensive and black or white thinking going on. You seem to fall prey to a number of fallacies in your reasoning. This is unfortunate, as it is making your comment unhelpful to the OP and inappropriate for this site.

            4. Myrin*

              I’m fairly sure GR’s questions were a nod to the commenting rules, where it literally states “If you’re speculating on facts or context not in the letter, explain how it’s actionable for the letter-writer.”

        3. AvonLady Barksdale*

          But this does not help the OP deal with the situation at hand. The OP can’t say, “Hey Jane, I notice you’re having problems with this– maybe you have ADD?” and she will still have the issues she’s having, namely that the work is not getting done efficiently. Jane may or may not have a disorder. She may or may not know she might have a disorder. It doesn’t matter, because the OP is not a mind reader– she, like all of us, can only deal with the information she has, and right now, the information she has is that the work isn’t getting done. We cannot “tread lightly” with information we do not have.

          From the other side, if I were screwing up and someone wanted to tread lightly with me because they assumed I had a disorder, then… what good does that do me? I will never know that my actions are affecting anyone and, worse, I will never be given the opportunity to improve.

        4. Observer*

          Well, either you are misunderstanding your training or your training is wrong.

          To comply with US law, you do NOT need to make assumptions and accommodations for disabilities that are undisclosed. To the contrary it is FORBIDDEN to make assumptions and treat a person differently because of this assumption.

          It’s always good to use inclusive design concepts when thinking about how to structure any given job. But the reality is that there is a limit to that, and sometimes accommodation means changes that put some level of burden on the manager / employer. Now the law REQUIRES that if the person has a qualifying disability, and it’s good practice in most cases (assuming that the burden is not excessive). But making those changes when they are not needed is, at best, a needless burden and can be actively counter-productive or harmful.

          The bottom line is that it’s neither realistic, reasonable or legal to make significant changes on the assumption that someone has an invisible disability.

          1. Observer*

            Well, maybe your training is not wrong – I’m realizing that you are probably not in the US, and I have no idea what the laws look like elsewhere. Sorry about that.

            The rest of my comment still stands.

    2. Sonya*

      I disagree. It is absolutely relevant.

      I agree that there is a baseline level of functioning that Jane may be able to reach, with or without medication. There is counselling aimed at assisting with developing better executive functioning skills.

      But this disorder is a disability, with legal protections and requirements for reasonable accommodations.

      Problem is, it’s often missed in women, and it’s arguably stigmatised in adults as compared to children, since adults are just meant to know how to adult.

      If Jane has this (and she may not even know if she does), she will not get better at her job by having her job security threatened. And all the strategies in the world won’t help if she cannot achieve baseline functioning. Usually that’s via medication, because adults *don’t have time* for trial and error, they need to function *now*.

      Ten bucks says she’d forget to go to the bathroom or lunch if she’s hyper-focused.

      I bet all her report cards said, year after year, “Jane could be a wonderful student… if only she just applied herself more”.

      1. OhNo*

        It might be relevant to Jane’s life and functioning, but it’s irrelevant to the question and the OP’s problem.

        As you state in your original post, the OP cannot ask about this specific issue. If Jane has not been diagnosed, or has been diagnosed and chosen not to disclose at work, there’s nothing the OP can do about it. The only thing the OP can do is to lay out the expectations clearly, and Jane will either meet them or not. Having an unconfirmed theory about the cause does not help.

        Until and unless Jane is in a position to engage in a formal accommodation process, the OP must proceed with the information they know for sure, which is that Jane is consistently not meeting the needs of the position in this regard.

    3. Sonya*

      Ah, but there’s several disorders it could be, with co-morbid symptoms and symptom crossover. And it is a delicate situation, because these conditions are often classified as disabilities.

      The OP ought to tread lightly.

      Just presenting an alternative perspective as a person interested in neurodiversity in the workplace.

      1. fposte*

        Every manager ought to tread lightly, because they’re supervising humans. There’s nothing special about this circumstance requiring additional kid gloves.

      2. LQ*

        When you say “tread lightly” what do you mean that isn’t not manage? Because the OP should absolutely manage this problem by being clear and direct. There is no other way to do this and anything that looks like “tread lightly” is essentially managing less or being less direct.

        What action should OP take that you would consider “tread lightly” while still getting the work that needs to get done done?

    4. valentine*

      I don’t get the constant “Not to diagnose, but…diagnosis” when it doesn’t change the advice.

    5. Sonya*

      I replied downthread. Without diagnosing. I specifically did not name any condition, but another commenter did. I noted there are several conditions that can affect executive functioning.

      All right?

      1. Myrin*

        I hope you forgive me for being harsh but there’s really no other way for me to say this – this sounds almost deliberately obtuse. You don’t magically circumvent the “no armchair diagnosing!” rule by simply not naming a specific condition.

      2. BuildMeUp*

        The rule about armchair diagnosing exists because speculating about things that aren’t in the letter is generally not helpful to the LW and can be really derailing in the comment threads.

        If you’re going to start speculating, it needs to be reasonable given the info in the letter, and paired with actionable, helpful advice to the LW. Just saying “but maybe Jane is neurodivergent” isn’t going to help the LW handle this situation.

        I would check out Princess Consuela Banana Hammock’s comment above. She brings up a specific issue she has struggled with. It isn’t necessarily the problem Jane is having, which brings it into speculation territory. *But* she then explains how she handled that issue. Pairing “hey, maybe this is what’s going on” with actionable advice makes it okay under the commenting rules, and gives the LW a potential solution.

  9. Me*

    We had a Jane. She was incredibly baffling. Didn’t prioritize appropriately even with explicit guidance, and worse, took initiative on things she 100% shouldn’t have and had to be cattle prodded to do the things actually in her purview. She simply couldn’t do the job. Be ready for that eventuality. We kept her far far too long trying to figure out how to get her where she needed to be instead of realizing she simply wasn’t capable. It’s not fun, but it is better for all in the long run. I hope you can turn Jane around with some clear pointed guidance. But if not, don’t drag it out hoping somethign will click.

    1. Letter Writer*

      There are a whole slew of other problems that are becoming a bit…much, so I’ve raised it with the rest of our team but we’re also so busy with a massive program overhaul that taking care of her is not anyone’s priority, if that makes sense.

      1. valentine*

        What are a few of the other problems? I’m wondering if they tie in or if there are so many different ones, it’s clear she’s not long for the job.

      2. Elizabeth*

        That may come back to bite you. Are you spending time & energy on getting her to do her work that needs to be going to the program overhaul?

        1. Letter Writer*

          Oh gosh. She doesn’t take decisions on things that she should be able to by now, instead coming to me to confirm. When she does take decisions it’s the wrong one or the wrong way. Recently big boss asked her to pull a report, and while she made the report in minutes (yay!), it had holes that big boss could fill with a quick Google search (bad!).

          Luckily she’s pretty far away from the overhaul, but since most of our time is spent on that I need the other trains to be running on time – which is where she comes in and…doesn’t do so hot.

          1. Ask a Manager* Post author

            She’s probably not right for this role — I would start whatever formal process your company requires (if it requires one), which will also clarify for all of you if that’s indeed the case.

          2. The Man, Becky Lynch*

            Oh gurl…

            If she were only stinky at the prioritizing and was otherwise turning out good work, I would have a lot more sympathy here but she needs to go. I would start transitioning her out now, even though it’s not an ideal time. It will never be a good time to fire her sadly, there will always be an excuse or something going on.

            You’re hauling dead weight right now and it can really poison your department and your own soul in the end.

            1. LSC*

              Exactly. If she has problems prioritizing and whatever she produces is not good, is she actually helping you and your organization or would her contributions be a net negative when you take into account the time needed to manage her? It might be easier to start the process to terminate her even if you don’t have time to hire her replacement right now.

          3. Me*

            I had a hunch it was part of a bigger picture. There’s a learning curve for most jobs. But if a job applicant requires certain soft skills and needs to perform at a certain level, like being able to figure how long it takes to complete a project be deadline, and they can’t do so…well it’s a sign they aren’t the right fit.

            Not saying fire immediately, but it’s worth noting. Does she fix the time management related to this specific task (shipping) but can’t apply the skills to any other task requiring time management?

            Our Jane would have been a lovely receptionist or in some role with very distinct duties. Unfortunately that wasn’t the role we had. She worked her 4 exhausting for everyone years. She never should have made it through probation. Just don’t fall into the endless improves one minute thing at a time but is still a swirling pit of hand holding.

            Oh and watch out for “excuses” – like no one showed me, I’ve never done that before, etc, etc. Our Jane never owned responsibility for a thing. If you don’t own responsibility for how you can improve at something you will never improve.

          4. Observer*

            Yeah, it sounds like you need to think about letting her go. And, no it’s NOT a good time. But you know what? It’s never going to be a good time. And the longer this lasts the worse any given time is going to be because things are going to snowball.

      3. NW Mossy*

        Of course that makes sense – you’ve got competing priorities too!

        That said, don’t yourself underestimate how much of your time and energy gets drained away when you’re dealing with a subordinate who’s underperforming, especially when they’re doing so in a way that erodes your trust that you can give them things and they’ll do them right and on time. The organization hired her to give you time back by lightening your load, but it sounds like the reverse is starting to happen. You’re having to maintain such a high level of oversight that the net benefits of another set of hands aren’t that great.

        It may be worthwhile to set yourself a clear goal of how much time you think is reasonable to invest over the next few weeks to bring her performance up to snuff. With that in mind, then keep track over that time – count the meetings you have course-correcting her, the time you spend doing things that should be on her, and so on. At the end of the few weeks, see how it played out against your goal. If you find yourself way over your estimate and don’t see significant improvement, that’s about as clear a sign as you’ll get that a well-handled firing may be your best option.

      4. Artemesia*

        The longer you let it drag on the harder it gets to fire her in many organizations. I’d prioritize the talk with her and then move to discipline and firing if it turns out she is not up to the job. I don’t know your organization but I have observed in other organizations, people who should have been fired and would have been easy to fire early on, end up stuck like barnacles and messing things up and being a missing stair for years.

    2. JediSquirrel*

      I’ve worked with people who just weren’t right for the job. On paper, they had all the right Legos. But in real life, they just couldn’t put them together.

      You go through the processes you have to go through to give them the benefit of the doubt, but in the end, sometimes it’s more fair to them, to yourself, and to the company, to simply part ways. It gives them a chance to move on to greener pastures, and it eliminates difficulties for your organization. Letting people go is never easy, but sometimes it just needs to be done.

  10. Meredith*

    My company has partially solved this problem by employing a production manager, whose job partially consists of helping grown adults prioritize their task lists. This is in addition to the task/project software we use (also implemented/managed by the production manager). I wish I were joking. In fairness, only one person REALLY needs his schedule managed, and the other just has a huge amount of work, including work that only touches his plate, so it makes sense for her to schedule him out just to see where we can fit other work into his schedule, or to be able to tell clients when we can start a project for them. The first guy… I got nothing. He rarely answers emails, is MIA when he “works from home” (at least once per week) and prefers chat. Fine. But he also needs to be told to do something more than once (again, even though we have task software) and so it just makes sense to go to the production manager and have her put it on his list, which she reviews with him weekly.

    It’s potentially one of the most frustrating parts of my job. As Alison has alluded to, I’m one of those high performers at my company who will probably eventually leave, partially because of the failure to address this.

    That said, OP’s situation doesn’t seem terrible – yet. OP, if you are the person who is best at task prioritization and have the ability and willingness to help, maybe you can try a system where you proactively review her priorities with her. Does your company have project management software? Is there a way to flag tasks as high priority and let her know anything flagged needs to be done by X time frame (end of the week, end of the day, whatever)? It’s perfectly possible she will start to learn and you will be able to gradually backoff on the hand holding. How long has she been in this job?

    1. Letter Writer*

      Wowza, didn’t even know a role like that was a possibility!

      I mentioned in another comment but Jane, me, and the manager have weekly check in meetings to review her to-do list, see if she’s overwhelmed or has any questions, and give her line of sight to upcoming tasks. I do try to flag deadlines and priorities here, but I’m open to hearing anything else that could help!

      How long she’s been in the job is another problem. We’re at about 8 months now and she still asks minor questions about 10 times a day. I don’t mind the questions, but some of these things she should know well enough now to make a decision on her own.

      1. Meredith*

        While you have the ability to help set Jane’s schedule, did you help hire her in the first place? Are you or the manager in charge of things like promotions, raises or disciplinary action? It’s probably much more frustrating when you have no ability to implement consequences. It’s definitely a good idea to flag this stuff to whoever has the ability to manage Jane’s consequences and hope you’re not at a company who thinks mediocre-to-incompetent is better than nothing. (Obviously, official PIPs and other tools might help.) Good luck!

        1. Letter Writer*

          I did help hire her, but I ultimately do not have authority over promotions, raises, or disciplinary action. I’ve started flagging it to others, but I see a lot more of the issues since I work more closely with her.

          1. valentine*

            I don’t mind the questions, but some of these things she should know well enough now to make a decision on her own.
            If you haven’t already, you can say this and ask what her system is for retaining such information. But don’t give her a multiple choice. Do you see her take or refer to notes?

            1. fposte*

              I would agree with this. At this point everything gets made literal and specific–what you want her to do, how you want her to do it, when you want it by, what you want her to stop doing, etc.

      2. RandomU...*

        Have you started pushing back on those repetitive questions?

        Jane: Where do find X
        You: Where did you find it last week when you were looking for it?

        Jane: How do I do Y?
        You: Did you take notes the last time we went over this? or Why don’t you give it a try and we can review tomorrow.

        Honestly, seeing your other post about her performance… I’d bide time until you do have time to address the performance, but in the meantime I’d spend some time getting your documentation ready for a PIP.

        1. Lana Kane*

          My go to in this situation is “At this stage, I’m going to ask you to start referring to your resources before asking. These instructions are already documented. I’m happy to help if you follow the directions and it’s still not working.”

        2. Meredith*

          One issue is that the OP is not in the position of authority to request or implement a PIP.

          1. Ask a Manager* Post author

            I might have missed a comment from the OP where she says that, but otherwise it definitely sounds like she can, at a minimum, request a PIP.

          2. Letter Writer*

            A few things here: she does take notes, which make me feel better, but it doesn’t help if her notes aren’t good, so that’s something worth looking at. Further complicating this is that some of the questions she has are one-offs, so we’ve talked about enough similar situations that I think you should be able to figure it out, but there’s one odd detail that throws her off. Perhaps I need to do a better job of saying “What would you do based on what we talked about earlier with x situation?”.

            I don’t believe I have the authority to put her on a PIP – I also don’t think that’s something my organization does – so that’s something I need to look into.

            1. Ask a Manager* Post author

              If your org doesn’t do PIPs, the question is: How do they handle it when someone isn’t working out and might need to be let go? That’s the question to raise, first with your own manager.

      3. NothingIsLittle*

        Does she have those deadlines in writing somewhere? It might be worth having a follow-up email with all the deadlines in it so she can reference that. I know that you mention below your shipment example had an emailed deadline, but that it was within its own email. At best, an emailed list will help her realize her priorities and at worst you’ll have a record that the deadlines didn’t take her by surprise.

        1. Glitsy Gus*

          Yeah, I’m wondering if, say a shared Outlook calendar or something so all three of you have the same dates in the same place?

          At the same time, given the other things you’ve mentioned, Letter Writer, this is kind o a last ditch attempt. I think it might really be time to have the, “I need you to be able to have a handle on these things in the next two months or else we may not be able to continue on here.” conversation. It sounds like there are too many things just not coming together.

      4. The Man, Becky Lynch*

        8 months is waaaaaaaaaaaaaaaaaaaaaaaaaaaaaay too long for her to be acting like this. If it were within the first three or if she was in a complex role, I’d say that it’s still on pace but no, this is an assistant role. Taking 8 months and still asking these questions constantly is proof she’s a bad fit and needs to be removed.

        If you find yourself asking the same question, you should write down the answer and look at your notes. The first step here is to ask her why she’s not retaining the information.

        I don’t think she’s just doing the “Fun” projects she likes even. I think she’s just doing the projects she understands since she’s struggling on so many levels.

        I seriously am praying they will cut her loose if you present all these issues. The point of an assistant is so that you and the other managers have time to do your jobs better! This is the anti-assistant.

        1. Artemesia*

          This. The groundwork needs to be laid with management that this person needs to be moved out because she can’t do the job. 8 mos. Wow.

  11. That Girl From Quinn's House*

    One thing that used to happen at one of my former jobs, was that assignments given well in advance often ended up with the details drastically changed or the task canceled entirely in the few days leading up to the deadline.

    So if you were someone who managed your time and completed an assignment a day or two early, you often ended up doing it over when the details changed, or throwing out hours of work when the task was canceled. For example, one time my boss entered her staff performance reviews into the computer a week before they were due, but HR pushed a software update to the program deleting them figuring “reviews aren’t due for another week so it won’t affect anyone since no one has submitted them yet.” They were lost, unable to be recovered, and she had to do them all over again, at the last minute.

    Is this something that happens often at your workplace? Or perhaps, it’s something that happened at one of Jane’s former workplaces and she’s picked up a bad habit that needs to be explicitly extinguished?

    1. Letter Writer*

      Ouch! Luckily no that does not happen in our workplace, otherwise I would be very irritated.

      This is her first job out of college, which may also be a factor.

      1. That Girl From Quinn's House*

        The first-job-out-of-college might be something worth probing further. I know I was advised, especially as a woman, to not take on “unpleasant” tasks lest I be pigeonholed at a lower level, and because I was eager to show my “value” I’d focus my attention on projects where I knew I could “shine” and thus be a candidate for promotions.

        In retrospect, it’s cringey. I made a ton of mistakes in prioritizing an unimportant yet highly visible project over some very important but not glamorous gruntwork! I did get solid performance evaluations all along so it must not have been a problem, but it might be worth discussing with Jane, because it’s often really hard to tell the subtle differences between what makes someone a successful employee in general vs. a successful employee in a particular role/for a particular supervisor.

      2. RC Rascal*

        College students have lots of control over when they complete assignments, and the work mostly doesn’t impact others. She may be someone who habitually procrastinated in school, and then pulled all nighters to compensate. That works in school, but is a terrible habit in the workplace.

        1. Kiki*

          Yes, school also doesn’t throw scheduling curveballs the way many workplaces do, so the adjustment can be hard. In school you have a syllabus handed to you every semester and you know exactly when things will be. In most workplaces, work gets assigned to you when it gets assigned to you, so waiting until the last minute is a much worse idea.

      3. Mockingjay*

        Other factors you might want to consider:

        -Workload. You said Jane is part-time, but is the workload itself more than part-time? Rote tasks can add up quickly.
        -Skills vs. Type of Work. Assistants can be assigned a very wide variety of work. As a junior, inexperienced employee, Jane may not have the skills to do all of the tasks she has been given.
        -Experience. Even if the tasks assigned are within her skillset, it takes a few years to learn how to quickly regroup mentally when switching tasks, especially due to changes in priority.

        If you truly need only a part-time employee, you might need someone with more experience who can handle changes on the fly.

        1. Working Mom Having It All*

          Yeah, the skills thing immediately jumps out at me.

          Complicated time management issues where there are somewhat unspoken deadlines that aren’t the official deadline, and lead time that needs to be built into things that may not be apparent to a casual observer, are usually not features of entry level part time admin work.

          It sounds like OP’s company is really looking for someone with 1-3 years of experience in this exact type of admin role, not so much someone fresh out of college who comes in a couple days a week to help out.

      4. Lady Jay*

        As somebody who teaches college students, I find this significant. College students do not always have great time management skills, and in fact some aspects of college life promote a culture of doing everything at the last minute (the stereotype of “all nighters,” for instance, or peers who model waiting until the last minute, or a lack of explicit instruction in courses about time/project management.)

        What that means for Jane is that while ultimately, she may not work out in the role, a little more (direct, explicit, targeted) coaching about what professional time management actually looks like may be helpful.

      5. Artemesia*

        You are meeting with her once a week but have apparently not made clear that 1. she is royally screwing up deadlines routinely 2. she has not mastered the basics of her job. This is a management fail. You are already spending the time, the issue is not being dead clear about the standards and her need to meet them. I hope you have discussed the steps for firing and replacing her with whomever has the authority to do so as it past high time to begin planning for that. Perhaps she will be transformed by a little management, but maybe not if she hasn’t caught on in 8 mos.

    2. RandomU...*

      Oh I would be on fire mad! This is also the reason I always do performance reviews in a document outside of the system vs. in the system, then transfer. I’ve had one too many completed reviews go “Poof” on me.

  12. Arjay*

    I think it’s important to be clear about expectations of progress. It sounds like with a four week deadline, you might want to see 25% completed each week, whereas Jane may be thinking she can do 100% in week 4 and be just fine. Setting intermediate deadlines and checking in on progress might help both you and Jane.

    1. Yorick*

      Yes, I think intermediate deadlines is a good idea. I would absolutely have planned to devote all of week 4 to do the whole shipment, and if I knew/thought I could finish in time, I would not get it if someone went into a panic and asked a bunch of people to help.

    2. Letter Writer*

      Yeah, this is definitely my next step with her and something I’ve started doing with smaller tasks!

    3. OhNo*

      It would be good to flag any information you have on how long tasks take, if it doesn’t take too much time on your end to figure that out. For example, telling Jane that a project is due in four weeks and will take at a minimum 60 hours, so absolutely must be started by X date might help.

      It’s possible that she just isn’t familiar or comfortable with doing that mental math on her own. But, of course, that’s putting the work for figuring out those details on OP’s plate, which might not be sustainable long term.

    1. Letter Writer*

      You got it! I love reading updates myself, so I’ll definitely be sending something in!

  13. timeforbreakfast*

    Since she just joined your organization recently, she could be putting off task X in part because there is some ambiguity about how it is supposed to be completed and for some reason she isn’t comfortable asking for clarification. Of course, she should be asking anyway, but if this is the case, it suggests that making yourself more explicitly open for questions (at least while she’s getting started) might help.

    1. Letter Writer*

      Well, she’s been here for about eight months now and she has tracked a path in the carpet to my desk with questions every day, so I’d like to think it’s neither of those things. Certainly though, yes, something to clarify with her.

      1. Hey Karma, Over here.*

        Please don’t let eagerness overshadow ability. She’s trying hard, but just not getting it. I think writing in at this point is a great idea. I think the comments offer a lot of insight as well as suggestions, so you should definitely try a redo with Jane. “OK, you are not prioritizing tasks the way that we need you to. I’d like to help you with that. Starting now, I will…” and insert you plan here.
        But be prepared for it not work. Be prepared to have to start the hiring and training process over.

  14. LilyP*

    Just be careful you don’t ever act like the boss in the first linked question! If you’re giving her something with a hard deadline but want it done ASAP or if you’re expecting to see certain progress, say, a week before the deadline, you really need to be explicit about that.

    1. Yorick*

      I think this is what’s happening. It’s telling that LW says she always does a task with a deadline first, but in some cases that’s not a great way to go about things (like here, where there are tasks with a far deadline).

    2. Antilles*

      if you’re expecting to see certain progress, say, a week before the deadline, you really need to be explicit about that.
      That depends on the kind of progress though. The shipment seems like a perfect example here:
      No, OP did not lay down a specific expectation of how much should be done by the last Monday of the month…but OP clearly laid out that the shipment needed to get out by the end of the month. And there’s no way the employee was going to meet that deadline – it took four separate employees to actually get the boxes packed and out the door. So the employee effectively *did* fail to meet the schedule, even though the shipment ended up getting out on time.

      1. Kesnit*

        We don’t know that Jane would have missed the deadline. Yes, 4 people ended up working on it, but we don’t know how long it took them, or what else they were doing at the same time. If it took a week to get it done, but each of them only worked a few hours for 1 or 2 days, it isn’t unreasonable that one person could do it in a week if they did nothing else. We don’t even know if it took 4 people an entire week. LW may have jumped the gun and panicked without cause. Some people just over plan. (My wife is like that. If it takes 2 hours to get somewhere, you can bet she’ll want to leave 4 hours early, just to be on the safe side…)

        Also, a “week” can mean any number of things. For example…
        The shipment has to go out on Friday, Day 28. LW talks to Jane on Monday, Day 17. Technically, that would be in “Week 3,” but is in the very early part of the week and still gives Jane 11 days (almost half the time originally given) to complete the project.

  15. Annonnomouse*

    The one hard example you gave was this: 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? Hadn’t gotten to it yet.
    but you didn’t actually say to her, this needs to be done by the end of this week (or some other time when you actually wanted it done by), you said by the end of this month. So that doesn’t read the same as “You must do Thing X this week, even though the deadline is a month away.” If the deadline is a month away, and it’s literally, go pick something up” I probably wouldn’t prioritize it over something that is due next week either.

    It actually doesn’t sound like you’ve literally said to her, “You must complete Thing X before beginning on Thing Y, regardless of their deadlines.” Try that first.

    1. Eleanor Konik*

      I think the problem there was that she presumably should have known that the task requires more than a week to complete, because she’s done it before.

      1. valentine*

        you didn’t actually say to her, this needs to be done by the end of this week (or some other time when you actually wanted it done by), you said by the end of this month.
        The end of the month was also the end of the week OP was asking, probably T minus 5 days.

        1. fposte*

          Right. And yes, intermediate check-ins and, with first-timers, estimates of the packing time might help preclude problems. But the fact is that there are plenty of entry-level employees who can practice this level of time management without their supervisors monitoring them, and it’s not an unreasonable thing to want in an employee. So while I’m with the OP’s effort to try to make Jane succeed, I also think it would be reasonable for the OP (or the manager with the authority) to consider Jane to be insufficiently independently governing for this role and to let her go.

    2. Letter Writer*

      I like the phrasing you’ve suggested! In the example I gave – an office-wide email was sent out that everyone needed to have their shipment due by June 31st so I assumed she would understand, but I think your phrase definitely needs to be tried out!

      1. Annonnomouse*

        How should she have understood anything other than “my shipment is due by June 31st” if that’s what you said? I think you need to be much more explicitly clear with what you mean, and not expect her (or anyone) to read your mind.

        1. valentine*

          Annonnomouse, what do you think wasn’t clear? The fact three people helped means Jane couldn’t do it in a week.

          1. Liane*

            AND there’s Fact 2 — This wasn’t Jane’s first time, per the OP’s letter, at doing this task. Therefore Jane should have known from the previous time/s she did it, that getting the things out the door by deadline was going to take more than a several hours/ a few days.

            Heck, even if she’d only worked with smaller shipments, Jane should have been able to reason it out: “It took 15 hours of my 25 hour workweek to get X boxes shipped. This is 3X boxes, so I should probably plan on starting by next Monday *At the latest.*”

            So the problem is *highly unlikely* to be “LW didn’t give poor Jane clear–or any!–directions for carrying out a task she’s never done before.”

          2. Kesnit*

            We don’t know that, since we don’t know how much work everyone actually did or how many days it took them. If it took 4 people working over 3 days, that doesn’t mean it would have taken Jane 12 days. If the 4 people only worked 3 hours a day for 3 days, Jane could knock it out in 2-3 days alone. LW says he talked to her in the 3rd week, but that could still be 11 days before it was due. (Monday, Day 17 for shipment on Friday, Day 28.)

        2. Antilles*

          Except that she still didn’t meet the deadline. It took four people scrambling to meet the deadline – so no, she did *not* meet the deadline.
          When you say “due on the 31st” that means that in whatever hours remain between today and the 31st, you need to be able to complete the task. So if the task takes around 60 hours of effort, you need to budget time like that. If it’s the 15th and you haven’t started, then you can say “well, I still have two weeks, no worries”. If it’s the 29th and you haven’t started, then um, you actually missed the deadline – even though you technically still have time, you’re clearly not going to make it.

          1. fposte*

            This is a really interesting observation that I think speaks to a lot of time management–that “too late to do it on time” is already late, whether it’s leaving the house for work or preparing a massive shipment. People who struggle with time management often don’t grasp that, and in fact because the OP is *good* with time management she may not realize that the interim steps that are intuitively obvious to her aren’t occurring to Jane.

            1. Letter Writer*

              I think *this* is really where I’m stuck. There are a lot of suggestions to provide her short-term deadlines and all that, but I don’t even know how to identify those since I tend to them sort of intuitively at this point, if that makes sense.

              1. Ask a Manager* Post author

                Your job here is to be very clear about expectations and how she’s currently falling short, and to paint a very clear picture of what acceptable performance looks like. If you can give her helpful suggestions and coaching, do (including things like pointing out “if something is due on the 31st, you need to plan backwards and think about how long each step will take and allow a buffer for things that might go wrong”). But ultimately it’s reasonable to say “I need someone in this role who can meet deadlines and prioritize independently.” It sounds like she may not be that person.

              2. LQ*

                …tell her to do it? I don’t mean for this to sound snarky and I’m afraid it will. But why not push that task to her.

                “I need these boxes ready to ship by the 30th. Can you make a quick outline of when that’s going to get done and some check in points along the way?”

                You don’t need a full on project plan for these (I’m guessing, maybe you do need more Project Management…) but ask her to take 30 minutes (no more) and have that outline to you by the end of the day. You can look at it and figure out what’s wrong. It’ll be easier for you to look at something like that and edit, and it will teach her the skill.

                I wouldn’t do it for everything, but anything that’s going to worry you or that’s multistepped it might be worth it.

                1. Observer*

                  This is an excellent idea. A lot of the suggestions have been putting a lot of the planning burden on the OP, and it’s just not reasonable. This pushes the task where it should be while giving Jane some support. And it will be a lot easier to clearly see (and document) if Jane is actually capable and willing to do the job.

          2. Kesnit*

            No, we know Jane did not meet LW’s arbitrary deadline that Jane was never informed of. There is also no indication that all 4 people had to “scramble” to get the job done. LW said 4 people ended up working on it, but nothing in the letter says they had to work extra time, or that they each spent massive number of hours on it.

        3. NothingIsLittle*

          I’m not sure I understand what you’re trying to say here. If my shipment is due by June 31st, it takes 40hrs for me to prepare it (which I should know because I’ve done this task before), and I only work 20hrs a week, then it needs to have been seriously started at least two weeks ahead of the due date. That’s not reading anyone’s mind, that’s basic time management. It’s pretty clear that the employee in question doesn’t have a grasp of that, but it’s not that OP is being unclear, its that employee doesn’t have the necessary skills to succeed in her job.

          Part of understanding that your shipment is due by June 31st is understanding the necessary steps for it to be ready by that time.

          1. fposte*

            Yes, that’s what I’m seeing too. This is something Jane has done once already–she knows it’s not a last-minute task. But because of skill level, mental mapping, or whatever, she’s not clocking that she needs to know in advance when to start the project, where she should be at what date, etc.

            What I’d probably do in a situation where there’s room for coaching is name the challenge–time management–and ask her to set her own mid-completion targets and targets by time, complete with estimates of duration, and share them with me. I want her to be able to be accountable for the plan and not just get a bunch of check-ins that keep her on task, and I want (again, if there’s room for coaching) a chance to go over her thinking with her and discuss problems I see in her assessments.

            But I don’t know that I’d have the time for doing that–it would depend on the job, the workplace, and what else Jane has to offer.

          2. Annonnomouse*

            I may be reading it wrong, but here’s what I see op saying:

            1. I gave Jane a task once before that she failed to complete and others had to pitch in to cover, though I don’t know if she learned anything from it. (in other words, OP failed to teach Jane anything about it)
            2. I gave Jane the same task again later, and told her she had one month to complete it. (I again failed to give Jane specific instruction about how I wanted the task completed, and “assumed she would understand”)
            3. When I checked in with Jane regarding the task about a week before the deadline I gave her, she hadn’t yet completed it and I freaked out.

            (I don’t see anything from OP regarding how long this task actually takes, and if op made sure that Jane is aware of that time requirement)

            So yeah, I don’t fault Jane here, until and unless the OP explicitly says to Jane,
            “You need to budget X hours for this, and it should by Y% completed by Z date.” or some variation thereof.

            1. fposte*

              Except that what that describes is a pretty common situation that a lot of employees manage better than this.

              I think, as with Sonya’s comment, it’s easy to go to a binary, in this case “is Jane bad or is the OP bad?” And I don’t think that’s a useful approach; in many, perhaps most cases, the answer is “Neither.” The question is whether Jane can do the job well enough with the resources provided, and whether a “No” means the job needs reshaping or a better-suited employee should be put in the role.

              From what I’m hearing, it sounds like Jane’s a bad fit for the job, and they quite possibly can find somebody to do it a lot better. That doesn’t make Jane a bad person (and it may mean they need to sharpen up their hiring practices), but she can be a good person and still not be somebody who gets to keep a job that’s not working.

            2. Artemesia*

              She has been there 8 months and has done it before. Jane is failing. But yes the OP is failing to manage. She is meeting with her every week but has not clearly communicated to Jane that she is failing and exactly how. Jane is asking repetitive questions daily, but the OP has not clearly communicated how inappropriate this is and that is signals a failure to learn her job.

              1. Letter Writer*

                Artemesia – this is perfectly reasonable! I very well could be failing, which is why I came here for help! :)

                I think a lot of what’s holding me back is that this is also my first job out of college, so I’ve never had so much authority over someone. While I want to help her I wasn’t entirely sure how to even start which is why I was asking for advice.

                1. SierraSkiing*

                  One way my first boss out of college nudged me to make decisions on my own was a conversation that went something like this, a few months into the job:
                  Me: “Hey boss, I’m almost ready to send off the X report – how do you want me to do part Y?”
                  Boss: “Oh, you don’t need me for that! At this point, you should handle Y on your own. Can you tell me how you would handle Y?”
                  Me: “Uh, I guess I’d do [technical details here].”
                  Boss: “Yep, sounds about right. Just make sure you consider [small detail] as well, and from now on you don’t need to check in with me about Y unless something really unusual comes up.”
                  And from there out I handled Y myself. Before that, I thought I was being a more responsible employee by checking everything with my boss – I didn’t understand that part of my job was to take those decisions off of my boss’s plate.

                2. NothingIsLittle*

                  Being honest with you, I’m not sure you can help her at this point. There are a lot of things you could try, as the comments have mentioned, like being incredibly specific about her tasks and micromanaging her, but if she doesn’t want to change, you can’t make her. “You can lead a horse to water,” and all that. I don’t think she’s necessarily beyond help, but it doesn’t really sound like you’re prepared for that to be the case and you really should be. She might just not be suited for the type of work that you’re doing.

                  I think another big part of the problem is that you’ve mentioned in your comments that you don’t have the authority to discipline her? If she knows you can’t do anything about her insubordination, she’s less likely to fix the problem. It might not be malicious, just that she might think it’s not actually a big deal if she’s not going to get into trouble for her actions. It could be worth getting whoever does have the authority to discipline her to deputize you, since you mentioned no one has the time to deal with it.

                3. Artemesia*

                  And you are getting great advice here. The most important of which is that you have to be firm and clear on expectations. She is still asking many questions every day after 8 mos when you expect her to be working on her own and, well, assisting you not making more work for you. This should have been dealt with 5 mos ago — now it needs to be clearly communicated that she should have mastery of the job and not need so much of your time answering questions. Apparently you have not made it clear that this level of hand holding is inappropriate.

                  This might be something she can learn as she doesn’t have clear professional norms or it might be that she is incapable of being sufficiently competent and independent. But she needs to be told clearly what her behavior should look like.

                4. Cherries on top*

                  Maybe you (LW) aren’t right for (the managing part) of your job (right now)? Which is something that also falls on your employer. Communicating to others what you want/mean is a skill, especially when people don’t think/work like you (people are different).

                  (Jane seams to be a problem too.)

            3. BuildMeUp*

              Yeah, I think you’re misreading the timeline. It’s more like this:

              1. LW gives Jane the packing assignment. Jane completes it successfully
              2. Some time later, Jane gets the same assignment again. LW, having seen her do it before, assumes it will be completed the same way this time
              3. Instead, Jane puts it off and, a week before the deadline, three additional people are needed to complete it

              So it sounds like, since Jane completed the task before once, she should know how much time it takes. And that’s why the LW assumed she would understand when she needed to start.

              1. motherofdragons*

                I find myself wondering what was going on in Jane’s mind that prevented her from applying what she did successfully the last time to this latest task. If I was her manager, I think I’d include that question in our discussion as well, to help understand the situation better but also to model a reflective process for her so she can start doing that more effectively on her own.

                1. Kiwiii*

                  I mostly wonder if she received more specific instructions or instructions directly to her to complete the assignment the first time and that the group email this time didn’t ping as an Assignment to her in the same way an individual email or direct conversation might have.

                2. EventPlannerGal*

                  I would assume that if she finished on or ahead of schedule the last time, she then thought that this time she wouldn’t need as much time as she had allowed for previously and could get away with putting it off.

                3. lasslisa*

                  I can’t nest another layer but I hear my own little always-late optimistic voice coming out of EventPlannerGal’s mouth. Last time I finished with daaaays left! Obviously this time I should wait longer to start.

                  Admittedly I work a lot on things that are prone to last-minute changes that can invalidate past work. But it’s definitely my weakness.

              2. Kesnit*

                No, here is the timeline…

                1. LW gives Jane the packing assignment. Jane completes it successfully
                2. Some time later, Jane gets the same assignment again. LW, having seen her do it before, assumes it will be completed the same way this time
                3. Jane knows what she did before and assumes this will be the same. Instead, LW freaks out early and, rather than asking Jane what is going on, decides Jane is screwing up and drags everyone in.

                Yes, Jane has done this project before. Why is everyone assuming that Jane blew it off? By LW’s own admission, Jane still had a week (maybe more, if LW spoke to her on Monday and it had to go out a week from Friday) to meet the deadline. If Jane did the project in a week (or less) last time, why would this be different? LW assumes a week isn’t enough time, but I’m sure LW has lots of projects going. Jane likely has fewer, so has more time to put towards this specific project, and maybe can complete it in a week.

                It would be a different if it was the night before and Jane had done nothing. But that isn’t what we have here.

            4. NothingIsLittle*

              I think you might have missed where OP said, “she’s done it successfully before,” in the original letter.

              If she’d failed before, though, I’d agree with you.

            5. fhqwhgads*

              I think you are reading it wrong? What I see OP saying is:
              1. I gave Jane a task once before and she did it, and on time.
              2. I gave her a very similar (possibly larger version) of that same task and told her it must be completed within a month. I assumed based on her having done it before that she understood approximately how long it should take to complete.
              3. When I checked in with Jane regarding the task a week before the deadline, she had not yet begun, and I freaked out.
              She didn’t tell us how long it should take but it’s strongly implied she gave Jane a month and freaked out with one week to go, and roped in extra hands at that point, because it was known to the people in the office who have done this that it was not possible to do in one week.

              If I’ve done X before I know how long X takes and it’s not on my manager to tell me every single time “you need to budget X hours for this” unless the current task is in some way significantly different than previous occasions. Nothing in the letter suggests this was some outlier that wouldn’t fit previous velocity for this type of task.

    3. Essess*

      Also, it says that the OP checked in a week ahead of time and it wasn’t done yet. The next thing is to specifically ask the employee “how long do you think that task will take you to complete?” This lets you know whether the employee had a grasp of when she should have started it and lets her know why you are asking to much earlier than she might have planned to start it and give you a coaching point about realistic time frames for tasks if she was underestimating the time.

      1. Kesnit*

        THANK YOU!!! You are the first comment I’ve seen that doesn’t automatically think Jane screwed up. Maybe Jane really can do it in a week (or less).

    4. LJay*

      But she wasn’t going to have it done by the end of the month.

      For this example I’ll use 60 hours of work as an example.

      I don’t think OP would have cared if the assistant did it 3 hours a day for 20 days starting on the day it was assigned, or 5 hours a day for 12 days starting on the day it was assigned, or 5 hours a day for 12 days the last 12 days before it was due.

      The problem was that she had 60 hours of work left, and only 5 days left to do it in before the end of the month. So, assuming the assistant is not regularly expected or authorized to work 12+ hours a day, the assistant had no way to meet the deadline.

      So even though the end of the month has not actually hit yet, this wasn’t about not hitting a soft deadline that the OP hadn’t articulated. It’s about the assistant not hitting the hard deadline that she was assigned at the beginning of the task.

      1. Kesnit*

        You are assuming 60 hours of work. What if the project only takes 20 hours? Jane has (worst case) 5 days left (could be as high as 11) to complete it. 4 hours a day and it’s done. Or 5 hours a day and she finishes a day early.

        1. Mindovermoneychick*

          Because otherwise 3 people would not have pitched in to get it done? I assume they did that because all involved at that point knew it was required to meet the deadline? At least that’s my reading.

  16. Alton*

    I wonder if part of the problem could be that while deadlines are clear, Jane doesn’t always have an accurate understanding of how much time is needed to complete the task in time (including allowing enough of a buffer to deal with any complications or delays). For example, I can see putting off the shipping task if there was a whole month to do it and there were other things that needed to be done sooner. In general, I think it’s common that people aren’t always going to get around to things until closer to when they’re due, because other things come up. But it sounds like Jane didn’t allow herself enough time to do it and ensure that she could meet the deadline. It sounds like in cases like these, there are really two deadlines: when the work must be done by and when you want Jane to start working on it to make sure it’s done in time without you needing to step in.

    If this might be part of it, maybe it would help, when talking to Jane, to talk about allowing enough time to complete tasks and planning ahead.

  17. No Longer Working*

    Maybe having multiple projects or tasks makes her feel overwhelmed, and she handles that by doing the easiest ones first. Whenever I felt overwhelmed with too much to do, I made a list and asked my boss or his assistant to tell me the order of priority for the list. When they stuck me with a new task, I asked where on my list of priorities it should go. Asking about priorities instantly relieved my stress and I was able to tackle one task at a time without freaking out that I couldn’t do everything at once.

    Perhaps a daily check-in and priority list would help her immensely.

    1. That Girl From Quinn's House*

      This is how I used to do my homework. I’d do the shortest/easiest assignment first and leave the longest, most complex one last. The logic behind it being, if the complicated project bogged down, all of the other work was completed and I could stay up late working on that one project, instead of having to risk cutting it short and also doing a shoddy job on my other assignments because I was now exhausted.

      1. No Longer Working*

        That’s fine to do when nothing is deadline-affected! I liked getting small things out of the way first myself. I also prioritized things that other people were waiting for, if possible.

    2. EventPlannerGal*

      I think that’s probably a lot of what’s going on. I would also add that IME, it’s the small/easy tasks that people get the most mad about not being completed immediately (“all I asked was for you to send one e-mail! Why hasn’t it been sent yet?”), and so it’s very easy to get bogged down in a million small tasks that people are telling you to do *right now* and lose sight of the big, long-term stuff. OP, if your assistant is dealing with multiple people giving her different tasks, how good is she at saying “can that wait as I’m working on the shipment for OP right now?” or similar?

  18. Shay*

    The problem isn’t that Jane cannot prioritize – the problem is that Jane is ignoring your instructions, needs, and requirements. This doesn’t sound workable to me.

  19. Adaptive Coaching*

    I believe there’s adaptive management / adaptive coaching needed for every employee.

    Most people can work on their own and be productive. Micromanaging these people will harm productivity.

    For people like Jane, who can get distracted easily into doing easy / shiny things and can be talk minded and miss the bigger picture, a bit of micromanaging is required. – say, you have 20 tasks for them to complete, assign them only the high priority tasks for this week, have a per week or even every day meeting to see what they have done. Give feedback right away and tell them you want to work only on this for time being. This will be a time/energy suck for you, but will get the job done and no more mad scrambling at the end.

  20. AdaptiveCoach*

    I believe there’s adaptive management / adaptive coaching needed for every employee.

    Most people can work on their own and be productive. Micromanaging these people will harm productivity.

    For people like Jane, who can get distracted easily into doing easy / shiny things and can be talk minded and miss the bigger picture, a bit of micromanaging is required. – say, you have 20 tasks for them to complete, assign them only the high priority tasks for this week, have a per week or even every day meeting to see what they have done. Give feedback right away and tell them you want to work only on this for time being. This will be a time/energy suck for you, but will get the job done and no more mad scrambling at the end.

    1. Ask a Manager* Post author

      That’s not a reasonable thing to do for more than a short period. You can try it for a few weeks to see if it gets her back on track, but it’s reasonable to decide you need someone in the role who can prioritize independently.

  21. Owlimentary*

    This is a really interesting one to read for me – I left my previous job in part because I was managing a Jane and I’d just run out of cope to retrain him/explain stuff to him. We couldn’t replace him imminently because we were massively short-staffed, and it just meant I had to do a lot of hand-holding and prioritising for him.

    I’d definitely say, if she’s not receptive to attempts to guide her towards what you want (clear, obvious guidance, obviously), then it is worth considering not keeping her on. Managing someone who you have to keep a constant eye on in case they’ve not done something is so so stressful and I wouldn’t wish it on anyone.

    Meanwhile I found a better job where I didn’t have to manage another person – bliss.

    1. Artemesia*

      If you have to micromanage an assistant you might as well not have an assistant. Glad you were able to move on and out from under this.

  22. iglwif*

    I think there are several things that could be going on here, but based on what LW has said in the comments about coordination meetings with the other manager, I’m landing on the side of “Jane’s problem isn’t not knowing how to prioritize, it’s choosing not to follow instructions”.

    I once co-managed someone who didn’t get projects done, and after a whole series of efforts to adjust her workload, help her prioritize, improve communication, and so on, it became clear that she just didn’t like some parts of her job (the ones that affected my team) and wasn’t gonna do them. She now works somewhere else.

    1. Artemesia*

      I am reminded of Pippa the assistant in Bellwether by Connie Willis. Yes there are people out there like this who make more work as assistant than they provide in assistance.

  23. LittleLove*

    I worked at a print shop where every job is time-sensitive. A new employee — young man — did the ‘fun’ stuff first even when he was given clear directions to do the jobs in order assigned. When called on it by the middle-aged female manager, he mumbled something derogatory about working under women. He was out the door within minutes.

    1. Observer*

      I’m always amazed when I hear these stories. Not, unfortunately, that people are that prejudiced, but that they are that STUPID.

      1. Artemesia*

        The awful ones are where they are NOT out the door in minutes. We have had a number like that here.

  24. Happy Ending*

    I supervised legal assistants. One in particular was allowed to unofficially leave early/come in late by the partner she worked for, who then needed others to step in and complete her work. She didn’t do things in any kind of order, and sometimes it was illogical so that others had a tough time picking up/figuring out where she left off. I met with her about this specific issue, as others above my pay grade needed to step in regarding her attendance issues and the partner. Even with talking to her, I couldn’t discern any pattern to her thought and work process. Finally, she told me she felt I was “oppressing” her. At that point, I admit I gave up trying to understand her process, or lack thereof, and told her flat out out how she needed to do things in the future so any other assistant picking up her work for completion could finish it without a lot of extra work and checking of her work. Luckily, she left not too long after that, as did the problematic partner.

    1. The Man, Becky Lynch*

      This is an excuse given when someone cannot explain their thought process even to themselves. It’s the age old “show your work” that teachers will require a lot of times, so they can go back and see what you’re messing up and what you need to be reminded of. “You’re forgetting to carry the 3.” etc.

    2. LCH*

      ugh, i had an asst like this. i would ask her why she did things (when i noticed problems with her work) and she would just say, “i don’t know.” yes, we had guidelines, instructions, hands-on examples, etc. but i couldn’t actually force her to use them. like grab her hands and force her. i could just keep explaining over and over how to do stuff. it didn’t seem to stick.

  25. Auntie Social*

    We had a “Jane”–we listed her projects on a clipboard with the due date and an “A”, “B” or “C” priority.

  26. IwasJane*

    I see both sides of this. I was a Jane – I had terrible prioritization skills that landed me on a PIP. However, it was only once I was on a PIP that I got some of the training / coaching / feedback that would have been helpful to receive back when my manager first got frustrated with my productivity. Instead she let me flounder for months and then I got fired. So I appreciate the Letter Writer is willing to invest time and energy into coaching! That said…Jane does need to be showing progress. I might have been struggling, but I walked away from that job with better prioritization / time management skills than I started with. (And I had been job searching long before the PIP – I knew the job was a poor fit!).

    Letter Writer – good luck. I hope Jane is able to benefit from your help and willingness to coach. One strategy that I had which was very helpful was the difference between a to-do list and a plan. It’s all well and good to have a to-do list of stuff and deadlines, etc. but you need to actually have a PLAN for your day / week / month if you’re actually going to push through and accomplish the *right* things. That, more than anything else, really helped me get a handle on prioritizing my work and helping me understand my entire work load, instead of just endlessly churning through a never-ending to-do list.

    1. Letter Writer*

      That’s a really good point between a to-do list and a plan! How did you learn the difference between the two? How can I help someone identify the difference?

      1. Escapee from Corporate Management*

        A plan looks at the desired outcome and outlines the steps required. A great plan does that and incorporates the time required for each step, the interconnectedness across steps, and potential obstacles. For example, a shipment may require one day to prepare, but if it first requires approval from a government agency that takes two weeks, and that agency closes on federal holidays, you may need to budget three weeks for that shipment. A to-do list are the daily/weekly actions that Jane will take once both of you agree to the plan.

        As a former project manager who spent my life outlining this to people, I recommend you require Jane to put a plan together for major projects before she starts work (and make it clear that the plan is due the day after you assign it). She will almost certainly need help from you the first few times, but that is your role as a manager. Once Jane comes back to you with a plan of action, you can review and modify it. It’s okay if she doesn’t get it right the first time; that is part of coaching her. If she isn’t improving by the third time, you will know she is not a good fit for the role.

        Hope this helps.

      2. IwasJane*

        @LetterWriter – For the plan, we started by developing a list (in excel) of my daily, weekly, and monthly recurring tasks so that I handle on my workload. My job was about 50% recurring things and 50% project work / special requests, so this made sense.

        Then every Friday, I would look ahead at the next week and created a daily plan for each day of the upcoming week. My template was:

        **A weekly goals page – what were the larger goals for the week? So in your example “Begin packing shipment” would be a good weekly goal.

        **Five “Daily Task” pages that had a list (with check boxes) for the stuff I HAD to accomplish that day and they were listed in priority order. As I developed each day I would write a time estimate down beside each task, to ensure I wasn’t trying to over-fill my day. I also had a few blank lines for any same-day new task that cropped up, and a box at the bottom to write down important notes or new tasks that got assigned during the day but didn’t need to be completed same-day, but that I didn’t want to forget about. I had breaks built in for handling reading / replying to email and items from my recurring task sheet.

        **Every morning I would photo copy my Daily Task Plan and print out a calendar agenda for any scheduled phone calls or meetings (and set up reminder alarms on my phone). I usually took about 2 hours to read email and handle recurring daily tasks from the recurring task list, and then I would devote most of the rest of the day to tackling the Daily Task Plan. Since it was already sorted in order, I didn’t need to spend any time thinking about what to do next. I could mark up my sheet with any notes, challenges, delays, questions, etc. and then at the end of the day compare my marked up copy to the photo copy and see:
        Did I accomplish everything? If no, why not? Did something take significantly more or less time than I had budgeted? If so, why? I would then check in with tomorrow’s plan. If something didn’t get completed today, could it be moved to the next day, and what impact would that have on my other forecasted tasks? (Or did I need to stay and work over time and get it done that day?)

        A to-do list is just a list of things you hope to do. It’s not sorted by priority, it’s not a “time budget” , it hasn’t taken into account how the various tasks interact with each other or with outside work flows / deadlines. A plan is a list which has taken into account more than just “this is a thing I need to do.” So a “to-do” might be “print name tags for employee event by Friday” but a plan would be: Monday: Ask Fergus for final guest list, check supply closet for name tags and order if not enough, and prepare mail merge file. Weds: Run mail merge and print name tags. Friday: Drop off name tags to front desk

        I’m not going to lie: getting everything written down like this took a lot of time, but it really worked. I’m in a job with a more reasonable work load now and don’t struggle nearly as much, but I still find myself making detailed time plans when I feel like I’m getting overwhelmed or I’m not spending my time on the “right” things.

        You are already meeting weekly with Jane, which is huge. Maybe use some of that time to walk her through “let’s plan out this task” and see if she can get the hang of time management.

        And know that if it doesn’t work out, it’s not the end of the world for her. I would have been more successful at my job if I’d had stronger time management skills, but ultimately, it was never a job that I was going to be really great at. At some point, if she isn’t improving, the job isn’t the right fit and that’s just a reality everyone has to face, including Jane.

        Note: I used time-management templates from a company called Ink & Volt. They have a $10 print-your-own-planner PDF that you might share with Jane if your workplace will cover the cost. Out of all the tools I tried, I personally found it the most useful, but everyone is different.

        Good luck, and I hope Jane is able to see that you are working to help her succeed!

  27. Sue Wilson*

    OP 2 things:

    1. You need to be her manager. Someone else rarely giving her non-time sensitive tasks but also having hiring and firing ability doesn’t make sense at ALL when the grand majority of her tasks are something you oversee, and the failure of her tasks are going to be on you. This mid-manager stuff where you have to deal with all the frustration of an employee but can’t control how anyone views the seriousness of those frustrations are never going to make you happy. Is this just a title problem (i.e. the manager is the only one supposed to manage?) Regardless you should be able to do her performance evals.

    2. She’s just procrastinating. If you want to do the work, you can walk her through her thought process. Emphasize the seriousness of not doing the project at the right time and walk her through where her thinking made things more difficult. I.e. “how long did this take you before” “2 weeks” “so why didn’t you start it before the two week deadline?” etc. This convo would have much more force if you can also emphasize that not getting a handle on prioritization could lead to job loss, but since you’re not her manager you can’t.

    1. Artemesia*

      This is why the OP needs to line this duck up with her manager to know what leverage she has and make it clear that this assistant is more work than she provides. 8 mos in, she almost certainly needs to be fired.

    2. Letter Writer*

      It’s partially an artifact of a previous team. In 2016 Manager managed Coordinator (me) and Assistant (Jane), but given 3 of the 4 left it became more reasonable for Director to manage Manager and Coordinator, so the only person left for the Manager to manage was Assistant.

      I am realizing that I have to be more explicit and a little more blunt in what I want and how it needs to be done.

  28. M*

    I would also suggest talking to your manager about this and see if you all can have a meeting with Jane. Maybe the manager is giving her other priorities. I say this because on my old team we had a couple coordinators, a manager and other team members (I was the director). One coordinator thought they were at the same level as the manager, which is usually not the case and sort of started to tell assistants and other team members what to do when it was not their job to do so. They also tried to get an assistant to do their work which was another big no-no! (They were told multiple times verbally and in writing that this wasn’t the case and the coordinator was ultimately let go). So I know you say here that you and the manager have the same authority, but maybe you don’t? Maybe everyone is on a different page regarding Jane? Usually a coordinator is managed by the manager. Also, I would recommend talking with your manager and director (if you haven’t already )to talk about Jane and the org chart as it may be helpful.

    And I apologize if I am wrong on this one, but I think it never hurts to have a staff meeting to get the information and then bring everyone to lay out what is expected of everyone on the team. GL

  29. Lobbyist*

    I don’t have time to read all the comments, so I apologize if someone else has already suggested this. I had an admin like this once and what I did was check in with her every morning — to see if what she thought was important that day was the same things that I thought were important that day. It only took a few minutes but it kept us on the same page. And, after about 6 -12 months of this, she finally got it and I only had to check in a few times a week.

  30. GS*

    I think Alison’s advice is good, and a lot of the commenters. I will throw out a different perspective, though. I work more along the lines of your assistant – I work on things I’m in the mood for/like more when given some flexibility. I also don’t necessarily do something that is a month or 2 months out, just because it has an actual deadline. I like to get longer-term, non-deadline work done too – it’s often times more important, and furthers MY goals vs someone elses. For example, an internal customer wants some piece of data from me, needs it in two weeks. Do I work on that, or do I work on an ongoing process improvement project that is also important, but has no deadline? The process improvement project might be something that will get my work noticed at a higher level. I would typically work on the process improvement project, esp. if that’s what I was feeling like doing that day.

    I had a boss like you, who would give a deadline, but the “real” deadline was DO IT IMMEDIATELY no matter when it actually needed to be done. She drove me nuts. I’m glad you’re being clear with your assistant to prioritize things – thank you for that, my old boss never did.

    Also, just one thing for you to keep in mind. You say you always do things with a deadline first, no matter how far out. I’ve found that a lot of times this can really hamper your career because it keeps you from focusing on more long-term non-deadline projects. These can sometimes can have a much bigger impact on your business, and your career progression.

  31. msk*

    Related to the topic, but a little different–I’ve noticed people who get an assignment from someone high up in the food chain and fail to understand that they need to do that right away. They’ll do something like routine filing because they always do that first and concentrate on their other routine tasks. Maybe it’s because they understand those well, and a request from someone high up is more daunting. But, even if someone at the top doesn’t specify a deadline, assume they want their requests handled quickly.

    My order of task ranks–big, big boss request, then big boss request, then boss request, then coworker request (always important to help peers, since you count on them to help you when needed) then normal work with deadline, then routine work without deadline. Been handling things in this order for 30 years and it’s never failed me. Of course, emergencies are their own priority list–even big, big boss *usually* agrees that a business emergency (customer or client facing) goes to the head of the list.

  32. Freya*

    If you’re having weekly check-ins, why aren’t you using these to get status reports on all projects / tasks and check what progress has been made? Isn’t that a big part of the point of doing such a check-in? I’m a little surprised that you’re meeting weekly and not going over this stuff with her.

  33. animaniactoo*

    OP, I skimmed a lot of posts, so apologies if this has been brought up already.

    I think it could be useful to call out the pattern to her and then ask her why she thinks she’s struggling with this the prioritization and carrying through on the direction to work on some stuff first. She may have some insight that you could either help unpack and figure out solutions for, OR she might have thought processes that will continue to rain unchecked as you’re not aware that they’re the underlying thing. For instance, if she thinks that it’s fine to start something else even though you want the other thing done first, or she believes that doing the other sets up the something else for success but waiting would cause it to fail – that’s something you can say “No. This is not an area of your job that you get to make that kind of choice about, you need to do it in the order that I asked you to. If you think there’s an issue with my priorities and that I’m missing something, then you should raise that with me and I will decide if it’s important enough to change.” or a belief that it’s always better to check with a human than her notes, so she’s not doing much note-taking and organizing about the decision stuff that she should know by now, but keeps coming to you about. Maybe

    It’s possible that she’s just not capable of doing the job, but it’s also possible that she has learned a lot of stuff about “owning your job” and other stuff that is leading her wildly off-course. Or that she has an underlying disability that she thinks she’s managing fine or maybe isn’t even aware of herself but knows she struggles with areas of X and can’t seem to figure out why.

    I would also be very clear about any offers to help – she may not want to do it your way, and that would be potentially fine. As long as she is figuring out some new system that works for her. So something along the lines of “Other Manager and I spend what is probably more time than is reasonable to try and help keep you organized and able to meet deadlines. At this point, I/we need you to have more ownership of keeping yourself on track. I’m willing to work with you on setting up systems that you can rely on to do that for yourself, but I/we need you to understand that even if my particular suggestions don’t work for you, this can’t continue the way that it has been and you need to figure out how to get it under control.” Ask her to vet any system she’s thinking of with you so that you can discuss any problems you can see with it and she can take those into account.

    1. animaniactoo*

      Also – on the “wearing a path in the carpet to my desk” and particularly in looking for confirmation on decisions. It sounds like she does not trust her own judgment, as proven to herself by almost always getting it wrong when she goes ahead on her own. Again, there could be something underlying that in terms of an unconscious self-sabotaging. But I think you need to talk about this as “We need a better way of managing this.” and ask her to e-mail you with her suggested course of action, her thought process for it, and ask for your confirmation that she’s selected the right option. Somewhere in here, she’s missing the connection for a-to-b in terms of context/importance, and you’re probably not going to find it unless you can gather this kind of stuff up and show a pattern of where it happens. (Is she always trying to avoid spending a nickel and ends up spending a dollar? Thinking every supply order is a case of “better to be safe than sorry” and goes overboard on how much she’s buying or how soon it needs to be there?)

  34. CM*

    Alternate analysis: Jane might be leaving herself an appropriate amount of time to do the actual work, but not building in a buffer in case something goes wrong. The solution to this is to have a conversation where you talk about that issue specifically, ask her to build in more time going forward, and then (for a limited period of time) agree to check in about how much time she’s leaving herself to do the task. So, she would say, “I figure it’s going to take me two days to pack the shipment, but I’m leaving a two day buffer in case something goes wrong,” and, based on the data you both have about how long the task has taken in the past, you can decide whether that sounds reasonable.

    I personally don’t think it’s reasonable to insist that everything with a hard deadline has to take first priority, or to try to tell Jane exactly how she needs to organize her to-do list. I get that it’s possible that the OP feels more comfortable, psychologically, if they choose to prioritize their own work that way, and that’s fine. But I think that, when it comes to working with other people, the issue is more “Are you leaving a reasonable amount of time to do the work?” and not “Did you do it as early as you possibly could?”

    1. Letter Writer*

      That’s a good point! I recognize that my work style is different than hers, so I’m willing to be flexible as long as she – as you mentioned – leaves enough time. I’ve found that she really does not and ends up routinely staying an extra 15-20 minutes after her scheduled time to finish tasks. It’s less “did you do it as early as possible” and more “did you plan your time out enough to complete the task by the deadline AND leave a buffer in case something goes wrong”. That’s where I went a little nuts over the shipment because there’s no way she could have finished by herself having started a week out from the deadline. That’s where she needed to give herself more time to both complete the task and provide a buffer.

  35. The Bill Murray Disagreement*

    (Possibly lone) voice of dissent here: giving someone a deadline that’s 4 weeks out is a pretty long deadline and it will naturally feel to many people like that is work that has more runway than immediate and day-to-day tasks. I’m not saying Jane is a stellar employee — what I’m saying is that this particular example you shared sounds more like a mini-project (multiple things needing to be coordinated; relatively large effort – as evidenced by needing multiple people tp ‘crash’ it and get it done). This isn’t necessarily a prioritization problem; this sounds more like a problem with expectations & abilities. It’s a different skill to get a list of tasks and be able to tackle them in priority order than it is to look at a larger ‘project’ of work and break it down into its component tasks and balance them against other day-to-day work. That second skill sometimes comes innately, but usually it requires seasoning in the job. I honestly think you’re not setting the right expectations here with Jane.

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