my lovely but bumbling boss is driving me crazy

A reader writes:

I’ve worked for a small educational institution for two years. The job is an excellent fit for me, and I don’t consider moving on.

The person I report to is the head teacher, who has worked here for 20 years. She is a gifted teacher and is justifiably loved by her pupils and their parents. As an educator I greatly respect her, and I’ve learned a lot from her.

The problem is, she is so scatterbrained and disorganized that I’m starting to lose my mind! And it just gets worse all the time. In the past few weeks alone she has:

– lost the office key

– lost the supply closet key

– lost a bunch of application papers containing sensitive personal information (we spent hours searching for those papers, and in the end had to ask the applicants to resubmit them)

– lost her parking ticket, thus trapping everyone else at the gate for half an hour and incurring a hefty fine

– somehow forgot to show up for an in-house meeting that she herself had initiated

– somehow got her coat zipper stuck, making everyone else late to leave by 15 minutes until she managed to disentangle herself

Stuff like this happens all the time. To her credit, she’s always very apologetic and never blames other people or circumstances for these mishaps. Everybody else manages to shrug it off, but they don’t work with her as closely as I do and don’t suffer the effects as much as I do.

Recently she has been hinting that she wants me to make up for her shortcomings by somehow smoothing the way for her, by providing daily reminders. That is NOT the job I signed up for, and I absolutely refuse to do it (thanks for teaching me about boundaries!).

I keep hoping that she’ll get her act together, but I doubt it will happen any time soon.

Considering that I’ll probably be working under her for the next decade until she retires, is this something that I’ll just have to learn to live with? Or should I leave this otherwise wonderful job because of an incompetent boss?

Yes, it sounds like if you want to stay at this job for a while, you’ve got to find a way to live with it.

There might be some practical steps you can take that will mitigate some of this, but not all of it. For example, you could advocate for someone other than your boss having a copy of the office key and supply closet key. But there are no mitigation measures you can put in place against losing her parking tickets or getting her zippers stuck.

If you were her assistant, you’d have more room to step in, and you could do things like remind her of meetings or create automated reminders and be more active in tracking paperwork that comes into her possession. But that’s not your job and you shouldn’t do that work. (The exception to that is you’re in a position where it wouldn’t be weird to have that type of involvement, even though you’re not her assistant, and you’d find it satisfying/enjoyable and would see some professional benefit from it. There are some jobs like that, where you can make yourself indispensable and become a sort of high-level advisor. But from your letter, it sounds like the opposite of what you want, so don’t get sucked into doing it.)

So assuming your boss isn’t going to get her act together and you can’t get her act together for her, can you live with the situation for however many years you’re both there, knowing that it’s not going to change?

Sometimes it’s easier to that if you can mentally reframe what’s happening to see it as funny rather than irritating. Can you see her as an amusingly bumbling character from a book or movie? An Inspector Clouseau? (Piglet from Winnie the Pooh also keeps coming to mind.) Can you find a way to just find it entertaining? I don’t mean to downplay the very real inconveniences she is causing you and others … but when you don’t have the power to change that, humor can be a weirdly effective way to cope.

If you can’t really get there and you feel like jumping out of your skin every day, I do think you should probably consider whether it makes sense to stay — both because that’s terrible for your quality of life and because you’re not going to be the best version of your professional self and over time that can have ramifications you don’t want.

But there’s some comedy gold here if you can get to it.

Read an update to this letter

{ 408 comments… read them below }

  1. Omnivalent*

    Why not suggest to the boss that they get her an executive assistant? Phrase it as choosing someone who has professional skills at managing the tedious details that it doesn’t make sense to leave your boss to handle, thereby freeing her up to focus on her high-level tasks.

    1. Regina Phalange*

      Depending on what kind of school it is, the boss may not have the power to do that…teachers rarely have control over budgetary decisions like that (unless the boss is very high up in a private school setting)

      1. Omnivalent*

        They might not, but it is also signaling to Boss that these are tasks somebody who is not the OP should manage as their actual job, rather than things that Boss can make the OP responsible for through hinting at her.

        1. quill (and the bees agree with me)*

          Yes. For example, the on-site facilities people should have their own copies of the keys, and a spare should be kept secured in the office. Now it’s not on Head Teacher to keep track of the keys.

          If your email system allows you to use shared calendars, insist that meetings be scheduled on that so that everyone can see all the meetings (and it will bother you five, ten, fifteen minutes before) or if this is a classroom where not much is done on computers, tell her something like “I keep a note of all my meeting times in the gradebook because that’s the first place I look every day.”

    2. Nea*

      This is good framework. In OP’s shoes, I’d try to combine it with the equally good suggestion downthread of making an intern the assistant. It’s a win-win situation. Boss gets freed from dealing with minutia, intern gets valuable work experience, OP isn’t having to deal with all these distractions.

      1. The OTHER Other*

        I suppose there have been worse internships, but IMO an internship spent making sure the boss doesn’t lose her keys or get her zipper stuck would not be valuable work experience.

        1. Nea*

          I can’t justify the zipper, but keeping track of office equipment like keys and paperwork and keeping management on track for meetings was a large part of my tasking when I was an office manager.

          1. Lucy Skywalker*

            Is it really that uncommon for adults to get their zippers stuck? I sometimes get my zipper stuck, and I always figured it was the same for anyone else. I am awkward and have terrible fine motor skills because of my disability, so maybe that’s the reason. Is getting a zipper stuck something that most typical people outgrow?

            1. Metadata minion*

              I get zippers stuck sometimes, too! That seems like a weird thing to add to the general complaints about forgetfulness (though I’m curious why it kept everyone *else* from leaving). In my experience, it’s more down to the quality of the zipper than my personal mindfulness.

              1. quill (and the bees agree with me)*

                I’m guessing it prevented OP from locking up because Head Teacher was still in the hallway struggling with her zipper. Or it prevented Head Teacher from unlocking something so they could leave… which is another reason to have multiple other people be key-carriers.

            2. Neurodivergentsaurus Rex*

              I don’t have the best fine motor skills either but I do think it’s normal for adults to get their zippers stuck every now and again. I don’t quite understand how boss’s zipper made everyone late here.

            3. Kella*

              Perhaps the issue was not that she got her zipper stuck but that for 15 minutes she couldn’t get it unstuck *or* do whatever was needed to allow everyone else to leave and deal with her zipper later? I could imagine it being very frustrating if all she needed to do was let everyone out and lock the door behind them (or whatever was necessary) and she wouldn’t do that because she was focused on her zipper, for 15 minutes.

              1. Gan Ainm*

                Yeah I think I would have said “hey can you fix that I’m the car / parking lot, I have an appt I need to get to.”just to not be trapped there.

                1. Koalafied*

                  Yeah, it sounds like these issues are all being exacerbated by am apparent power dynamic where the less senior/tenured teachers don’t feel comfortable telling the head teacher, “Tabitha, the rest of us are waiting for you to do X – would you mind setting aside the zipper for a minute and doing that so we can leave?”

                  It’s one thing to have a chaotic person in the workplace. It’s a much worse thing to have a chaotic person in the workplace who everyone feels they must go along with at all times without complaint, including when the chaos is directly resulting in their time being wasted.

              2. EmmaPoet*

                That’s how I read it. I’ve had zippers get stuck, but if it was going to take me a minute to fix, I’d let everyone else go rather than hold them up.

            4. fhqwhgads*

              It’s common to get stuck occasionally. It’s not common to get stuck in a way that affects anyone other than you.

            5. The OTHER Other*

              The LW mentions that the stuck zipper made everyone else late by 15 minutes. How, I don’t know, but yes that is very unusual. Everyone gets a zipper stuck now and then, but hopefully not for 15 minutes and not making other people 15 minutes late.

              1. New Jack Karyn*

                I imagine it’s something like, she had to arm the alarm system, or there’s a policy that no one can be alone in the building, or they were at a remote site and had all ridden over with the boss.

        2. KO*

          I scrolled and didn’t see this as a comment so I’m going to add it. If this is a rapidly worsening behavior, it sounds like this person might have a medical issue affecting her memory. I’d find a way to suggest she go for a checkup.

          1. Chili pepper Attitude*

            I worried about that too. If she has another 10 years to retirement she does not sound that old? Too young to have changes like this that are getting worse?

        3. Xenia*

          Maybe not if you frame it as “make sure boss doesn’t loose her keys” but if approached from the perspective of “here is a position where you will get to exercise your patience, creativity, and problem-solving skills in managing up to and handling a very disorganized person”, then you have some skill building. Being able to efficiently wrangle someone who’s nice but not a great coworker is a valuable management and coworker skill.

      2. Humble Schoolmarm*

        Unfortunately, school interns are there to practice teach with supervision. Asking someone in a (usually unpaid) student teacher role to take this on would be highly exploitative.

        1. just a random teacher*

          This. When I was doing my student teaching year, I was paying my college a great of money to be there, and needed a certain number of hours of documented successful supervised teaching experience to get my teaching license. If I didn’t get my teaching hours, I couldn’t get my license and wouldn’t be able to turn the degree I was going into debt for into a job the next year. I wasn’t there as a general volunteer or to do office work, but to teach classes in my subject area while the regular teacher watched and gave feedback.

          You might be able to find a responsible high school student who wants an “office aide” period and can be trusted to do actual tasks unsupervised (some students with aide periods are very useful, others are not and are just there because they have a hole in their schedule), but they have their own studies to do and certainly can’t follow an adult around all day and keep them organized.

        2. Starbuck*

          Also student teachers are not just unpaid but usually they are *paying* to work (via college credits) so it’s even more inappropriate to ask them to do something that does not benefit building their teaching skills.

      3. Unicorn Parade*

        I don’t know if it’s state or school dependent, but I work in Marketing and was explicitly told that none of our interns should ever be doing office manager or assistant work. It gets on my nerves because I have less seniority than most of the staff so I get stuck doing that stuff instead. The interns do a pretty-involved research project and make recommendations, and they help with Marketing stuff like writing romance copy and press releases, but we cannot ask them to make copies or act as an assistant to staff.

    3. Aerin*

      This was my immediate thought. OP shouldn’t be forced to act as Boss’s assistant if they don’t want to, but it sounds like Boss desperately needs *someone* in that role.

    4. Gnome*

      I was going to say the same thing. Even a part-time position, intern, or whatever could be valuable. For those of us with difficulties in executive function, a little help can go a long way
      Definitely do offer low key things… like suggest there be a backup set of keys or show her how to set reminders in her phone or digital calendar, where it will help and not cause you burden… But outside help might be the best bet.

      “You’ve got so much on your plate these things are bound to happen. Maybe it would be helpful to get someone in a few hours a week to help with X and Y so you can focus on Z” goes a long way.

      1. Nanani*

        Things that are one and done, like making backup keys, good.
        Anything more than that risks pushing LW into the role they Do Not Want, sadly.

    5. Gingerblue*

      It’s wildly unlikely for a teacher at a small school to get an assistant, as much as it sounds like she needs one.

      1. Ella bee bee*

        If this is outside of the US, she is not really just a teacher. A head teacher in Britain refers to something that is closer to what a principal is in the United States. So makes a little more sense to have an assistant.

    6. Wendy*

      I’d be afraid that she thinks she already has an assistant – the OP. “Why should we pay for all that when I have you?”

      1. Gan Ainm*

        Maybe, but it seems pretty clear that’s not officially part of OPs job, so I would want to bring it to light so I could shut down that kind of thinking quickly.

    7. Double A*

      Teachers don’t get executive assistants. “Head teacher” doesn’t usually mean principal; in my experience, it’s more like a department head. They still teach the same as everyone else, but have some leadership roles.

      1. londonedit*

        Not in the UK – head teacher/headteacher is the principal (the term used to be headmaster/headmistress, but most schools have switched to head or headteacher now). You have Head of Department roles as well, and those involve teaching as well as overseeing the department, but a Head would be in charge of the school and probably wouldn’t teach.

      2. Batgirl*

        No headteachers are the head of the school. My headteacher has an assistant for just her personal use, but it’s a large secondary school. Primary school heads tend to have one administrator doing everything.

    8. Momma Bear*

      An EA wouldn’t help with the keys, parking, or coat thing.

      Maybe OP can sit down with this boss about specific work-related things and come up with a better SOP for things like the applications.

      OP can also do things like ask for a spare office key, not carpool with Boss/leave the parking garage first, etc. I would only carpool with a specific coworker at Old Job because he was reliable. If he wasn’t driving, I drove myself and paid the parking because it was better for my mental health and the client was very unhappy when people were late. I figured it was not my job to babysit the PM and it mattered more that *I* was on time.

      1. Thunderingly*

        I didn’t read that as they were carpooling, but pictured the boss stopped at the gate for a long time looking for her ticket, with a line of cars having to wait behind her.

      2. Underrated Pear*

        I know this is straying from the point of the letter, but I didn’t see anything suggesting that the OP carpools with her boss. The parking gate thing used to happen allllll the time to me at a former gym – the person exiting doesn’t have their ticket, can’t get out, and then there’s a lineup of 20 cars winding up the levels of the parking lot because no one can move until the car in front does. How quickly the situation gets resolved depends on the offender’s stubbornness in trying to find the lost ticket, whether or not there is a gate attendant, and/or whether or not there is an easy option to just pay the fee using a credit card at the gate (which still holds everyone up, but at least for only 2 minutes). It’s SO annoying, particularly at the end of the day when people are in a rush to get out, get to daycare pickup, etc. Unfortunately, if someone is super prone to losing things, I don’t think even a personal assistant would do much good unless that person literally holds the ticket for her all day every day and presents it to her at the exit of the parking garage!

    9. Gouda*

      Even if this was a financial option, the reality is right now there’s a massive hiring crisis in childcare and education. It’s a good idea in the long term, but ultimately unhelpful to the OP in the present moment.

    10. Selina Luna*

      I might also suggest to your boss methods for entering or exiting the school that don’t require daily ticketing. My school has parking passes for teachers that we stick to our windshields or to our back windows. There are different ones for students as well. The security guard team walks through the parking lots 3 times per day to check passes and that’s it. No one has to pick up or drop off tickets that risk getting lost. If you’re using a public parking structure that has ticketing every day, it might be worth talking to their management about setting up a pass system for all of the groups that have employees who must use this structure to park. I bet the boss is not the only one struggling with this.

  2. Justin*

    Well, if this truly causes you distress, you might have to leave over time, but otherwise, maybe you can set up a day (or two days) to help her set up some of these things so they’re out of your hands (ie helping her set all this up on her phone/comptuer/google calendar etc etc). That might not be your job at all, but if it’s worth it to you, you can set aside a bit of time on a given week for that and then be clear you can’t help after that.

      1. Gnome*

        If it’s a whole day, I agree. On the other hand, offering stuff like “I set my phone to remind me to X, I could show you haw if you think that would be helpful” is more friendly one-off offer/suggestion than likely to become part of the workload.

        1. Omnivalent*

          With a boss like this? No, it’s more likely to signal to Boss that her hinting strategy worked and the OP is open to helping Boss with assistant tasks. This is a boundary that needs to be firm. A boss who keeps everyone else waiting for 15 minutes due to a stuck cost, and who tried to slough off admin tasks by dropping hints, is someone who cannot be expected to understand a just this once.

      2. Ashley*

        The varies greatly depending on workload, but it isn’t always a bad thing to be the boss’s right hand go to person. If the OP is interested in expanding or changing their role over time this can help.
        But honestly, if I know people are going to be routinely late for a meeting I would rather just text them or swing by their office then waste 20-30 minutes of my time because they forgot. It can be a slippery slope I know but I hate waiting.

        1. Green Beans*

          Yeah, I have a strict no-assistant-work policy. As a woman, I’ve found that any offer of it will be taken as a sign that my magic uterus will be able to organize and manage all the tedious, detailed things no one else wants to do, just with no effort or time invested, thus negating the need for any professional recognition or credit.

          If I wanted to be an admin assist (and develop the skillset to be a competent one), I would have picked a different career path.

  3. Sloan Kittering*

    I’ve also had good luck working to get like your boss an actual assistant (who is not me). Is there an intern program you might tap? A grant for part time admin support? Someone who wants to shadow and learn from this person who can also be charged with keeping keys? Make it clear what the role entails and that babysitting is involved, but jobs like this can be a very valuable entry into the field for young people and they may be fine doing it.

    1. Nea*

      This kind of experience is absolutely invaluable for someone angling to get their foot in the door as an office manager.

    2. kitryan*

      If any of this is feasible, I strongly recommend it. Our company’s big boss used to make my life so complicated with his car service needs that it was turning into a huge issue. One week we were never working w/service A again, (never mind that many other execs liked them best), the next service B was out, then it was service C, and since there were only 3 or 4 services, we were back to A again in no time. And could I make sure he never had Driver X again, could he always have Driver Y, etc.
      Combined with everyone else’s cars and all the other reception duties, it was a nightmare. Then he decided to get his own driver and it was like a weight had been lifted. Suddenly none of this was my problem anymore. Combined with office management deciding to move everyone to Uber and make them responsible for managing their own car requests, and it was a freakin miracle. (I still hate Uber personally/morally though).
      Anyway, I’m not saying that this boss can just hire their own assistant or something but having these sorts of tasks become someone else’s problem is just beyond wonderful and as others have said, not a bad learning experience for someone going into admin/office management or to get a feel for the school workings/environment.

  4. Artemesia*

    Only thing you can do is enforce your own boundaries and distance yourself emotionally. If she asks you again about ‘reminding her’ suggest she set reminders on her phone for important events; ‘this is what I do when I have a meeting or important event’. Once. After that just smile and nod and view it as entertainment.

    Does she have a boss or is she at the top?

    1. The OTHER Other*

      Good point, if she is the (or even a) boss then she may be able to do more than just hint that she wants help with these things. If she is NOT the boss, why isn’t that boss part of this solution? Answering my own question, I’m guessing her popularity and skill as a teacher insulates her such that everyone snickers and says “that’s the way she is!”. This would drive me batty. True, it’s comedy gold when you hear about it or see it on TV, but in person when you’re stuck in the parking lot behind her trying to get home… not so much.

    2. Rose*

      If your boss asks you to do something you don’t want to do or plan on doing, deff do not just smile and nod lol

    3. Jinni*

      I know this may sound weird, but can you leave before her? Avoiding coats and parking at least. I was stuck behind a ‘lost ticket’ person just last week in a public lot and it was kind of annoying, but that was one day where I had nothing else on the schedule (I was, fortunately, leaving the appointment).

      Keys are a different issue that I can’t think of a solution for. My mother made me wear them around my neck. But I was a ten-year-old latch key kid).

      And as far as losing applications. That feels like a serious data breach where maybe someone (not LW/OP) needs to manage that. It’s one that could come back to bite.

      1. Olivia*

        If this is about a school in the United States, I would be seriously concerned about a FERPA violation. (FERPA is kind of like HIPAA but for schools.) If it were me, I might think of that as an opening to a conversation with someone higher up. I work in public education and I have emailed HR or supervisors on two occasions where I saw other staff being really negligent/careless with student info. And since she had to ask a bunch of people to resubmit forms, my guess is it would not at all be apparent that the complaint came from you (as opposed to other things that only you would know about). Assuming the person who talks to the teacher about it keeps it anonymous, it could be any one of a number of parents who brought it up, as far as the teacher knows. This wouldn’t necessarily be an opening to mention all or a lot of the ridiculousness going on, but if there were other instances like that, I would definitely mention those too.

  5. OrdinaryJoe*

    Reframing and letting go is what’s saved me over the years with similar bosses. I also took some pro-active steps that didn’t ‘cost’ me much in terms of time or additional responsibilities, such as sending ‘friendly reminders’ about upcoming meetings or asking a question that could also serve as a reminder about a meeting. Like, “Hey, do you want me to bring X for the Blah Blah Meeting at 2pm today in Hall B”… and making sure I had people’s contact information personally so I could let them know if we were running late, directions had gotten misplaced, etc.

    But accepting that some things are not your problem and only trying to control what is yours to control and letting go of what isn’t, can be very freeing!

    1. smirkette*

      This is a great idea. And you can do so strategically for the really important things to save yourself from having to do it all the time. Pick your battles.

    2. Anonymous Coffee*

      Because of the hinting, boss might take this as OP got the hints and will do this for everything, which not something OP wants it seems.

    3. Shhh*

      These were the kind of strategies I used with my last boss. It didn’t solve the problem but it made it feel more manageable to me until I could find another job that was a better fit for my career goals. It got me to the finish line even when it wasn’t perfect.

      The other thing I did was pretend I was on a The Office-style sitcom.

      My boss and coworkers at that job were really ridiculous.

    4. Green Beans*

      I wouldn’t give any reminders – that’ll quickly turn into “I’m late because OP didn’t remind me.”

      OP, don’t do any extra labor. Just sympathize with her when she complains “oh yeah that’s tough. I hope it works out better next time/calendars are rough, huh?” and let it be her problem.

    5. MigraineMonth*

      “[W]hen you don’t have the power to change [things], humor can be a weirdly effective way to cope” may be my life motto.

      I’m on one cross-departmental project that should have taken 2 months, but due to weird processes and communication barriers has stretched to 14 months with no end in sight. I’ve had to accept that I don’t have the power to finish the project if the project lead and stakeholders don’t want it finished, and I’ve decided the whole thing is hilarious.

  6. Cambridge Comma*

    Some of these things might have technological solutions that might be helpful to everyone, not just the scatterbrained. Locating devices on the keys, paperless applications etc.

    1. m_sparkles*

      This seems to have gotten buried but I completely agree. If you can find tech solutions that only require one-time set-ups which solve an ongoing problem, then I would try this! I bought my partner a Tile for both his keys and wallet and he uses the Find my phone feature frequently. It really has helped.

    2. Angstrom*

      Exactly. Take personality out of it and turn it into process improvement: “How do we ensure appropriate access if the key is lost?”

      1. quill (and the bees agree with me)*

        Better, because there should have been a key policy LONG ago, like, since the building has been open, dig up any of those old policies (someone like an office admin should do that, not OP,) and make sure they are all accessible somewhere.

        “Policy states that Head Teacher, Facilities, Office Admin, and Head Of Lunchroom all have keys to open the supply closet” is a lot easier to handle than “Head Teacher has the only keys.”

    3. PeanutButter*

      Also LW and co-workers now have a built in holiday or birthday gift ideas for the boss – Velcro closure coats! (I kid, I kid)

    4. leela*

      My school keeps all keys in a keybox in the staffroom, each set on their own hook. Keys need to be signed out (name and time) and signed in. The school office has copies of all keys in a similar box.

    5. MCMonkeyBean*

      Yes, I understand some places are very out of date with their systems so it may not be feasible but it is honestly hard for me to imagine now having only physical copies of documents! It also seems like while OP should not be responsible for helping the boss maintain their schedule or things like that, it might be worth offering to be the keeper of some of the more frequently lost physical items if doing so prevents you from having to deal with her losing things in the future.

      At the very least it sounds like she should certainly not have the *only* copy of some of those keys. That should probably true anyway just in case she was unexpectedly out of office or something.

  7. Myrin*

    I’m sorry, OP, this sounds like it would be justifiably infuriating if you had to deal with it every day but for me as an outsider, I’m sitting her wheezing while I imagine all of you getting stuck in a steadily growing line behind her because she’s blocking the only door by way of zipper malfuction.

    1. Kat*

      I know it’s not funny to OP but when I got to the coat part, I was dying laughing. Perhaps this is a “you have to laugh so you don’t cry” scenario?

    2. WellRed*

      I cannot for the life of me understand the zipper situation. Why did this hold up a bunch of people?

      1. Myrin*

        I assumed she got stuck in the only exit and in such a way that she couldn’t simply move out of the way OR slither out of her coat.

          1. Imaginary Friend*

            I assumed it was another lock that has only one key, and everyone has to be out before the door can be locked, and she couldn’t leave because coat zipper and it was very very very cold outside. (Merely “cold” outside means she could have walked quickly to her car and I would have been biting my lips to keep from suggesting just that.) But I still can’t figure out how that held up multiple people. Maybe they were all going to an event together?

      2. SimplytheBest*

        I mean I have absolutely been in a situation where someone is in some kind of mild distress and there’s nothing anyone can really do while that person fixes themself, but you’d look like a dick if you just peaced out.

    3. Humble Schoolmarm*

      I suspect it might have something to do with most teachers instinctive drive to jump in and help with such mishaps (which do happen regularly in schools, just not usually with the adults).

  8. Office Lobster DJ*

    She got trapped in a coat and it meant everyone had to stick around an extra 15 minutes? I’m dying for more details. I’ve gotten trapped in a coat myself, but it was very much a Me Problem.

    In a nutshell, my advice would be to (1) find the humor if you can and (2) protect yourself from inconvenience where you can. For that second part, I mean trying to stay a step ahead of her when it comes to things that could affect you.

    1. ecnaseener*

      Yes, please LW come back and explain that! Did she get stuck to the doorframe or something, or did everyone just feel too awkward to leave??

    2. Name (Required)*

      Yeah, I can’t imagine why her getting a zipper stuck would cause everyone else issues. Just leave her to it – she’s an adult and a stuck zipper is not something anyone else should feel obligated to assist.

      Frankly, same with the parking ticket. If she lost her ticket and people are backed up behind her trying to leave, ask her to move out of line so other people can leave. Surely she’s not so self involved that she expects everyone else to not leave?!

      1. Cj*

        I’ve lost my parking ticket before, and you just pull up, tell him you lost it, and pay whatever the fee is.

        I also make sure I have my ticket in hand before I ever pull out the parking spot, so if I can’t find it right away, I am looking for it without people waiting behind me.

        1. Laney Boggs*

          You can’t really do it now since self-service kiosks are the norm, but at manned parking garages my mom always tucked her parking ticket on the dashboard – never even left the car.

          1. Gracely*

            It’s generally advised not to leave your parking ticket in open view in your car, because that invites car theft.

              1. Patty Mayonnaise*

                Not the OP but theoretically if someone was looking to steal a car from a lot they might choose a car with the parking ticket visible to get out of the lot easily over one with no ticket.

                1. Bluesboy*

                  Also, if I have been parked for 48 hours and I see you have only been parked for 10 minutes, assuming the ticket doesn’t show identifying info (like your number plate) I could smash your window to get your ticket and get out more cheaply.

          2. Anononon*

            Even at self-service kiosks/garages, a lot of them have the option to pay with a credit card at the gate when you leave. Where I park for work, there’s the option of either paying at a separate kiosk in the elevator entrance area or with a credit car at the gate before leaving, fully automated. I always just pay at the gate when I leave because it means I just leave the ticket in my car and don’t have to worry about it.

            (Very rarely, there have been card read errors, but fortunately the parking garage does have an office w/ at least one employee there, so I’ve been let out within five minutes or so. Also, there are multiple exits, so they can direct people to other exits if necessary.)

      2. Double A*

        I’m guessing they were on some kind of field trip or professional development where they took a school vehicle or at least carpooled.

          1. New Jack Karyn*

            It can be hard to say to your boss, “Hey Zarathrusta, can we just get to the car? I know it’s cold, but if we walk fast, we’ll get there and have the heater on in a jif.” Easy to think, sometimes not so easy to say out loud.

          1. misspiggy*

            This boss sounds very like me, and I have learned that I can’t have zip-up or lace-up items, because it ultimately inconveniences other people. Same with hard copy documents in my sole possession, and so on. Risk assessment training for the whole team or just the boss might help bring out some mitigation strategies, if the boss is aware of her foibles.

      3. CowWhisperer*

        When I taught at an alternative education building, we had to arm the security system, exit the building, and manually lock the front door.

        Now, due to extreme peer pressure, staff and faculty were at that door by 9:05pm or the rest of us were calling, yelling and pestering any stragglers because 7:55am was rapidly coming and sleep is precious.

        We were all roughly peers as well. None of us reported to each other.

        A scatterbrained administrator….may have destroyed our agreed-on closing procedures……

    3. So they all cheap ass rolled over and one fell out*

      This was my thought as well. It’s a lot easier to find amusement in a bumbling coworker if you aren’t so directly impacted. It doesn’t make a lot of sense (from what’s written) why everyone was stuck for 15-30 minutes. Nor even why OP had to spend so much time looking for lost paperwork (“Good luck finding it! If I come across it I’ll let you know!”) and keys (“OK, I’ll do something else that doesn’t require supplies, let me know when you find that key!”)

      1. Lynn Whitehat*

        I’m picturing a parking garage with one exit lane. So if one person sits in front of the kiosk for an extended time, no one can get around them.

      2. SimplytheBest*

        Your boss says important paperwork is missing and she needs your help looking for it and you’re going to just tell her “good luck?”

        1. New Jack Karyn*

          Yeah, and it’s got private student info on it, and it’s an application they need for something. When it affects students–especially those who’ve held up their end of the deal–it’s hard to just let someone flounder.

        2. So they all cheap ass rolled over and one fell out*

          If you’re at the point where you’re considering quitting a job you like just because you keep getting sucked in to this battiness, what do you have to lose? Might as well try leaving the ball in her court whenever you can. Boss knows she is bumbling and needs to start really recognizing that it’s not her fault that she is bumbling, but it is her fault if she lets everyone else suffer for it.

  9. Confused227*

    I don’t understand her getting a zipper stuck making everyone 15 minutes late to leave?? Unless it was stuck in the only exit door?

      1. goducks*

        But why would her being the one to lock up mean that nobody else could leave? I could maybe see that it meant that one person had to stay if two people are required for lock-up, but everyone?

    1. Butterfly Counter*

      I was guessing that it was a meeting that didn’t start until she extricated herself from the coat. It took so long that she started the meeting late and couldn’t catch up?

    2. DANGER: Gumption Ahead*

      I’m guessing she was driving or had some key role to play in whatever was going to happen next.

    3. Been There Done That*

      Maybe they were all having to carpool to get somewhere….Again….not sure how a stuck zipper would cause you to be late. If you can’t get into the coat, just take it with you and work on the zipper in the car. If you can’t get out of the coat, just keep it on until you get someplace you can work on it.

      1. So they all cheap ass rolled over and one fell out*

        If she can’t keep track of her parking ticket and/or keys, don’t let her be the one who drives the carpool.
        If she causes a meeting to start late, have a shorter meeting.

        1. Momma Bear*

          Right. Some of this can be mitigated by others being proactive. While I wouldn’t want to abandon my boss, I might make the suggestion to just keep the coat on and continue on to the meeting. Something I am trying to teach my kid is how to make do if things are not perfect – as in maybe you don’t have the right shoes, but we need to get in the car so find *something* and get in the car. Maybe boss is not 100% perfectly prepared, but better to just go than be late?

    4. Trombone*

      If you have a coworker stuck in their jacket, you don’t think you would stop everything and try to help them? I honestly can’t imagine not doing that. She’s clearly the type that will be making a lot of noise/big deal about this. Hard to ignore . . .

      1. rubble*

        but they all don’t have to stay. that’s one or two people, tops. and at a certain point you should be able to ask the person to just drive home in their coat so you don’t have to be home late.

      2. short'n'stout (she/her)*

        Pretty sure that getting someone out of a jacket with a stuck zip could only usefully be done by one other person. Everybody else would be in the way, and might as well just leave.

    5. Public Sector Manager*

      At my old high school, the custodians would lock the front doors at 3 pm and would have to unlock them when the teachers left at 5 pm in order to keep the general public from wandering through the school after school let out. There were sufficient fire exits, but that would have triggered the alarm.

      Anyway, I envision that the boss has the only key, so the boss having a stuck zipper required everyone else to wait by the door until the boss arrived.

  10. So long and thanks for all the fish*

    What is the OP’s actual role here, and why does she work more closely with the boss than everyone else? I feel like any practical advice beyond internally learning to live with it or moving on is going to heavily depend on this answer.

      1. Cj*

        But there are surely more l teachers besides just the OP and her boss. I am also curious to know why they work more closely with the boss than the other educators do.

      2. Myrin*

        That doesn’t answer the question (which I’d wondered myself), though – because surely even in “a small educational insitution” there’s more than one regular teacher (OP), right?

      3. So long and thanks for all the fish*

        She doesn’t necessarily say that, by my read- she works in education, and respects her boss as an educator. You don’t have to be an educator to respect someone as one.

    1. Betty*

      I’m thinking it might be like a Montessori school…each classroom has a head teacher and an assistant teacher

      1. So long and thanks for all the fish*

        This was what it sounded like to me, in which case I’d think there could be a lot OP would do to help her boss that didn’t fall into personal assistant territory- making the office organization system clearer, putting a big shared calendar on the wall, figuring out an alternative system for keys, generally trying to take ownership of the practical parts of the office that the boss is having/causing issues with so the boss can see that it’s handled and she doesn’t have to be the one to do it. She could still try to do some of that if she’s a teacher and there isn’t anyone who is supposed to be the office manager, maybe by roping in her peers so they can all take little pieces? If the boss is as nice and good at the rest of her job as OP says she is, I would guess she’d be receptive to other teachers volunteering to try to make the office run better, particularly if they were careful about how they pitched it.

  11. Doug Judy*

    As some who is the bumbling person, I often frame it in terms of a wacky sitcom whenever I find myself in a frustrating situation due to my clumsiness or other lapses in organization. Trust me, I’d love to be the type that always has it together, and while I’ve made improvements, I am the person who will spill water all over the table at dinner just trying to pass the salt.

    1. Anon Y Mouse*

      Oh goodness yeah. I am the person who does stupid things with keys. Public stupid things, that inconvenience other people. I only do it at about a rate of once in three years, but it’s enough to make me feel that everyone I ever worked with remembers me as the Key Ditz.

      It’s its own punishment. I don’t expect other people to fix it for me though.

    2. Pippa K*

      I’m generally against stereotypes with one exception: the Absentminded Professor. It me, as they say, and it’s sort of nice that other people have a ready-made pattern for understanding me :-) I try not to inconvenience others with my scatterbrainedness and they politely don’t laugh when I give lectures with my sweater on backward (yes, sadly) or lock myself out of my office once every semester.

      1. Eukomos*

        If it makes you feel any better, I’m one of the people who helps professors get into offices they’ve locked themselves out of and it’s really, really common. Doing it only once per semester puts you in merely the moderate-frequency group. It is possible other workplaces don’t have such a chronic issue with this, though, I’m not sure.

  12. Anonym*

    This brings to mind an increasing pet peeve – colleagues who frequently ask you remind them of things. Unless you’re their assistant, this is ridiculous and unreasonable. Manage your own sh*t. I have no actionable advice for OP, my apologies, but you do not get to ask colleagues or employees to manage your work (or your life) for you. They have their own minutiae to manage. Get it together.

    I wish OP luck in coming to a satisfactory conclusion with this situation.

    1. Van Wilder*

      I’d like to add to this: family members that ask to be reminded of something. No, husband, ask Siri.

      1. mreasy*

        I accept it from family but not coworkers. Like nope I had to learn to write multiple reminders for everythjng, so can you!

        1. MCMonkeyBean*

          Yeah it’s a normal thing to say in my house between me and my husband, but honestly it’s usually less about wanting an actual reminder from them and more that just the act of saying that out loud makes your own brain more likely to remember. (But also doubling the number of brains that know the information does make it less likely to be forgotten!)

    2. ecnaseener*

      The most effective way to avoid this, I’ve found, is cheerfully warn them that you’ll probably forget. (Obviously this is advice for you and not for LW, since you’re talking about colleagues not a boss!)

    3. Lacey*

      Yes. They can’t remember, so they need to figure out how to fix that. Themselves.

      See also, coworkers who request that you resend an email they can’t find – all I will do is do a search for it, which my coworker can do too!

      1. Gumby*

        The email thing is so my manager. I try to just tell him search terms to use to cut down on the whole “it’s easier to ask Gumby than to search my own inbox” factor or will tell him the time and date it was sent so he can find it if his emails are sorted by date but it still doesn’t stop it. Was once on a mtg. with him and he had me resend something I had sent the day before! “I sent it yesterday. At 6:34 p.m.” “I don’t see it here, just resend it, it will be faster.” Gaaaahhhhhhh! (Also, you are sharing your screen and for some reason looking at 6 a.m. so. )

      2. Emmy Noether*

        I actually do resend emails to coworkers if requested – my inbox is organized and I’m good at the search function, so I can either sit there 10 excrutiating minutes while they scroll through their inbox, look for the search bar, mistype 3 times etc, or I can search and resend in about 15 seconds. It doesn’t happen so often that trying to teach them would lower my total time investment, so I do the thing that is quickest and least frustrating in the moment. It’s not my job to train them.

    4. Kella*

      If it’s related to a project we’re working on together, I really don’t mind someone saying, “If you haven’t heard from me by [Date] can you send me an email to remind me?” Usually the answer is yes, I can do that easily. If it’s something unrelated to me, like remind me that I have a meeting at [time] I would be a lot less inclined to say yes.

      1. Green Beans*

        Yeah, I tell people to follow up with me if they haven’t heard from me by date – especially if I’m busy! But that’s more like “I have a lot of competing priorities and this is more important than you than for me, but I still want to get it done.”

    5. A Poster Has No Name*

      Wait, you have coworkers that actually expect you to remind them of things? They’re not just saying “Remind me to submit the TPS report this afternoon” as a way to remind themselves, by saying it out loud, to submit the TPS report?

      Granted, I don’t do this with coworkers, but my husband and I do this to each other constantly, and rarely do we actually expect the other to do the reminding. It’s all in saying it out loud, making it less likely you’ll need the reminder later.

      1. Koalafied*

        I’m surprised too like, what are you being asked to remember for someone else?

        The only context in which I really encounter this is when Person A mentions something casually at happy hour/lunch/on the subway/etc and Person B says, “Can you send me an email or remind me about that when we’re back in the office?” I think it’s reasonable to decline responsibility for keeping track of things that were raised outside of the usual context and where you don’t have your computer or your desk notepad handy.

        I can’t imagine a scenario where someone says, “Hey Koalafied, remind me to submit my timesheet this week,” or whatever, instead of just making a reminder in their calendar or on a post-it note or something. Then again, I’ve never understood people who ask easily Googlable questions in online groups, not because I think it’s lazy or imposing a burden on others…but purely because I can’t imagine having the patience required to wait for responses, nor the blind confidence in others required to trust that the answers I’d get would actually be correct. I likewise wouldn’t ask someone else to remind me of something when I could write it down or put it in my calendar myself because I trust human memories far less than I trust written documentation.

    6. Anonymous Hippo*

      Yeah, me too. Mainly because I have a terrible memory, and I still manage to handle all my stuff. So I usually answer, “I have a terrible memory, don’t rely on me. But here is x, y, z, tools that I use to help me remember stuff” They usually stop asking LOL.

    7. just another bureaucrat*

      You stop me in the hall and ask me to do something for you? I’m going to forget by the time I’m back to my desk. You want something, you email me a reminder note.

  13. The Cosmic Avenger*

    This probably doesn’t help the OP now, but it sounds like their boss should be in charge of teaching evaluation and professional development, but not have any real administrative or facilities duties. They need a separate office or facilities manager or administrator, who can run meetings (that are not purely about teaching evaluation), and be in charge of supplies and other things. That won’t help with the zipper and parking issues, but those can happen to anyone at any level, and aren’t really made worse by the poor delegation of responsibilities here.
    But if you stay, OP, you can try to work towards getting someone else to be responsible for these things. If not you, an additional dedicated office/facilities/admin manager.

    1. Dramatic Intent to Flounce*

      And paperwork. Clearly someone else should be in charge of keeping track of paperwork.

      Maybe that role can be delegated to another teacher, maybe you need some sort of administrative role, but yeah, it really does seem like everyone would be best served with these tasks splitting.

    2. Batgirl*

      Or at the very least some automated systems for things they can’t misplace. Those forms should be submitted and saved online.

    3. Shirley Keeldar*

      Right, this sounds like the sort of (smallish?) institution where a lot falls to the boss by default, because there’s nobody else who should obviously be handling it. But that could change. Janice can be in charge of the key to the supply closet, Eduardo can be in charge of boss-coat-removal duties, and so on. Maybe some of this has systematic fixes so that the boss is not in charge of so much granular detail since, obviously, that’s not her strength.

  14. Esmeralda*

    Can your employer hire an assistant for your boss? Even a part-time assistant?

    Because otherwise, you’re gonna pull your own head off some day.

    And to be clear, I have a ton of sympathy for you and maybe half a gram of sympathy for your boss. She knows this is a problem. What is she doing to resolve it? Nothing. Because she’s a broken stair, and everybody just jumps over it and she never has to fix it.

    And btw, those lost applications? Which it sounds like were never found? That’s horrifying. If you’re working at a school, that’s a potential lawsuit.

    1. Gingerblue*

      Yeah, the rest of this is annoying but harmless, but the part about the applications was hair-raising.

    2. Marion Ravenwood*

      If it’s in the UK or Europe I’m pretty sure that would count as a GDPR breach as well. Or at the very least you’d need to warn the applicants that their data had been lost and they might be at risk of fraud etc.

  15. Dust Bunny*

    Put the various keys on a large, obnoxious keyring and get one of those tags that pings to your phone. (My personal keys are on a ring with a rein clip that I can clip onto my handbag.)

    We all wear our office keys, ID tags, and keycards on lanyards. Non-routine keys (showcases, locked cabinets, etc.) are on large, hard-to-lose rings and have very specific resting places–replacing them incurs a painful fee that in and of itself is a big incentive to not lose them.

    The part about the paperwork with sensitive information, though, is really disturbing here. You (plural–y’all as an office and an institution) need better information-handling requirements and she needs to have real consequences for losing things like this. If somebody’s SSN gets stolen because she left their application in the cafeteria you’re going to have much bigger problems on your hands than a harebrained boss.

    1. Dust Bunny*

      I would also suggest that you minimize the number of separate keys if you can. If various keys can be contained together on one right a) you won’t have so many rings to manage and b) the rings will be bigger and harder to lose.

      You might also put them on lanyards for users to wear, as well. Much harder to lose that way.

      1. After 33 years ...*

        Our keys for classrooms, photocopy room, dept main office etc. are each attached to a piece of wood, typically 10 -20 cm long. They still get mislaid.

        1. Dust Bunny*

          Lanyards, then. Don’t want to wear the keys? Tough rocks; that’s what you get for losing them.

          1. After 33 years ...*

            Until you forget the lanyard at home …
            Having duplicates/quinticates is the only thing that’s worked.

            1. Dust Bunny*

              I loop mine around the handle of my handbag. Can’t leave it behind (my car key fob is also attached so I literally cannot leave without the bag) and it can’t fall out.

            2. goducks*

              The only thing that really seems to work for chronic key-misplacers is biometric or pin-code locks. Even if you have spares and a designated keeper of the spare, when the key-misplacer borrows the spare, it rarely makes it back to the keeper of the spare.

            3. Dust Bunny*

              But at some point, people simply need to take responsibility for things they do over and over again and figure out a system that works for them. If the boss here doesn’t have any real incentive to fix it, all the solutions proposed by other people aren’t going to stick.

        2. Esmae*

          My boss got so sick of people accidentally walking off with keys that he started tying them to ethernet cables.

      2. Empress Matilda*

        The problem with that, is it allows her to lose all the keys at once! Right now she’s “just” inconveniencing the people who need to get into the supply closet, but at least the filing cabinets are accessible. Or vice versa, or whatever the situation is. As soon as the keys are all on one ring, she’s going to lose them all, and then OP and the others won’t be able to access anything!

        As someone with ADHD, I can assure you that it’s possible to lose nearly *anything,* regardless of how large or brightly coloured it is. The biggest advantage to the size and colour is it makes it easier for other people to find once I’ve lost it!

        1. NotRealAnonForThis*

          Yup. There’s no “taking responsibility for it” or “just remember where you put it”. Its just…gone. Freaking POOF. I have Tiles for the really important things, and I make the limited use stuff very, very, very obvious. As in “Hey, what’s Yoda doing on your desk?” obvious.

          1. NotRealAnonForThis*

            (Adding that, since I *know this*, there is no way in Hades I put myself into a situation where I am responsible for losing something akin to these applications.)

          2. Empress Matilda*

            Yup. My new favourite example is my personal trainer, who somehow managed to lose a set of 25 pound weight plates – in his own apartment, which can’t be any bigger than 400 sq ft. Like…how??? Only a fellow person with ADHD would understand how easy this actually is! :D

        2. Your Local Password Resetter*

          Absolutely. I’ve misplaced or forgotten rings with dozens of keys, on multiple occasions.

    2. The Rafters*

      Different law, same result. As someone who has HIPAA pounded into them on a regular basis, I can’t believe this would be simply swept under the rug. It still hasn’t been located?! This is a huuuuuge deal.

      1. Dust Bunny*

        Yeah, I also work in a setting where HIPAA applies to some material. When we had a fax machine, our fax number was one digit away from that of a local medical specialists’ office, so we kept getting people’s medical records! Fortunately, we’re medical-adjacent and a very controlled environment so we could be depended upon to shred them and then notify the sender of the error, but that was dumb luck on the part of all the doctors’ offices who were sending us records by mistake.

    3. Sabina*

      One of my admin jobs involved being “Keeper of the Keys” for a law enforcement agency. Who loses keys as often as cops? No other type of worker that I’ve ever met. One of my favorite “cops with keys” trick: officers rolling Code 3 to some critical situation, jumping out of their patrol car, and somehow locking it with the keys inside and the engine running. Then there was the rookie who needed a padlock for his work locker. I have him an old one we had lying around and told him he could have it but he would need to take it to a locksmith and get a new key made, the old key was lost. He took it and before I could say anything closed it shut around a belt loop. So…he had to go to the locksmith and take off his pants so they could key it (I assume he stood there with his duty belt, gun, etc. still on, just no pants).

  16. smirkette*

    It may not be possible for her to change (everyone has different strengths and weaknesses), so unless there’s budget for an admin assistant to take this stuff off of her plate or an appropriate way to redistribute time- and organization-specific tasks, I’m afraid the only thing you can do is try to reframe the situation for yourself. When I’ve had to work with people with similar issues, I’ve reminded myself what I do value about them when they get on my nerves. Being a great teacher and treating people kindly are huge. I once had a lovely boss who was always 5–10 minutes late to every. single. meeting but once I accepted this was just always going to be the case, I adjusted all meeting agendas to take care of housekeeping stuff the top of the meeting so that when they came in late it wasn’t a big deal.

    1. Dust Bunny*

      Or they could replace her with someone who can do the other tasks and doesn’t lose stuff all the time.

      1. evens*

        Good idea. Get rid of a teacher that parents and students love because she loses keys and gets stuck in her coat.

        1. Dust Bunny*

          I in no way said that. They could put her back in just teaching and get an administrator who can actually do the job. She doesn’t need to be *head* teacher.

          Her forte seems to be teaching. That she’s been there a long time and everyone loves her doesn’t make her automatically deserving of a job she’s actually really screwing up. She can still be a teacher, just not the one in charge of so much.

    2. anonymous73*

      That’s an excuse. If she’s genuinely unable to change, then she shouldn’t be in charge of keys of applications that include sensitive information.

    1. Esmeralda*

      I’m sure the OP is not exaggerating.

      No doubt plenty of those people are seething inside. But they are not doing anything about it because, for instance, they know or fear they will get in trouble if they try, or they’ve tried in the past and it did not good, or they’ve decided to save their capital for more significant issue, or they’ve decided to save their time and energy for other issues.

      I’ve worked in places like this. My own office in the past had a director like this. They were valuable enough that they got an assistant (eventually), before that the associate director dealt with it (in addition to all of the rest of her job).

  17. ZSD*

    As someone who used to work in university admissions, I’m most concerned about the lost paper applications with PII (personal identifiable information). Can your institution switch to online applications with a secure submission process? If you have the budget, there are plenty of third-party companies that provide the software to manage applications securely, but it also shouldn’t be too hard for your own IT people to come up with a small-scale, secure application system, if that’s all you need.

    1. CommanderBanana*

      I can’t imagine wanting to attend an institution that contacted me and said “hey we lost the only physical copy of your application – you know, the one with sensitive info on it? – and need to reapply, UwU sowwy!”

    2. Jen*

      Agreed, that really stuck out to me and could cause serious issues. You cannot mishandle that stuff. It can cause serious problems.

    3. Typing All The Time*

      Yes. A relative of mine was to start a new job and the office staff lost his paperwork with his banking information. It was never found. Relative had to put privacy guards in place. He ended up turning down the job.

  18. Jean*

    OP, I commend you for not allowing her to make her executive dysfunction yours to manage. If she needs an assistant, which it sounds like she does, she needs to hire one and not just expect someone with an already full time commitment to another role to take on those responsibilities as well. Keep pushing for that, and if she keeps resisting, you will either need to accept this part of working with her, or find a new job with a boss who can function normally.

  19. Anti anti-tattoo Carol*

    I had a boss like this! Amazing, warm, empathetic, talented, and groundbreaking in the field. And she was 10 feet of chaos in a 5 foot body. I think everyone around her just sort of “filled in” or planned around things she was involved in. You couldn’t count on her to show up on time, or to get things right, or to use the same filing system everyone else used. It was exhausting. The cost-benefit analysis the new ED did came out in her favor (staff time lost to covering for Amelia Bedelia was not more expensive than the immense value added by Amelia Bedelia). We just all restructured around her until she retired. Basically, accounted for needing extra time, support, etc. I wouldn’t recommend this; it’s very missing stair and can breed resentment. But it is what we did and now everyone just sort of remembers it with a fond eye roll because they all loved her and were frustrated by her in equal amounts. Since I reported directly to her, I bore the brunt of her chaos (eg, me banging down her door because she missed another high level meeting where I had to advocate above my pay grade, and seeing her little glasses pop over a pile of papers, followed by LOTS OF SINCERE APOLOGIES but no behavior changes).

    PS: I was promoted so I didn’t have to advocate above my pay grade anymore. It was her retirement gift to me. She’s a good egg, despite the chaos.

    1. Chlorite*

      The language of Head Teacher makes me think UK schooling, in which case there’s a regional HR or governance of sorts that occurs outside of school staffing. I would honestly start documenting these occurrences. Someone can be a fantastic classroom instructor AND be terribly equipped for leadership. Losing paperwork with PII, not showing up to meetings you’re leading, and misplacing keys for supplies and security are pretty concerning to me. If Head Teacher would like her way smoothed, it seems the correct person being elevated to her administrative duties (and compensated accordingly) would do that effectively.

    2. PT*

      I worked with a woman who was similar to this, too. She was not a boss, she was a Llama Trainer.

      What it turned out was she had been having microstrokes that were nuking her memory. She was getting to the point where she’d lost enough of her memory that she couldn’t do her job fully and needed to retire. But she was in desperate financial straits and could not afford to retire. Because she was a nice person, everyone pitched in to help her out where needed.

      It never hurts to be kind, in my opinion.

      1. Colette*

        But being kind isn’t necessarily covering for her. It might be raising the issue so she can be moved into a job where she’s a better fit, or letting her bear the costs of her mistakes so that others don’t have to, or asking her to move out of the way so everyone else can go home, or finding a new job and letting her work with someone who won’t be as frustrated with her mistakes.

  20. Wintermute*

    The one thing I would do is take steps to structure it so I rely on her inputs as little as possible. I am not sure how her being tangled in HER coat means I can’t leave, or her being unable to find HER parking ticket. If there’s anything that can be done it’s probably structuring things so when she bungles something you can shrug your shoulders and go home on time leaving her to fix her problem.

    And honestly that might help encourage her to solve the problem, too, if other people are putting a lot of labor and mental energy into solving the consequences of her mistakes for her, perhaps having to face them down herself will encourage more conscientious behavior.

    1. OrdinaryJoe*

      Yes – second the … HER problem doesn’t mean it impacts you/everyone. I think highly organized people often feel the need to try to ‘save’ people (guilty, for sure!) but that often just creates problem stress for everyone

    2. Important Moi*

      I would offer for discussion purposes, the Boss makes it others people’s problem.

      – Being tangled in her coat? She complains to everyone (while untangling?) and is retaliatory to those who don’t show empathy or sympathy to her situation in the form of not helping Boss and going home.
      – Being unable to find her parking ticket? Boss is sitting in her car at the gate and can’t find the ticket. If she gets there before people who their parking tickets, this is affects more than her. She doesn’t move her car. She stays in place while searching for said ticket and time is ticking for everyone else. That’s inconsiderate. She may also be retaliatory to those who don’t show empathy or sympathy to her situation.

      1. Kella*

        There’s really nothing in the letter to suggest the boss has retaliated against people who don’t help her out. Yes, it sounds like she’s acting in an inconsiderate way but the retaliation point is total conjecture.

    3. MsSolo (UK)*

      I sort of assume with the parking ticket that she was front of the queue to get out, and couldn’t find it to scan so everyone was stuck queueing behind her (depending on the set up, once a queue formed it might not have been possible for her to pull out of the way without everyone else in the queue moving first)

    4. Pay No Attention To The Man Behind The Curtain*

      For the parking ticket it sounds like you pay at a booth as you drive out of the lot/garage and if you don’t have your perhaps validated ticket, or ticket showing a time stamp, you pay a maximum fine; so she’s at the booth frantically searching her purse/pockets/car for her ticket while cars are lining up behind her, until the attendant manages to get her to pay the fine and move along.

      Maybe similar with the coat — she’s the teacher and the class can’t proceed without her… that one we don’t know all of the circumstances, they could be leaving for the day (sure leave her behind) or leaving on a field trip (she has to be there).

      1. Wintermute*

        And that’s why my biggest advice is **structure things differently so she isn’t the required input** wherever practical. Don’t park behind her, don’t make it a situation where if she can’t leave no one can leave, whenever that’s practically possible at least, it’s usually not terribly difficult to at least mitigate a known impact.

        1. Batgirl*

          Yeah the structure sounds bananas. Which is not surprising because the head teacher is not someone who would structure a school well. I think OP should start pressing the boss to make things easier for other people to get what they need. What if someone else loses their parking ticket? What if the headteacher becomes ill and noone knows where the keys and papers are?

        2. Empress Matilda*

          Agreed, I think this is the most practical solution. If OP thinks she might be retaliatory as Important Moi suggests above, it might require a different approach, but this should be the end goal regardless.

          For the coat -does everybody need to leave at the same time as the boss? Why? What other options are there? The parking situation is a bit trickier since you don’t have control over procedures or the physical space, but it’s worth exploring. Maybe she could keep the ticket in the car instead of bringing it inside? Maybe the parking company has an app that she could use rather than a paper ticket?

          To be clear, this is still a lot more emotional labour than you should have to do – this should definitely be a Boss Problem rather than a You Problem. But since it does appear to be a You Problem regardless, maybe putting some energy into it now will make things easier for everyone in the long run. Good luck!

        3. sb51*

          Also, don’t make the structure so that ANYONE can block things if possible — she blocked the parking exit by being absent-minded, but a single point of failure means that a car issue NOT caused by absent-mindedness could trap everyone there indefinitely. Or “person X has the key but just had an emergency in their classroom and is unable to step away”. And “documents with personal information have a VERY specific process so that no one can lose them, even if the building catches on fire while they’re holding them”.

          For the meeting she called & missed, it’s unrealistic to remind her, but — as a fellow absent-minded person — perhaps a brief discussion of “how long should we wait for you/what should we do to mitigate the impact on our time if you’re unexpectedly unable to make a scheduled meeting” would be OK, since she’s aware of the fact she’s going to do this again.

          1. Underrated Pear*

            I admit I don’t fully understand the zipper thing, unless people just stayed because they felt an obligation to not leave her stuck by herself. But as someone who lives in an enormous, parking-garage-dependent city, I’m cracking up at these suggestions of just “restructuring” a parking garage to make more exits. She is not the first to have caused this problem, nor will she be the last, and I don’t think the school is going to undertake a potentially multi-million dollar construction project to alleviate it. (But believe me, as someone who used to be stuck on a near-daily basis trying to exit my former gym, I was absolutely seething in sympathy on behalf of the LW.)

            And just to clarify for those who don’t deal with this kind of parking structure on a daily basis – at least in my experience, in areas where they are ubiquitous, there is (1) often no attendant, and (2) absolutely no physical way to pull over unless there is no one behind you.

            1. Underrated Pear*

              (I’m commenting a lot today!) But I feel I should clarify, so it doesn’t seem like I’m just snarking on other commenters, that my point in the above post was ultimately about circling back to the LW’s original question of “do I just have to live with this?” I don’t think it’s particularly helpful to the LW to discuss additional hiring* or restructuring the parking garage, since neither of these things seems financially realistic for a school.

              *This might be a stronger possibility in a different sort of industry, but in a primary/secondary school, I doubt it.

    5. Kella*

      Yes, I was also struck by the coat and parking examples how those really shouldn’t have caused such a problem for everyone else. After a minute of searching, the parking attendant should have insisted she pullover or something to continue searching for her ticket so everyone else could go home. Perhaps the boss made that difficult (ie: No, no, just give me a minute, I’m sure it’s here somewhere) but that seems like a kind of enforcement it’s reasonable to put on the person in charge of parking tickets.

      With the coat, it’s unclear why everyone was held up. It sounded like she had lock up after everyone or something similar, her coat got stuck, and rather than let it be stuck and deal with it after locking up, she continued to wrestle with it, unaware of just how much time was passing or that it was impacting everyone else. If it’s somehow not possible to avoid her necessary role in everyone being able to leave, it seems like it would’ve been very reasonable for someone to ask her to stop messing with the zipper, after the first minute or two, and let everyone else first so they could go home. That is made slightly more difficult by the power imbalance but doesn’t seem like it would be totally out of line to do.

      I’m not saying that everyone is responsible for her problems or that they should fix them for her, but that if her actions are impacting others, people don’t have to just stand by and watch her do that indefinitely.

    6. Broadway Duchess*

      I wonder if this is a place where “we all leave at the same time” because family? I had this problem when I was in college and working retail, but I also did an internship in a medical office where they did this. I didn’t quite fit the culture there because I didn’t hang out after my shift was over, but my coworker definitely did the slow walk out, everyone leaves at the same time. And in a Chicago winter, donning outerwear can take awhile.

  21. Mockingjay*

    I’m not sure that looking at Boss as a bumbler is good advice. The Boss is causing real problems: incurring fines; losing documents with Personally Identifiable Information (PII), which is a HUGE deal if the LW is in the U.S. (Privacy Act); forcing protracted waits on other people.

    In the long run someone this ineffective in small matters is likely not that good at the real stuff of managing. She might be an excellent teacher, but as many, many letters herein attest, being good in a role does NOT automatically translate to being a good manager. LW, I’d spend the rest of the school year looking at how well she manages the other responsibilities of Head Teacher besides instruction – is she supportive of teachers? Compliant with curriculum and administrative requirements? Runs efficient meetings? Etc. Then decide whether you want to work under her for the next 10 years.

    1. glitterdome*

      I once had a boss who couldn’t figure out how to get off an elevator on the correct floor. They had to be chaperoned everywhere because they legitimately should not figure out how to get from point A to point B on the same floor. It got unfunny REALLY quick.

      1. Jaid*

        I was listening to an episode of Radiolab, where they interviewed a woman who would get lost in weird ways. It turns out her hippocampus wasn’t developed properly and the condition even had a name! “Developmental topographical disorientation”. It is akin to face blindness…
        Giuseppe Iaria is a cognitive neuroscientist at the University of Calgary researching the condition.

      2. Dasein9*

        Oof! I did once work in a place where one needed to use stairs or elevator to get from one side of the building to the other, even on the same floor, but I hope that was just an extraordinarily dumb design and not a common thing.

      3. we don't talk about wakeen*

        To be fair sometimes I zone out on an elevator and just automatically get off when it stops even if it hasn’t reached my floor yet. But I haven’t yet needed anyone’s assistance to get back on and finish the trip.

  22. Anastasia Beaverhousen*

    If this is regular behavior I question if she IS a good teacher. How does she manage to organize her classroom, her students and provide feedback in a timely manner if she can’t get her coat off? Is she actually good or is she “likeable”. There is a difference.

    1. Anon…*

      I question this as well. If she’s losing applicant materials with private and personal information, then I can’t imagine she’s managing to keep track of student assignments. I remember in grad school, I had a professor that everyone loved, but as a student she drove me absolutely nuts. The biggest issue was because she couldn’t remember her policies and due dates they were constantly changing, it was maddening,

    2. London Lass*

      Some people are totally switched on in some areas and utterly in incompetent in others, including things others among us might consider basic skills. I can easily believe that an excellent teacher could also be a terrible administrator.

      1. After 33 years ...*

        Absolutely; different skill sets and priorities are commonly involved. I would never lose a student assignment, but I have mislaid an exit ticket to a parking garage. I would never come to class unprepared or lose my place in a lecture/seminar, but I can lose track of where I am during grocery shopping. Anything connected with teaching is high priority for me, so it gets my full attention; other personal/domestic things can rank lower.

        1. Gouda*

          Totally agree. At a fundemental level, in teaching, the priority is anything that directly involves the students — the actual act of teaching, grading, relationship-building, etc. When you move into an administrative role, this is no longer always the case, and that adjustment (if it ever really happens) is huge.

      2. Anti anti-tattoo Carol*

        Yep. Boss I mentioned in a different thread was truly, 100% amazing at the functions of her job that she held as an individual contributor. I am not kidding when I say that the educational model she created was utilized by others in her field, and she was lauded for her empathy and ability to tailor her work to individual needs. When she was promoted to a high level and given a team plus administrative duties, it all went to chaos. Her brain just didn’t do those other things. There was no ability to compartmentalize the “admin/boss” duties from the “educator” duties. We’re all just wired differently! Unfortunately, depending on your workplace, you’re often asked to do things outside of your abilities because of staffing or budget issues and it all just piles up.

      3. Dokes*

        Yuuuuuup. “Absent-minded professor” is a stereotype for a reason.

        Acquiring knowledge and sharing it in a classroom setting is a totally different part of the brain from “did I eat this morning” and “where did that bill I need to pay go”.

        1. Dust Bunny*

          However, it’s reinforced by not requiring people to do better. Absent-minded professors are stereotypically followed around by wives, assistants, and grad students who pick up their detritus because it’s apparently not fair to ask them to allocate a little bit of their “genius” to figuring out how to do this themselves.

          1. Chili pepper Attitude*

            I’m married to an absent minded professor (we learned many years after marriage that he was on the autism spectrum). If I don’t pick up all the pieces he mostly solves his own problems. But not always. He really cares which products we use, like toothpaste, but almost always buys the wrong one bc he does not read the labels properly.

            I noticed at a work event that a bunch of admin staff (it was all women) just seamlessly tag teamed him to get him to the podium on time and then told him where to sit etc. So I suspect this happens a lot at work.

        2. Omnivalent*

          The reason it’s a stereotype is that the absent-minded professor was expected to have grad students and a wife handling all of those “unimportant” little tasks for him.

          It’s so much easier not to think about or notice things when others are assigned to think about and notice them for you – especially when they have less actual or social power to push back.

        3. Underrated Pear*

          Yes, and many “absent-minded professors” are brilliant scholars but terrible, terrible teachers. I’m not trying to suggest that that’s the case with this teacher… but *in general* I agree that empathy/caring and organization/planning are two separate but very necessary skill sets if you want students to be both supported AND learn effectively.

      4. Wintermute*

        Amen! “domain competence” is a very real thing.

        I think there’s sometimes an assumption where if someone is bad in an area of their job they must be equally bad in them all, or that someone with issues at work must have them at home or vice versa– but that’s just not how people work. I’ve met some very successful professionals that simply could not translate some of those exact same skills, the very ones they used all day at work, from the office to a hobby or a side business.

        1. marvin*

          I think energy level is a factor for this too. I am very on the ball and organized at work but slack off a lot more in my personal life because it takes a lot of mental effort and sometimes I’ve got to prioritize keeping it together in the arena where I could get fired if I do badly.

    3. Popinki*

      THere are a lot of soft skills a good teacher has, like being able to build a rapport with students, present the subject material in a way that’s understandable and enjoyable, enforce discipline without being labeled that mean teacher all the kids hate, or having a genuine love of and enthusiasm for teaching.

      If she’s got those her superiors are probably willing to overlook her bumbling through everything else like the Tasmanian Devil.

      Though count me in with the others who want to know how the heck she made everyone else late because her coat zipper got stuck…

    4. Dutchie*

      Apart from the domain competence mentioned by Wintermute (a term I have always needed, but never knew existed), there is also the option that this boss has found a way to organize her workflow extremely well, digitally. Especially if she works in higher ed, the way she interacts with students about assignments might /also/ be completely digital.

      I know several people who are completely lost when they need to handle anything that is not digital, because it doesn’t fit into their organizational system that consists of a carefully selected bunch of seven different apps that are all somehow interconnected. They so rely in the reminders and workflow in their laptop, tablet and phone that a piece of paper just kind of disappears.

      Now, I’m not saying it’s necessarily professional and it certainly wouldn’t explain missing meetings, but it is possible that her teaching duties are part of an organizational system that just cannot contain keys or pieces of paper.

  23. The Prettiest Curse*

    I have a family member who was a LOT like this with work and non-work things, until she retired. She still does stuff like this every so often, but it’s nothing like as bad as it was previously. So I think much of this may simply stem from being very overloaded and stressed. This means that it might be worth looking at whether there’s anything that can be done to have others take on some of the items which have the most impact on staff members when the boss forgets or loses something.

    There may not be the money to hire an assistant for her, but (as Alison mentioned), someone else could be a key holder, assuming that there aren’t weird school district rules around keys. It might be worth looking into changes to the parking barrier too, since she’s probably not the only person who will ever lose a ticket.

    If some of the minor issues are tackled successfully, she may get better at remembering major things. There’s only so much information that you can easily hold in your head at one time, and the fact that the boss is forgetting minor stuff indicates that she has reached her limit.

  24. KWu*

    This seems like kind of a “I/we shouldn’t have to ___ if only Boss would ___.” I very much sympathize because I also spend a lot of my life baffled at how tasks that I feel “should” be very easy are very difficult for other people. It’s an easy bias to fall into though that because something is very easy for yourself, or seems commonly doable for other people you see in similar situations, that the person who keeps not doing is choosing to keep living their lives this way. Maybe so, maybe not, but you can’t really tell from the outside.

    It helps me with being more patient if I think about the things that I’m bad at and *I don’t care that I’m bad at it* (not enough to do something about it immediately anyway) that probably do cause other people some frustration. An example would be like…when we first got a house, there were times when my parents said they didn’t want to visit and have the neighbors associate them with how unkempt our yard was then. It just wasn’t a priority for me at all at the time (new house, pregnant with 2nd baby, etc.) but I tried not to take their judgment personally.

    In OP’s case, what I’d probably be getting frustrated with is my feeling that Boss’ apologies are not really sincere, because if they were sincere, surely they are generally intelligent enough to come up with ways not to have the same problem again more than a couple times and they’re choosing not to do so despite the inconvenience to other people. But it seems like Boss is just not very capable in this aspect, yet has many other work skills that are very valued.

    Oh, I also think it’s jarring if you feel you are a generally competent person yourself, to see other people who are really good at some things and really bad at other things. It’s a little frightening, in a way, because it’s perhaps suggesting that you yourself will run into things where putting in effort won’t necessarily help you get any better, which causes anxiety over how little control we have over outcomes in the world. Ultimately though, all you can really do is set your own boundaries and accept that some amount of avoidable delays are unavoidable at this job.

    1. Mimi*

      I like this thing about keeping in mind stuff that you yourself are bad at and don’t care enough to change, or intend to be better at and yet somehow haven’t managed to quite take care of. There are good suggestions elsewhere in the comments for systemic changes to be less dependent on someone else’s (dis)organization, but in terms of not being frustrated, I think it’s important to remember that my competence and your competence aren’t exactly the same, even if a particular set of tasks feel easy to me.

      My mom used to have a boss who was an organizational nightmare but very good at other aspects of her job (though not this degree of Amelia Bedelia). My mom got through it by deciding that this was how it was going to be and accepting that, and then working on mitigations to make her life easier (e.g. insisting on a regular 1:1 in which they went over all the things mom was waiting on from boss). Eventually mom got fed up and retired, but it worked well for several years.

    2. Sangamo Girl*

      Very good point. My very sincere answer to “What is your weakness?” is that I’m very organized and unorganized situations can be very frustrating for me. But not everyone has the skills I have. Now this situation, on the face, seems to go beyond merely unorganized but I’m sure part of it is that she’s just not capable.

      1. KWu*

        I have this too! Or some phrasing of like, “I know I like clear goals and structure and sometimes the environment we work in has a lot of ambiguity to navigate. In those cases, I’ve found that ___ can help me continue to make progress,” etc.

    3. Dust Bunny*

      Well, it’s one thing if I’m bad at arithmetic and public speaking if those things aren’t a big part of my job and don’t cause problems for people around me.

      It’s very much another if I’m losing office keys, holding up the line of cars, and *losing applications with sensitive information on them*. It’s not OK to be bad at stuff like that and OK with it. That is stuff that is affecting other people a whole lot.

      1. Anon Y Mouse*

        The thing is, though, that self-knowledge is not the cure for disorganisation. I am like this. I hate it about myself and constantly struggle to do better, but the 2% of times when my efforts don’t succeed are way, way more noticeable than the 98% of times when they do.

        The other thing is that it’s possible to screw up in a subtly different way each time, neatly evading the strategy you had put in place to avoid doing the stupid thing you did last time.

        It’s a stressful way to live.

        1. Omnivalent*

          It’s also pretty stressful for the people who have to live with it.

          We can sympathize with Boss without implying that the only kind and empathetic choice for the OP is to suck it up and become her boss’s Girl Friday.

          1. MCMonkeyBean*

            No one is saying that OP should act as the assistant and OP has specifically said they won’t be doing that. But if she doesn’t want to make changes herself and the boss is not likely to change then what option is there for OP other than to just accept this is how it is? Reframing it their mind may be the only way forward.

        2. Dust Bunny*

          But maybe this person needs to not be the one to hold this job. Let her teach if she’s so good at it but find a head teacher who can handle the other parts of the position. This seems like a pretty straightforward case of doing =/= managing. Plenty of peope (myself included) are great at what they do but would be much less great at managing people who do what we do.

          1. KWu*

            Whether the Boss should be in her role isn’t in OP’s purview at all though. I’m assuming that even with the difficulties of working with her, the pros outweighs the cons for whoever is the final decision maker there. The applications thing really is very concerning, but it doesn’t seem like there was a coverup about it happening either. If the people in charge of deciding whether Boss should hold the role are aware of the potential consequences to those applications having been lost, they can choose to do something about it.

      2. Sharon*

        Is there someone else this can be escalated to? If it’s a work performance problem, shouldn’t it be addressed by someone higher up the chain, not lower down? That person can help figure out how to solve the work problem, whether it’s developing new processes that mitigate the issues, hiring an assistant, helping the boss work on her skills (maybe some kind of EAP or organization skills training?), or potentially even letting her go/putting her on leave if the problem is serious enough.

    4. anonymous73*

      If you have things 1 through 5 that are critical to your job success, and you manage to mess up 2 or 3 of them on a regular basis, maybe you shouldn’t be that job. Yes everyone has weaknesses, but it’s not up to other people to help you overcome those weaknesses. Supportive, yes. But it’s up to YOU to figure out how to fix and/or improve upon them.

    5. Koala dreams*

      Yes, I think you have a good point. A lot of suggestions in the comments aren’t practical when it comes to dealing with your boss. You’ll have to decide if you can deal with the boss or not, and if not, start job searching. If you decide to stay, you’ll only make yourself miserable if you expect your boss to suddenly change for the better.

    6. Daisy Gamgee*

      Oh, I also think it’s jarring if you feel you are a generally competent person yourself, to see other people who are really good at some things and really bad at other things. It’s a little frightening, in a way, because it’s perhaps suggesting that you yourself will run into things where putting in effort won’t necessarily help you get any better, which causes anxiety over how little control we have over outcomes in the world.

      In a comment full of good advice this is a particularly wise and useful point. *makes a note*

    7. Gumby*

      I definitely have things that I am bad and and don’t care enough about to try to fix. Some of those are things that I suspect that even with work I would not be good at and since I hate failure, I just decided I didn’t care. Deciding not to care out of fear of failure is a suboptimal coping mechanism. However! I also make sure that the rest of my life fits around those shortcomings.

      I really try to make sure *my* shortcomings do not affect other people. The making people late would drive me particularly bonkers – five minutes delay is annoying but half an hour? No matter how crowded that parking garage exit is with that much time you can get enough people to back up to get the head teacher out of the flow of traffic. Further, I avoid jobs where my shortcomings are a central skill required to succeed in the role. I think for the head teacher “properly handle documents that contain PII” would be a pretty core requirement.

  25. I'm just here for the cats*

    This sounds horrible! Maybe if she asks you again about reminding her you could give her some tools she could use o her own.
    so if she says ” it would be great if you could you remind me about XYZ going forward” and its not in your job (your not her assistant) reply with “You know I’m busy with my own tasks that it would be hard for me to do that. But I found that making lists, using time management software, etc has helped me so much.

    If there’s anything you use like Microsoft todo or google calendar task list or anything like Asana maybe you could show her how it works and how you use it to help her? But really there is only so much you can do.

  26. I WORKED on a Hellmouth*

    Hi OP! If you choose to go the “I’m not leaving so I guess I’ll have to laugh at it” route, you can always recount the most ridiculous events of the week on the Friday open threads–I used to do that almost every week back when I worked at The Most Horrible Place on Earth (with the Most Horrible Boss). Obviously it was a very different situation to yours, but I can tell you that it definitely helped to write up the most noteworthy things and present them as entertainment, and it was also nice to have other members of the commentariat chime in or make jokes or otherwise be supportive. It might help you reframe things if you decide to stay!

    1. Esmeralda*

      When is the book coming out? Seriously, I’m glad you don’t work at the Hellmouth any more, but I was awfully sad when the postings stopped…

      1. I WORKED on a Hellmouth*

        Heh, I’ve actually been channeling some of the Hellmouthness into horror short stories, but they basically just live on my computer. :D

    2. irene adler*

      Man those posts were entertaining/frightening/awe-inspiring! Such an insight into human behavior.

      1. I WORKED on a Hellmouth*

        Every now and then I’ll log onto FB and one of those memory posts will be there from my time at the Hellmouth, and… they tend to really floor me! I’ll suddenly be reminded of, like, the time a resident threatened us or the time there was a reverse burglary (resident snuck into the office after hours to slip her late rent into the check bag) or something horrible that Hell Boss said or did and wonder HOW I COULD HAVE EVER FORGOTTEN.

    3. Mimi*

      I did this with my blog when I was living in a foreign country. Somehow the knowledge that I was going to get a GREAT blog post out of something made inconveniences like being stranded in some random town for hours with no transport much more bearable. I think it helped me to see them as the great story they would one day be, even in the moment.

      1. I WORKED on a Hellmouth*

        That’s so smart! What a good way to take out some of the anxiety that you can experience while traveling!

    4. RagingADHD*

      I thought the much-requested rule about “no running blog posts” also applied to Friday?

      If LW wants to start a blog, they can always swing by and drop a link.

      1. I WORKED on a Hellmouth*

        Nope, posting about your week at work in the anything-goes-open-work-thread violates no rules and is absolutely fine. Alison herself has said so.

  27. bee*

    I do think that some of these things are actually workplace problems and not on your boss — one person shouldn’t have the only copy of all the vital keys (what you do if she was out sick??) and it’s wild to me that your applicant information wasn’t stored anywhere but in one single hard copy (no digital backups?) It seems to me that it’d be within your purview to say “hey this is a bad system” and let your boss handle it from there.
    And a lot of the other stuff is a Her Problem. Why on earth would you stay and watch her struggle with a zipper? As a bumbling person myself, that would make it soooooo much worse.

    1. I'm just here for the cats*

      I thought the same thing with the zipper too. Like was she blocking the door? I understand the car pass thing because there might not have been a way for her to backup or anything. But if your leaving and she’s struggling with the zipper couldn’t everyone say “By Lucinda have a great night” and just, you know, leave. Unless its like someone else has to be with to lock up or something. In that case couldn’t she have just left the coat stuck, walked outside, and then got it taken care of?

    2. Littorally*

      This is a good point.

      I read once that the purpose of a bureaucracy is to ensure that the work gets done regardless of the competence or incompetence of any given individual within the system. It sounds to me like that mindset might be useful here — how do you structure things to minimize the opportunities for this person’s weaknesses to cause major problems for everyone?

      1. bee*

        Oh I like this! I also think that while people who struggle with executive functioning (like the boss, or myself) might expose more flaws in the system, optimizing it for The Most Bumbling is also going to help out everyone. We’re all human and all make mistakes, and a better set of systems will catch those mistakes as well — anything that relies on everyone functioning perfectly all of the time is not actually workable in real life.

    3. Overeducated*

      Agreed – I don’t think some of these are issues where OP can refuse to help because you don’t want to act like your boss’s assistant, some of them are issues where you really need a better process or system. Relying on one person as a failure point reflects on your institution as a whole and not just your boss. Think about it as strengthening the organization and making it more redundant and fail-safe, not just enabling your boss.

  28. Nea*

    LW, I’m on team “get an intern” but here are some suggestions you can pass on that might help without making Boss your problem to keep organized.

    – Can there be duplicates of keys kept in a safe location? If not (and even if so) would Boss be willing to wear her keys on a very brightly colored lanyard?

    – A Place for Everything And Everything In Its Place: The parking pass needs to live somewhere. On a badge holder on the lanyard, in the map pocket of her car, wherever. The parking pass needs a home.

    – Japanese point and call. (Google-able phrase will lead to articles explaining the system) This requires training so it may not work for either you or boss, but if someone can get into the habit it’s amazing. This is where you don’t just have a mental checklist, you actually point at something and call out what/where it is. I’ve got a 6-item point-and-call for leaving my house and another for leaving my car and it has saved me from leaving the coffee maker on/forgetting to put up my hang tag when I park/trying to leave without my keys So. Many. Times!

    You’re on your own with the coat zipper, though.

    1. Roy G. Biv*

      Japanese point and call — interesting. I think my new welcome mat (exit mat?) must subscribe to that. It has a check list on it: keys, wallet, phone, glasses. My partner and I used to take turns leaving the house without phone or wallet, but not since this mat entered our lives.

  29. Pucci*

    Seems there is a lack of awareness of how her actions affect others. If you can’t find your parking ticket and others are backed up behind you , you either pay the fine right away or find a way to move out of everyone else’s way; you don’t dig around in your car for a half hour.

    1. Empress Matilda*

      Lack of awareness, and lack of consequences! At least, lack of consequences to *her* – there are certainly consequences to everyone around her. So far everyone seems to be shrugging their shoulders and going “Oh, that’s just Bumbling Betsy doing her thing again,” and then waiting for her or working around whichever problem she has created. There should be some procedural updates for sure, but I think also some cultural updates, to let people know that it’s okay to leave before she does, or to ask her to move her car if she’s blocking the exit from the garage, etc.

  30. Lifelong student*

    Has there been a marked increase in these events recently? Not diagnosing- but wondering if there has been a change if there is another root cause – which OP may or may not want to explore or bring to someone’s attention.

    1. Keira*

      I was wondering if I was the only person here seeing red flags for cognitive decline in OP’s account. OP’s boss needs an assessment. Sadly, it would be considered unprofessional for OP to suggest one or to contact the family to suggest it.

    2. Wintermute*

      I immediately thought the very same thing.

      In my opinion it’s not really diagnosing (which is saying ‘that sounds like X Syndrome to me!’) but rather just flagging that a sudden drastic decline in memory coupled with motor skills (an adult does not ‘get stuck’ in their own clothing for prolonged periods by and large unless there is some form of impairment) is a massive red flag for… for something bad upstairs.

      Speculating on WHAT that bad thing might be would be getting into diagnostic territory, but simply saying “this could have a medical origin and it might be a sign they need to be assessed by a professional” is both incredibly reasonable, as well as unimpeachable in terms of accuracy– we can’t know what, we can’t even know IF, but we can know that the picture painted shows troubling possibilities that would cause many people with medical credentials to want to take a deeper look.

      1. Metadata minion*

        “an adult does not ‘get stuck’ in their own clothing for prolonged periods by and large unless there is some form of impairment”

        Do other adults really never get zippers catastrophically stuck? If it happens really frequently, I agree that there’s something wrong with either your fine motor coordination or the zipper, but I’ve definitely had zippers eat my t-shirt in a way that took a good while to unstick. The head teacher sounds like she has some serious executive functioning issues, but the zipper part sounds to me like the sort of thing that happens to everyone at least occasionally.

        1. Empress Matilda*

          The zipper thing could definitely happen to anyone! And from here, most of us can see an easy solution – all she would have to do is say “Please don’t wait for me, I can fix this on my own. See you tomorrow!” But if she does have some kind of executive dysfunction going on, she may not think of that in the moment – she’s just stuck on the immediate problem of the zipper (pun definitely intended!).

        2. Wintermute*

          Maybe it’s just in how it’s presented but I read it as “stuck and truly unable to extricate herself” rather than just “couldn’t get a stubborn zip up” because she couldn’t walk or move to let people leave and couldn’t just deal with it.

  31. CommanderBanana*

    Sigh. Or imagine it as working for Mr. Bean. Yeah, she needs an executive assistant. The ‘losing the only copy of applications containing sensitive info’ is really not ok, and to be honest, if I had applied to a program that then asked me to reapply because the only copy of my application had somehow been physically lost, that would be a huge red flag for me.

    I don’t want to run afoul of Alison’s moderator note, but I had a similar experience working for – you guessed it – a very small nonprofit with an executive director who had been there since the Dawn of Time, and yes, you can probably extrapolate what it was that was happening. Eventually the board noticed after a few incidences happened at large conferences and couldn’t be explained away and he finally retired, probably years after he should have. It was very sad but by the time it finally happened, the staff were just relieved that he had stepped down.

  32. Budgie Buddy*

    I wonder how this lady is with students. Is she routinely forgetting important parts of her lesson plan or not showing up to classes? She must be keeping it together somehow, at least mostly.

    This does sound like a situation where a person bumbles (consciously or unconsciously) because they are comforted by being forgiven after bumbling. (Uhh I may have been reading “Games People Play” by Eric Berne recently.)

    The coat zipper does make me wonder if this is partly a cry for attention. Why did that have to be everyone else’s problem?

    Usually the counter is to not have a big reaction or soothe the person by minimizing the harm done. Which is harder when the person bumbling is also your boss at work… :P But OP is right to maintain her boundaries and show she’s not the ideal audience for this behavior.

    1. Sylvan*

      Good point about the students. I’m sure we’ve all had a teacher who lost an essay and gave someone a 0 for it, or something like that.

      I had never heard of people being comforted by being forgiven for bumbling, and creating problems because of it. That’s really interesting. I’ll check that book out.

      1. Budgie Buddy*

        It’s an older book, and some of the analysis is…questionable…but a lot of the scenarios seem straight out of a Captain Awkward advice column. Sometimes human interactions just aren’t based on rationality, but maladaptive coping strategies.

    2. Attractive Nuisance*

      I have a friend like this, and it used to drive me insane. But it became a lot easier once I just stopped giving any bumbling-related emotional support to her and honestly started acting a little oblivious to her issues. Oh, you’ve finally arrived 3 hours late to the bachelorette party you were supposed to help set up? No problem, we got it all set and we’ve been having a great time without you. Don’t reward her by acting super happy and relieved that she finally turned up. Don’t let her failures or absence derail your plans – let them derail HER plans.

      1. hodie-hi*

        Spouse has always been similar to the person described by the OP, especially with keys, wallets, other stuff. I realized that my daily reaction of assisting the frenzied search resulted in a lot of stress and resentment since my own routine was disrupted. I rarely misplace my own things.

        I discovered that if I stayed in bed and even pretended to still be sleeping, I no longer participated in this daily panicked ritual. I wait until the tornado of stress had departed before I started my day. Spouse somehow survived and was forced to mind their belongings better. My whole day shifted at least an hour later, but my workplaces were always OK about that. My mornings became much calmer and smoother and I no longer started my day in a bad mood.

  33. BronzeCat*

    I’m a bit wondering if your boss is going to you to request reminders as the result of some kind of accommodation request where she didn’t want to disclose to you specifically, but received approval from her boss or HR or something? I know schools are different, but how much transparency would necessarily be involved in this sort of process?

    1. Zephy*

      I would think if the boss is basically asking for accommodations in the form of an executive assistant, it would be much easier to just hire one of those rather than try to force other employees to take on that role, but then again…

  34. Hiring Mgr*

    I get the idea of reframing it as humorous, but I don’t think that would work for very long here – according to the LW this is getting worse as time goes on, and already things with PII have gone missing, plus all the other stuff.

    So if this continues to get worse, it has potential to be more serious than a bumbling Inspector Clouseau type..

  35. Bumbler*

    This Boss is me (not literally but I’m exactly like her). We do apologize but cannot get our acts together. I’m brilliant at my job and have learned some coping skills obviously. But I do put Apple trackers on everything, nobody allows me to keep company property at home (like marketing stuff), when I fly with others they double check the seat pocket and overhead bin. They all come tell me when they have done weird things like I do so we can laugh together. We know all of this is very annoying for others. Medication does not help me.

    1. Squidlet*

      Sounds a lot like me, fellow Bumbler! I’m really good at the parts of my job that require conceptual and critical thinking, and joining dots in a way that others don’t, but I have to work exceptionally hard to keep simple admin tasks under control (although medication does help).

  36. Nanani*

    Can you encourage your boss to hire an actual assistant who is not you?
    Because it sounds like she wants an assistant.

  37. Sylvan*

    This sounds so frustrating for you!

    I have some similar issues from ADHD (no opinion on whether she has it or not!). If she is asking you for assistance, in addition to suggesting an executive assistant or someone similar, you might avoid taking on her responsibilities by making a few suggestions that she takes ownership of. A few things that help me:

    – Using location-based phone reminders
    – Using time-based phone reminders in advance, such as a reminder to prepare for a meeting 30 minutes before it begins
    – Taking pictures of things she thinks she might forget or misplace (examples: car in a crowded parking lot, important paperwork set down somewhere)
    – Keeping frequently-lost items in her purse or other bag, whether carrying them constantly makes sense or not
    – Duplicate items (examples: keys, masks, and travel-size personal hygiene items, stashed in my car and at work)

    If you’re not sure how to bring up advice like this, you can just say it works for someone you know who kept losing their key/forgetting when meetings were occurring/etc.

  38. BiscuitGirlyGirl*

    In addition to the things discussed already (making multiple copies of keys, etc.), is there a way that an entry-level person could be brought in part-time (at minimum wage or slightly above) to just act as her “keeper”? I understand this woman. She’s me. Scatter-brained and disorganized but exceptionally good at the core functions of her job. People like that are worth keeping, and the main requirement for her assistant is “being really organized”. There are plenty of folks like that, and no experience is necessary to keep her schedule, remind her of meetings and deadlines, organize her office. etc.

  39. Cold Fish*

    Am I the only one confused as to what boundaries OP is enforcing? That you are intending to be unhelpful? I get being frustrated by boss constantly losing things and causing disruptions but it doesn’t sound like she is doing it on purpose. And I’m missing what boss is asking OP to do that is so far out of line. I mean, I’d get it if boss was treating OP like her assistant but that is not the impression I get from the letter.

    Note: I tend to be hyper-organized at work and it is very much in my nature to try and implement procedures that eliminate inefficiencies (I’m kinda lazy that way) so I’d definitely see myself offering suggestions to boss like “hey, can we keep the office/supply closet/janitor closet keys in top drawer of X file cabinet so we can find them when needed?” or “Lets put all the applications in this file as we receive them so we don’t lose any”. I guess I wouldn’t see anything like this as above and beyond so that may be part of my problem.

    Note 2: I have worked with many people who say things like “remind me about to bring X up at meeting this afternoon” or “remind me to call Y about Z” who don’t actually expect me to remind them about anything. It’s more of a habit/memory thing they’ve developed to remind themselves. I would assume boss was doing this unless boss was coming back after the meeting with “I told you to remind me of X” (Yes, I found this habit annoying but not nails-on-the-chalkboard annoying)

    1. HelloHello*

      The boundaries are that OP isn’t going to start acting as an executive assistant for boss by giving her a five minute reminder before meetings, checking after meetings that the boss hasn’t left anything important sitting on the table, taking over paperwork the boss is supposed to do but is forgetful about, etc. That type of organization and administrative work takes time and effort, and if you start doing so, it can become an expectation of you rather than something you are kindly doing to be helpful. The OP isn’t an administrative assistant, and is drawing boundaries around what tasks she takes on that are outside her job description, to avoid being treated like an admin or having her time used up on administrative tasks.

    2. animaniactoo*

      I expect it’s stuff like “call to remind me of meetings in future” and “keep track of my schedule and send me a reminder list daily” and other seemingly small stuff that actually takes up a large amount of brain space when that’s not the kind of stuff your brain is focused on – or needs to be to do the job you did sign up for.

    3. Dust Bunny*

      I think it’s the frequency. We all misplace stuff occasionally, but it sounds like the boss does it a lot and does it with important things.

      Come on: Holding everyone up because she lost the parking card or got stuck in her coat? Losing keys all the time? Losing sensitive applications? That’s out of line. This is someone who can’t actually do all the necessary parts of the job effectively.

    4. Rusty Shackelford*

      Am I the only one confused as to what boundaries OP is enforcing? That you are intending to be unhelpful? I get being frustrated by boss constantly losing things and causing disruptions but it doesn’t sound like she is doing it on purpose.

      It doesn’t matter if Boss’s actions are intentional. The boundaries OP is enforcing is that she is not going to fix the problems by holding Boss’s hand. A person doesn’t have to be bad to be a boundary stomper.

  40. Ssssssssssssssssssssssssssssssss*

    I completely sympathize.

    I am an executive secretary and I work with one of these. No amount of reminders, short cuts, emails, guides, instructions and texts will work in the long run.

    My disorganized person will welcome the initial organization attempt and praise it to others and to the person who organized it and then unconsciously will resist it with every fiber of her being because nothing sticks. And she is also a wonderful, empathetic human being who is a great activist. But I’ve learned to work around her brain, not with it.

    It’s not a perfect way to work, I point out. It’s been three years, I know fully well what I’m working with and I still have moments of “OMG, what have you done to ruin my document/ work flow now?!” several times a year and rage silently at my desk.

    1. Empress Matilda*

      My disorganized person will welcome the initial organization attempt and praise it to others and to the person who organized it and then unconsciously will resist it with every fiber of her being because nothing sticks.

      Hello, and welcome to my brain! I don’t know about your person or OP’s person, but in my case it’s at least as frustrating for me as it is for everyone else. Which I know doesn’t provide a lot in terms of practical advice, but at least you know you’re not alone?

  41. blackcat lady*

    I see many people above have recommended an assistant or intern – that was my first thought.

    I also see Sylvan just above me mentioned ADHD. I was wondering about an underlying medical issue. Has the boss always been like this? Is it getting worse? How old is boss? It’s out of bounds to ask the boss but I do wonder if her doctor has evaluated her for ASHD or early onset memory issues.

    Disclaimer – no, I’m not a physician.

    1. Ally McBeal*

      I wonder if even a couple sessions with a professional or life coach would help. Boss could get advice/ideas for implementing her own system of checks and balances to keep herself on track. The thing is that Boss has to WANT to change, and I’m not getting the sense from OP that that’s the case.

  42. velomont*

    There’s a book called “The Artist’s Way” by Julia Cameron and in it she describes a type of person she calls a “Crazy-maker”. Crazy-makers are charismatic people who create vortices of chaos that end up controlling everyone around them through wasting and stealing time.

    I have a sister who is one and I once had a colleague who’s one and it’s brutal. If you work for a crazy-maker (and it sounds possible) you really have to have solid boundaries.

  43. AthenaC*

    Without offering any sort of opinion one way or the other on whether there is anything medical or what that medical condition may or may not be, and without going into detail on specific individuals I’ve worked with before and their specific diagnoses, treatments, and other non-medical adaptations –

    (Is that enough pre-emptive qualifiers in order to avoid an inaccurate “armchair diagnosis” comment deletion?)

    Are you close enough to your boss to recommend she go to the doctor and get evaluated?

    1. Dr Sarah*

      This was very much my reaction. I agree we can’t and shouldn’t diagnose her, but it sounds as though she should be talking to someone who *can* see whether a diagnosis is in order. Since the OP seems to have a good relationship with her, it’s quite possible that it would be reasonable for her to have a gentle word suggesting that discussing this with her doctor regarding assessments might be helpful.

      Given the nature of her job, the boss should already be aware of the existence of neurodiversity issues that can affect executive functioning. Maybe the OP could introduce this as “I was reading up last night on executive functioning issues, and I hope you won’t mind me saying this, but some of the things the article said about adult diagnoses really rang a bell in terms of what I see you doing. Was this something you’d ever thought about yourself?” Obviously the OP is better placed to know whether this would be OK with the boss, but I definitely think it’s worth seriously considering.

  44. Former call centre worker*

    I used to work for someone a bit like this. Highlights include losing her laptop by leaving it next to her car as she was leaving instead of putting it in the boot, and having to get someone to climb into a skip to retrieve some important papers that she’d been carrying around in a recycling bin that the cleaner obviously threw out.

    In this case I was the assistant so it’s a little different, but I think the advice to reframe it as comedy is good. I actually really liked working with her, and could see that a lot of the disorganisation came from her being so dedicated to our aims that she put all her energy into that instead of leaving some room for things like remembering to write meetings in her diary.

    I think you can end up honing your psychic powers over time, so that when she comes to you saying “I was supposed to call someone about something, can you remember who and what?” (or other problem applicable to your roles) it becomes predictable what she’ll forget and you’ll be able to stop problems happening in advance or work out what she’s trying to remember.

    1. Squidlet*

      I once drove 2km with my phone on the roof of my car … luckily it had a really good rubberised grippy case that prevented it from sliding off the roof and onto the road.

      I also (on a different day) drove around an underground parking space, reached the exit and couldn’t find my ticket, and had to squeeze out of the exit lane and back into the main parking area. After spending 10 minutes searching my car, handbag, and pockets for the ticket, I found it … on the roof of my car, with the coins from the pay station.

    2. Hlao-roo*

      I love the “carrying important papers around in a recycling bin.” XD

      I can imagine that to her, it was such a convenient way to transport the papers. Sturdy! Perfect dimensions! And to everyone else, it looked like … recycling. Definitely a great nugget of comedy gold right there.

  45. animaniactoo*

    A bunch of this sounds like stuff that needs to have systems set up to prevent mishap where possible.

    • Yes to the somebody else has copies of the office and supply closet keys.

    • Applications and other essential material are immediately copied/scanned and filed as a backup.

    Stuff like that – you incorporate it not just as a question of *her in particular*, but as a question of maintaining function in a “hit by a bus” scenario. Even though, in this case, you would be doing it because of *her in particular*.

    1. Dust Bunny*

      I’m seeing a lot of “there should be copies of the applications” and, yes, the applications should absolutely have backups, but that doesn’t negate that the copies the boss had are now possibly out in public with people’s personal information on them. This would 100% get you disciplined or worse where I work.

      The institution needs better info-handling practices and the boss needs real consequences for mistakes like this. This isn’t comedy.

        1. Dust Bunny*

          But it doesn’t sound like it’s been brought to the attention of people whose hands it might not be out of. The application thing is a serious transgression.

  46. Queen of the File*

    Along the lines of requesting help in the form of an intern or assistant, it’s possible some coaching sessions may offer some solutions. I live in a bit of a chaos cloud that sounds a bit similar to your boss. Where my workplace was not in a position to help me out, I did decide to spend some of my own time and money to get some advice and strategies for forgetfulness and general organization from a life coach. In my case, I sought out a coach specializing in adult ADHD (not a comment on OP’s boss or any kind of diagnosis, just that that type of coach’s skill set might be a good match for anyone with the kinds of challenges described).

    A past colleague in an executive role with similar challenges worked with an executive coach for awhile that also offered some strategies for managing a lot of little things they were continually losing track of.

    1. librarianmom*

      This is an excellent suggestion, especially considering that you can bet your bottom dollar that her disorganization is affecting her personal life as well.

    2. Ally McBeal*

      I just commented this in reply to someone else! Should’ve kept scrolling :)

      Boss could think of it like one of those consultants who comes out to help you organize your closet or other trouble areas in the home, but for her brain instead of her closet.

  47. Paloma Pigeon*

    I think this is going to be my 2022 mantra: Establish Systems so you don’t have to rely on One Person. Lost a key? There should be a backup. Lost a parking ticket? There should be a protocol to address the issue when it inevitably arises. This shouldn’t be OPs responsibility, but I think it’s fair for OP to point out that someone should set up some protocols to avoid mishaps like those, in order for things to run smoothly. The paperwork loss is more egregious and OP has standing to suggest online portals for submissions – it will protect the company and can be easily accessed by approved staffers.

    1. kiki*

      Yes. It does seem like the head teacher’s nature is making these issues apparent more quickly than they would be otherwise, but it’s common for keys to get lost or for somebody to lose their parking ticket or even misplace some paperwork– there should be systems in place to ensure these events aren’t big deals. Trying to wait for the head teacher to get better the current systems is just going to make everybody frustrated. It’s worth the extra investment of time and money to set up more resilient systems even if it “shouldn’t be necessary if head teacher more organized or less scatterbrained.” Head teacher is who they are and it seems like they’re valued by this school– make systems that actually work for the parties who have to use them.

  48. The organized one*

    I don’t think “I won’t take any of this on” necessarily works here. Are you part of a team? In a working team, people with the best skills take on different tasks. Especially in education. I’m organized. So on my team I set up the calendar. I communicated with parents. If she is disorganized, why is she getting the paperwork? An organized colleague should set up the system for that. I ended up in charge of a lot because I liked doing those things. If you don’t, then don’t take it on, but setting the group up for success seems better then letting someone flounder.

  49. Shangrila*

    One of the best things that happened to me after being emotionally and professionally entrenched with two prior bosses…was to land a job where I rarely saw my boss. It was eye opening to have a job where I wasn’t emotionally and professionally responsible for my managers, their work, and their problems. I was never an assistant but I’m apparently naturally talented at managing up. My first thought for this letter was to question why ANY of this is LW’s problem to the extent that they are considering leaving the job. Disengage from the boss as much as possible. Stop allowing it to be your problem.

    I also don’t think a boss like this is a funny, ah-shucks sitcom hero. I wouldn’t want to work for Gillian or Nemo. What a resource and time drain.

  50. ArtK*

    Are the Powers That Be aware of her issues? In particular, losing documents containing PII. That puts the whole organization at risk.

    I don’t understand the parking ticket preventing others from leaving unless she blocked the exit and wouldn’t get out of the way. That’s simply inconsiderate and *not* a “lovely person.” Same with the stuck zipper. Why could nobody leave if she couldn’t get her coat on?

  51. anonymous73*

    If I was an outsider, I might be able to find the humor in this, but in your position, it would drive me batty. If there are ways to keep her more organized so she doesn’t lose everything, I would try making suggestions (especially when they affect your job). And make sure there are backup solutions so she isn’t the single point of failure for important things (like the possession of the keys for example). But as you said it is not your job to “fix” her. It is her job to come up with her own ways to avoid being an unorganized mess. If you haven’t already, you may want to have a heart to heart with her and explain this. There are ways to solve these problems, but she has to want to find ways to solve them, instead of just laughing it off and apologizing.

  52. January*

    I had a superior like this. The trouble for me was that he expected me to “manage upward,” and it eventually bit me in the ass. I was essentially babysitting a third party while they prepared an involved document for us, for a government deadline. My superior wanted oral updates and refused things like calendar flags and emails because “I’m not going to read that.” My only instruction was to “get the damn document, we’re ready to submit it.” The third party took while (which I made my superior aware of) and the morning it was due I handed it to him with my edits. He then exploded and told me that he didn’t have time to run it by my grandboss or the board, which I wasn’t even aware he needed to do. He then wrote an email excoriating me for not making the third party get it to him in a timely manner, and I had nothing in writing to show that I was constantly telling him “Don’t forget about X, it’s due on Date.”

  53. Cheap Ass Rolex*

    I definitely second the Inspector Clouseau comparisons! Have a Pink Panther films marathon, and when she bumbles again, just think to yourself, “I am examining the wax!”

    Besides that, though, if you can get to a place where people are fine not waiting for her, she’ll be less of an inconvenience. If you establish norms where no one has to wait around at work just because her zipper is stuck, or where you all will explicitly leave without her for something if she’s late, that can take a lot of the pressure off. It sounds like she’s gracious about things, so this might be doable.

    Also, bake in some failsafes to your planning as much as possible – wiggle room is a must. Don’t carpool with her, don’t schedule things close to deadlines, and give her the college-professor rule of “we’ll wait for 15 minutes for you and then assume the meeting is cancelled”.

    Obviously, this is a lot of workarounds for someone’s incompetence, but she’s your boss and otherwise you like the job so this may be what it is.

  54. kiki*

    I understand that this isn’t your job to manage but unless you’re able to hire on an admin assistant or office manager, it would probably be best for your own sanity to organize some of the low-hanging fruit. What does she have difficulty most? Is it losing things? Make sure everything possible has triplicates and keep at least one copy somewhere your boss isn’t going to start taking from. Get a bunch of those tile tracker things and put them on everything irreplaceable (binders full of important documents, original keys, etc.) Does she lose paperwork when she takes it home? Suggest a policy barring paperwork with sensitive information from being taken out of the office. Suggest a policy to scan all important paperwork so it cannot be truly lost.

    I would also ask her what she wants to do when she’s holding things up. Because she’s the boss, people probably feel weird about asking her to move her car out of the way or blocking people from leaving because her zipper is stuck. If she forgets her parking ticket, that shouldn’t actually affect anyone else– it should really be between her and the parking garage management. I’m not sure if I completely understand the zipper thing, but I actually would not want anyone to watch me struggle with my zipper for fifteen minutes– I would request that everyone leave and try to make room for them to do so! Maybe she gets really absorbed with what she’s doing and doesn’t notice that she’s affecting other people? It might help to start asking in the moment, “Is it okay if you pull around to search for your ticket so we can get out?” Is it okay if we head out while you figure out your zipper?”

    1. RagingADHD*

      Yes, that struck me as odd, too. What’s going on with the culture or the policies that nobody can leave until she leaves? Normally the primary keyholder is the last to leave, not the first.

      Simply empowering people to go about their business while she sorts herself out seems like it would reduce LW’s frustration by about 50%.

  55. Just Me*

    I mean, to me it sounds like some of these are directly related to your work and can be pushed back on, while others may be just-her issues. Forgetting to show up to her own meeting and losing papers with sensitive information is a big deal, but I don’t see how her coat zipper getting stuck is necessarily a work issue?

    But as Alison mentioned, you can work around it by building a system of fail-safes and reframing it as “People are fallible and make mistakes so we have to make sure there is a check in place to make sure these things don’t happen” such as quick check in meetings in the morning with the team to make sure everyone knows what needs to happen that day, making internal audits a regular part of your processes, etc.

  56. higeredadmin*

    There can be a lot of reasons that someone struggles with executive functioning, including ADHD/ADD or perimenopause/menopause. Teaching/academia also has a habit of promoting people who are good teachers/researchers without looking at management skills, so you end up with some pretty interesting management. You could easily be dealing with a combination of the above. There is probably not a budget to hire someone to help her, but maybe having a frank conversation about how this is impacting you and working with her on some practical solutions? (And maybe it isn’t just you stepping in to help – as noted above, a lot of solutions are collective such as making lots of copies of keys.)

  57. Emily*

    Has anyone so far suggested just talking this out with the boss and finding a solution together? What would this boss recommend if she had a bungling child in her classroom who couldn’t remember to do their homework or kept forgetting their gym clothes? Since she’s a ‘lovely person’ maybe she also has the self-awareness to see that the solution isn’t ‘ask mom to remind me’, but to implement some strategies to remind herself of important things (keys, appointment times, location of important documents).

    1. Goody*

      Ooh, this gives me an idea.

      “Hey boss, can I pick your brain on ways to help Student?” Then cite examples taken from what Boss is going through, tweaked slightly to fit (for example, a lost group project instead of applications, a bus pass instead of the parking ticket) and see what sorts of ideas Boss comes up with.

  58. Sparkles McFadden*

    I say stick to keeping boundaries, LW, and stay for the stories you’ll be able to tell in the future. Alison is correct, there is comedy gold here. Even if you don’t want to be a work-story raconteur, framing things in that way can really help you distance yourself from the situation.

  59. ThursdaysGeek*

    I had a boss who claimed to be ADHD and would assign work and then forget she had assigned it, and assign the same or different work. I had a good relationship with her, and told her I was going to work on what I wanted to work on. If she assigned work, I would listen, but if it didn’t match up with the direction we were going, I’d tell her I was going to ignore that and keep working what I was working on. So we acknowledged the issue, communicated about it openly, and it worked quite well.

  60. KK*

    I haven’t read all the comments so maybe it was mentioned but I would show her how to set up alerts on her phone for meetings. Have TRIPLICATE keys made for the office and supply closet. For documentation, I would encourage her to make an extra hard copy AND soft copy for you. It might be extra work for HER but really this is HER problem that you can only help so much with.

  61. it’s funny because it’s true*

    My dad has long referred to his workplace as a sitcom, and regularly frames his weird work stories as “Guess what happened in today’s episode,” which feels like a good example of implementing Alison’s advice here

  62. Martha*

    For everyone wondering how she could be a good teacher is she’s this disorganized –

    My husband has severe problems with executive function, yet runs a successful contracting company. The way I’ve come to see it is that he has X amount of EF to use, where most people have XX, and he uses it ALL for work. Meaning that when he gets home he’s used up all his EF and is a complete tornado. On weekends he’s remarkably more functional at home.

    1. Batgirl*

      People who are excellent at X often get stuck in a hyperfocus of supreme X excellence which ignores all the pedestrian and real life details that go alongside it.

  63. RagingADHD*

    Look, if your boss is only 10 years from retirement, this isn’t a matter of her “getting her act together.” Her act is together. According to you, she is an excellent and beloved educator, a good mentor, and a kind boss who apologizes and never blame shifts when she messes up or inadvertently inconveniences people. That’s a damn sight better than a lot of people are doing.

    She is also clumsy and loses things. What you’re seeing now is baseline, and isn’t going to change. She may have expended a lot of effort when she was younger trying to make it change (or maybe not) but either way, this is just who she is and the way she functions. That is her life, and you can bet your sweet bippy it is a lot harder to BE her than to work for her.

    She probably could benefit from a PA, and you could always recommend that she hire one if it’s possible, even part time. She would certainly benefit from clear systems for things like paperwork and keyholding, and if office systems and policies are part of your role, you can put something in place. But whatever the approach may be, wishing or hoping that she will magically transform into a different person is the thing that really will drive you crazy.

    1. Anon Y Mouse*

      Thank you for this compassionate response, from someone who sees herself in this lady (and doesn’t like being this way at all).

      1. RagingADHD*

        There is a very strong tendency in our culture to worship and moralize organization and efficiency, to the point that being weak in these skills is seen as a major character flaw, while actual meanness, greed, dishonesty and cowardice are excused as minor foibles.

        There are even folks on this thread insisting that the boss is doing all these things on purpose just to get attention. Seriously? That’s what five-year-olds do. If the boss had the emotional maturity of a five-year-old, it would show up in her teaching, mentoring, and relationships with the parents. Which it apparently does not.

      2. Batgirl*

        Totally. I have gotten a lot of my executive dysfunction together, but I know I could never be a headteacher. I actually don’t know how anyone could be one without superpowers; it’s incredibly demanding and would completely overwhelm my coping mechanisms. I don’t understand how OP thinks someone like this can “get her act together” as though the solution is sitting there and the boss just simply can’t be bothered implementing it. These traits have almost certainly bothered her and cost her in her life. If she hasn’t solved it yet, she isn’t going to.

    2. Small town problems*

      Yes 100%. There’s things that can be managed, but you aren’t going to change someone.

    3. Caraway*

      This sums up my thinking pretty well. You are certainly welcome to draw a hard line on not keeping your boss on track, but I don’t think she’s going to change at this point. I think you need to consider whether the annoyance of taking on some “assistant” tasks like reminding her of meetings outweighs your annoyance at her being late, again, for her own damn meeting.

      My last boss was like this, a bit (not to the same extent). Kind of absent minded, prone to missing meetings or showing up late without anything to take notes with, etc. It frustrated me, but I decided I’d be less frustrated by swinging by his office to pick him up than I would be by a meeting no-show. You might come to a different decision than me, but I think this is the choice you’re facing, if you’re determined to stay.

  64. Alton Brown's Evil Twin*

    It sounds like saddling the boss with things like keys is not the best for the organization. In addition to soft leadership skills, and given her reputation among parents and students, she should be spending more time on pedagogy, instructional design, mentoring other teachers, etc. and less on the administrivia.

    The school ought to figure out how to get her working on things that does well, instead of handing paperwork. It sounds like boss recognizes this to some extent – which is why she’s trying to push stuff onto OP. If isn’t the right person for this, then somebody (or a committee of somebodies) ought to take on the role of XO.

  65. beloved but in some ways incompetent*

    Sorry that her incompetence is impacting your pleasure in your job.
    Outside of the box thinking.
    I am her. Yep, embarrassing but true. Not Principal but head of a department in a k-8 school.
    If there is no funds for a part-time assistant, this is what has worked for me.
    Parents LOVE me. I have had a parent volunteer (various ones 2 half days a week) to keep me organized for over 15 years.
    Mail gets opened, things get filed, invoices get paid, paperwork gets done by deadlines.
    Keys, IDs, parking passes etc all have apple ID finders on them.
    Keys are duplicated and kept on site.
    Every important paper is scanned onto a share drive.
    Deadlines are on a shared calendar. Many reminders.
    Meetings are on a shared calendar. Many reminders.
    Zippers- keep spare coats on site- step out of the stuck one. put something else on.

    There came a time when instead of trying to be someone else, I recognize that I have other gifts.
    I spend my time on those and allow others to help me with my deficits.

  66. Keymaster of Gozer (she/her)*

    Ahh, you have my boss from 2 jobs ago. Great with our suppliers/board meetings/clients but would forget common sense stuff, wouldn’t put reminders in her calendar, would be late into work 3 days in a row because she forgot where she’d put her car keys etc.etc.

    All I could do was offer to help by downloading/installing/showing her how to use a ‘reminder’ application on her phone for basics, sticking a post it note on her laptop to remind her to book appointments in her calendar as soon as they were set up and gentle reminders that although ‘information management’ was the department that didn’t mean I could manage her life.

    That wasn’t a fun conversation but I objected to being told I had to remember her medical appointments. I have enough trouble remembering mine.

    Beyond that, I just tried to shrug off as much as I could. I mean, I have to keep a running notepad of my own duties these days (menopause brain fog), I got no time to do someone else’s.

  67. bluephone*

    I can be pretty scatterbrained/forgetful/ADHD/whatever you want to call it but I’ve been on the other side of “someone lost the important materials I sent then so I had to resubmit them” enough times to lose all sympathy for this lady. She may have lost application materials instead of FMLA paperwork but it’s still a pretty egregious “oopsie doo tee hee!” gaff. So whether the OP wants to be her boss’ personal assistant or not, someone at that school NEEDS to step in and make sure subsequent application materials aren’t messed with again. Please tell me at least one applicant (or their parents) read you all the riot act for that because honestly, this school is acting way too glib about it.

    1. New Jack Karyn*

      OP didn’t say the breach was laughed off with an “oopsie doo tee hee!” That’s uncharitable of you.

  68. Pobody’s Nerfect*

    This is not armchair diagnosing but an actual fact: recent surveys have shown that half of all women consider (and often go through with) leaving the workplace completely, reducing their hours, or changing their job responsibilities when they are going through the worst times of their perimenopause and menopause. Rollercoaster hormone changes and plummeting estrogen during those times have a very real and proven detrimental effect on brain function and cognitive abilities. Brain fog, memory problems, mood changes, depression, anxiety – these are very real and very difficult symptoms for people going through perimenopause and menopause, and it absolutely has an effect on workplaces and people in them. I’m not saying this is the issue with this woman, but it’s a very real issue that all employers, coworkers and employees need to be aware of and educated on. Women themselves often aren’t even aware it’s the reason behind their distressing symptoms.

    1. No Tribble At All*

      This is good to know… but I feel like this encourages employers to discriminate against women even more. Even if I don’t have kids (pregnancy brain, maternity leave, “distracted”) I’m a liability when I get older anyway :(

  69. Sara without an H*

    I keep hoping that she’ll get her act together, but I doubt it will happen any time soon.

    Hi, OP — First off, for your own mental health and happiness, stop this! Your head teacher will not change. Ever. Repeat that until you believe it.

    You also cannot fix her, nor should you try. Don’t pick up your boss’s hint that she’d like you to try to manage her. It’s not your job and is unlikely to be successful. You might, at most, offer to take a look at your internal processes and see if there are things that can be changed, such as having backup copies of keys available or how application paperwork is processed. (Oh, and please keep your own copies of anything related to your own work, such as pay stubs, performance reviews, etc.)

    For the rest of it, I like Alison’s suggestion that you reframe your manager’s disorganization as a form of entertainment and get whatever amusement you can out of it. Short of finding another job, it’s the only way out.

    1. More dopamine, please*

      +1 to this. Thinking that the boss just needs to “get her act together” demonstrates a lack of empathy/acceptance to the way this person actually IS. Accepting that just is the way the boss is, likely due to unchangeable neurological and personality factors, will help OP respond with more grace and maybe get creative about workarounds.

  70. A Ruler - Measurement, not Royalty*

    I have learned that working in education is such a mixed bag. It’s like each school, heck, each department within a school, is it’s own little company run by a CEO who have never seen a functioning company run. There is no one way to do things, and nobody has any power to tell anyone else how to do their job.

    Unfortunately I don’t have much more advice than to try to see it as comical, because in fact the whole industry is comical. I’ve learned to set up systems that work for me within this horribly broken system. It’s a lot like life: I can’t make anyone else do anything or behave in any way, therefore it’s up to me to work around the world.

    1. Batgirl*

      Yep. I don’t think people understand that teacher managers are just people who were good in the classroom, and not at all trained/mentored or have even witnessed competent management, budgets or admin. It’s like asking an actor to do your taxes. If you have a good teacher manager it’s almost entirely a fluke.

      1. kiki*

        Yes, I love some of my former teachers but looking back at some of the work advice they gave me… yikes! A lot of my teachers had never had any jobs outside of teaching and it showed in their advice.

  71. L'étrangere*

    This I think is a place where throwing a bit of technology at the problem would be a good thing. If my friends in their 80s can tearfully thank me for introducing them to the joys of google calendar, I think your scatterbrain can get the hang of it. Make and share with her/other staff a calendar of important school events. It won’t be extra work for you because you need reminders of those too, and you might well be able to get other participants (just don’t let her edit because you could easily have a zipper situation on your hands). Do her a favor and show her how to do a parallel one for herself, as her personal life is likely to be even worse. Introduce her to electronic tags, they won’t save the parents’ confidential data () but you can get back the office keys. Maybe the entire school can chip in to get her tags for her car keys for her birthday etc. She’s gotten away with this kind of disorganization so long she probably has no idea how it affects other people. As you try to introduce innovations, be sure to tell her that it’s because you’re worried about the level of stress she’s under because of this chaos, that she’s precious to the school, that y’all can’t bear to think of losing her because of some stupid accident, freezing to death in a ditch with her zipper halfway up… But in any case the stress is getting to everyone else too (probably the kids!) and you need it to ratchet down a bit

  72. Mayflower*

    She is a gifted teacher and is justifiably loved by her pupils and their parents.

    I doubt that she is a great teacher. I have a 7th grader and some of his teachers are like this – mind boggling incompetence covered up by a “lovable” personality. A small number of students and parents like them but most suffer the consequences: endless “technical issues”, poorly assigned homework, late or incorrect grading, missing materials, etc. And it goes on for years… these problem teachers are well known among my child’s friends, their older siblings, and other parents including those whose kids went to school years ago.

    You are not hearing from the victims of your boss’s incompetence because of the power imbalance. I wish I could report some of the teachers but I can’t! It won’t do anything other than antagonize them against my kid.

    This is a classic missing stair problem. Everyone knows how bad these teachers are but everyone enables them. Please don’t enable this person.

    1. Shangrila*

      This. It also reminded me of the coworker I had, in education, who was surviving on the basis of her pre-decline reputation. Everyone loved the colleague she had once been and refused to point out the incompetence, missed deadlines, 3-hour meetings that regurgitated decisions and discussions she had forgotten on a weekly basis, fines, unhappy students, etc. She was a lovely person, though.

      1. Lizzie (with the deaf cat)*

        Hi OP, I think it would be useful to expand your options a bit. Get your resume up to date, and start spending 30 minutes a week just looking at alternative employment options.
        There are practical ideas up above, for sure, which might take the edge off a bit. But, you have been there for two years, and this person’s behaviour has already taken a toll on you. Can you really endure another ten years of this situation? Forty hours a week times 50 weeks a year times ten years – that’s 20,000 hours of irritation or anticipated irritation. And that takes us to 2032. I think you might only be fit for a long lie down if you wait for her to retire! Of course, many things could happen- some practical things might help, she might win the lottery and retire early, etc etc. Maybe give yourself a deadline, you have written here how it affects you – do another letter in say November this year describing how things have changed, or not changed, and whether you feel the work environment is more tolerable or not. Best of luck to you!

    2. New Jack Karyn*

      She certainly can be a great teacher. It’s easy to globalize things when we look at someone else, but we actually compartmentalize in interesting ways. Someone can be very skilled at managing all the things that feed directly into student learning (lesson plans, assignments, grading & returning papers, pacing curriculum, etc.) and very unskilled at all the other moving parts of being a teacher.

  73. Goody*

    Things that help for ADHD me and will probably be helpful for OP and Boss:
    – Tile tracking devices on key rings, and in wallets, car, and tote bags
    – A dedicated “landing pad” for keys, wallets, facemasks, etc right inside my front door (Boss could set up something similar on her desk, a filing cabinet, whatever she has in her workspace)
    – Google calendar for appointments (although I must admit there’s still gaps here, mostly from scheduling something verbally)

    I agree that this should not be part of OP’s job. An executive assistant or maybe even an organizational coach could be brought in to get Boss set up and comfortable with these changes.
    And for the keys, a second (or even third) set should be made that Boss can’t access, including Tiles on those rings just in case. And multiple people should use the tracking app.

    Good luck!!!

  74. Rebecca Stewart*

    Regardless of why she is the way she is, as someone who has executive function issues and has lived with people with them and raised people with them…. All you can do is to protect yourself from the consequences of her issues. Make extra keys. Don’t assume she will remember anything. Follow up on things. Several times.
    At a certain point, as someone with these issues, you just hit bottom and realize This Is Not Working For Me. And then you’re open to diagnoses and therapy and meds and learning different coping strategies. But you cannot get someone to that point where they will cooperate in learning new ways to function until they are at the point that they’re ready to do it. In that aspect it is a lot like dealing with an addiction, cause you can’t make someone be sober, either.

  75. Red5*

    Like many others, I’m lost trying to understand how getting her coat zipper stuck equals no one can leave until it’s unstuck. I wonder how much of this problem-solving the OP takes on that maybe she just doesn’t have to? Maybe just try treating the boss like a competent adult (whether she is or isn’t) and letting her know you trust her to fix her problem(s)? For the coat jacket scenario: “Oh, I’m sure you’ll figure out how to get your zipper unstuck. I’m just going to squeeze around you so I can get going.” For the lost parking ticket: “I hate it when I misplace my parking ticket! Would you mind moving aside while you look for it so I can pay and get through? I have an appointment I can’t be late for.” When she’s misplaced something that you don’t need: “I haven’t seen the supply closet key, but I’ll keep my eye out for it!” How much can you cheerfully tell your boss you have faith she’ll figure it out and then disengage? Good luck!

    1. New Jack Karyn*

      In re: the zipper. They were on their way to an off-campus meeting or training or some such, probably carpooling with the Boss as driver.

  76. Beautiful, talented, brilliant, powerful musk-ox*

    I would like to provide a little perspective from someone who struggles with this. I was diagnosed with ADHD as an adult and we’re still trying to figure out which medication is best for me. I HATE that I’m like this. I feel immense guilt if I space on a meeting or lose something important. It is a frustrating state of existence and finding systems that work with my particular brain has been a seemingly never-ending cycle of trial and error.

    I know my own feelings about the matter don’t change the effects that my issues have on others. The suggestion about viewing her as amusingly bumbling honestly stings a bit because this sort of thing can feel so defeating and exhausting (I understand that the suggestion is for the sake of LW’s sanity and I get it; I just also know how frustrating having your own brain betray you is and having that considered “bumbling” feels…uh…not great). It’s hard to know what the person is attempting to handle under the surface. Your boss might be trying out various organizational methods only for them to fail a few days in. And if she is, hey, she may finally find a system that works! But it takes time, patience, and effort, and sometimes it seems as if outsiders view the inability to immediately pull a 180 as laziness or lack of care.

    Just my two cents. I obviously have no idea if your boss has the same issues that I have. And I fully understand how disorganization can frustrate those around the person; they’re still in charge of their actions and finding a system that works for them. It can just take awhile to find such a system.

  77. Chilli Heeler*

    OP: a word of caution on the advice to avoid frustration by appreciating the comedy:

    Like your boss, I’m frequently forgetful and bumbling, and I HATE this about myself. I find it extremely embarrassing, and I work very, VERY hard to combat this tendency. I don’t want a reputation as a screw-up, even if (maybe especially if) it’s a “lovable, wacky, hilarious” screw-up. So when I do make a mistake, you can trust that I find it 10 times more annoying and frustrating than anyone else does.

    But I’ve also learned that if I show how upset I actually am, it only draws more attention to my mistake. So if it’s not an error with serious consequences (like some of the examples you gave), I may make a little joke of it, or treat it like a sitcom-esque situation. Again, this does not mean I actually find it funny; it means I am trying to present myself as a responsible, competent person who has the occasional mishap and doesn’t get ruffled by it.

    If someone laughs WITH me about my mistake, that’s fine. That means they’re taking my cue that this is not a big deal, and will probably forget about it before I do. If someone laughs AT me – e.g. laughing at something I’m taking seriously, or recounting it as a story to entertain people who weren’t there – that’s AWFUL.

    Clearly, your boss already has a reputation as a screw-up, so that ship has sailed. So if seeing the funny side, a la “oh, silly Boss; there she goes again”, helps you deal with the annoyance, then great. But please do your best to keep those thoughts to yourself and not joke about it with others. And definitely don’t joke about it with your boss, even as a gentle ribbing, and even if she laughs along when others do this. I always laugh along. I never find it funny.

    My suggestion is instead of viewing her mistakes as comedy, you try to view them with empathy. Imagine how you would feel making that mistake, after a lifetime of such mistakes, and how you would like others to respond. I appreciate when my mistakes are treated with patience and compassion, followed by a quick trip down the memory hole. And if the mistake is too serious to just forget about, please know that reprimands are neither helpful nor necessary. I’m already shaming myself more than you ever could. Instead, I just want focus on how to fix it, and how to prevent it in the future. Again, patience and compassion are the best I can hope for.

    1. Budgie Buddy*

      This is a good point – Boss may be the type to lean into the Bumbler role because of the positive affirmations it elicits (“It’s not a big deal; everyone loves you; let us drop everything to help you”), or she may be even more frustrated than everyone else and would rather be given a moment of privacy to sort her stuff out without inconveniencing everyone. In both cases the response is the same – de-escalate and take attention off boss’s mistakes.

  78. Monica Roscoe*

    Why does her losing a ticket or having her zipper stuck require other people to stay later? Can you not leave her wrangling her zipper? Or, in the lost ticket case, why didn’t she pull over so other could get around her?

    1. Rusty Shackelford*

      Yes, it sounds like there’s a lot of… I don’t know what to call it. Coddling isn’t the right word, but just… inability to leave her to deal with the problem herself? Why would people wait 30 minutes behind her instead of requesting that she move? What about people who *didn’t* work with you who were still stuck behind her?

  79. theletter*

    I think a lot of this comes down to the job duties of the ‘head teacher’ role – is she the owner/founder/manager of this organization? If that’s the case, the org has come to the point where getting an EA with some IT skills at the very least, and it sounds like she has very much earned that privilege both in the work she’s done and the organizational work she doesn’t have the bandwidth for.

    If she’s more of a departmental head, then a lot of same things apply – and why she would be in the position of sole key holder, sole paperwork manager with IT duties, transportation manager, and not have/not be able to use calendar reminders? Who (above her) dumped that work on her?

    But I think a lot of this just needs to be tackled as it comes – lost keys should be replaced with numbered keypads, or app-enabled keypads, or spare keys being held by facilities managers. As for the supply closet – in our app-enabled world, how concerned are we that someone will steal our post its? Can someone else manage the safe-keeping of the scientific calculators?

    Is the lost paperwork the result of a lack of IT resources? or a lack of IT understanding? or a consequence of an large, open office that hasn’t had a re-org/clean-out in the past five years?

    As for the missed meetings, that’s usually one of two things – calendar alerts that aren’t working, or the state of being so popular/important/heads-down that no amount of calendar alerts would make a difference. There’s people who just haven’t set up calendar alerts yet, and there’s people who are basically The Prince Of The Show from Monday-Friday, and have to have handlers. Is she (or should she be) the bride at a big wedding, desperately in need of a coordinator? If she’s the bride, someone (hopefully a professional admin) is going to have to be the coordinator who can extract her from low-priority-but-high-energy-suck situations and send her to the high-priority meetings/tasks.

    While there’s a lot of comments that emphasize not becoming the assistant, there’s a lot in the original letter that speaks to a tiny, non-profit, highly potent but small budget outfit. Ultimately, you can work towards growing the organization (hiring more people, which increases the budget needs, which then requires more funding, which requires hiring more people, and la-di-da, you’re not a small organization anymore) or you can work towards growing your own skills, which means wearing more hats and taking on more side work until she’s able to pass the leadership torch to you completely.

    Ultimately, one or the other is going to have to happen before she retires.

    while you contemplate the available career paths, there’s probably some things you can do right away that would actually just be a kindness, rather than putting you in an assistant position – check and make sure her calendar alerts are working correctly. Suggest and/or implement a solution to the lost keys problem. Make a note of the parking pass placement, or suggest outsourcing transportation duties. The lost paperwork situation should inspire five whys or a root-cause analysis session, and there should be iterative action steps coming out of that for everyone involved.

    Don’t make her struggle for longer than a minute with her coat! Ask if she’d like a hand. If it happens a lot, maybe it’s the coat that’s a problem. If you just saw a coat in her favorite color for sale at TJ Maxx, she might find that interesting.

  80. Gouda*

    There is a lot of advice here that’s outside the norms of an educational setting — it looks like this is a preschool or other setting without a dedicated “principal” who would have an admin assistant in charge of things like keys and documents. If this is a head teacher/assistant teacher dynamic… it’s not your job, exactly, to help them be organized, but it is your job to help your classroom be organized, and sometimes that involves picking up some slack for the other person.

  81. e271828*

    This much chaos, particularly if it’s getting worse, cannot be good for the teaching environment, which is already stressful. LW, you need to start tracking how many times this person is disrupting the workflow around her. It looks like classic “missing stair” influence, where everyone is (mal)adjusting their behavior to accommodate someone’s distorting, negative effect on the group because no one wants to confront them about it. The students you serve deserve the best efforts of the staff, not “comedy gold,” and the faculty don’t deserve to waste time on ghosted meetings, inconsiderate parking queues, or zipper hostage situations.

    I’m wondering how many students didn’t reapply after their applications were lost.

  82. Radical Edward*

    I’m of two minds about this situation. On one hand, I agree that reframing as comedy gold is helpful to prevent mountains being made out of molehills (I like the idea of a weekly share in an anonymized blog or with friends over coffee). On the other hand, the story of the lost PII made me gasp audibly at my screen! That’s serious business, and in my opinion it’s the sort of thing that everyone at your place of work has a responsibility to try and mitigate *if they’re aware that it happens* regardless of individual job descriptions.

    I have experience working in multiple countries with very strict laws and workplace regulations governing the safety of personal information. The situation OP describes would have gotten my boss severely reprimanded, if not demoted or fired (it would have depended on the relative size of the loss and the prestige of the client). In a school setting the repercussions would have been worse, honestly.

    It sounds like you might need to take a hard look at real vs perceived responsibilities at your workplace – because no amount of ‘that’s not in my job description’ will help you if something goes pear-shaped and public perception doesn’t agree. I have had to adjust my own willingness to take on this kind of extraneous PA work in the past, simply to cover my own ass – and it was worth it (for me), because I kept both my job AND my reputation intact. The fact that my boss came to rely on me for things that shouldn’t have been my responsibility in the first place was just an unintentional side effect. They weren’t going anywhere, and I wasn’t willing to suffer the consequences of their preventable mistakes while I was working under them.

    TL; DR you might want to consider separating these incidents into Personal and Professional columns, and strategically intervene in Professional ones where it makes sense to do so.

  83. Shangrila*

    It reads to me like the boss is being infantilized and enabled. Although, I once had a boss who would go through the roof if anyone left the office before her, as she felt she her work needs required instant tending and seemed to enjoy being doted on. No one liked her.

  84. moneypenny*

    I am married to someone with ADHD so this letter rings particularly true for me. Rather than cruise-direct her life, which is the path of least resistance for her, offer to help her set reminders in her phone. Provide her a little bin to put papers she may need, etc. enable her to help herself. The more someone else is responsible for her, the absolute less responsibility she’ll have to take. If you choose to help her in these days, help and then back away. It’s up to her from then on to manage her brain. Might she have ADHD? Could be worth finding out.

  85. Klem*

    Agree with finding the humor! I’ve been the assistant to someone just like that. How do you remind someone not to lose the company credit card, or not to leave all their chargers in a hotel room, or their wallet by the pool? The letter made me laugh out loud remembering my time with my former brilliant-but-hopeless boss. It was a bit of extra work, but she never, ever blamed anyone but herself and was grateful when I started managing her, to the extent I could anticipate what might come next :)

  86. Bucky Barnes*

    I feel like this is so similar to my situation except instead of bumbling, I have a procrastinator who just this morning told me to not let them forget to do something today. I am not their assistant and I work with them more closely than some of my coworkers.

    I’ll be thinking about this response a lot.

  87. Small town problems*

    I’ve had two direct bosses and one grand boss that could be described like this, and I could also be described like this somewhat.

    How close is this person to retiring? That might give you a way to reframe, if you can deal with it for X years.

    I lose my keys a lot, and those apple key tags are the best thing I have ever spent $30 on. I will say that all of the people I mentioned above would have been helped by these too, but one wouldn’t have been able to figure it out or remembered how to use it / that they had it.

    Sometimes people just kind of bumble and are neurotic, sometimes there’s other stuff going on. Doesn’t really matter either way.

    I would also say that in a smaller organization especially, a lot of “not my job” becomes your job, and it can get stressful. With any of those bosses, hiring an assistant for them would not be an option, or they had a type of assistant whose job it wasn’t was.

    Disorganized people can be brilliant, but there’s a tax that comes with that. And some things can be funny, but oftentimes its just stressful, and sometimes it gets worse, especially if the person has to be removed and has been the pillar of the organization.

    I would recommend leaving.

  88. OP*

    Re: the zipper thing. She was our ride to a certain location, with another car following. We obviously couldn’t leave without her.

    I have to admit to laughing at the thought of her blocking the doorway while we all piled up behind, as some commentators suggested!

    1. Rusty Shackelford*

      I’m still confused. Was her zipper caught on furniture or something, so she couldn’t leave?

      1. Asenath*

        I’d guess she was either partially unclothed, or not ready for winter weather due to the zipper malfunction. Until I finally got fed up and took it to a tailor, I had a nearly new outdoor jacket with a zipper which very frequently malfunctioned in a way that left the jacket open, except for where it was held together by the slider, as it would merrily unzip as soon as it zipped. And it was a royal pain to get the zipper working again so that I could close the front of my jacket.

        1. Rusty Shackelford*

          But that would mean people waited 15 minutes because she couldn’t close her coat, which is insane unless they were at an Arctic research site.

      2. Shangrila*

        Seriously. 15 minutes is a long time to be fiddling with a zipper while everyone waits. And waits. And waits. And waits. After 30-60 seconds, most people would just say eff it and get going, right?

        If I was stuck, I would probably leave my coat after 5-8 minutes, unless I risked dying of exposure.

        It sounds either like a power play or someone who is really tuned out…

  89. Clare*

    Apologies if I’m repeating a thread however has illness been considered? Some of the things OP describes could link to a level of cognitive degeneration. That could be why the HT is seeking additional support? I may be completely wrong however that occurred to me

  90. wobbly*

    Is it your job to figure out how accommodate what might be any number of disabilities? No, it is not. Would it be kind to do so? Yes it would. How much time would it take, really, to do the one-time tasks of making sure that spare keys for everything are on-site and setting up a joint calendar to which all meetings will be added and which will ping her phone to remind her? How much grace would it take empathy to someone when they are in the embarrassing position of getting their zipper stuck or forgeting their parking ticket?

    Agreed that no armchair diagnoses are apt, but I do hope that those who have known boss longer have noted and spoken up if any of this is new or has gotten progressively worse. Sometimes coworkers are the ones in the best position to notice memory declines due to age or illness, and it’s a kindness to encourage someone to see a doctor when that happens.

  91. KW*

    I know the comments prohibit armchair diagnosis, and I agree. But there’s any way to tactfully urge your colleague to visit their physician for a cognitive assessment, this might be in their interest.

  92. Ancient Llama*

    Came here to say Piglet is getting a bad rep, watch Piglet’s Big Movie. I also was thinking Columbo, who always seemed bumbling but actually had a lot of experience and “solved every case.”
    I’m sure I’d be frustrated, and agree not to take on some task. But we all have strengths AND weaknesses, and a good team strengthens each other by filling in each other’s gaps. Is there something she provides that fills a gap you have? I always like when Allison reframes a situation, and that might work here.
    Plus several suggestions others made for tech solutions and backups that would benefit everyone.
    But ultimately you need to make the choice for yourself like AAM suggests.

  93. Bibliotechgeek*

    I’ll admit, when I saw this title of this query, I was afraid it might be about me! I am the bumbling boss at times and it’s pretty embarrassing. But perhaps I can share some perspective from her side? For me, it’s that I have so very much going on, way more than any of the other employees. I try really hard to be organized, but occasionally I forget to put something on my calendar or even forget to check my calendar altogether. I’m m the director of a small nonprofit, so hiring an assistant is financially out of the question. My staff have taken to reminding me to check my schedule, to put things on my calendar, or asking me if I remember I have certain upcoming meetings and honestly it is so helpful to me. I’ve often wondered if they resent me for my scatterbrained nature, but they seem good natured about it. I try to make sure I thank them, and regularly acknowledge the help they give me in this regard. And I also am consciously working on improving this. I wonder if OP would be willing to try and help her boss develop some organizational skills? Not as a long term measure, but as a teaching moment? Or find some Continuing Education opportunities that teach this skill and suggest them to her boss?

  94. Cyclopath*

    Scatterbrain teacher to

    The fact that she is asking you to do these things gives you an opportunity. This is where you can make suggestions for how these can be solved without you doing things that are not your job.

    I think an assistant who specializes in scatterbrained people is the best way to go. There are virtual assistants who specialize like this, and the good ones can come up with systemic solutions.

    In terms of practical solutions for the problems you mentioned:

    More than one person should have a key. But I think the best solution is to put locks on every door that have digital codes that can be used by people who don’t have keys.

    Why did her zipper being stuck cause a 15 minute delay for everybody? Was she stuck to the only exit door? Think about this. What would need to be in place so that next time, her getting her zipper stuck does not cause others these types of problems?

    The parking lot should be rearranged, so that if someone realizes they don’t have their parking slip, they’re not blocking the exit, and can pull away to let others out. This is a fire hazard.

    An assistant who is experienced with scatterbrained people, or even a one-time consultant, could take a look at your letter and make it suggestions about things to put in place in your school so that her problems do not become other peoples’ problems.

    Is you have the type of relationship where you can suggest specific things to her, I’m going to list the things I do. I am a scatterbrained person, and I used to cause all sorts of problems for myself and others. These are the things I have put in place that have really minimized the danger and inconvenience I caused myself and others.

    I put locks on the doors with digital codes that can be used if someone doesn’t have a key.

    Every physical object has a place where it lives. My priority, whenever I’m using a physical object, is to get it back to the place where it lives immediately after I’m done.

    Every physical object has a back up. Multiple keys, multiple pairs of scissors.

    Everything that can be made electronic, is electronic. I scan everything in as soon as it arrives. You guys really should go to electronic applications, and someone’s job should be to scan in hard copies immediately.

    I got a phone, watch, and computer, that sync calendars. This can easily be done with Google calendar. The most important things I do whenever a meeting is scheduled is put it into the calendar and schedule alarms. My rule is that whenever there is an alarm, I check the phone or watch to see what I am supposed to be doing. I have three different things beeping at me for alarms. This is also something a virtual assistant could do, call her before every meeting.

    My phone is backed up to the cloud, and I have a back up physical phone that lives somewhere specific, if I lose my phone, I can immediately restore and start using the new phone.

    My priority is not inconveniencing others. If my zipper is stuck, I do everything I can to make sure this does not cause problems. If I’m supposed to lead a meeting and I can’t take my jacket off, I still lead the meeting. If I can’t find my parking slip, I pull off to let others out.

  95. Rue*

    anyone who ran an organisation that size in the private sector would have an assistant, she should have an assistent. I am mindful of armchair diagnosing but remember that there are plenty of reasons this could be happening beyond thoughtlessness.

  96. CoveredinBees*

    If my mom weren’t retired, I would wonder if OP’s boss was my mother. While she doesn’t have ADHD, my mom has found ADHD coaching websites to have some particularly useful information. Only because your boss has asked you to help out do I think you have standing to look into it and offer some resources if you think they’d be genuinely helpful. A lot of what they list could be useful for non-ADHD people, myself included. That said, you know the relationship best so it might not be well-received. Or you simply don’t want to get that involved in it. Both are totally understandable. This is more of a half-measure to maybe help the issue without getting roped into managing it.

  97. Zahra*

    Whether or not she has any kind of diagnosis, the behaviors in OP’s letter match behaviors common in ADHD people. So, OP *and* head teacher would benefit from looking at the strategies ADHD people have said to be helpful and/or effective. Throw technology at it is my favorite one: calendar (with appointment start time that are 15-30 minutes earlier than actual start time for those appointments where I need to go elsewhere), reminders, alarms (I have one for trash/recycling/compost pickup days, for example), etc.

  98. AMW*

    Your boss and I are very similar…if she ever finds something that works for her, please let me know about it too!

  99. Jesshereforthecomments*

    Isn’t losing a bunch of documents with personal info a compliance issue? That would not go over well where I work. In fact, people get fired for that.

    I agree that you need to reframe this to help ease your own frustration, but you also need to keep a running list of things that are legal & compliance violations, as well as safety (missing keys) and efficiency issues that are dragging down morale and ability to get work done. There’s got to be someone above her to report to if needed?

    Lastly, within reason per your job description and role – don’t solve problems she creates or clean up her messes. She should be experiencing the consequences of her chaos. And are you guys getting paid OT when her stuck zipper or other antics stop you from leaving on time? Maybe you should…

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