what are the most ridiculous requests you’ve ever seen made of assistants?

by Alison Green on April 16, 2026

Next Wednesday is Administrative Professionals Day, so let’s talk about the weirdest or most ridiculous requests you’ve ever seen made of assistants. To start us off, here are a few that have been shared here in the past:

•  “In my first job out of college, my boss asked me to dry his shoes, which got wet in the rain. He plunked them down on my desk and said he needed them dry for a meeting in 15 minutes. I’m still not sure what he expected me to do because at a certain point, only time can dry things. The hard, unabsorbent paper towels from the bathroom weren’t going to cut it. I was a receptionist but in no way a personal assistant.”

•  “I once had an office-assistant-type job at a wedding and event venue. Turns out, my MOST ESSENTIAL duty, which was not listed in the job description and did not come up in the interviews, was to make the GM’s meal-replacement shake at lunch and then check on him every half hour to see if he finished it, remind him to finish it if he hadn’t yet, then wash the shake container and return it exactly to the correct spot in the cabinet. Other work needed doing? If it was in the afternoon, it wasn’t getting done.”

•  “We had a new associate one year who, come to find out, had grown up very well-off and was accustomed to being waited on, and then expected the support staff at the firm to take up where their household staff left off. I don’t even think they were a month in when their practice group chair came and had a chat with them about the fact that their administrative assistant was, in fact, not their personal assistant. For example, the AA would not be picking up any coffee order on her way in (much less the ridiculous one the new associate wanted), nor would she be getting their lunch every day. We also don’t ask our assistant, who sits further from the supply closet than they did, to get up and get them a single pen or two file folders, especially when the AA is working on a deadline filings or client billing. First year associates were generally expected to walk themselves the 10 feet to the supply closet and get their own stuff. The AA would also not be placing all of the first year’s calls, picking up their dry cleaning, nor getting their personal credit card billing issue straightened out.”

Please share your own in the comments.

{ 162 comments }

{ 162 comments… read them below or add one }

  1. Medium Sized Manager*

    We had a new office manager (hired from within the existing org) who was technically junior seniority wise to some other managers but not responsible for being anybody’s specific admin. They decided that she was responsible for ordering their lunches every day and dealing with the delivery drivers. They were just toooo busy walking around and talking about how busy they were/spending hours in a meeting room eating said lunches and being soooo busy. The COO asked less of her!

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  2. Assistant*

    My time has come.

    The dumbest request I’ve ever gotten as an assistant: going out every morning to buy multiple avocados for the CEO to choose from. After she chose her preferred avocado, I had to slice it in half, put cayenne pepper on it, and serve it to her on a plate. With chopsticks.

    She once asked me to put the whole avocado setup on a paper plate in a ziploc bag so she could eat while driving to the Hamptons (again– with chopsticks). I made the more senior assistant handle that one as I didn’t want to be liable in case her dumb ass did something on the road.

    (I’m sure I’ll think of others, but this is the prime example of Dumb Shit Asked of Me in the Course of My Job)

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      4. FormerAssist*

        I was really expecting it to say “After she chose her preferred avocado, I had to return the others to the store” and I was already feeling the 2nd hand embarrassment lol.

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    3. Susan Calvin*

      … trying to figure out how to eat a sliced in half, and not otherwise prepared avocado with chopsticks is going to haunt me for the rest of my life.

      I feel like I’m stuck on a puzzle in one of these old point & click adventure games and applying the “use X with Y” prompt to random inventory items in desperation!

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        1. MigraineMonth*

          I’m certain that the incident report would have explained the role the cayenne pepper played in the fatal crash.

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          1. RLC*

            I worked with volunteer firefighters, EMTs, and first responders during my career and “person eating avocados with chopsticks whilst driving and causing a crash” would be fodder for MANY cautionary tales to be later told by those who responded to the incident.

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        1. PurpleShark*

          I don’t know, avocado is kind of slimy and eating it with chopsticks would be challenging. Then again maybe she had a driver?

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          1. Another One*

            That was my thought.

            I suppose she could have been on the Jitney with the rest of the Hamptons plebeians.

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      3. B’Elanna*

        In fairness, I’m sure Guybrush Threepwood (mighty pirate!) would think of something very clever to do with avocado + cayenne + chopsticks.

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      4. Fungus Among Us*

        >Eat avocado with chopsticks.

        You can’t eat the avocado with the chopsticks.

        >Eat avocado with one chopstick.

        You stab the avocado with one chopstick. It slides all the way down and drops into your lap. You lose control of your car and end up upside down in a ditch. It is now pitch black. You are likely to be eaten by a grue.

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      5. Lady Lessa*

        As far as I am concerned, the pepper might make the avocado edible, but with chop sticks? I can’t imagine how they could be used. (as you can tell I am glad to give away any and all avocados that someone else wants. The texture bothers me, and they don’t seem to have much taste)

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        1. Hannah Lee*

          I’m picturing some variation of what people do to avocado pits with toothpicks, when the are trying to root them in a glass of water.

          Stab the avocado half all the way through with one chopstick, and then stab it at an angle with the other, then use the 2 chopsticks together to maneuver it close to your mouth to take a bite.

          I have zero idea how that would be done while driving to the Hamptons, unless ‘driving to the Hamptons’ actually means ‘have a 2nd assistant drive you to the Hamptons while you sit in the back seat eating your half of peppered avocado with chopsticks’

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        2. Unauthorized Plants*

          I’m imagining that the CEO had a very odd preference for underripe avocado, but while that resolves the chop sticks quandary it raises other questions (I will take ALLL your avocados, I adore them).

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    4. Seeking Second Childhood*

      Appropps of nothing, thank you for this thread… it’s saved my ADHD self from the rotting avocados I’d set to ripen too long ago.

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    5. Caliphate*

      Was your boss in fact Miranda Priestly?? Because what.*

      *Although I really want an avocado with tajin right now.

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  3. Alton Brown's Evil Twin*

    A good friend of mine started as an assistant and then worked her way into HR. In her early days, she was assistant to rather loud VP. When he got really pissed off at something he would throw his PBX phone against the wall – smashing the phone and often damaging the drywall. She had to deal with facilities and the landlord, and never really told them how the phone & wall came to be broken.

    This happened at least once every nine months. Sometimes she was in his office when it happened and the phone whizzed by a few feet from her head. She always had an extra phone in her desk so she could do a straight swap. He never apologized, but he did mellow out significantly by the time I went to work there. Her ability to maintain a poker face during these tantrums was legendary.

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  5. v*

    At an engineering firm, I was the receptionist, admin, and somehow also accounts receivable. Because I had heard “we were going to hire three people but you were so great that we’re going to give you a couple thousand more a year to do all three jobs,” and was young enough to be flattered.

    One of the engineers was younger than me and very high-handed. One night right at five o’clock he popped up at my desk and said “I’m going to need you to stay late to do this MASSIVE photocopying job that will take a few hours. But I’ll stay to keep you company.”

    I told him that he could do his own damn last-minute after hours photocopying because I had a life and plans and he didn’t ask nicely. He was actually a much nicer coworker after that, to his credit.

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  6. ATW*

    I was an assistant at an art gallery. One of our clients rented art from us for home stagings. One day, the client tells us that her payment to us was returned to her and asked us why. We had no idea why because we didn’t return it. My boss wanted me to call the bank and ask why. My boss didn’t even give me account details or anything. I just had a copy of the bank statement that our client had given us. Well, the bank can’t tell me that information because I’m not the account holder. My boss keeps asking me to do this a few times and I repeat that the bank can’t tell me this info because I’m not the account holder. Our client had to contact their bank or my boss had to contact our bank. Eventually, our client had to call their bank and it was discovered that it was the client’s bank that did this. The client’s bank thought it was a fraudulent transaction and refunded the money to the client.

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  7. Parker*

    When my boss couldn’t park in her preferred spot in the parking garage, she’d leave her car in the loading dock, come inside, and throw her keys on the reception desk. I was supposed to go park her car for her and then, of course, retrieve it again at the end of the day since she didn’t know where it was in the garage.

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    1. DEJ*

      I know of a CEO that did park in the loading dock and an assistant would have to turn the car around so that the CEO didn’t have to back out at the end of the workday.

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  8. Peanut Hamper*

    I was not an administrative assistant, but the boss was a nepo baby who considered everybody there his assistant.

    Every once in a while he would drop cash on my desk and tell me to go buy beer and goodies so we could have a beer Friday.

    He would also call me into his office, pull a $50 bill out of his wallet and tell me to go pick up a bottle of bourbon for him from the liquor store down the road. This was usually in the afternoon, but sometimes happened at ten in the morning.

    No, I don’t work there any more.

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  9. Darcy Mae*

    This might be stirring a hornet’s nest, but here goes –

    In some circumstances, an AA being responsible for coffee and lunches is not an unreasonable demand.

    This is obviously office dependent – if there are six AA’s in the office and this is not an office norm for the position, it’s tone deaf for someone to start demanding that an AA provide this service. However, I don’t think it’s an out of line request for an AA that supports ONE exec to handle this kind of thing, particularly if they are non-exempt employee paid hourly. I know someone who worked for years under this kind of situation; both she and her boss (company owner) had the understanding that some strange requests would come her way under the heading of “take care of this for me so I can handle business matters”. My friend dealt with all kinds of personal matters for her boss, up to and including picking up sick kids from daycare. Friend’s attitude was “I’m being paid hourly whether I’m picking up coffee or reviewing timesheets. When my 40 hours are up, I go home or get overtime.”

    I will say that this friend would have told her boss to pound sand had they presented her with a pair of wet shoes, however!

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    1. umami*

      I could see ordering lunch in if the boss doesn’t get a chance to take a lunch, but … maybe I’m old, but the coffee thing seems more like a movie schtick. Are admins really expected to pick up coffee orders on the regular? I could see if coffee isn’t offered onsite and it’s needed for a meeting or something, but otherwise this seems really strange to me!

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      1. Parker*

        I was an office admin from 2011 – 2017 at two different places, and I made and picked up lots of breakfast, coffee, and lunch orders. I regularly made coffee and tea in the office too.

        I don’t know what things look like ten years later, but I imagine they’re not that different.

        Honestly, I didn’t mind. I got paid for my time, got a nice break from my desk, and usually got my own meal or drink order covered for the trouble. It was cheaper and quicker to pay me instead of paying delivery people.

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        1. AVP*

          I was a few years ahead of you, but same! Loooved taking a little walk around town, grocery shopping for office snacks at the fancy cheese store, taking lunch orders pre-app, all of that.

          The one that surprised me most was that my boss lived in the same building as our office, and had all of his personal and business mail delivered to the same box. My first week, I dutifully sifted out anything that looked personal and left it on his desk for him to open. I got called in for sort of a formal talk with my manager who said actually, he doesn’t have any personal mail, literally anything that comes in is yours to deal with. If it’s a card from his mom or an invite to a wedding please make sure he sees it, but the rest is all yours. Including his personal financial statements, medical tests, his kids’ college bills and grades, etc!

          (I was fine with this as a job duty but thought it was wild that they’d give a random 22yo so much access and trust.)

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      2. Teaandviolets*

        As an office manager/owner’s admin assistant in my early 20s I regularly went to the 7-11 up the street from us to fill his two bucket-sized cups with diet coke and pick up pastries. He paid for me to get a coffee and pastry as well, and I got to take his very sweet dog along for the ride so I never minded a bit.

        Now when he wanted me to draft his emails to his match.com connections though, that was a slightly different story!

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    2. lunchtime caller*

      totally, coffee and lunch is a very normal request for a high powered executive since they’re usually in back to back commitments and we can’t have them passing away from hunger! And when I’m being paid six figures to do it, I don’t mind in the slightest. But if a junior person I also support started asking for that when their time is less valuable than mine in terms of dollars and it takes away from me supporting my top executive, it would be completely wild.

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    3. Pay no attention...*

      I agree but the line can get pretty gray quickly. We had a ED who would ask his administrative assistant to go to the store to pick up toothpaste for him or eyeglass wipes…and that sounds reasonable if he needs these in a professional capacity, right? But when it got to be doing his entire personal grocery shopping, that’s outrageous. Picking up sick kids should be too far too — that gets into a ton of liability problems if there was an accident for both the AA and the employer… is this workman’s comp? would the company insurance cover it? Is the AA on her own and possibly going to be sued personally? Would the company get sued by the other driver since this was a work requirement?

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      2. Unpopular_Opinion*

        Are there any job descriptions that don’t include the all encompassing, “other duties as required”?

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    5. Betty*

      Former admin here. Sorry, there is no reason to have to make someone coffee or fetch personal lunches in the year 2026. Ordering catering for meetings and events, fine. But I refused to fetch someone’s food for there normal meal/coffee times. It’s an incredibly outdated practice that I successfully pushed back against for 15 years.

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      1. Annie2*

        Really? I have definitely asked my assistant to grab me food at lunch, but only on the odd occasion where truly I will not get to eat unless it shows up at my desk because I’m handling something extremely urgent. I always tell her to get something for herself, too (on me, obviously). Asked nicely and as part of an ongoing relationship of reciprocity and respect (I am usually the one doing coffee runs and bringing back her chai latté with oat milk) I really don’t see an issue with this.

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    6. Goober*

      If you’re told in the interview that those are duties of the position, not matter how ridiculous they seem (go read about some of the things personal assistance have to do for movie stars), then you have no one to blame but yourself because you agreed to it.

      If, on the other hand, you’re hired to do filing and paperwork, with no indication of that kind of personal assistant duties, that’s on the company for being dishonest.

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      1. MigraineMonth*

        It also needs to be a reasonable level of support for the number of people you support. If you’re supporting one exec and aren’t snowed under with other duties, maybe it makes sense to pick up their coffee and lunch and deliver it to their private office.

        If you’re supporting 15 people on a lower tier, that wouldn’t be reasonable. Maybe you put in a catering order or make the first pot of drip coffee, but personalized service doesn’t scale.

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    7. Seeking Second Childhood*

      If she’s asked to pick up coffee *on the way in* chances are she’s not clocked in yet. Off the clock or off the relevant insurance plan are both a hard no.

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  10. ticktick*

    My boss made her long-suffering assistant read through long legal agreements line by line, to compare what we had sent to the customer with what the customer sent back to us, because she neither trusted the redlines that the customer had made, nor the Compare function in Word. This was done using a ruler as a guide on two physical printouts of the document.

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    1. Abogado Avocado*

      Sorry, but I don’t find this out of line. This is legitimate work and this is how it was done before the age of computers. As has been said above, it’s work, the AA is being paid for it, and once 40 hours is up, they go home or get overtime.

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      1. Thegreatprevaricator*

        Because there are computers now and it add hours to the task? Because it’s weirdly prescriptive?

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      2. Strive to Excel*

        I’m pretty sure this is the Word equivalent of printing a 20-page Excel sheet and using a calculator to do the sums instead of trusting the SUM function at the bottom. If this was done in 2000? I can see it. But starting by about 2015 or so this would be very silly. Apart from it being the least efficient possible way to do it with the tools available, it’s also the most error-prone!

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      3. Anonymous*

        Nope. I do this kind of review all day every day, and this is absolutely an absurd request. There’s a line between old-school and just being abusive in the guise of thoroughness , and this is well past that.

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        1. Unpopular_Opinion*

          Well, to be fair, we don’t know what year this was taking place in. Tiktik refers to it in the past so….

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  11. cleanmachine*

    I was an AA at a small nonprofit. My regular duties were stocking supplies, scheduling appointments, connecting callers to the right person in the organization, plus “additional duties as assigned”. These included replacing the chains and flappers in toilet tanks, replacing door handles, and once, lugging a 100lb floor cleaning machine up two sets of stairs to get rid of the results of a disastrous art project. I loved that job.

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  12. Red Shirt Alert*

    My second day working for a renowned surgeon & dept. chair (& big muckety muck overall) gave me his wife’s phone number to assist her with her afternoon social in 3 days. (Note: attendees were just her friends and social climbing assets.) I was so shocked, my spine grew unexpectedly and I told him that I was a state employee and would never perform any personal errands for him and certainly not his wife. To his credit, he just said ok and never brought it up again. I actually think he respected me for speaking up and the 4 yrs I worked for him were some of the best in my work life.

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      1. i like hound dogs*

        Ugh yes … I struggle enough with knowing what’s in my realm of responsibilities; this would have stressed me out so much, wondering “am I supposed to do this? Is it valid for him to ask me to do this?”

        Good for you.

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        1. JB (not in Houston)*

          Even in that case, though, the boss is the person who actually asked Red Shirt Alert to do it, so the boss is the problem in that situation.

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    2. Hannah Lee*

      This is from the other side of a situation like that – A friend’s husband at the time (in the 70’s-80’s) worked for a large bank, and was an up-and-comer. It was a common thing for that bank to promote people to different locations as they moved up the ladder, coordinate the relocation process, help the family settle in.

      At one point, he was promoted to from a smaller office in a laid back MidWest locale to Houston, into a position in which he was expected to do a lot of socializing with various country club movers and shakers along with other assorted mucky-mucks. My friend was at the time stay at home mother who was socially adept but never had socialized in that scene.
      One of the things her husband’s assistant was expected to do, as part of her normal job duties, was to take my friend shopping and help her get a new wardrobe for that kind of 1 percent socializing, and coach her on the who’s who of attendees, local customs. And also guide my friend on how to plug in to various foundations, charitable organizations, ladies-who-lunch activities. It was like a 1 on 1 finishing school the assistant was expected to do in addition to all her other Administrative Assistant duties, often after hours.

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  13. tired designer*

    My sister, a photography student, got a job as an assistant for a well-known art photographer. It was meant to be a job as a *photography* assistant, but she was essentially bait-and-switched into being the woman’s personal assistant. I can’t remember exactly when she quit, but it was shortly after the woman made her do her kids’ school project, à la The Devil Wears Prada.

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    1. hypoglycemic rage (she/her)*

      the devil wears prada is the first thing I thought of when I saw this post! I love that movie so much and cannot wait for the 2nd one.

      I am an admin at a law firm, and I would NOT have lasted working under miranda.

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      1. Fungus Among Us*

        I worked for someone who was so eerily similar to Miranda in bearing (and even looked a little like Meryl Streep) that the first time I saw the movie, I spent the entire time feeling like I was still at work. A while after I’d left, an unhappy coworker hosted an office showing of the film on the boss’s birthday and, to everyone’s amusement and perhaps also relief, she didn’t get the reference at all.

        The redeeming grace is that she wasn’t like that intentionally and never asked for anything personal or inappropriate for work – but she delegated in the same detached, flat tone with no further instruction and expected us to make the thing magically happen, no matter how hard or time-consuming the task was.

        (I’ve since come to love the movie and Miranda, but for a while there it was a little fraught.)

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    2. omelet*

      I experienced the low-rent version of this. I was hired as “photographer’s assistant” for one of those old-timey photo places, where you dress up as a cowboy or Victorian lady or whatever.

      The base job was already somewhat ridiculous (involved a lot of lacing corsets, wrangling hoop skirts, and rearranging fake bottles of whiskey). But my boss was also extremely regressive and expected me to do a variety of extra tasks, including but not limited to:
      -Ironing his laundry
      -Shining his shoes
      -Learning close-up magic tricks
      -Listening to his (probably made-up) Vietnam War stories

      He would also regularly tell customers that it was my first day, even after I had been there for well over a year, I think just to humiliate me.

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  14. honeygrim*

    When I worked as a leasing agent for a real estate company, I was briefly assigned to assist one of the property managers. This mainly meant I had to answer any calls for him since he was very busy and was rarely in the building. But it also meant I had to answer calls for him even if he WAS in the building since many of the tenants in his properties caused him a lot of headaches. He had a weird sense of “honesty,” though. So if he didn’t want to talk to someone (as identified by the receptionist who was routing the call), he would step out of his physical office and stand just outside the door so I could then answer the phone and say say “I’m sorry, ‘Bob’ isn’t in his office right now, can I help you?”

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  15. thankful to no longer be her assistant*

    When I was an assistant, my boss made me input every day when Mercury would be in retrograde into her calendar.

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    1. The OG Sleepless*

      That one sort of makes me chuckle. At least it wasn’t very time consuming, or sounds like it wasn’t.

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    4. Unpopular_Opinion*

      Yeah I think I’d have just picked random days and see how it affected her mood or whatever on those days… the Retrograde Placebo Effect.

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  16. see you anon*

    Not the most ridiculous request, but one that consistently baffles me in my current admin role is when folks ask me to call the credit card company (for corporate/work-provided cards) to resolve an issue on their behalf. I understand that they’re busy with their work (I work in healthcare), but I have to explain to them that as the cardholder and account holder, they have to be the one to call as the credit card company doesn’t know (or care) who I am, and therefore won’t talk to me. Again, not the most ridiculous, but I’m always have to take a beat for financial-related requests when I have no authority or delegation on the accounts/cards.

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  17. Georgia Carolyn Mason*

    Right after college, I worked as a department admin at a very prestigious medical school, which included scheduling meetings, setting up and breaking down meeting rooms. Fine. This included ordering and setting out food. Fine. This included throwing away items left in the conference room, bringing leftovers to the break room, wiping tables, etc. Fine. HOWEVER. I wasn’t in the room during lunch, so maybe they replaced the MD/PhD published researchers with animals from the zoo. This would explain the food on the floor, under the table, and on one memorable instance on the wall. Which I was expected to clean up, including once being ordered to crawl under the table to wipe up a blob of tomato sauce. In a skirt and pantyhose. Which I did. (I was 21 y’all.)

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  18. Jane Bingley*

    The EA at my first big job was responsible for preparing lunch for the CEO every day. She cooked it at home the night before and warmed it for him (always on the stove, no microwaves allowed) and served it to him at the same time daily. Every other task on her agenda was dropped for lunch. It took at least an hour a day, between prep and dishes afterwards.

    When I left that company for an EA role, I joked with my boss that I wouldn’t be able to cook his lunch every day. It became a running joke between us.

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    1. zinzarin*

      This–to me–is the winner.

      Even if the groceries are paid for and the EA was paid for their time cooking at home, this is bananapants.

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      1. Unpopular_Opinion*

        Honestly, if the CEO was single and the EA older, I could see it being a “tsk tsk. You need a wholesome meal at lunch. Not that fast food. I’ll start preparing your lunch for you,” kind of thing. Especially if this was 30 or more years ago. I was an AA in 1993 and our Office Manager in charge of all of us, was always fussing over the boss in a sort of maternalistic way.

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        1. Amateur Linguist*

          Yeah, I had a cup noodle almost every day for a while and one of my colleagues did say she didn’t think it was healthy. Given what goes into those things, she was probably right.

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  19. AnanaBanana*

    I worked at a company where the CEO has a tendency to wander, forget mealtimes, and will become hangry or functionally useless. Rather than packing or purchasing food, he expects his assistants to magically divine when he needs to eat and what kind of food is needed. His assistants either have to locate him and feed him, or will send the nearest staff to do so. He is well-connected and generally polite, so they just put up with it. I am baffled that a nearly 50 year old man cannot feed himself… but maybe I shouldn’t be? He’s somehow never held any other kind of job except executive suite.

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    1. The OG Sleepless*

      Meh, I once texted my daughter from bed to get her to let the dog out of my room. I think she was in bed too.

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  21. Fergus*

    I worked at a position as the only Java Software Engineer as a Senior Java Software Engineer for a project for the DOD. I was there for about a year and all of a sudden I was getting orders from the business analyst for things that had nothing to do with Software engineering. I shut that shit down from square one I had no clue why she thought I would do it. It wasn’t my background and I had no experience doing it in the first place. She didn’t like it that I refused and I didn’t care.

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    1. Unpopular_Opinion*

      Yeah, I’m a Senior Cybersecurity Engineer and people will come to me or email me instead of IT Support to ask me to “fix this weird error I’m getting” or “x keeps freezing” etc.. and I’m constantly having to say, “I am NOT a PC technician and that is not a cyber problem; it’s a PC problem. Call the helpdesk.” Although for nicer colleagues, if it’s something I do know, I’ll often tell how to fix it.

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  22. Bunny Girl*

    I used to work at the front desk of a gym with a friend of mine. One day the boss called the five front desk women into a meeting and said that summer that he would like us all to start taking shifts advertising outside the gym. In bikinis. He then went on to say that he didn’t hire any of us for our experience or skills, but because we all “weren’t hard to look at”. A few of the other women seemed fine with it, but my friend and I, who were both a tad older, were fuming. We both quit shortly after.

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    1. NMitford*

      In college, I worked in a bank. They rolled out a new advertising slogan of something like, “Let us show you how good a bank can be” on radio and television. But, then, they handed out salad-plate sized buttons for the tellers (all women) that said, “Let me show you how good I can be.” That lasted one day and then we revolted en mass and refused to wear them one second longer.

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  23. NMitford*

    The maintenance man at a high school where I work was arrested one weekend on drunk driving and couldn’t make bail. So, I was directed to go down to the city jail and see if I could get his key ring because there were literally doors that we could not unlock when school opened that Monday. I was like, “I’m genuinely not sure that that’s how they handle inmate property in jails” and got out of it. Like, was I supposed to sign in as a visitor and then asking him to hand over the keys to me in the visitors room. Seriously.

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    1. A. Lab Rabbit*

      IIRC, they would have confiscated his keys and anything else like that when they locked him up, so you shouldn’t have had to meet with him. (Although this may vary by jurisdiction.) But still? Going down to the police station to get these? That’s something the principal or somebody with some authority should have handled. That was a completely ridiculous request!

      Reply ↓
      1. NMitford*

        Exactly. I admit that my knowledge of jail procedure was entirely based on tv shows, but I just knew that no one was getting those keys until he was released from jail and they handed them back to him.

        Reply ↓
      2. Unpopular_Opinion*

        Also, there should NEVER be ONLY ONE set of keys! That’s just a single point of failure waiting to happen… and it did.

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  24. my new cat is prettier than me*

    I was an Executive Assistant for an extremely wealthy man. He wanted me to make a catalogue of his watch collection. The problem was, I didn’t have access to the watches, just the boxes and some paperwork. No pictures. Most of the paperwork was in French, which I only have elementary knowledge of, and the names of the watches were not listed. Somehow I managed to do it. Shortly after, I was fired via email after I left for the day.

    Reply ↓
    1. Anonymask*

      Unrelated: yay to your username change! I’m always happy when someone invites a new friend into their lives =] Here’s to many wonderful years you will share together, and many more happy memories in addition to those you shared with past pets.

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  25. No Thanks*

    One time my boss told me to pull together the building permits for renovations he was doing on his house (which had several adjacent units he was renting out). Permits were part of my job, but the ones needed for my company’s work were extremely simple and straightforward compared to building permits, which I didn’t understand and absolutely was not qualified to handle.

    I walked into the local building inspector’s office with a disaster of a permit packet, a million questions it was not the inspector’s job to answer, and the knowledge that there were a million more questions I didn’t even know enough to think of. The building inspector was really no-nonsense and frosty with me – until he realized that we both hated my boss, after which we got along great.

    Reply ↓
  26. TessMcGill*

    Sad to say the dumbest thing that was ever asked of our Company Admin was that the admin, who had existing health issues, was asked come in during COVID lockdowns – not for any good reason as our sector was largely non-operational at the time, but rather because the Exec Director was absolutely incapable of doing their own job and needed the admin to be present as a human prop. Our admin, inevitably, became seriously ill with COVID and was hospitalised, and is still suffering long-term effects.

    Having hospitalised the first one, the same ED asked a different admin to update the lead image in the company newsletter no fewer than eight times – a process that took over four hours and went past the end of the working day – before deciding the first option had been the best one after all.

    I wasn’t either of the admins but I left in solidarity shortly after.

    Reply ↓
  27. Queer Anon*

    I was once asked to walk to the other side of a large room (maybe 50′ across) to pick up a small hand-held tool for someone and bring it back over to them. There was no earthly reason they could not have done this themself, they just didn’t want to. (I wasn’t even this person’s assistant, I was a coordinator between departments with an ill-defined list of duties, but this was definitely not one of them.)

    Reply ↓
  28. Wilma Flinstone*

    I was asked to buy a birthday present for my boss’s grandchild. Not ‘pick up a thing I bought’ or ‘go buy this specific toy the kid wants’, but ‘go shopping and select something a kid would like and get it giftwrapped.’ I’d known this boss for 2 weeks. I didn’t know anything about his family, let alone met any of them. I have no kids and have no point of reference to anything kids like.

    It was a temp gig, so I was disinclined to tell him to pound sand. The errand did get me out of the office for the better part of the day, which I considered a win. I told him the line at the wrap station was hella long. (shh!)

    Reply ↓
  29. AnonAnonSir!*

    My first ‘official job’ was under the title of Operations Manager, but was treated more like office assistant/GM’s personal assistant/general dogsbody. I can’t think of the most ridiculous request per say, but I remember the most borderline-illegal one was being told by my General Manager ‘hey Anon, one of your colleagues is applying for a new role and has put me as a reference, write something for me would you?’

    Not only did it feel horribly inappropriate (particularly as she was more senior than me and I hadn’t actually done any work *with* her) but I’m pretty sure the delay that came from me pushing back on this was what led to her not getting the role.

    Reply ↓
    1. Lee Plum*

      “ borderline-illegal one was being told by my General Manager ‘hey Anon, one of your colleagues is applying for a new role and has put me as a reference, write something for me would you?’”

      That is not in the slightest bit illegal, and it’s honestly not even that unusual. You might not have been the right person to make the ask of, but it is pretty common for people who write recommendations to ask somebody else to write it up. It’s one of those annoying tasks that nobody likes to do and so they offload it to someone else. Hell, sometimes they ask the person who needs the recommendation to write their own.
      Now, we can debate whether or not someone should be able to just write a damn recommendation because it’s really not that big of a deal, however, whether or not it’s a big deal to write a recommendation is not the same as saying it’s illegal to ask somebody else to do it and then sign your name on it.

      Reply ↓
      1. Darcy Mae*

        I know an admin that writes up the first draft of performance evaluations for her boss’ direct reports. He does modify the reports before they go out, but he likes his admin to do the first pass since she’s better at knowing/remembering the good/bad things that the employee did in the previous year. The employees receiving the reviews have been known to say “Wow! I didn’t even know you noticed that I did that!”

        Reply ↓
  30. ZombieVsUnicorns*

    My boss asked me to write his sons’ papers more than once less than a dozen. He had three sons.

    I did not, just provided comments and typo corrections.

    When two of the sons started submitting robopapers for me to edit, I did the bare minimum, hoping they’d get caught. They didn’t but I was not going to be an accessory.

    I work as an admin in a law firm so no, this is not within my duties. And I have real work to do.

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  31. CzechMate*

    I once had a boss who had an ongoing legal dispute with a neighbor about a fence. He would come to our shared office space and dictate threatening emails to his neighbor that our admin was supposed to type up and send from his personal email address (it was something like [ownername]thegreek@gmail.com. Also, he was like a fourth-generation American). I do remember one email being along the lines of, “I’LL HAVE YOU KNOW THAT MY LAWYER WILL BE IN TOUCH FORTHWITH WITH ADDITIONAL DOCUMENTATION. YOU MESSED WITH THE WRONG GREEK!”

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  33. AdminProfesh*

    I’ve been an administrative professional for 10 years and, boy, the stories I could tell of disrespect and disregard for the profession as a whole. I am currently Executive Assistant to the President of our organization, and I still have people coming to me to tell me that a faucet is broken in one of our facilities. Like, okay, thanks for telling me, but I’m working on booking a last-minute international trip, planning a 75-person week-long offsite, speaking with corporate consultants on 2-3 executive level initiatives, getting my executive’s taxes paid, and running the company’s 5-year business strategy.

    Reply ↓
    1. Spreadsheet Queen*

      Unless there is a dedicated Ops or Facilities person (that everybody has easy access to knowing they exist and contact information), a facilities problem is totally what people go to an Admin or Receptionist about.

      At my job, I generally go to the Receptionist. She reports directly to our Ops person, but is more accessible. Both our Receptionist and our Ops person would have to be out of office before I’d go to the EA to the President of the company though. I’ll give you that.

      Reply ↓
      1. Amateur Linguist*

        Yup! As receptionists we were employed by our organisation’s facilities and we still classify them as such now we’re part of a dedicated facilities org. It’s much easier to have that sort of arrangement as a receptionist knows the building inside out and back to front. My former colleague even kept a hammer in drawer to repair the pins on the vestibule door hinges.

        As reporting and helpdesk facilities got more sophisticated it became more usual to ask them to raise a job on the system for issues that could wait, but for quick fixes like the door hinges or something like a blocked toilet, we would be the first people to know and would be in more of a position to get someone out quickly than they were.

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  34. InsAnon*

    I was forwarded an email by an underwriter and asked to, “please forward this email to so and so”.

    ….not the sharpest crayon in the box today are we?

    Reply ↓
  35. I've been here the whole time*

    I was a temp, doing admin work when I was about 8 months pregnant with my first son.

    I was at a construction company that stored old equipment in a 200 year old barn behind the office. I was asked to
    1 – clean out the barn and
    2 – find all of the old desktops, take out the parts and repurposed them into new laptops.

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  36. Writes Neatly, Apparently*

    At my first job when I was 19, I took messages for my first boss – personal, professional, didn’t matter. He was old school. I’d pick up the phone and manually write down a message if he wasn’t available because he didn’t like checking voicemail.

    One day, he marched out of his office and said, “Your handwriting is too neat.”
    Me: “I’m…sorry?”
    Boss: “You’re writing too neatly, it’s too slow. You should write faster. Time is money.”
    Me: “O-okay?”

    Since I naturally had very neat handwriting at the time, I had to practice writing more messily solely to take his messages….which I naturally did on company time.

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  37. Happy Penguin*

    This was when I worked at a toxic doctor’s office. I was admin assistant to his wife, the practice manager, and my desk was closest to the bathroom. She always wore a headset and once took a call while in the bathroom. When she was done with the bathroom part, she came out and motioned for me to flush the toilet for her so her caller didn’t hear it. We laughed about it afterwards, but I recall saying THAT wasn’t listed in my job description!

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  38. Cats Are Better than People*

    I’m a teacher and have been a department chair for more than 20 years. I managed the Career and Tech department so most of the teachers came from industry. One year, we hired a diva of a man who wanted someone to run his copies, answer his emails, and grade his papers. Seems he was a Super Important Engineering Manager in his former life but he learned real quick that no one was here to cater to him.

    He lasted a single semester.

    Reply ↓
    1. NotBatman*

      That is hilarious. I’m in higher ed now, and I’m remembering this one for the next time someone in business complains that academics are lazy and incompetent.

      Reply ↓
  39. my cat was prettier than me*

    I was an Executive Assistant for an extremely wealthy man. He wanted me to make a catalogue of his watch collection. The problem was, I didn’t have access to the watches, just the boxes and some paperwork. No pictures. Most of the paperwork was in French, which I only have elementary knowledge of, and the names of the watches were not listed. Somehow I managed to do it. Shortly after, I was fired via email after I left for the day.

    Reply ↓
  40. cncxch*

    I was on crutches and got asked to rush my boss’s girlfriend’s late job application paper portfolio that he had put together and basically done to the late night post office but since it wasn’t work I couldn’t expense it and had to take public transport. Then commute home 90 minutes.

    I was so happy when he married someone capable of doing their own job applications and mail, unfortunately he didn’t marry her while I was still working for him.

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  41. Basketball Lesbian*

    Worked the front desk/crisis hotline for a DV shelter, and about a year in a new program manager was hired who decided that, in addition to handling both in-person and over-the-phone crises from people in active danger, I was also her personal assistant. The most egregious instance was when she came down to the main floor of the shelter for a meeting (her office was on the third floor, old building so no elevator), realized she’d forgotten her laptop, and asked me to “fetch it” from her office because she “didn’t want to take the stairs again” and I had “younger legs.” She was…not someone I trusted to answer the crisis phone if it rang while I was gone.

    Working for that woman made a difficult job much, much harder.

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  42. unanon*

    My job was not in any way to be an assistant. Neither I nor my coworkers had assistants. We got a new coworker who had an assistant in his previous job. Our common boss made the department’s admin do this guy’s admin work because he was used to having an assistant (instead of telling him this job didn’t include one). One day she was out, so said coworker arrived at my office to ask me to copy something because the copier was so tricky with all those buttons! Without moving from my desk, I said “I put the paper down on the screen and push the button that says “copy”.” He never asked me to help him again.

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  43. Amh*

    My boss at a legal staffing company once sent me to a church to light a candle of remembrance to honor her late husband, asking me to be sure to pray for him on her behalf. She told me she was too busy to go on her own (I was her EA; she wasn’t) and I heard her explaining to her adult children the heart rending emotions she felt while she lit the candle.

    It was my first job out of college and I a great deference to authority, and so I did it. Even the prayers, although we did not share a religion.

    Reply ↓
    1. ursula*

      Ok I work in law and I have seen some shit, but my jaw literally dropped over this one. That is absolutely wild.

      Reply ↓
  44. WantonSeedStitch*

    I was an admin for three years to the president of a tiny medical software company. Most of my duties were pretty standard, if sometimes annoying (the specificity of his coffee order was obnoxious, as was hand-carrying two cases of Diet Coke several blocks from the store to the office). I would place office supply orders–pretty normal. But when I ordered new binder clips, I had to dump out the plastic cylinder of clips and flip up the tabs on each one, then put them back (at which point they never fit properly into the cylinder anymore and I had to kind of jam them in). This was because my boss was too busy to do this himself when he wanted to use a binder clip.

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  45. Return of the Mack*

    My long-time boss, who in almost all respects was wonderful, had me “stuff his pencils.” He’d have me get a box of 12 mechanical pencils, and 12 packs of refill lead, and stuff each pencil with one full refill box of lead. It’s not the wackiest request ever, but it was one of those things that really gave me the ick.

    Reply ↓
  46. SkiddamarinkADinkADink*

    I was an assistant director once for a professional summer theatre in the southern US and the director expected me to cut music he wanted in scenes and be ready to both have an play those sound cues the next day. When I pointed out that the sound designer might be a useful person to ask for that (the music, not playing the cues in rehearsal) he said that wasn’t necessary because it was just for rehearsal.

    I happen to know how to edit sound, but he didn’t know that. (And guess whose cuts were used for the show without any sound credit?)

    Other notable highlights of that job, though not prescribed by the director, were running around having pre-meetings with everyone before they met with him so they would know the information he would have expected them to magically read his mind about and slipping backstage at rehearsals to problem-solve while the director hair-petted the lead who threw a fit every time anything went slightly awry (and did nothing to actually deal with the problems at hand).

    Reply ↓
    1. The OG Sleepless*

      My daughter is a sound engineer. She works in live sound. Things like that are exactly why she has no desire to work in film. (One of her friends was working with a shoot at a lake near Atlanta, and the director wanted to shoot a scene on a Saturday afternoon. Somebody pointed out that a lot of boaters were out on the weekend and the sound of the motors would be in the background, and maybe they should do the shoot on a weekday. The director said “nah, y’all can just take it out in post.”)

      Reply ↓
  47. Felix Unger*

    At my first job, I wasn’t an assistant but my desk was closest to the door from the elevator. You needed a keycard to open the door or you could enter through either of the reception desks one floor up or one floor down and then take the stairs. One of the bigshots had decided he didn’t want to carry a keycard or take the stairs, so he would just knock on the door until somebody let him in. That was me for the first few days I was there, but then one day I was on the phone. Instead of putting the person on hold, I kept talking (you know- doing my actual job) even as the knocking got louder and the bigshot started yelling “Hello???” A couple of times he yelled at me specifically by my physical description since he hadn’t bothered to learn my name. Eventually he got in somehow, and he yelled “Thanks for your help, asshole” at me loud enough for the person on the phone and my manager (who was down the hall a way) to hear.
    My manager asked what happened and she went to HR, who apparently talked to him. I never heard him knock on the door (or even talk to me) again. I’d like to think he started carrying his card or taking the stairs, but he probably called his secretary to let him in every day.

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  48. Got_the_Tshirt*

    I was working at a Big8 accounting firm and for a brief period of time I had to put eye drops in the eyes of one of the senior partners.

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  49. my cat was prettier than me*

    Oh, I have another one! This was right when Covid lockdown started, and hand sanitizer was a hot commodity. One day one of the bottles went missing. The VP told me to call facilities and report it stolen. We were one of hundreds of offices in the building (this was in the John Hancock tower in Chicago), so I don’t know what she expected them to do. Search the other offices? I’m sure they had much more important things to worry about.

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  50. I&I*

    Temping in what was supposed to be a receptionist’s position, I was given the order to print out some photos for the CEO.

    The CEO was not a nice man. It was an open plan office and when he got in a mood, everyone could hear him yelling down the phone for ten- or fifteen-minute stretches. So disobeying him was definitely not an option.

    By ‘some’ photos, I mean about 60. From a printer that could only print 10 pages at a time. You had to go collect them each time and reset.

    The printer was on the other side of a large, one-floor company office.

    The other side from the reception desk, which everyone got angry if I left unattended.

    And by ‘photos’, I mean pictures of the unbelievably lavish, must-have-cost-as-much-as-a-wedding party he’d thrown for his tween daughter.

    Oh, and hiking back and forth across the office at maximum speed was done while I was visibly six months pregnant.

    The office had a ‘Keep Calm And Carry On’ sign on the wall. I did not keep calm, and the day my temp role ended I did not carry on with that agency.

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  51. Lord Doctor Fergus*

    When I was working as a lab student, my boss came in one day with some complex woven fabric that was some kind of seat material. The outside and inside some kind of soft fabric woven into some stiffer fibres that ran perpendicular to the overall fabric.

    He said: “I need you to work out the overall fibre surface area per square centimetre of this fabric.”

    When I stared at him, he added: “Don’t worry, I brought my daughter’s old toy microscope for you to use.”

    I count it as a point of pride that I did (by means of unravelling, careful weighing, and yes using the toy microscope to compare fibre widths to lines of known gauges) come up with a justifiable estimate.

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  52. Hellbent on Peace*

    Oh let’s see…now, please note that I was not a personal assistant. I was the office manager of her small but lucrative business.

    – bought all of her 4 kids’ school supplies and organized them into the binders as she requested, and wrote their names in everything. Watched her take them all apart to count and be sure everything was there.
    Then she told me to put it all back together and walked off.

    – I was responsible for making sure her HUSBAND paid the Amex card bill that was in her name. I had sent 2 reminders before drafting the most professional email I could pointing out that after 30 days, there would likely be a report to the credit bureaus about it. Radio silence for about 8 minutes during which I swear I could feel the rage building in her from somewhere across town. Husband calls and gives me checking account info to pay the bill (because that’s faster than just paying it himself??) His normal conversational tone was gone, presumably ground up under her stiletto heel.

    – the post office lost a package with a $10 pair of pants for her son. I filed a claim with them and went there every other day on her instruction to badger them to see if they found them yet. Turns out she never picked them up when they originally were shipped and were sent back. The company re-sent them and I picked them back up. I apologized to the post office staff a few times as they stared me down and insisted that I sign for the pants.

    – installed a tracking system for her staff to ensure they were working hard. I negotiated hard for the staff to have 8 minutes a day per person to use the bathroom. She wanted 3.

    – she wore a pair of earrings that was inventory for sale – they were worth thousands. Then she lost one. We all had to stop what we were doing and look in every nook and cranny for them (spoiler: the only place we could not look was her desk, because she already checked there and needed us to look where the earring would actually be) She accused people of stealing it and had someone identified that she was considering firing if we didn’t find the earring.
    Turns out that she had taken them off during a phone call and it fell down behind a stack of papers on her desk.
    Was that the last time that she wore inventory? No.
    Was that the event that inspired her to clean up her hellscape of a desk? Also no.
    Did we all hate working there? You betcha.

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  53. The Dread Persephone*

    I was an executive assistant to the general manager of a Navy Exchange, which is basically a Target (we sold groceries, clothes, household stuff, electronics, jewelry, even designer goods) on a Navy base. He was also in charge of several smaller outlying stores around the base.

    One year, he couldn’t get a manager to volunteer to organize and run the annual inventory of all the stores, and somehow decided it would be easier to make me do it. I found myself, someone who wasn’t a people or project manager, running a massive project.

    I had to:
    -create 2 days of overnight shifts for a few hundred people
    -train said people on how to use the inventory equipment
    -create signage about store closures
    -assign the “right” number of people to inventory each section of each store
    -organize transportation for people without vehicles
    -track all the inventory numbers as they came in
    -manage breaks for everyone and provide enough food for snacks
    -troubleshoot inventory equipment issues
    -make sure people weren’t sneaking any of the tiny food items in the middle of the night as they counted candy bars and chips in the convenience stores
    -and, my favorite, keep the GM from falling asleep at 4 am by pushing coffee and small talk

    I hated it, and apparently did it so well that I had to run it every year until I left for a new job.

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  54. many bells down*

    I have worked as an EA/PA but my boss was totally professional. I was once asked to take his young daughter shopping at the bookstore and I accidentally stole a book, but that’s on me.

    The most fun errand was when he asked me to bring his vintage Mercedes to get a new stereo installed. I stepped out of that car and have never had so much attention from nearby men in my LIFE. It was a pretty cool car.

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  55. Lemonfork*

    I worked for a tiny org, with a tiny office space. The boss refused to buy the city’s trash and recycling services because the rolling bins would have to be visible in the main space and that would “look unprofessional.” Instead, multiple times a week I was tasked to take office trash home to dispose of in my own residential bins. I even handled some bulky trash disposal piece by piece from a renovation prior to my start date.

    Reply ↓
    1. NotBatman*

      That is BONKERS, and I think might be fraud??? Not you, but the boss dodging municipal waste fees by putting you on the hook for illegal dumping.

      Reply ↓
  56. Not Tom, Just Petty*

    Story from my mom, 1953.
    Background:
    She was the executive secretary to the president of a medium sized company in Pittsburgh that made and sold steel mill things to steel mills. The president was late 20s/early 30s party boy whose dad was CEO but let son run things, pretty much. And son did a good job, pretty much. (So he took the jet to the Bahamas without telling anyone for a week. My mom ended up telling on him to his dad when son was MIA for three days, but over all, ok guy.) Typical Mad Men stuff, she learned all the different types of alcohol glasses and mixed drinks. Nothing shocking for the 1950s.
    Story: President Jr. came in one Monday and puts a box with multicarat diamond ring on mom’s desk. “Mail this back to XYZ Jewelers.”
    Yep, his proposal had been rejected.
    My mom looked at it and confirmed he meant put it in an envelope and mail it. He did.
    She didn’t.
    She called the jeweler who thanked her madly for not putting a multicarat ring in an envelope and dropping in the mail bin. Instead he sent a pair of armed security guards to pick it up.

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  57. Not Everyone Can Wear Sandwiches*

    I was a lab tech. And while picking melted labels out of the printer with tweezers was “other duties as assigned” building the company a new website was well out of my abilities. I gave it my darnedest finding DIY website builders and getting a quote from an actual company, but my boss thought that because I knew enough HTML to add italics to a blog post he should be able to get a new website out of me for free. While I did my normal job.

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  58. AG*

    I was once in a meeting with an executive to review a document. The executive called in her assistant to look up whether the adjective describing the arrangement of furniture is spelled “setup,” “set-up,” or “set up.” Then she made the assistant go through a 5-page, single-spaced document to make sure all the “setups” were spelled correctly.

    I said, “let’s do a quick search and replace” and was shot down, because “[the assistant] can do it.”

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  59. Blue Spoon*

    This wasn’t even a job thing, but my AP Calculus teacher in high school once asked me to proofread an angry letter her friend had written complaining about her (the friend’s) son’s soccer coach. I was a teenager who was bad at calculus and didn’t have a strong sense of boundaries, so I did it in order to stay on the teacher’s good side. Y’all, the letter was so bad. Stream-of-consciousness, treated punctuation as suggestions, hard to follow from one idea to the next. I did my best with it, and I guess she was satisfied. Hope things worked out with the soccer coach.

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  61. Lemonfork*

    Oh! When I was in college I worked part time as a personal assistant for someone in a niche field of antiques. My boss wasn’t able to drive, so I drove her to a regional meet-up for this field, which was pretty snooty. The moment I, a young person, walked through the door, a woman (without making eye contact, saying anything or acknowledging me whatsoever) flipped the handle of her dog’s leash into my hand.

    (The implication = You’re the help, walk FiFi.)

    I was stunned, but walked the dog, which was a lot more enjoyable than the meeting. It was a very cute little foofy white dog. But also – the audacity! I wasn’t HER assistant!

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  62. Spreadsheet Queen*

    I once worked a temp receptionist job for a real estate company. I answered the phone and occasionally had to mail merge and print something, but mostly was really, really, REALLY bored.

    One of the realtors was a member of the Junior League, and at one point they had lost the original files for their handbook, which needed updating. So, she brought in the handbook and I retyped the entire Junior League handbook of my city’s local chapter into Word in my downtime. I don’t think I ever typed more than 50 or 60 wpm, so it kept me busy for a while.

    I was there a couple of months before they finally hired someone* permanently. Nice people. They wrote a nice card and gave me a gift (a couple of very nice brass candlesticks) as a going away present – totally not what you’d expect at a temp job.

    *I was not in the market for a permanent receptionist job. I had left one career, and was temping until I could find a position in some random new career I hadn’t thought of yet.

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  63. NotBatman*

    Second one reminds me of the time that, while working as a server at an events venue, I got involuntarily added to a wedding party. The bride’s gown had a large train and it was very windy out on the lawn where she was supposed to process. So (near as I can tell) the wedding planner asked if someone could be found to carry her train, my manager glanced around and saw me first, and next thing I knew I was processing down the aisle in front of 300-odd strangers, trying to keep this giant piece of silk taut but not too taut while appearing in several thousand photos that I’ll never see.

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  64. LadyByTheLake*

    This is from a firm where I was a young associate, and although it happened before my time, it was legendary in the firm. A senior partner was unusually paranoid about filings. When a filing with the court was coming up, he would make his assistant get the exact number of pieces of paper to be filed and practice walking across the street to the courthouse the day before the filing was due. If she was carrying the wrong number of sheets of paper, she would have to do it again. Another assistant would also have to practice walking about ten feet behind the first assistant, so that if something happened to the first assistant, the second assistant could swoop in, pick up the papers, and continue across the street to the courthouse.

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  65. Fox Wit*

    I was a teenager and this was my first foray into semi-professional work. I have no idea how I ended up with the job, but for about 3 months I worked for a self-employed professional (I can’t recall if he was an accountant or a lawyer or some such, but he was a professional). My job was to type up checks on an electric typewriter. This was the early 90s, so it’s not as far-fetched as you might think. Still inserting each individual check and lining it up against the ribbon took more time than me simply writing it out. And I had pretty neat handwriting as a kid. But such things were verboten. Once a week, I came in for 2-3 hours and would type up a bunch of checks.

    As jobs go, it might have been the most straightforward job I ever had! I knew exactly what I had to do and how I had to do it.

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  66. Amateur Linguist*

    The reorganisation plans at my org have been put on hold, but they need wider geographical coverage over the whole region and can’t necessarily just dump people and rehire in the areas that are underserved. So they wanted to create an administrative ‘helpdesk’ service where managers would be able to request our services through a ticket system, a bit like when someone requests a purchase order to be raised through the finance team.

    Unfortunately, my line manager and I presented them with the reason it wouldn’t work — as part of her team I have a lot of duties that require ongoing engagement and relationship building with local customers, suppliers and delivery teams. I can minute meetings well, and often get asked to do stuff by colleague relations, but the ones I know well are the people I work with month in, month out and can coordinate actions and so on with the general team. It just can’t be boiled down into fungible actions that a helpdesk can assist with. Additionally, at the moment someone just sends me an email asking if I can do such and such, and I can get it done quickly. A cab rank system means that not only do management not know who will be handling their need, they will also have to fill out a form every time they need something done and that just takes up more of their time than anything else, and undermines the consistency of what they get out of us.

    So they are working on a new plan to square the circle. I don’t think it would be budget friendly right now to just employ who they need down in the SW, and my manager and I included a proposal for individual admins to be attached to specific regional delivery management teams but cover for their regional colleagues if something comes up that needs coverage. I don’t mind that as I have a lot of spare capacity, and it would get me mentally (if not physically) out and about across a wider area. There are also some people who really can’t cope with the job as it stands who should have been performance managed out, but our public sector isn’t brilliant at doing that (they tend to gold plate existing worker protection such that it’s way easier to fire someone for bad behaviour than it is for poor responsiveness.

    I’d be protected in redundancy and if the worst comes to the worst I’ll get a nice lump sum that would keep me going for a long time (my contract is way above statutory minimum) but I suspect I will be kept on because it would be more expensive to make me redundant! But the whole scheme was poorly thought out, and credit where credit is due — they listened to the objections and paused the process while they explore different options. And the HR lady running the consultation also needed me for an investigation note-taking this afternoon, so cultivating that contact would have someone to vouch for me on the inside.

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  67. Cookies for Breakfast*

    Former office assistant here. This was my first job, at a small company ran by a husband and wife not much older than me, with the rest of the management team made up of their close friends. During my interview, the owner assured me (unprompted) that personal errands would never be part of my job. And yet, the happiness of their household found its way into my job duties time and time again. Here’s a compilation of perplexing requests. There are probably egregious ones I’m missing, because I’ve chosen to put a lot of my time there out of my mind.

    – Let Husband’s elderly father drive me to a wholesale store that was very out of the way, so we could buy replenishments of office supplies in bulk together. This was, most certainly, to help him fill his day, as he opened and closed the office, and didn’t seem to have much to do other than that (but you bet he was on the payroll). There was no reason we couldn’t have ordered online.
    – Order an expensive bottle of champagne from a very famous luxury department store’s website, and have it delivered to the hotel Wife’s father was staying at during a visit, as a welcome gift from Husband. What’s ridiculous about this is that Husband was generally a thrifty guy, and the bottle probably cost what some of us made in a week. As office gossip had it, Wife’s father was as close to an oligarch we could imagine, and Husband was terrified of him. The hotel was the Ritz.
    – Write a letter to the couple’s local elected representative to ask them to speed up Wife’s citizenship, on account of her outstanding contribution to the country’s economy. My guess is Wife asked Husband to do it for her, he forgot, and delegated it to me last minute. Heaven knows why. I was in my early 20s, an immigrant, completely unaware that writing to representatives was a thing, and clueless as to how you’d even address them. She did get her citizenship in the end, but I don’t know if my effort sped up anything at all.
    – Go on Amazon to order a new coat stand for the office (which was not customer facing and had an overall “where dreams go to die” vibe), under strict instructions from the operations manager to spend as little as possible, but make sure it didn’t look cheap, or Wife would get very upset. What low-cost, mass-produced coat stand doesn’t look cheap on Amazon? I’m sure she hated my choice, but it did its job (storing coats), so we kept it.

    This was also the company where warehouse assistants were constantly monitored on packing speed and reprimanded if they clocked in a minute late, in the name of punctual customer service – but the day the owner asked half of them to leave work and travel to the other side of the city to lug a very bulky snooker table up the stairs to his apartment, all was absolutely fine. For all we knew, he didn’t even play snooker.

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  68. Annie O*

    I was not an assistant, but a veterinary technician/pet groomer/dog trainer. I worked across a few different locations on a contract basis. Think grooming at one place on Monday, training facility on Tuesdays and Saturdays, clinics on the other days, etc. One place that requested my services was a boarding facility (mostly dogs, a few cats) that claimed they wanted additional help from someone with “medical experience.” This was common for me if a boarding facility had a medically complicated boarder (diabetes, Cushing, etc.) that they wanted more specialized care on site. I showed up only to find that the woman who owned the kennel did NOT want medical for the boarders, but for herself. She wanted me to apply antibiotic ointment between her toes 3 times per day, as well as rides to various medical appointments. Additionally, her house needing cleaning so I would need to do that too. Clearly this woman needed or wanted a home care aide, but did not want to pay for one. She was very angry when I told her “I am here to provide animal care only, and it is alarming that you are not feeding, walking, or checking on your boarders (she wanted NOTHING done with the animals until after her needs were met) and this needs to be reported as neglect.” She was very irate that “nobody wants to do an honest day of work anymore” since all of her attempts at hiring a kennel assistant have failed when people quit after just a few days. I said “well, this is not an animal care job, so I am leaving after I feed the boarders and clean kennel runs.” I called the humane society who handled neglect/abuse complaints (I worked there multiple days per month as needed when they had more work than help) when I left and informed them her facility would require an inspection. I heard shortly thereafter that she closed her kennel. This woman was not an invalid, she just seemed unbelievably lazy. Found out later she needed rides everywhere because her license was revoked after her 4th DUI years before.

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  69. sofar*

    I’ve told this story before, but as a temp at a small family-run real estate firm, I was tasked with reading the CEO his emails.

    Every email he received, he’d hit “fwd” on and send to my email address. I was tasked with printing said emails out and reading to him twice per day. Even one-line internal emails from other coworkers. Even the spam. And I’d have to explain why it was spam to him. If I deleted an email as obvious spam, he would say, “I got 25 emails, you only ready me 15?”

    I honestly wonder if he just could not read.

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  70. ghost_cat*

    Boss did not like having to use a taxi. When he needed to travel for work, two of us would follow him to the airport so that one of us could bring his car back to the office. And yes, one of us would then drive it back on his triumphant return with another person following behind.

    It should surprise no-one that I had to go to court years later as a witness for the prosecution for fraud charges relating to his travel acquittals.

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  71. The cat is on my lap now*

    The owner, who lived in a different city, believed in Feng Shui. Not just as a design aesthetic, but as serious life guidance.
    Our building had three elevators and the AA was only allowed to take number one, regardless of which one arrived first or was crowded, because his Feng Shui expert told him that her taking elevators number two or three would decrease business success. She had other rules about movement around the office inspired by the expert, too.
    (Non-desk staff were not expected to do this.)

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  72. Museum Worker*

    I was the personal assistant for a model and socialite in London in the early 2000s. She made me use dating sites (this was pre-app), pretending to be her, until I narrowed down the bachelor pool sufficiently for her to wade in and talk to the men herself. She would occasionally give me my orders for the day clad only in a thong. She was fond of saying, “I don’t like ugly people.”

    The most bizarre errand I was sent on was to take her teenage daughter shopping to teach her about “being mixed,” as I was from the same ethnic group as the girl’s late father. I didn’t last beyond a few months.

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  73. HR Exec Popping In*

    I was a receptionist at a healthcare facility right out of school. The Head of that facility did everything old school. Easy job, nice people but the facility Head was very old school. Think lots of dictation of memos and letters. But the one odd thing I had to do was his family’s personal Christmas cards which I had to sign by each member of the family in their handwriting. So I had to practice forging the signatures of Director, his wife and their two kids.

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  74. Done*

    After my first year of law school, I was hired for the summer by a law firm in my hometown as a law clerk/paralegal/administrative assistant/whatever Weird Lawyer needed me to do.

    I mentioned I was on the swim team in college. He would swim for exercise a few times a week. I had to give him swim lessons.

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  75. Former Media Grunt*

    Maybe outing myself, but I was allegedly a professional assistant, not a personal one, for several years to the top guy at our org. Things I was supposed to do: manage calendars; answer phones; organize client meetings; and read, edit, and project manage my own projects and those of another senior person. Things I ended up doing: washing and arranging a weekly fruit bowl; setting out, bussing, and washing his lunch dishes because he required real flatware to eat his takeout salad off of; sourcing, purchasing, and coordinating freight shipping for a butcher block kitchen cart for his London flat; wire requests for his 35-year-old niece’s monthly allowance; planning a 70th birthday party for his friend who wasn’t even tangentially related to our industry; and, my personal favorite, coordinating with his fishmonger (!) at his weekend house when there were (frequent) issues with his weekly order.

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  76. Grandma Moses*

    Ah, 1984. Vanessa Williams nude pictures were published in Penthouse. My 58 year old boss sent 23 year old me to the drugstore in our tiny midwest town to purchase 5 copies. Good times.

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  77. Nudibranch*

    Was told to take bosses shirts home to iron as wife was out of town. He did not want to spend money on dry cleaners. I was very young and powerless. I did.

    Was tasked to babysit for bosses protege so she could work nights and weekends. Which meant I had to babysit nights and weekends after already working a 40 hour work week. I did.

    Insistently told and threatened, so I had to come into work for an all day training meeting after I’d called out sick with a fever, cough and dripping head cold. I came with my med and full box of kleenex, sat in the back–no one wanted to sit near me, unsurprisingly–until training was done. Surprisingly, I retained no information received during training, which was not pertinent to my work either.

    Was informed I would be letting boss’s hired consultant’s female assistant (lover? he was married) live with me rent free in my tiny 2-room rental during their 6-month stent of temporary employment as boss was religious and did not want to pay for their lodging together, only for male consultant. Luckily, I got out of that due to telling them all my landlords would not allow me to have another person stay with me. Thank god I had that excuse, because oh the melodrama and guilt-tripping that ensued. P.S. There was no money or benefit to me offered to take on a roommate who I would also be expected to chauffeur around town as they had no vehicle. I assume I’d also be expected to entertain them nights and weekends, when she wasn’t needed by her ‘boss’.

    I can probably think of a few more instances, but I won’t take more of your time.

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  78. not an essential worker*

    For a while I worked as a receptionist at a recreation center that had a policy of never closing for anything. When we were anticipating a big snowstorm, the center manager asked me to spend the night at the center with her to be sure I could work the next day.

    Cannot stress enough this was not a hospital or a fire station or anything you really need to operate in a snowstorm. The risk was that the center manager would have to charge the two people who would still show up to swim in a snowstorm. Of course, there probably wouldn’t be in lifeguards either…

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  79. Melonhead*

    I think I may have posted this before, but years ago an attorney I worked for looked down at his shoes, decided he needed different socks (he wasn’t leaving the office that day), and sent me to Saks in his big ol’ Mercedes to get him a pair.

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