'My boss... asked me if he could borrow $1000': 25+ Bosses who had ridiculous requests for their employees

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Remy Millisky • Writer and Editor
Jul 29, 2024 5:00 PM EDT

Bosses can ask their employees to do the most ridiculous things, even when it falls outside of their job description. A lot of job descriptions will list out all of the daily tasks the employee is expected to do. Then, there will be a line that says something like, "Additional tasks as needed." That leaves a lot of room for a manager to request help with things that their employees really shouldn't be doing, but will be strong-armed into doing anyway. 

The people answering u/thekutsi's questions have a few good examples of this. They wondered, "What's the craziest thing your boss asked you to do?" and hundreds of workers replied to share their tales. Some people were asked to work at odd hours or drive places they shouldn't be driving. One person who worked in a hotel kitchen revealed that their boss wanted them to use expired milk in the food products! At least they and their coworkers revolted over this revolting idea, and refused to use that milk. A lot of people quit their jobs after these incidents too, which is probably for the best. 

Next up, this dad had a silly idea for a joke gift for his kid, but he neglected to actually get them any kind of nice present after the prank was over…

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  • 01
    ROSS
    via Paul Hanaoka on Unsplash
  • 02
    What's the craziest thing your boss asked you to do?
    via u/thekutsi
  • 03
    roseandbobamilkt... Order a 3 story fire escape ladder for a 5th story office. When I looked at him incredulously and asked if he meant a 5 story ladder he said, "We just need to have the ladder. People can jump."
    via u/roseandbobamilktea
  • 04
    NOOWOFFICIAL Used to deliver pizza for Domino's on an e-bike. The e-bikes we used had a bunch of wiring underneath the saddles. One day the wiring caught on fire while I was delivering an order, so the fire started burning underneath my (also obviously the batteries stopped working so it became very tough to ride
    via u/NOOWOFFICIAL
  • 05
    the e-bike). Asked the shift manager of that evening if I could get another e-bike to use for the rest of the evening. He told me "as long as you're not on fire yourself you're using this e-bike". Quit my job shortly after that.
    via u/NOOWOFFICIAL
  • 06
    ha1fway decent I used to work at Taco Bell and on the receipt there was a little online survey at the bottom. My manager told me to go through the trashes to find receipts that people had thrown out so that we could fill them out ourselves so our store would
    via u/ha1fway decent
  • 07
    get a better rating. I was a stupid 17 year old so of course I did it. We used to give ourselves perfect reviews all the time actually.
    via u/ha1fway decent
  • 08
    Led_Halen My old shop owner used to have us techs pour coolant down the toilet instead of disposing of it properly. After enough of us raised a fuss he started dumping it in the street himself.
    via u/Led_Halen
  • 09
    ArtFreek Worked at a college town pizza place that paid me $5/H plus tips under the table. It would get insanely busy on days when there were football games and boss required all hands on deck. 12+ hour days were not uncommon when there was a game. I got to the store at 10am (2 hours before opening) and
    via u/ArtFreek
  • 10
    worked until 3am the following day. By the time. 2am rolls around and the crowds finally die down and we start closing shop and cleaning up, my boss pulls. back the entire front counter (which was on wheels) to reveal dozens of little roaches scattering everywhere. He gave me a
    via u/ArtFreek
  • 11
    broom and told me to "clean up" the roaches. I waited for him to go out back to smoke his cigarette, I took everything from the tip jar, and left. Never went back.
    via u/ArtFreek
  • 12
    Mo... A long time ago I worked at a grocery store. They decided to no longer get the cleaners that came in with special gear to clean out the compactor, presumably to make extra money. The compactor began to stink to high heaven. I'm talking rotten meat, produce etc.
    via u/MorkSal
  • 13
    So they asked me to climb inside and clean it. I laughed at them and said no. I told all my co-workers to say no. One did not listen and went in and cleaned it, he had to go home because he stunk so bad and reeked for days afterwards.
    via u/MorkSal
  • 14
    There is a reason a specialist comes in to clean it, wears a Hazmat suit and has the machine disconnected with another person standing there making sure no one turns it on.
    via u/MorkSal
  • 15
    baconpoutine89 Worked at a convenience store and my boss actually asked me if he could borrow $1000 to pay for part of the beer delivery because they wouldn't have enough. Quit not long after that.
    via u/baconpoutine89
  • 16
    Implicit Hwyteness My first "real" job out of college was one I lucked into. I ended up working for a local business in a role kinda-sorta related to my degree, but my responsibilities were light and I was honestly probably paid more than I was worth. Essentially I was a glorified office IT guy, but in a specific professional field.
    via u/Implicit Hwyteness
  • 17
    Sort of an office troubleshooter crossed with an intern. Anyway, my boss, who is honestly a really nice guy, ended up tasking me with running some cables from our office to his house across an empty lot he owned in between the two. And he wanted them laid in a trench in some kind of waterproof conduit. And I had no help. So basically he
    via u/Implicit Hwyteness
  • 18
    wanted me to plan it out, search out and price the materials, submit that to him to actually purchase all of it, potentially arrange equipment rental(s), go out and dig a trench and run cables through a pipe, figure out how to run the cables (and pipe) through one or both buildings' walls, etc. Basically way above and beyond anything I was doing there day to day and both
    via u/Implicit Hwyteness
  • 19
    barely and only technically related to my job since one of them would have been an ethernet connection. After apprehensively talking it over with him for a few days he started to realize how big the project would be and decided to go in a different direction, much to my hidden relief.
    via u/Implicit Hwyteness
  • 20
    IMakeBrew My boss at a grocery/retail store told me to pour 4 big jugs of this industrial glass cleaner down the sink drain in one of two public washrooms, they've been in the back so many years one chewed through the plastic and melted all the paint off the shelf, honestly don't
    via u/IMakeBrew
  • 21
    know how I didn't damage my vision with the chemicals in the air, long story short I ended up with a few chemical burns on my arms and hands with not as little as an apology.
    via u/IMakeBrew
  • 22
    markste4321 Would we like to go 'on call' (for free) if the one person scheduled for the Saturday shift needs help or calls in sick. A weekend away for a team building exercise paid for by ourselves, including travel, accommodation, food & expenses. In our own time. No thank you
    via u/markste4321
  • 23
    imlittleeric My boss had me put together a remote control inflatable shark in a closet in secret
    via u/imlittleeric
  • 24
    Blue-And-Silver Worked in food and beverage at a hotel, I had lots: We were told to continue using expired milk products (we didn't do it) The chef, who had a massive ego even for a chef, convinced the hotel to let him put on these super pretentious 20 person
    via u/Blue-And-Silver
  • 25
    private dinners, at $85 per ticket. Each time they would sell less than half of the tickets, so we were asked to buy the remaining tickets ourselves and give them to family members, all so they could pretend the chef's latest vanity project was a success. I was once asked to cut my vacation short because my boss realized none of my co-workers had any clue
    via u/Blue-And-Silver
  • 26
    how to do my work while I was gone. (I was on the other side of the world at the time) Once, while I was on disability due to an injury, my boss angrily called me demanding I explain why I had missed a mandatory staff meeting. I could keep going for hours. Hospitality really is a industry to work in.
    via u/Blue-And-Silver
  • 27
    Solelbis I've worked at my job 2 weeks and ran the store on my own at least 5 times. Had one day of training lol
    via u/Solelbis
  • 28
    rosesforthemonst... Run a nursing home laundry room with no experience and no training. I didn't even know how the machines worked. Industrial laundry machines are not like your home washing machine. The extent of my training was having an under qualified supervisor telling me "you'll figure it out".
    via u/rosesforthemonsters
  • 29
    inevitabled34th Asking me to stay late. Doesn't sound so bad, but this guy would sit in the office all day playing games on his phone and watching videos. When it would get busy he would come out for ten or 15 minutes for vanity purposes to show he was "just like us." You weren't like us, Steve. You did all all day and then asked us to
    via u/inevitabled34th
  • 30
    sacrifice our lives for your fast food place. He paid me $8.30/hr in an area that had a median rent cost of almost $900/mo. The only reason I took the job was because I was in a rough spot and they were the first one to get back to me. But I would've shoveled for $8.31/hr. you, Steve. I still can't believe
    via u/inevitabled34th
  • 31
    you busted my for needing to go to the ER for crippling chest pain. I hope you're still working for that company.
    via u/inevitabled34th
  • 32
    P13r15 I had a boss that whenever we weren't busy at night (which wasn't very often, but still) or if it was raining, he just said we will be closing and that I should come in tomorrow X amount of hours earlier (X being the hours we closed earlier than we should've.) As if it's my fault for bad weather or low foot traffic, and as if it's my responsibility to cover those
    via u/P13r15
  • 33
    hours. In the beginning when I first started I am ashamed to admit that i did it a couple of times, but after that I always answered that I had other responsibilities and couldn't. I should mention I was a full time employee that worked split hours 6 times a week, 10:00-14:00, and AGAIN 19:00-23:00.
    via u/P13r15
  • 34
    BusConfident1756 I worked at an independent retailer. The owner pocketed a lot of money and never wanted to spend anything. We had a massive rat infestation. Instead of getting help my boss had me create a position just for wiping rat ; and of beer six backs before off being put out
    via u/BusConfident1756
  • 35
    XarumeR I stock overnight at Walmart. The average speed 1 pallet of goods takes to stock is roughly an hour and a half for the dairy section when you work on it by yourself. My boss asked for it to be done in 20 minutes.
    via u/XarumeR
  • 36
    [deleted] I worked part time at a restaurant in my teens. My boss once asked me to go on an emergency drive to a store for more supplies. My problem: I didn't have a license, and had only just started to learn how to drive.
    via u/[deleted]
  • 37
    My boss's solution: "it's okay, just don't get pulled over!" (She was stressed and not thinking straight, and quickly realized that it would be better to ask someone else.)
    via u/[deleted]
  • 38
    wo... I work on a 24/7 open call center wich sells tickets for ferries, I was in the night shift which is 00:00 to 08:00 am, there was huge caller amount and my supervisor asked me can I work another 8 hours without timeout, let me sleep
    via u/wolizxcv
  • 39
    viniciuscarv I was an intern in a small engineering office, drawing floor plants and such, but my bosses always pushed me to do more and more. I woke up one day (during the pandemic) with a bunch of messages from one them asking me to go somewhere more than 30km away so we could demolish a concrete ladder. Just went back to sleep.
    via u/viniciuscarv
  • 40
    [deleted] Pressure wash a grill plate, I worked in a kitchen
    via u/[deleted]
  • 41
    Due_Boysenberry... Marry a guy so he could come work in America.
    via u/Due_Boysenberry
  • 42
    PunkThug Well, mine is really tame compared to all of this. My boss had a couple of youngins. I get along well with kids and I babysat for them occasionally. Little one had a rough time going to sleep around 2 or 3 and started demanding that Uncle punk thug read her a story every night. So for a
    via u/PunkThug
  • 43
    good three or four months, she would hold the phone. while I read her The Hobbit. Took about 15 minutes on average and my boss insisted he pay me out of pocket
    via u/PunkThug
  • 44
    talldarkandanxious I was an intern. Supervisor calls me up on a Saturday to ask if I could deliver a thumb drive by car to Cape Cod. They'd pay a flat rate and reimburse for gas. I told her I wasn't sure since I'd literally just been in an accident. She
    via u/talldarkandanxious
  • 45
    paused and said "So do you think you can do this for us?" I ended up driving like four hours round trip in the rain to deliver a piece of plastic. Made like a $30 courier tip though haha.
    via u/talldarkandanxious
  • 46
    taoshka I worked at ampm and my boss was terrified of rats. We had mice, and instead of hiring an exterminator, he brought me cotton and an air horn and instructed me to use air horn to herd/scare the mice out the open back door with the
    via u/taoshka
  • 47
    cotton in my ears, while he hid in his office. I felt like such a idiot but I did it. Shockingly it was ineffective /s.
    via u/taoshka
  • 48
    pinkflufffybunbun I have 3 of them 1. my first job: I worked the 12th day in the row and had a 3 sweet days. of sleeping ahead of me. My boss came and said I'd have to come in all 3 I said that I'd have to work 20 days in a row if that's true he said idk immediately sat down and wrote my
    via u/pinkflufffybunbun
  • 49
    resignation (I work in logistics at a very specific airport and everyone is looking for office workers there so the next day i had a new job don't do this if!) 2 I was ok vacation in another country no one has my actual phone number and my work phone was (obviously) off They searched me on FB and
    via u/pinkflufffybunbun
  • 50
    insta and asked me to work the next day, I just sent a picture back of the beach, boss said I'll pay your ticket back... I said No and blocked him 3 still same job as 2 // had a work accident and was brought to the hospital, got 8 Stiches on my right (dominant) arm obviously could work for 2 weeks Came back to work, boss demanded to see the
    via u/pinkflufffybunbun
  • 51
    Stiches I said no, he tried to rip of the huge I reported him to HR band aid,
    via u/pinkflufffybunbun

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