The wildest requests bosses have made to their employees: 'He would just drop the kid's assignment on my desk and expect me to do it'

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Ally Perry • Writer and Editor
Jul 6, 2026 7:45 PM EDT

Sometimes, the smallest amount of power will do crazy things to a person.

Being a boss comes with great responsibility, and an unfortunate number of individuals who are put in this position believe that they have the right to use that for their own personal gain. Good management involves balancing the goals of the company with the needs of employees, but there are times when managers are only interested in themselves and not much else.

The reality is that almost everybody who has experienced the working world has had issues with a bad boss. They are a lot more common than we would like to think. Leadership is important in most workplaces, but a lot of people who claim to have that quality could not be more wrong, and the work suffers as a result. Problems with management remain one of the top reasons that people choose to leave their jobs, so it is important not to ignore any bad behavior that is displayed by a manager. It can be the difference between a team that runs efficiently and achieves its goals and one that struggles under the weight of toxicity and poor planning. It really is that serious.

 

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  • A female employee sits at a desk, looking down and pinching the bridge of her nose
    via Getty Images (Unsplash+)

    A female employee sits at a desk, looking down and pinching the bridge of her nose

  • A common sign of a boss who has a deluded sense of self-importance or just doesn't know how to manage is that they will make unreasonable requests of their employees. One of the most important qualities in a manager is understanding the professional limits of other people that they work with, and treating them with the required respect while doing so.

    Naturally, bad bosses usually bypass this logic and can have some strange ideas about what employees will be willing to do for them as a result. At least the most outrageous tasks make for an interesting story, and a warning not to tolerate certain kinds of behavior in the workplace.

     

  • What's the most unreasonable request you've received from your boss?

    I used to fly for a self made billionaire. He was very tight with money most of the time (unless it was for pet projects or basketball games). At the time we only had one plane. He was out of town with it and his wife had used a chartered plane for her trip. Since I wasn't working that day I headed to the gym early so I could beat rush hour traffic.
    via Aarunascut
  • As I was getting in to my car the boss called. He just rattled off a list of things I needed to go buy and put in their refrigerator for his wife since she'd been gone a few days. I just said okay then called one of the guys at the hangar and gave them the order.
    via Aarunascut
  • I want to point out that I was not above doing that. But between the boss and his wife, they had 5 assistants. 5! Fetching groceries is not in a pilots job description. But that's the way they were. If they were paying you they felt they could ask you to do anything. We all had their security code and code to
    via Aarunascut
  • garage so that we could drop off items left on the plane or even collect things before a flight. That was no big deal. But asking as to grocery shop was a little over the line.
    via Aarunascut
  • writing_mm_romance I once had a boss send me an email at 1230am with a list of things he wanted updated in our system, I started my day at 7am and saw the email, just as I read it I received a very angry email asking why the updates weren't completed yet. Mind you the
    via writing_mm_romance
  • changes were going to take a couple of days to build and implement. This was also the same man who in company wide meetings was a vocal proponent of work life balance and ensuring you don't live for work.
    via writing_mm_romance
  • After 11 months I was laid off and it was the best day of my professional life.
    via writing_mm_romance
  • A female employee looks at her smartphone while sitting down
    via Getty Images (Unsplash+)

    A female employee looks at her smartphone while sitting down

  • Dish Relative5853 When I was 17, I worked as stock boy at a Woolworths in a small town. The store was on the main street and stretched about half of the block. Along with stocking the shelves, I also had to sweep and mop the floors at closing. One day the manager asked me to scrape up some gum, not off the floor inside, but off the
    via DishRelative5853
  • sidewalk. He wanted me to scrape all the gum off the whole sidewalk. This was 1978. Gum was very popular. So, on a Saturday afternoon, I scraped the gum off the sidewalk. At the end of my shift that day, I quit. My boss was really surprised, but I said I wasn't going to scrape gum for $4 per hour.
    via DishRelative5853
  • Funny_Associate_376 Someone ran into me whilst driving a company vehicle. The side was all crushed in but the vehicle was drivable. When I got back to the office the boss asked me if I would get it repared using MY insurance !
    via Funny_Associate_376
  • Deansdiatribes Asked everyone who worked from them to get tested for organ compatibility kidney i think it was..
    via Deansdiatribes
  • ShalomRPh I guess it depends on how much the pay is. I used to work overnight as a pharmacist, back when there were still 24-hour pharmacies. I wound up taking out the garbage, even cleaning out the disgusting horrible microwave in the break room with burnt on cheese on the walls, even though I never used it (and
    via ShalomRPh
  • hadn't even been asked to, but it offended my dignity to see it like that). I was literally the highest paid employee in the building, but I didn't care. You want to waste your money paying me pharmacist wages with night differential to be a janitor, I'll be a d in janitor.
    via ShalomRPh
  • A female employee leans over a desk to look at a laptop
    via Getty Images (Unsplash+)

    A female employee leans over a desk to look at a laptop

  • JustSomeGuy_56 I was working as an IT consultant. One day the boss told me his stepson was in college studying Computer Science. He was stuck on a bug in his latest assignment and asked if I would take a look at it. Sure. It was a very simple program and I quickly found the bug. I wrote a long note explaining what the problem was and how I solved it.
    via JustSomeGuy_56
  • A week later the boss brought in the kid's next attempt at writing a program. It was clear he had no concept of what he was doing, but I helped him out again. From then on the boss would just drop the kid's assignment on my desk and expect me to do it.
    via JustSomeGuy_56
  • retiredhawaii Take their car in for a tune up and just wait for it. Got paid to sit in a garage for most of the day.
    via retiredhawaii
  • Shatnerz_Bassoon I worked as an accountant and my boss once got me to research lizard for her kids homework. She also got me to contest a parking ticket once too
    via Shatnerz_Bassoon
  • lotic_cobalt As a teen I worked at place that sold food. There was a tree out front. I was told to wash the tree.
    via lotic_cobalt
  • Significant-Theme253 I was an HR Manager. She knew I painted and she liked the painting in her office but not the color. It had too much green and she wanted me to change it to blue. She left the painting in my office, and this is where it forever lived.
    via Significant-Theme253

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employee workplace bad bosses entitled people
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