15 weird, hilarious, inappropriate jobs bosses asked their staff to do…

In my last post I talked about the 20 Most Creative Excuses Employees Give for Not Coming to Work. Because I’ve been on both sides of the encounter, felt the need to balance things with these weird; hilarious; inappropriate and in some cases even illegal things bosses have asked people to do.

In my own case, I’d been promoted to be the PA to a military officer. On my first day he called me into his office to ask me to buy a birthday card for his wife whose birthday it was the next day. Wow. I knew nothing about him; didn’t know his wife; had no idea whether they were a happy couple; a couple who enjoyed a laugh or were even a couple facing divorce. No pressure then.  He said his wife loved the card I chose, so I got to live to fight another day. But very strange.

Another boss asked me to type up his step-daughter’s homework (which I was not happy about). I did it for a while until he let it slip that his wife did his step-daughter’s homework for her. At that point I said ‘I can’t do this’. He didn’t push the issue. But once again – strange and totally inappropriate on so many levels.

So I wondered what other ‘strange/inappropriate’ jobs other employees had been asked to do. And if I thought mine were strange, these will blow your mind.

  • Asked me to unblock a badly blocked toilet
  • Told me to go up on the roof of the building and help the janitor saw off the cage around the HVAC unit. I work in IT as a computer tech support analyst.
  • Sent me to help renovate a suite in the hotel where I worked as the doorman
  • Asked me to fill out adoption papers for my female boss
  • Openly asked me to go out and buy some dresses for his mistress
  • Asked me to put aside all my tasks and go and buy an inflatable playground for his 2 year old son
  • Asked me to ‘like’ all his articles on Linkedin
  • Asked me to babysit her 18-year-old, 6’5″ son.
  • My boss suffered from diverticulitis. During really bad attacks, he could only eat Jell-O. He had me go to a self-serve market, buy Jell-O with fruit salad and, because we paid by weight, had me remove the fruit before paying for it.”

How about requests that are just plain mean? My boss gave me a demotion and a short extension to my contract position. I asked what would I be doing? The response was ‘training the new full time person’.

Requests that are plain ‘illegal’? My direct supervisor asked me to take his professional designations testing. He asked me to do it because I had already passed the same test two years prior to him.

Every boss should know they will be caught out sooner or later. I worked at a sporting goods store in college and my manager instructed me to tell a customer trying to return $500 worth of merchandise first thing Saturday morning that we could not because our POS System wasn’t working for credit card returns. I refused, so he delivered the message. Turns out the woman was an executive at [a major credit card company] and called him on his BS to his face. Happy to hear he is likely out of a job now

Every boss should also understand Karma: She gave me all her wedding invitations to address. They should be handwritten according to proper etiquette, but I played dumb and typed them all, complete with messily corrected mistakes. By the way, this was not a private business owned by her, it was a publicly funded agency. That’s why I went passive-aggressive, and quite creatively, I thought

Bosses PLEASE don’t do this to your people. Remember that the worst thing a boss can do is abuse the people who work for them.

If your job is to tell me how to do my job, then you should at least know how to do your job.

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