45 of the Weirdest Things Bosses Have Asked Their Employees to Do

45 of the Weirdest Things Bosses Have Asked Their Employees to Do
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11 min read
This story originally appeared on Business Insider

In a perfect world, your manager would always be a totally sane, rational human being. Unfortunately, we don't live in a perfect world.

Last week, we asked readers what weird things their bosses have asked them to do. From dumpster diving to covering up affairs to unclogging toilets, here are some of the strangest answers:

Watch the O.J. trial.

"My boss asked me to watch the O.J. trial and explain it to her. I was living in Germany and she thought that, as a Canadian, I might have a better insight into the whole mindset. She paid me my full wage to sit with her and 'explain' the reasons behind the trial, the chase and just about everything O.J. Easiest job ever! I was so sad to see the trail end and I had to go back to my regular job." -- Anonymous 

Run his entire company.

"My boss asked me to run his entire company for the first full week without even being there to tell me a single employee name or what he wanted done. Strange." -- Curtis, Nashville  

Make sure her spray tan was even.

"My boss asked me to make sure her spray tan was even." -- Anonymous, Austin

Fill out adoption papers.

"My boss asked a coworker to fill out adoption papers for her." -- Anonymous 

Print a giant, canvas-sized prints of his face.

"My former boss asked me to urgently locate a company that could print giant, canvas-sized prints of his face. They were needed for a party, apparently. He also needed two gold thrones. After the party the giant prints of my boss' face were put up in our (tiny) office and we used to turn them upside down if we were annoyed at him." -- James, London

Buy dresses for his mistress.

"My boss asked me to buy dresses during work hours for his mistress, while using his car to go around from store to store until I found the model and size he wanted." -- Anonymous, New York City

Be Santa Claus.

"My boss asked me to be Santa Claus for his kids at the staff holiday party." -- Anonymous 

Have a "happy ending."

"My boss asked if I wanted to get a 'happy ending' massage together on a business trip." -- Anonymous 

Buy drug paraphernalia.

"My boss asked me to go buy a pipe for her to smoke her weed out of because she had a party she was going to later that night." -- Anonymous 

Tape up her boobs.

"My boss asked me to double stick tape her shirt to her boobs. I'm a woman but it was still awkward in every way." --Anonymous 

Handle cyanide.

"In 2008 I was required to get a summer co-op as part of my business degree. Obviously, finance jobs were tight at that time, so, in order to meet my co-op requirements and graduate, I (along with other classmates) were jumping at every approved co-op job possible. Somehow, a hazardous material cleanup company found their way into the approved employers. One day, I walk into work (the office was in the basement of their home) to find a few large boxes on my desk.

"I naturally open up the boxes with a box cutter, and find a bag of white powder inside. At this point I ask my boss what is in the boxes I've just opened and they start screaming to leave the room. Apparently, they had been cleaning out a recently abandoned gold mine and had come across a few cardboard boxes full of sodium cyanide.

"Apparently it is used to extract gold in the mining process, but it is also extremely toxic. I had just opened a box with a box cutter, and nearly sliced into the plastic bag of a toxic chemical. The boss then told me that they had put it on my desk because they wanted to find a purchaser for the multiple boxes of cyanide that were sitting on my desk.

"I spent the next month cold calling different companies asking them if they wanted to buy multiple boxes of cyanide. All of this because of what was happening with the housing market. Thanks Lehman Brothers, you almost cost me my life." --Anonymous 

Fish for Koi.

"My boss asked me to catch Koi fish from the pond." -- Anonymous 

Mess with a customer.

"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 bulls -- to his face. Happy to hear he is likely out of a job now." -- Michael, Connecticut 

Smile for the camera.

"I worked in a Japanese restaurant and was asked to go stand under the camera and look up and identify myself, just so that my boss' friend could check if he knew me or not. And the way he asked me was not even polite. I felt like a dog. I quit the next day." -- Anonymous, Los Angeles 

Buy a bouncy castle.

"My boss asked me to put aside every other task and look for an inflatable playground for his only 2-year-old son." --Anonymous

Fudge promotional testing results.

"My department manager asked me to fudge on promotional testing results, as she had promised an employee the job who was out on medical leave due to an accident. I discussed it with her. I explained why I wouldn't do it. Morally, dishonest, unethical, to name a few. I asked myself, 'if caught would this person defend you in court?' Likely not. I was sweating it. Next morning, she called me in to her office. She rescinded." -- Anonymous, Central Valley California 

Act as a valet.

"Park his car in an underground city car park -- it was a very tight space, and his car was missing the driver side mirror." --Mark 

Pluck her nails.

"My boss asked me to pluck her nails." -- Vaibhav, Ahmedabad

Watch "Snakes on a Plane."

"My boss asked me to go home and watch Snakes on a Plane and Deep Blue Sea." -- P, Missouri 

Stomp on trash.

"My boss asked me to stomp down the garbage in the outside dumpster ... in August." -- Bill, Centennial, Colorado 

Like all his LinkedIn articles.

"My boss asked me to help like all his LinkedIn articles." -- Anonymous 

Check in at a hotel for a client.

"I had to check in at a hotel near the office for a client, because his mistress was coming to town and he didn't want his name to be on record." -- Anonymous 

Reschedule surgery.

"My boss asked me to reschedule my long lead time colon surgeon appointment as it inconvenienced him. I was bleeding at the time, he didn't care." -- Paul, Melbourne

Sit there and look pretty.

"My ex-boss once asked me to sit there and look pretty. He was such an a--." -- Anonymous

Decorate his man cave.

"Find a good quality used pool table, a mix of lamps (retro) and cow skin rugs to outfit his 'bunker room' -- which he used as a work space/boys only office/den/function space." -- Anonymous 

Cover up an affair.

"My boss, a school principal, asked me and a couple of other teachers to lie for him during an evaluation from his superiors. He was a married man and was having an affair with one of our (married) educational assistants. They spent many afternoons in a hotel room, leaving her position unfilled and being very open about the affair. She was fired. He was transferred to a small school as a 1/2 time principal." -- Lynne Hamilton, Ontario

Take a test for him.

"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. Maybe not the weirdest, but definitely pretty slimy." -- Anonymous

Babysit his 4-year-old daughter.

"Babysit his 4-year-old daughter, whom I had never met before, for the day because the nanny wasn't available that day." --Anonymous

Go up on the roof.

"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." -- Steve, Montreal

Transfer an entire Rolodex.

"My boss asked me to hand write their entire Rolodex of contacts in to a new address book." -- Anonymous, New York 

Lie to his wife.

"My boss asked me to lie to his wife if she called and looked for him while he was on a short trip with his female business partner." -- Anonymous 

Renovate suites.

"My boss asked me to help renovate suites in the hotel where I worked (I was the doorman)." -- Anonymous 

Buy a keg of beer.

"My boss asked me to buy a keg of beer for the office party (also assigned me to be the designated driver)." -- Anonymous 

Train replacement.

"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.'" -- Anonymous

Buy tampons.

"I am a male employee. My boss asked me and a female co-worker to go buy her tampons." -- Anonymous 

Babysit her 18 year old.

"My boss asked me to babysit her 18-year-old, six-foot-five-inch son." -- Anonymous 

Handle a urine sample.

"I was asked to take my boss's urine sample to the lab for testing." -- Ingrid

Scrape gum off the sidewalk.

"My boss asked me to scrape gum off the sidewalk out in front of our building with a butter knife." -- B.E., Woodbridge

Become more cultured.

"My boss asked me to pay to go to Paris/London with the rest of our workplace so we could go to a one day trade show and become more 'cultured.' He ended up not bringing us to the trade show, although he now tells people he brought us there, as if he paid for the whole thing." -- Anonymous

Buy special jello.

"He asked me to run to the drugstore and buy him toenail clippers. Thankfully, he didn't ask me to do the clipping. He also 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, he had me remove the fruit before paying for it." -- Karen, Toronto

Do the laundry.

"He asked me to take his dirty laundry to the cleaner." -- Victoria, B.C.

Address wedding invitations.

"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." -- Anonymous 

Dumpster dive.

"My boss asked me to go into a garbage dumpster bin to find a document that he threw out." -- Anonymous 

Stitch his cuff.

"He was a very tall man and could easily put his foot on my desk while standing on his other leg. He did that and handed me a needle and thread and told me to stitch his cuff which had given way. I looked at him like he was from another planet an grabbed my stapler and proceeded to put in about six staples and said that would keep him until his wife could repair it properly." -- Maureen

Unplug a badly blocked toilet.

"My boss asked me to unplug a badly blocked toilet. I was the executive assistant but the maintenance person was not on site." -- Karen, Winnipeg

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