The Most Ridiculous Requests Made By Bosses

Putting His Life On The Line

While working in retail, my General Manager told me to jump in the cardboard compactor to unjam it by jumping on it. When I did, I almost lost a foot and did lose a shoe. 

Think that was bad. It gets worse. I almost suffered a horrific accident because of his clear flouting of safety regulations, and the guy actually thought it was funny. 

Story Credit: Reddit/ComradeButterChicken

Inappropriate

My boss told me to wear more makeup and wouldn’t be upset if I dressed “differently”. I was a cashier at a fast-food chain. The worst part, I was 16 at the time. 

I don’t know how he ever fared, but given how much more informed the world has become on things that are just not okay, I wouldn’t be surprised if he was canned, or sued or something. 

Story Credit: Reddit/Plushymuffin

Corruption

In our company, we have a third-party auditor for our finances and stock. While the auditor was on-site, my manager handed me £900 and asked me to sneak it into the safe while the auditor was less than 1 meter away. 

Needless to say, I immediately walked out and have never looked back.

Story Credit: Reddit/Suberp_Witness8426

She Had To Be The Best

My supervisor was the most ultra-competitive person I’ve ever known. Her desire to not have anyone else grow but herself was crazy. She told me to not take the promotion I rightfully earned. 

She tried to talk me out of it by selling me lateral or even lower positions. She did this to me twice. Thankfully, my third promotion was out of her department for good.

Story Credit: Reddit/Outside_Shock7105

No Shame

I used to work as a work comp adjuster. Was told not to authorize a pain med that a 60-year-old woman had been on for decades. She had pretty frail health and her doctor had documented it in a way that met state standards to authorize it. 

Just quitting the med could cause serious health issues. I refused. I was told to quit or be fired. After I quit, the file was given to a trainee that cut her off. She was a cool lady. Made me feel sick.

Story Credit: Reddit/RosyClearwater

Condescension

My boss always tried to flaunt her superiority and used to parade around always making other people feel guilty about their lifestyle choices. 

My boss is a vegan. She told me: “How would you like it if you were the one getting stuffed for Thanksgiving?”

Story Credit: Reddit/Deleted

The Office Rat

Catching another cop planting evidence. I refused to not report it. Both he and my Sergeant got arrested which lead to a big investigation of all the open cases that the detective was involved in. 

I got labeled as a “rat” no one would respond when I called for backup someone left a dead rat in my locker, etc. This was all while I was battling cancer. Made me quit law enforcement altogether

Story Credit: Reddit/MrTeeWrecks

Going Too Far

Office politics are one thing but my boss clearly had a vendetta that I got stuck in the middle of. I’ve never had a weirder request in all my years of working. 

Take the assistant manager’s keys and go hide her car on the other side of the building while she was in a meeting with the district manager. She almost had me arrested lmao.

Story Credit: Reddit/p3nguLGOG

Stranger Than Fiction

It was only my second day on the job and my boss told me to lie to a customer about a server outage to conceal the fact that they were charging them for monitoring services they weren’t actually providing. 

It became clear that the whole operation was using junk old hardware and was barely able to keep the lights on. I noped out of that place as fast as I could.

Story Credit: Reddit/KratomHelpsMyPain

Be All You Can Be

So mine isn’t necessarily uncommon. I have lots of friends that work for corporate companies and get asked to fudge reports, embellish statistics, and stuff like that. 

My boss asked me to lie on readiness reports so that we look better. Thing is, I was in the army. The consequences for a lie like that don’t get any worse. 

Story Credit: Reddit/Deleted

The Weirdest Of Them All

I was barely out of high school. My first job was at a fast-food joint. Boss was a real weirdo in every sense of the word. I could actually stomach most of his antics but this was too much. 

Basically, one day he looks at me with a straight face, all earnest and stuff, and then proceeds to ask me to lick his toes. To this day, I never knew why, I just got out of there as quick as I could. 

Story Credit: Reddit/itsy-bisty_dumpling

We Kid You Not

There you have it. With workplace stories like these, makes a person kind of appreciate any other job right? If you’re a boss and reading this, hopefully, you weren’t taking notes. 

Life at the office can be hard enough with deadlines, targets, and the normal pressure of competing. Let’s maybe take it easy on the weirdness. What do you think of these stories? Have any of your own to share?