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36 Employees Share the Dumbest Things Their Bosses Have Done

Roy R. Oct 06, 2023 01:00 PM EDT

The corporate world is often a theater of the absurd, where bosses' decisions can leave employees scratching their heads in bewilderment. In this post, we've collected 36 jaw-dropping anecdotes from employees who've witnessed their bosses' most baffling moments. From peculiar policies to outlandish ideas, these stories shed light on the eccentric side of management. Whether you're a seasoned professional or just entering the workforce, get ready for a rollercoaster of workplace hilarity.

dumbest bosses What is the dumbest thing your boss has ever asked you to do? My previous boss wanted me to write a java program that would parse and organize incoming Outlook e-mail into different folders. I was like O_O. — Save

dumbest bosses Find a Chimpanzee to dress in a fireman's outfit and train it to run across the top of a massive lightbox that had fake flames along the top 18 feet in the air, that was part of the trade show set I had built for the company. He wanted the chimp to carry a little fireman's hose and pretend he was putting out fires because the company product was "so hot". This is absolutely true. — Save

dumbest bosses A former boss once told me he was sick of finding out things I hadn't been told about at work. So, he asked me to make a list of all the things I didn't know. When I tried to explain that this wasn't possible he told me to stop being argumentative. I gave him a blank piece of paper and told him I'd fill it in as soon as I learned what I didn't know. — Save

dumbest bosses Not to think. The direct quote was, "I pay you to do what I tell you to do, I do not pay you to think." The next day, he was all over my alfor continuing to copy flyers even though they were going grey (hot copier issue). He asked me "What were you thinking?" Apparently, the correct answer to this question was NOT "You don't pay me to think, you pay me to do what you asked." — Save

dumbest bosses I was once hired as a web designer at a company that sells machine parts. I was supposed to create and maintain their web page for them. On my first day at the office I was seated at my desk... which had no computer on it. I was told that I was to draw the website on paper and after it was approved I would get a computer. — Save

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dumbest bosses My old boss did not understand that servers require power. No, really. We had a farm of servers that ground through 3D renderings. He wanted to add more, I told him not without more power. He said the UPSs we have had plenty of open sockets, I told him that's not the same thing. Well, we ordered them and he said he would order more power circuits, but instead he just got in before me, plugged everything in, and blew everything up. And then blamed it on me. — Save

dumbest bosses I work for a company that helps rich Chinese kids get into schools in the US. This one absurdly rich guy pays my boss like $200 per hour for me and my colleagues to teach his son SAT words, analogies, US high school literature and history, etc. His son does not speak English, other than hello/goodbye/OK. But the dad keeps paying, so my boss keeps insisting that I spend hours a day trying to tell a kid who can't pronounce his own name what "gregarious" means, instead of teaching him the basic si he needs first — Save

dumbest bosses My old boss once asked me to wash all of the dishes in the break room. None of the dishes were mine and there wasn't even any soap. There were a few of the dudes who worked there who weren't busy and when asked why he didn't just get one of them (they actually used some of the dishes) he said "Nah, dishes are womens work". I refused to do them and nothing bad happened to me. — Save

dumbest bosses "Transcribe these perfectly good Skype guidelines so that it looks like our department made them." Why can't we just give them the fl directions that are already there!? — Save

dumbest bosses My boss: "Why didn't you bring your laptop to our meeting? Now you have to go back home, get your laptop so we can have access to the company's emails!" BIGGEST FACEPALM OF MY LIFE. — Save

dumbest bosses When I was going through Army basic training Ihad a drill sergeant tell me to dig up a metal sign post. I asked to speak freely and told him that there would be a large cement block at the bottom that we wouldn't be able to pull out by hand. He said "Think so? Dig." So we dug the hole, hit cement and was told to fill the hole back in again. I often wonder how many times that post had been 'dug up' just to keep a soldier busy. — Save

The workplace, with all its quirks, never fails to provide amusing tales. If these stories resonated with your own work experiences, our website is a haven for those seeking relatable content and insights into the professional world. From career advice to office humor, we offer a wide array of articles catering to employees' interests and challenges. Join our community, where you can share your own stories and find solace in the shared hilarity of workplace escapades.

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Posted by Roy R. About the author

Roy has been one of the internet's meme tastemakers for more than a decade. He and Phil started Thunder Dungeon in 2012 by posting the stuff they found funny, and it grew into viral photo and video creations, one of the largest meme community apps and one of the best sites for daily meme content. If you've spent any time online, you've probably laughed at one of his memes.