'Boss threw out 7+ years of employee files... because she hated paper': 25+ Employees with completely nonsensical bosses

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Aug 30, 2023 5:00 PM EDT

If you've ever had a boss that you are clearly smarter than, you know it can get pretty awkward really fast. 

We all want to think we're super smart and sophisticated, especially in the workplace. Many people try really hard to appear on top of things and in tune with exactly what's going on at their workplace from day to day. However, some bosses just don't care. It's baffling — they'll have a whole job that involves giving a darn about a workplace, and yet they'll happily sit in a back office and ignore everything. Then they rake in a six-figure salary for all their lazing about. Meanwhile, the regular employees often have a much better idea of what's going on in the workplace. But heaven forbid they try to tell the big boss how to do their job! That's how a lot of people found out just how inept their bosses really are. 

These folks below were cursed with some pretty dumb bosses. People shared stories of their bosses who were incompetent, lazy, or just straight up lacking common sense. Check out all of these hilarious stories below. 

Next up, this employee was told to stay in their lane, so they happily agreed — and ended up spending weeks without a scrap of work to do. 

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  • 01
    Motor vehicle - 'The former CFO asked me who was in charge of the finance department. I still don't know if it was a joke.'
    via Ant Rozetsky on Unsplash
  • 02
    Font - Employees of Reddit, how did you first find out your boss was actually just an idiot that makes more money than you?
    via u/ColossusXT
  • 03
    Font - Lauer99 When he told me instead of taking my new higher paying job I should just work more hours at my current one for him.
    via u/Lauer99
  • 04
    Font - adeiner I had a boss once who refused to register to vote because she didn't want jury duty and then got jury duty because that's not the only way they pick. She ended up serving for a week.
    via u/adeiner
  • 05
    Font - birb_in_disguise My manager (woman who's in nursing school) thought that women were pregnant for 12 months.
    via u/birb_in_disguise
  • 06
    Font - Peregrine2976 Dropped a ton of cash renting art from a museum's art bank for our (decrepit Chinatown) office. Then didn't have money to pay salaries.
    via u/Peregrine2976
  • 07
    Font - davidmitchellseyes. When they fired the woman who did HR (she wasn't qualified for it, and had no training to do it so whatever), and I overheard the owner/boss have this conversation with a co- worker. Boss: "So, what is HR anyway?" Co-Worker: "Human Resources" B: "Yeah, but, like, what do they do?"
    via u/davidmitchellseyes
  • 08
    Font - CW: "Well, they take care of employee conflicts, deal with internal complaints, stuff like that" B: "Well, we don't need that. Besides, you can do that" So now we don't have HR, and bonus, the co- worker they were talking to deals with conflict by telling people to "fill out a hurt feelings report". And yes, it is a family owned/operated business.
    via u/davidmitchellseyes
  • 09
    Font - Axl_Bundy The time he got really by/passive aggressive a few months after he hired me which finally boiled over when he got mad and said "I HIRED YOU BECUASE I THOUGHT YOU WERE GOING TO RUN THIS COMPANY FOR ME!" I'm a graphic designer by the way.
    via u/Axl_Bundy
  • 10
    Font - Queen_lucya Once I told my boss I was 1/3 done with the work I had to do He said "well you better hurry the others said they has finishes 1/6 of the work" He walked away and I just stared at him for a few seconds
    via u/Queen_lucya
  • 11
    Font - Lufernaal Asks me to do stuff that helps no one or makes nothing better. He has us doing stuff that he literally can't explain why.
    via u/Lufernaal
  • 12
    Font - kingslayer_07 When he keeps asking me why the inventory looks "dirty" (physically dirty) and doesn't care about the accuracy of it. My job doesn't even have anything to do with the warehouse. I'm an ops analyst
    via u/kingslayer_07
  • 13
    Font - My manager told me to mop the breakroom floor. I did. She freaked out that it was slippery (two seconds after I was done).
    via u/r/AskReddit
  • 14
    Font - LeftChoux My boss thinks he is a programmer. (SQL) He told me he did not like that I have one table that contains both active and inactive computers with a field that indicates active\inactive and told me (demanded) tha I should create 2 tables one for each computer state.
    via u/LeftChoux
  • 15
    Font - TheMonkeyMen I told my boss since he wouldn't listen to me we needed an industrial engineer to make our . dept/machine more efficient. He said, "no way in h are we bringing in an engineer." 3 weeks later my company hired an engineer and when they came to our Dept the engineer asked him what he wanted to do differently he froze turned and said, "well let's go talk to Themonkeymen he's worked here a long time he knows what needs to be done." ... this boss makes at least double my salary if
    via u/TheMonkeyMen
  • 16
    Font - K Onk abad84 He couldn't do basic math while pretending to have a master. Couldn't use Excel either...
    via u/abad84
  • 17
    Font - TheHealadin. The former CFO asked me who was in charge of the Finance department. I still don't know if it was a joke.
    via u/TheHealadin
  • 18
    Font - forumdestroyer156. She has no idea about basic 101 things related to our industry that a fresh intern could demonstrate on the spot. Now, every job I do I have to explain from the beginning what it is, why we're doing it and why it's important. She nods, makes an "insightful" comment, then forgets it completely. I'm the only one on my team with actual experience in certain areas, and naturally have to do all the work in those areas. When it comes time for the credit, it's a "team effort"
    via u/forumdestroyer156
  • 19
    Font - o davidmitchellseyes. Another one At my old job, (hardware, paint, tools etc) they promoted this weirdo. One of his first orders was for us to all start wearing big yellow buttons that just said "YES" in black block lettering. The idea being, that no matter what a customer wanted, we had to provide it. I asked them, "well, what happens if they're asking for a product that doesn't exist?". Which happened more often than you'd like. He said to "just figure it out for them". OK then, good ta
    via u/davidmitchellseyes
  • 20
    Font - And if he ever heard me telling a customer that "I'm sorry, but semi-solid water-based oil ceiling and boat paint in a matte gloss finish doesn't exist", he would come up, cut me out of the conversation, then sell them something that wasn't anywhere close to what they needed. Resulting in returns that were almost impossible to talk about with the angry customer without saying "I'm sorry but YES, my boss is an idiot".
    via u/davidmitchellseyes
  • 21
    Font - FoleyX90 When I created functions for similar procedures instead of copying & pasting the exact same code & modifying it in various spots throughout the program. "What if we hire a developer that doesn't know how to use functions?" Then we shouldn't have fing hired them.
    via u/FoleyX90
  • 22
    Font - donutshopsss I did business with company A while working at company B. Company A offered me a job because they liked how I operated. I went through an extensive interview process, they said I was great, they had my resume, knew my experience and specialties, what I was capable of, etc.
    via u/donutshopsss
  • 23
    Font - After a few weeks they kept telling me "you need a degree in electrical engineering to understand this" when they knew I had no understanding of electrical engineering and left that part of the job description out when they hired me. I was ped so I spent the next few months interviewing at other companies while getting paid a nice salary. I had another job before they fired me. No regrets.
    via u/donutshopsss
  • 24
    Font - One_2_Three I work in mechanical engineering. My bosses (multiple levels of management) not understanding the product and only sees unit sales. Expects a small team of 4 to complete a one year project in 3 months. "We can test on the customer's site, they will understand any failures." No they won't. This is what happens when a construction company buys a mining company.
    via u/One_2_Three
  • 25
    Font - jadepaint My boss laughed when I put my respirator cartridges in a plastic bag to keep them fresh (Standard procedure). He said "well there is air in that bag isn't there". SMH
    via u/jadepaint
  • 26
    Font - TheRealWooky Monster. When she told me I should have no problem with this new task because "it's not rocket scientist". Also, she says "pacifically".
    via u/TheRealWooky Monster
  • 27
    Font - zerobot She needed to send an e- mail to somebody really important. So she forwarded me a long e- mail exchange they had and told me which one of those e-mails needed to be replied to. Instead of replying herself she wanted ME to replay but she e-mailed me what I had to reply with. She included an image she needed me to insert into the body of the e-mail. She didn't know how to insert an image into the body of an e-mail and is why I had to send this e- mail from MY e-mail account on HER b
    via u/zerobot
  • 28
    Font - thematgreen Before I quit to be a stay at home dad I was inflicted with a supervisor named Vicki (name changed). Vicki was this arrogant idiot of a woman with almost no idea of how to actually do the work, yet her managers lauded her as the "Queen of Eligibility" because she schmoozed them well. On top of this, the company I worked for promoted from within, which is good, but provided no management training, which is bad.
    via u/thematgreen
  • 29
    Font - On the management side of it Vicki had no sense of humor, and no idea of how to professionally discipline a person. Another supervisor asked me to help with outbound calls and I jokingly refused and she joked back with me because we both knew that of course I'd do it. I heard her mention to Vicki she tapped me in to help and mentioned my joking around as a positive. Vicki didn't understand the joke and walked over to me, and in front of everyone berated me loudly about how I WILL do the w
    via u/thematgreen
  • 30
    Font - The other supervisor came and de-escalated the situation. She just had no idea how to handle people and her position gave her a false sense of power. On the work side of it she just knew nothing. You'd ask her a question, she would say she needs to get back to you, and then vanish. You'd ask her for an answer later and she would say you never asked in the first place. Even if you had e- mailed the question and she replied it didn't happen, because she didn't have the answer. I
    via u/thematgreen
  • 31
    Font - remember asking her a very simple question, clarifying if I needed to get a new eligibility form from a customer or if I could just use the one I had that had a white out mark on it. She said I should know this. I agreed, but since I didn't what should I do. She said she would need to get back to me, and when I asked why she said she didn't have time for this, and I told her she SHOULD have time since she is my supervisor and I'm an employee who needs help. ...I never got an answer.
    via u/thematgreen
  • 32
    Font - My team and I had problem after problem with her. She just couldn't do anything correctly, ever, and would never admit a mistake, just become aggressive when shown proof she was wrong. I left the company for dadhood and a week later a friend I had there let me know wonderful news. Vicki, who had been with the company for over 15 years, had been terminated. No specifics were given to the employees, of course, but the rumor was that she screwed up a massive project that could have gotten th
    via u/thematgreen
  • 33
    Font - (I was not even there when the project started) and then the other employees. Normally this would have worked, but this time the director was involved and she was gone.
    via u/thematgreen
  • 34
    Font - rgm480 He was afraid of me taking his job.
    via u/rgm480
  • 35
    Smile - PokyCivi I worked for a production company that never put a dollar into advertising our products.
    via u/PokyCivi
  • 36
    Font - [deleted] My first real job was at a company owned by a guy whose family owned a bank. He'd gotten a EE degree from MIT sometime in the 1950s, and he didn't keep up. His fragile ego wouldn't permit anyone who was better than him to stay in the company for long. He regularly hired someone who would get one thing working and shipped, and then he'd make their life miserable and the company would lose them to a competitor.
    via u/deleted
  • 37
    Font - ✪ [deleted] In my last programming job my main boss feared written communication and types with his two index fingers. He had every trait that describes a toxic micromanager.
    via u/deleted
  • 38
    Font - ravemama13 Working as a pastry chef for a catering company: My boss would eat the pastries I'd prepped for tastings, even though he was "on a diet" and "it couldn't be him." He finally stopped blaming it on the cleaning staff when the other manager threatened to look at the security cameras.
    via u/ravemama13
  • 39
    Font - Also, I had never worked in a commercial setting before that job, but I streamlined the inventory and ordering system two days after starting, showed them that their pricing model for desserts was bleeding money, and then gave my notice six months later when it turned out the boss had lied about there being health coverage. (I turned 26, so couldn't be on my parents' plan anymore.)
    via u/ravemama13
  • 40
    Font - elaxation I work in HR. My old boss threw out 7+ years of employee files, medical clearances, and 19 forms (which verify your legal ability to work in the US and have to be kept for a determined amount of time) because she "hated paper." She did not create electronic records of anything, which the government agencies that funded our programs wouldn't have allowed anyways for auditing purposes.
    via u/elaxation
  • 41
    Font - We were audited and fined 80K by the government for sany HR intern or person with the ability to google "how long am I legally required to keep employee files" would know. She made 6 figures more than I did.
    via u/elaxation
  • 42
    Font - buycuriousub She told me to look up something, what she asked me to look up she had access to. It took her 5 minutes to come to my office to ask me to look up something that would've taken her .3 seconds to look up on her own computer. Also she had no idea the other CSR had for years not charged people for services and the other was taking two hour lunches and two 45 minute breaks. She was an absolute idiot that was paying five people to do the work of two.
    via u/buycuriousub
  • 43
    Font - malsomnus - "I need you to update the version on production right now" - "Are you sure? This is a really big one, it means taking the website down for like an entire hour and we can't abort it in the middle either" - "Yeah, do it now" (15 minutes later) - "OH MY GOD WHY IS THE WEBSITE DOWN WE HAVE A SUPER IMPORTANT DEMO WITH THE PRESIDENT OF PERU"
    via u/malsomnus
  • 44
    Font - TransformingDinosaur He asks very ambiguous questions that cannot be answered accurately with a yes or no answer. Then he gets angry when you don't give a yes or no answer.
    via u/TransformingDinosaur
  • 45
    Rectangle - Wazards Spends money on "fun events" instead of hiring people when we are understaffed severely.
    via u/Wazards

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ask reddit boss in-the-workplace work stories workplace-story terrible-bosses coworkers dumb people employees toxic-boss incompetence overworked-employees workplace Horrible Bosses dumb bad bosses funny stories funny
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