October 10, 2023 | Byron Fast

Dumb, And Sometimes Dumber, Bosses

It’s not always easy being at the top. Do you know what else isn't easy? Working for a boss who is a few cans short of a six-pack. Taking orders from someone that’s not all there is like an exercise in infuriating futility. These nine-to-five Redditors have it bad, so let’s give them a chance to rant about their dumb bosses.

1. His Brain Was Pristine

I was in the middle of a meeting and I used the word "Pristine". I used the word while we were discussing backing up some files. My sentence was something like: "The files will be in pristine condition". My boss stopped the meeting and got angry. He thought I was making the word up. He said he’d never heard of that word before and told me not to use made-up words in a meeting or I'd be written up.


2. Get Thy Map M’lady

My mom was working at an old-lady clothing store in the South when a woman with a beautiful but peculiar accent came in. As she was checking out, my mom asked her where she was from, and she said, "Wales". After the woman left, my mom's manager got out a map so she could find Wales. My mom told her it was in the UK. Her reaction was hilarious. 

My mom's manager looked at her and said, "Oh, that's cute. Trish thinks Wales is in England," and then proceeded to look for Wales in South East Asia.

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3. A Galaxy Of Stupidity

This was the most ridiculous thing I've ever had to explain to an adult. We worked nights together, and on our lunch break we were commenting on the stars and such, and this supervisor was completely oblivious that the earth revolved around the sun. "This whole time I thought the sun revolved around the earth"! She was close to 40 years old.

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4. She Left Her Brain At Home

At my current job, our email was getting overhauled and we resorted to using our personal emails for a short time. One of the over 40-year-old women I work for came to ask me for help because she "left her other email at home". She wanted to know if she had to bring her computer in. I had to explain that email is in fact accessible from anywhere that has internet, and that it's not physically located on your computer.

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5. It Was A Monthly Problem

I had a very long "discussion" with my manager over a timetable she had created for monthly reporting. She couldn't understand that a calendar that had the first of every month as a Monday and gave every month 31 days would be wrong. She thought my objections were an elaborate lie on my part to excuse missing a deadline. I'd like to say it was satisfying to finally get through to her, but after two hours of arguing it was actually more depressing.

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6. It Did Not Calculate

I had to calculate a percentage of something for ordering some inventory. The result was 0.79 so I said, "ok that’s 79%". My boss chirped in and asked if I was sure. "Did you do that in the calculator"? I explained that I did it in my head. You know: .79 times 100 is 79%. She put it in the calculator and said: "Hmm...well, just put it in the calculator to make sure because I don't think it will work out that way every time".

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7. Not Full Of Hot Air

I work at a group home and we have to transport our residents in vans. The boss didn't want us warming up the vans when it was even well below zero because it wastes gas. In addition to this every single van we have has the low tire pressure indicator on, and she doesn't want to pay someone the hour it would take to add air to each van.

Driving with under-inflated tires wastes so much more gas than letting an engine idle for five minutes. She's an idiot.

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8. Next Stop: Hogwarts

My manager and I were having a conversation about Harry Potter while I organized movies we displayed at the front of our store. At some point, he brought up how Harry Potter can't be real, so I shrugged it off. He then pointed out that Twilight has a larger chance of being real than Harry Potter does. I didn't know how to respond immediately, so I just stared blankly at him for a few minutes and then gathered my thoughts. "Do you realize what you just said? Vampires aren't real, least of all ones of that nature".

Awful First Dates FactsShutterstock

9. A Quarter Of A Brain

I had to explain to a manager that a quarter past the hour means 15 minutes past the hour. He thought a quarter always meant 25. I had to tell him that quarters are one-quarter of something and not a fixed number. Then I went into how football quarters are 15 minutes, not 25 minutes. Sadly, he still didn't believe me. Some bosses cannot take advice or learn from underlings.

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10. What Was That Screen Thingy Again?

I had to show my boss how to take a screen capture on his computer. He ended up calling me a couple of times after that to ask me how I did that "screen thingy" again. He would try to hit the key but didn't know what to do after that. One of my coworkers ended up having the same question too. They are 26 and 24.

The same boss also asked me why his mouse wasn't working, but that was more of a "derp" moment since it wasn't plugged in.

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11. It Never Struck Him

I worked a summer job on a farm once, and when the weather turned bad, something ridiculous became very obvious. My supervisor thought that thunder and lightning were completely separate and non-connected things. He actually thought that they had nothing to do with one another. When I explained to him that actually yes, hearing thunder does mean that there's lightning close by, he laughed at me.

He honestly thought I was lying to him. He would not believe that thunder is the result of expanding air from the sudden heat of lightning.

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12. Mission Impossible

Recently I had to explain to my boss why I, as someone who does not identify as a Christian, would not be accompanying him on a mission trip with the intention of showing "Jesus videos" to "less fortunate ignorant, illiterates".

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13. No Fixed Address

I was working as an executive assistant for a boss who was incredibly paranoid. He had just bought a new house and asked me to take care of a lot of the details. He wanted to transfer his utilities, get the cable hooked up, all that good stuff. No problem, right? Wrong. 

He also told me that I wasn't allowed to release his new private address to anyone ever. "Not even the cable company"? I ask. Nope. Apparently, I am supposed to get cable and garbage service started at a house that cannot be disclosed.

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14. Rant Over Middle Name

I had a supervisor once that said he loved Obama—this was before he was elected—and was screaming about what the Republicans were doing to him. He said that they put up a billboard comparing Obama to Saddam Hussein. When I realized what was going on, I had to giggle.

I asked what it said, and he told me they had written "Barack Hussein Obama" and went on a rant. I had to explain to him that Obama's real middle name is Hussein. It took a few minutes, but I got him calmed down enough to laugh my head off at him.

They Weren't JokingShutterstock

15. She Wanted Her Money Back

My former supervisor, a woman in her 60s, purchased a wireless router for the laptop that the company had just given her and couldn't get it to work. Since I was the token guy in his early 20s in that office, she came to me the next morning. We went around and around for a good ten minutes, as I tried to sort out just what was wrong with it.

Finally, I went for the fallback of "Unplug it from the wall and plug it back in". This completely floored her. I spent the next 10 minutes convincing her that, even though it's called a "wireless" modem, she still has to plug it into the wall. She was downright offended and felt like she'd been ripped off when she bought it.

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16. It Wasn’t The Fear

I used to deliver furniture in box trucks, which, in case you didn’t know, are quite top-heavy. I was out on delivery one day, and it started storming badly. A tornado warning was issued, and sirens were going off in town. I pulled over to a hospital and went inside for safety. When I called the store I worked at and told them what was happening, what the manager said was infuriating. 

He accused me of being afraid of storms. I had to explain to him that it wasn't fear of storms that caused me to stop, but the fact that the truck would be blown over and I could possibly die. He just never understood why I stopped.

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17. This Was Not Touching

I worked with a doctor. He had this ridiculous and annoying habit. He would walk by something and touch the thing he wanted you to bring him. For example, while touching a stapler and walking away, he'd ask for you to bring it to him. It would have been just as easy for him to wrap his fingers around it and grab it himself.

The Worst Things People Have Ever DoneFlickr, Kurt Nordstrom

18. What’s In A Name?

My job is to represent employees who are in disputes with their bosses. One of the members that I represent contacted me to inform me that his manager would not pay him bereavement leave for his grandmother. When I spoke with the manager, he stated that the grandmother did not share the same last name as the employee.

I had to explain to him that his grandparent on his mother’s side of the family would not share the same last name, as it is customary for women to take the man's last name when married.

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19. Choose Life!

My former boss was a raw vegan, although he didn't start that way. It was a development while I was working there. So through his progression from vegetarian to vegan, he would tell us that he just couldn't eat eggs because they were chicken abortions. The first time he told me this I was just like "Yeah, yeah ok whatever".

After he mentioned it a few more times, I finally explained to him how chicken eggs are not abortions, because they're unfertilized to begin with. I continued to explain that through his reasoning, that meant that I, as a female, essentially have an abortion every month. He still refused to believe me, even after I explained the process.

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20. Orange Is The New Dumb

I had to explain to my dumb boss a bunch of things—things that most people just get on their own. First off, the brand of your computer doesn't have to match the brand of your mouse. Also, if you fax something to someone from one machine to another, and the image looks like there's not enough ink, it's not the fault of the first machine.

I just...I'll end up talking for years if I say everything this woman and I have argued about. Yes, argued. She doesn't quite understand that I'm just trying to help, and she tries to battle with me over things. Oh god, like the time I told her we ran out of oranges, and she refused to believe me. She said, "we couldn't possibly run out that fast". Look boss, there are no oranges.

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21. A Dust Up About Dust

I had to explain to my boss that light does not in fact create dust but does attract it. He was completely convinced that overhead lights for his concession stand created the dust that settled on the machines and registers. I explained this to him after he said this to me: "This light makes a lot of dust you need to wipe it off". To which I was like: "What"?

I explained to him the conversion of mass, how matter can neither be created nor destroyed, only altered. He came back with this: "If light doesn't create dust, then why is my front porch dustier than my back where the sun is less". I tried to cover my shocked face and said, "Then explain how dust gets in your attic where there is no light". This stumped him

He didn't believe me and got haughty and annoyed that he was being schooled by someone half his age. To this day he still doesn't understand it and continues to tell employees to "wipe off the dust that the light created". Sigh.

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22. He Was Gone With The Wind

I live in Grey County, Ontario, and over the last seven years, there has been an explosion of windmill farms in the area. I deliver party rental supplies and set up large party tents for my summer job, and one day I had to work with my boss. On the way to the tent location, we passed one of the wind farms in the county. That’s when my boss turned to me and said something incredibly stupid.

He said: "Why don't they just power those windmills with a generator, and then they will turn and make electricity". I then had to explain that what he proposed is impossible without being condescending and without stating that perhaps somebody would have thought of that already if it was a good idea.

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23. She Didn’t Go With The Flow

I was new at this job and was excited to go to my first team meeting. My boss was at the front and we were trying to figure out the organizational workflow. To my amazement, my boss starts writing everything down in paragraph form! Even though I was new to the company I had to put a stop to that. I took what she had written and wrote it on the board in a standard flow chart.

Her eyes totally lit up in amazement. I'm 25, fairly new to this profession, and she has been running this business for close to 30 years. Somehow in all her years of experience, she had never seen an organizational flow chart. This is a human resources-type gig, so I was absolutely flabbergasted that she didn't know how to make one.

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24. They Didn’t Correct

I'm a doctoral student in clinical psychology. A couple of years ago, we were reviewing a projective test used with children. It consists of picture cards that the child can construct a story from. The protagonist is a little pig. The students presenting the test explained that there is a different set of cards picturing a lamb instead of a pig to be used with Jewish people, because, you know, Jewish people worship pigs. That wasn’t even the most insane part. 

And then they added: Oh, and by the way, the same goes for Muslims. So I snap up, sit straight, repress a chuckle about how ignorant they are, and wait for one of the two professors to correct them. But, as I look at the professors, I see them nodding their heads! I was in total disbelief! So, I had to correct my student colleagues and professors.

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25. He Couldn’t Bear It

My boss had a nephew who was saving up for an operation to change his gender. My boss's comment really floored me. He said: "My nephew is going to be a great mother one day". I was a little unsure how to handle this situation. I gently said that his nephew was not going to be able to have children after the operation. My boss looked totally shocked.

I had to continue and tell him that his nephew wouldn’t be able to have children because they won't actually give him a uterus and the ability to bear kids". My boss looked so sad and said that his nephew was going to be devastated when he heard this.

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26. He Should’ve Known Better

On the first day of my new job, the annual Christmas lunch was being held, which I was invited to. Score! I sat down, and got told the boss was paying for everything. Score! I went up and introduced myself to the boss to have a chat and let them know how excited I was to work here. What he said completely shocked and surprised me.

He said two things in quick succession. He said he wasn’t having the steak because steak stays in your digestive tract for up to forty days. Two minutes later my boss says that he’d better not take his antibiotics if he’s drinking, because he didn't want to have an allergic reaction. I politely asked him what he was taking, and he provided me with the name of a brand of allergy tablet.

This was an antihistamine, not an antibiotic. So I explained about the digestive tract and the difference between an antihistamine and an antibiotic. Maybe you think this isn’t so bad and not so moronic. You may be right—except for one thing. 

My job was at the University Faculty of Medicine. The place they train doctors. My boss is a trained doctor.

Bad DoctorsShutterstock

27. Shut ‘Er Down

I work for a very small company and my boss called me late one Friday night and said there was something wrong with the computer at work. I rushed over there and found him sitting at the computer. What I saw was seriously confusing. The screen was showing a box that says, "Are you sure you want to shut down"? I asked him if he wanted the computer to turn off and he said yes.

So, I told him to click yes. I'm still not sure what he thought "shut down" would do to the computer...make it explode? This is the same boss that thinks anything you do on a computer is email. When we had to switch to paying taxes electronically, he'd ask if I had emailed the money to the IRS. Then, he would check the email constantly to see if they'd replied back saying it was received.

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28. He’s From La La Land

So, here’s an experience I had while working in a warehouse. There was a truckload of very expensive parts going to San Diego. However, the label had been mistyped and instead of having 'CA' for the state, it read 'LA'. This meant that the parts were put on a truck line that goes to Louisiana. I caught the mistake at the last minute and approached the boss.

I told him that these parts were supposed to go to California. The guy argued with me and said that the state read Louisiana. So, I asked him where the heck San Diego, Louisiana was. His reply was infuriating.

He said that he thought LA stood for Los Angeles. So which is it guy? Los Angeles or Louisiana? He had no clue.

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29. IT 101

When it came to my old boss, I felt like I was teaching a basic IT course. Here are some gems from the man who earned 15 times more than I did. He thought all email addresses needed WWW in front of them. I had to explain copying and pasting text about a hundred times. I also had to explain how the Internet doesn't just automatically happen wherever you are.

These were especially hard for him to grasp. It took an IT person explaining it multiple times for him not to get it. But that wasn’t the worst thing he did. 

Finally—and this is a big one—if you're going to sign up for "adult sites" that put malware on your computer, don't blame IT for having a bad firewall. Oh and by the way: don't use your wife's credit card and wonder how she found out you signed up for "adult sites". What an idiot.

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30. Barking Up The Wrong tree

I work in a lumber yard, which is kind of like a giant lean-to. There were 100 to 150 tall trees against the side of one of our building, One day, while eating lunch, my boss asked if I would cut down the trees. I laughed, figuring he was joking. I was so, so wrong. He got mad and told me to grab a hand saw and a ladder and make it happen. I had to explain that our property line ends at the edge of the building, and those trees are not ours and he'd need permission.

I also had to explain that people are trained and come with equipment to do things like that. That made matters worse and, after a hissy-fit at my refusal, he stormed off. Later he took my advice and called the people needed to bring them down. Later, I realized I indirectly taught my boss how to get rid of something I didn't want to go. I still miss the shade in the summer.

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31. Which English Do You Speak?

When I was working at a video store my boss was talking up a movie to a couple of customers when the assistant manager walked up and asked what movie he was talking about. He responded that it was called Easy Virtue and he didn't think she'd like it for two reasons. First, it was really quick-witted, and they used a fair bit of slang. So, if you don't pay attention, you won't keep up.

The second reason was that it was British. The assistant manager looked confused for a moment then responded—and I kid you not—"oh so it has subtitles"!. The booming laugh that emitted from one of the cashiers was fantastic. How she got to be a manager is beyond me. The girl legit didn't even know the order of the alphabet.

Why Would You Say ThatPexels

32. A Few Short Of A Full Plate

In a casual conversation at work—I guess we were talking about earthquakes—a superior wondered aloud why earthquakes seem to be concentrated in certain areas. I said something about the tectonic plates of the earth, and how they meet up and collide. After I’d finished, I was met with the blankest stare I have ever seen.

I tried to explain what tectonic plates were for a long time—in vain. Mostly because I had no idea the depth of the ignorance I was dealing with. Apparently, this person thought the oceans just go down to infinite depths? Like there is no earth under the oceans. I ended up getting out an old issue of National Geographic I had which showed the fault lines of the entire globe.

The weird thing is, this person wasn't some slack-jawed drop-out. They were quite sharp and had been to college.

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33. Heartless About Homeless

I came in to work with a copy of Big Issue once. For you non-UK dwellers, it's a magazine sold by homeless people trying to get themselves up and on their feet again, by buying and selling, and running their own business. My boss tried to tell me that the guy I bought it from was going to spend it all on booze and crack. I told my boss that it seemed unlikely.

I went on and said that he can spend the money on anything he wants, as it was his money. My boss disagreed and said "no, it's your money" He thought since I gave it to him it was mine. My position was that I had bought something from the guy, so the money was no longer mine. He didn't understand the concept, and the fact that he was bandying about a really rather unkind stereotype about homeless people made me drop the conversation. But come on dude, have some sense.

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34. Iconically Misinformed

My boss wanted a picture of her grandkids put on top of her standard Windows background—which was yellow tulips—for her desktop. I told her I could do it rather quickly. Then, however, I realized that I couldn't get into the folder that contained the yellow tulips. So, I decided to take a screenshot of her desktop, pasted it into "Paint", moved all of her desktop icons a row over, and took another screenshot to just puzzle the two pieces together.

Her reaction was…interesting. While I did this she freaked out about how she needed her icons, and I couldn't remove them. I told her it was going to be fine, I needed to move the icons so that they weren't on the actual picture of the background. She continued that her icons were very important. I asked her to trust me. I halfheartedly whited out around her grandsons in "Paint" and brought them onto the field of tulips, changed the background, and magically her icons worked.

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35. She Didn’t Know About Yesterday

I was running a trivia competition at my work and I asked this question: "Which band was Jim Morison the lead singer of"? To my shock and horror, no one got the answer. I told them it was The Doors and no one at my work had even heard of them. I was yelled at by my team leader for not making questions about more current people.

Her excuse was that she is 27, how is she supposed to know about bands from before she was born? She wanted questions about more popular artists like Beyoncé or Lady Gaga. I then asked if she had heard of The Beatles and she replied "I've heard of them, but I wouldn't know any of their songs or who is in the band".

Inside my head, I was like: "Seriously? You’ve only heard of them". Then all the people on my team—15 of them of varying ages—backed her up instead of me. They accused me of not knowing anything about the most popular, contemporary bands. Ugh!

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36. Not Up On the ABCs

So, basically, I have to create a large number of docs at work, a lot of them are lists in Excel that require numbering and lettering. The guy I work for is the only other person in my department and usually, his spelling and grammar are decent—not great, but decent. There is, however, one giant exception. In every alphabetical list he makes, it seems he doesn’t know where G and K go.

This problem is only associated with lists, as he seems to use G and K in words pretty well. When I first noticed it, I went back through previous pieces of work and the dude had missed them out every time. Usually, the lettering only gets about halfway through the alphabet, so I never get to find out where he thinks these two letters go.

He's much older, so I feel bad asking or pointing it out to him. I spoke to one other person to see if there could be a legitimate reason but apparently not. So yeah, my department head doesn't know the correct order of the alphabet.

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37. Bin There, Don’t Do That

When I was in high school, I got a job at an accessories store called The Icing. I had this totally clueless boss who every time we got a shipment in, would open all of the packages of little tiny earrings, necklaces, rings, and other itty bitty items, and throw them all into this giant bin. She would then proceed to spend hours wandering around the store, finding a home for each individual item.

I tried to explain to her that it would be so much easier if everything didn't all get dumped into a bin and mixed up. Like if all of the earrings were together in one bin, and all of the necklaces were together in another. It would be so much quicker to put things away since they would all go into one section. She clearly did not understand the concept of a lean workplace.

Even after I nicely explained it to her, she insisted on continuing to do things her way. It aggravated me so much, because I really could have cared less if she spent her time wandering around the store putting away merch, but she would stick me with it too. She would often open up tons of stuff, dump it all into a bin, then push the bin over to me and ask me to put everything away. Ughhh.

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38. Do You Wanna Go Faster?

Working as a developer for a company, it turned out my role was to run every online aspect of their business. This was a European-wide multi-million-pound business, 40% of which was now coming through the site. One of my, very-much-unwanted, roles was "advert designer". I'm not a designer, I'm a programmer—but my boss didn’t understand that.

So yes, I was soon standing in the CEO's office having him angrily telling me to "make the van look fast"! for an advert about next day delivery. I added some "speed lines", and he just yelled, "Faster"! So, I skewed the whole thing so it was leaning back a bit. Again he wanted it "Faster"! I then added a bit of motion blur and he came back with "Faster"!. In the end, I made the van yellow, and he was delighted.

What?! Give me coding any day.

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39. He Didn’t Approve

When I was in college, I worked at a coffee shop that was owned by a Christian fundamentalist. One day, he came in to drop something off while I was on my break. I happened to be reading the sixth Harry Potter book, as it had just come out. The owner was oddly quiet and left without saying much to anyone. This was strange, as the guy was actually quite friendly.

A day or two later, the store manager asks me to stop in. I swing by, and what she tells me leaves me shocked. She said that the owner wanted to fire me but she talked him down. She then showed me that he had made a termination form. In the "reason for termination" field, he had written: the employee was reading unapproved and immoral material.

The store manager then explained to him that you can't fire an employee for their choice of reading material when they are off the clock. And also that putting that in writing and filing it was a surefire path to a lawsuit. The third thing she had to explain to him was that Harry Potter was for children and not immoral at all.

I was not fired, but I quit a few months later. I made the manager a plate of cookies for going to bat for me.

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40. She Was Lost In Translation

I had to explain to my former boss that although I am Chinese, it does not mean I can "speak Chinese". I was hired as her executive administrative assistant and I worked so hard for months to keep the office together. She was nice—albeit crazy—so I let some of her slight prejudices slide and shrugged them off as harmless. Big mistake. 

One day she called my office and asked me to join her in her meeting with an investor. I was asked to make the atmosphere more casual and favorable by conversing in Chinese. I was shocked as I had never said I spoke Chinese to her or anyone. The truth was I did speak Cantonese, but as it turned out the investor spoke Mandarin.

After I failed to speak Mandarin to the investor, my boss called me back into her office. She gave me a verbal whipping and complained that I had misled her on my resume.

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41. Meetings To Look Forward To

My boss had the weirdest quirk. I had to explain to her that it wasn't expected—nor typical—for every single meeting to also include a small buffet of food. She had a PhD and zero work history and only had her orientation as a reference point for meetings. She would have me put out coffee, tea, cookies, half sandwiches, and desserts for every single meeting we had, even if it was only us. Gotta love academia!

If this wasn’t bad enough, she was kind of crazy about ingredients. She wanted no dyes in the food and to know where the meat came from. I couldn't have the same or similar foods either otherwise she would say things like, "Oh is this that hummus wrap we had last week? Maybe next time you could order us something different"? Apparently, she wanted to make sure she was eating a varied diet.

It got so bad that planning the food for a 15-minute meeting would take forever. And I would have to drive to a farm nearby to get her unpasteurized milk. Oh God. The flashbacks!

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42. She’s A Little Behind

I'm the local tech support, which means I'm the guy that knows how to power-cycle the router. One time, my boss asked me to help her with a document she was writing: her Christmas newsletter or something. She needed it to fit on a page, and it ran over. She was having some issue formatting it consistently. So, I figure I'll show her how to select everything, and where the margin and font-size settings are, and we'll be good to go.

My boss—and I don't mean this as a criticism—isn't very technologically inclined. She knows how to do lots of stuff, but hasn't really kept up to date with the modern equivalents of the technology she was used to. Consequently, her letter ran a bit long because she hit the carriage return at the end of each line. Just like you would on a typewriter.

I had to go through the entire document and take out all the carriage returns. Then I had to explain that, like, computers did that for us now, and you could just keep typing and it would figure out where to break the line. BUT I COULDN'T FIX THE FACT THAT IT WAS IN ALL CAPS.

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43. A Glitch In The Matrix

In my miserable time as a cashier and dishwasher at a restaurant that was also a grocery store, I had the task of mopping the floors every day. Unfortunately, my boss refused to let me stay an extra 15-30 minutes after the store closed to mop. This meant that I had to mop the floor while customers were still wandering around.

This, predictably, does not have the desired effect. They would have been better off having me mop the floors never. After a week of this type of mopping my boss calls me into the main office and tells me that the floors aren't getting cleaned properly. I tell him I agree and remind him that I asked if I could stay after and he wouldn't let me.

My boss responds with a blank, clueless, stare. I decided to repeat my request. "If you let me stay after, I could mop the floor after everyone leaves". The boss says again that the floors haven't been getting cleaned properly. I repeat my request, and he says that he can’t pay me overtime. I reply with the fact that the floors can’t be mopped when the customers are standing on them.

My boss pauses for a moment and then starts the whole thing over with: "The floors need to be cleaned better".

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44. She Eats At His Soul

These anecdotes about my boss would be fun—if only she wasn’t a total jerk. She holds rabidly onto weird and totally untrue "facts". Such as, a mouse can squeeze through a space the size of a ballpoint pen. I've seen mice, their heads are bigger than ballpoint pens. Also, she thinks I'm some kind of magical wizard for being able to whip up a basic flier in a Word document. I imagine her head would explode if I had Photoshop at work.

Just last week she flat-out asked me what Christianity was. She insisted to a Sikh man that if his beard is aggravating his skin, he should just shave it off. In an altercation the two of us had, I had to explain what I meant when I threatened "constructive dismissal". She accused me of making it up. She's been a manager for ten years—but that’s not all. 

She actually asked if chocolate and black Labradors came from Jamaica because they're darker than golden labs. She once suggested that we all dress as golliwogs for an upcoming fancy dress day. She thinks animal testing should be done on prisoners instead. She won't even hear you if you try to explain how reprehensible that is.

And by far my favorite: She had to be told, at the age of 35, that dragons didn't exist. This happened after she exclaimed "it's funny how you don't see them" and then "but didn't they hang around with dinosaurs"? The fact that I have to work under this creature eats away at my soul. I've reported her several times for some of the more offensive things but guess what? Nobody cares as long as we're still taking money.

Dumb, And Sometimes Dumber, BossesShutterstock

45. I’m Not IT But I’m Better Than You

Last week, my supervisor asked me over to her desk, saying there was a problem with her Outlook and that maybe I can help. Just so you know, I'm not in IT or anything, I just know more than her about computers. So, I go over there and ask what the problem is, and she says a bunch of her folders in Outlook disappeared a while ago. She said that now she needs to use them "for filing things" and doesn't know how to get them back or if they're gone forever. When I looked at her monitor, I wanted to scream. 

I told her to click that plus sign next to her inbox. She had no idea had to expand her inbox. She was so happy when all of her folders magically reappeared. This same supervisor had gotten an email from her boss saying she needed to start locking her computer when she left her desk. She then forwarded that email to me asking how to lock her computer.

She asked for help sending an email. She was sending an email with an attachment and kept writing the subject in the attachment line and not the subject line. I almost explained how she's essentially changing the file type from ".jpg" to ".jpgCUSTOMER3452" but just facepalmed on my way back to my desk.

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46. They Time Shared Their Brain

I worked for the Hilton's timeshare division—I know: it’s an evil place to work. At one point they hired a new management wizard who they said was going to revolutionize the timeshare industry in Hawaii. He implemented a new bonus incentive program which all the managers and HR were touting as our ticket to undreamed riches.

Apparently, they thought we were as stupid as the people who actually buy the timeshares. I did the math and made a disturbing discovery. I found that with exactly the same production, I would be making nearly $1,000 less per month than with the previous system. Their pitch was that if we worked 10 times as hard, we would make double the money we used to make!

I politely explained my feelings on this to HR, and they told me this was the deal, so play or bow out. I left two days later.

Reason I Was FiredShutterstock

47. That’s A Really Long Cable

Rewind to the summer of 1994 so things like Wi-Fi, cellular modems, data tethering, virtual private networks, and things like that are pipe dreams at best. A 256K ISDN line is considered blazing fast. I was working as the lone tech support for a small shop, mostly Mac but some PC. The owner of the shop is about as technically savvy as lasagna but demands (and gets, of course; he IS the owner after all) a then-brand-new PowerBook 520c.

At about the same time he announces he's taking a trip to China for two weeks. I set him up with an AC power travel kit and three or four pages of instructions in the event that something goes wrong with his Mac. I tell him very specifically that he will not have any network or email access. At the time we were using a proprietary non-internet-standard-based internal-only email system. I even wrote this down on the instruction pages.

Yeah, you know what happened. He gets back from China absolutely furious that nobody was responding to any of his emails. He pulled out his PowerBook while on the plane and started writing multiple emails, ignoring what I later learned were hundreds of error messages that had appeared on his screen.

I had to spend literally two hours explaining to him that he needed an ethernet connection on our internal network in order for email to work. In the end he never fully understood it.

Dumb, And Sometimes Dumber, BossesShutterstock

48. He Didn’t Have Work/Life Balance

My boss had one of those bracelets that make you have super balance or something. During my interview, I noticed it and laughed—and cried—internally. I always thought those things were so stupid. Well, I ended up getting the job and a few months later I asked how it worked. He sort of explained how it worked but it made no sense to me whatsoever.

I then very gently said it didn’t make sense that that little bracelet could give him super balance. So the guy stood up and posed in this weird position and asked me to push him. Obviously, I didn't push him hard because I didn’t want to make my boss fall in front of everyone and make a fool of himself. Apparently, he has done this, and no one has ever made him fall, so that’s why he believes it works. But then one day we finally turned it around on him. 

A worker asked him if he could try it out. The worker put the bracelet on and asked the boss to push him. The boss pushed him, and of course, the worker fell down. The guy on the floor stood up and said "This doesn’t work at all, I think no one pushes you hard enough". He gave the bracelet back and went back to work. The boss still uses the bracelet.

Dumb, And Sometimes Dumber, BossesShutterstock

49. A Map, Get Me A Map

I had to ship some retention samples and had the logistics manager ask why I listed "Russia" under country when that's the continent name. He's twice my age—I thought he was joking—but he just kept insisting I phone to get the correct shipping address. He explained to me there are eight continents: America, Asia, Russia, Europe, Africa, Greenland, Australia and, believe it or not: Canada.

He took me to a wall map to point these out to me. I tried to explain the continents were in bold over each landmass, and, when I pointed to Antarctica in a side box, he said that was the South Pole. He said he didn't know where the North Pole was but he was sure they weren't continents. He's been at his job for 40 years.

I had to show him maps online but he says this is all "new or modern mapping". He went on to say if I was older I'd remember the original continents before they were renamed. He still thinks those eight masses are the world's continents, and that teachers need to stop making up new continents as that's what's wrong with America today.

Dumb, And Sometimes Dumber, BossesShutterstock


Sources: Reddit,



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