March 8, 2023 | Eul Basa

Move Over, Michael Scott: These Weird Bosses Should Not Be In Charge

You never know what kind of boss you’re getting when you start a new job. Sure, you could get a good one, but a lot of the time, you get stuck with someone who has all the control and none of the competence. They can be mean, they can be strange, they can be downright terrible, or worst of all, they could be one of these people. Strap in: Here are the bosses who put even Michael Scott to shame.

1. Really Getting the Point Across

We had an anonymous feedback program. Our boss was mad with the feedback and the many comments about his short temper and how he would yell in meetings. The more he talked about how incorrect, unfair, and hurtful they were, the redder and angrier he got. He finally smacked the table and yelled, "I DO NOT! SCREAM! IN MEETINGS! OKAY?"

Quit On The Spot factsCanva

2. Prepared for Anything

One of my bosses was a nice, well-meaning person who just did some absurd things. He was like a real-life Michael Scott. We had kidnapping drills one day where we learned how to “not be kidnapped.” Notably, this was a regular, boring office in a regular, boring suburb. There’s no reason why kidnapping would be on anybody’s radar.

Also, a push-up contest happened. It was between my boss and a few other guys. Again, this is a white-collar office with middle-aged dudes in khakis. The next week, my boss couldn’t remember the nationality of our Hispanic colleague. He tried to “learn Spanish” to make her feel special when she returned from maternity leave. What he learned was NOT Spanish, and also she was from Portugal, not Spain. She knew like five words of Spanish.

There were many, many moments like these. Great boss. He genuinely cared about everyone in the company. He had his occasional moments of brilliance where he really got things done, but there were just so many moments of ridiculousness.

Weird Bosses factsThe Office (2005–2013), NBC

3. Running the Office

My boss actually did organize a "fun run" for the whole office. The course was just running around the building about 20 times until we eventually got to 5k. It was at 7:30 on a Saturday, and only 7 people showed up.

Weird Bosses factsMax Pixel

4. Clear Your Schedule

My boss got a smartphone to replace a flip phone. He came to me to learn how to use it. That became my job for the next week. With complete disregard for what either of us had to do, it was all about him learning his phone to the point where he was blowing off meetings and making excuses so I didn't have to go to mine.

The following week, he came to me because he discovered free online dating apps and asked if there was a setting where “fat chicks” couldn't message him.

Weird Bosses factsLibreshot

5. Never Want to Be Tangled in That Web

Long ago, my 80-year-old boss pulled me into his office. He said, “Paul, I've noticed that your shirts come untucked and that looks unprofessional.” I responded, “I'm sorry about that, Joel.” He went on, “I want you to start tucking your shirts into your underwear.” I didn’t know what to do and stood there mouth agape.

“Go ahead and try it now,” he said gesturing towards my pants. I said, “Joel, you know I have 15 women who report to me. I can't undo my pants in the office.” He stood up and said, “sure, you can,” and dropped his pants. My 80-year-old boss was standing there wearing a pair of Spiderman undies.

Weird Bosses factsCanva

6. After Inconsiderations…

My boss only hired people he could, "get a drink with." He was grossly under-qualified to manage, but he was good at sales and kept getting promoted. He made awkward, distasteful jokes and comments like asking an employee if he and his twin brother "shared" a girlfriend. We’d always have just really wasteful, pointless meetings.

Nobody knew how he spent his days; his assistant manager did all the heavy lifting while he would wander around making conversation. He showed up to a meeting with his superiors having done zero preparation, and they kicked him out. He finally got fired for using the phrase "kung flu" with a Chinese employee back in March.

Bad Houseguest factsPexels

7. Symbolic Homonyms

I’m a public-school teacher where the principal is technologically illiterate. When the #MeToo movement was all over the news, he held a staff meeting to discuss how it might impact staff and students. He didn't understand hashtags or how to talk about them in a public setting and discussed the “pound” Me Too movement. It was so brutal.

Worst Co-Workers factsPxHere

8. Commemorating Teamwork

My boss got really excited while organizing an office picture day. At the time, I was his sole employee.

Weird Bosses factsCanva

9. Most Vocal Supporter

A boss I had made Chewbacca noises regularly because he thought a co-worker’s name vaguely sounded like Chewbacca. (It did not). He used voice-to-text extremely loudly in his office, but only to send really personal messages. He shouted the same 7 references to old movies and awkward hip-hop song lines 100 times a day. He insisted on greeting all our international coworkers who, by the way spoke perfect English loudly, in "their language" and would then look around for approval afterward, even though he almost always messed this up.

That said, he had good sides too. He never hesitated to go to the mat for us whether we deserved it or not, and he gave really sage business advice. He even came to each community play I did in the four years I worked for him and told everyone else in the office how good I was in it for the following month and chastised them for not coming. When things really got serious or bad in my life, he couldn’t have been more accommodating. He was a weird guy, but he may be the best boss I’ve ever had.

Weird Bosses factsUnsplash

10. Doesn’t Hold Water Glasses

I had a boss who would stop us in the middle of our work and hold company-wide meetings talking about his crazy conspiracy theories. Aliens, Illuminati, whatever, we were in the conference room watching his ridiculous Powerpoint slideshows. Mind you, we were a freaking furniture-making company. One month he got so caught up in his deranged theories that he didn't order wood to make any furniture for an entire month. I don't know how he hasn't been fired.

Worst Co-Workers factsPxfuel

11. Knows What He’s Doing

I worked for a boss who rarely thought about what he said before he said it. During my interview, he asked what my weight was. When he was thinking of selling the company and was walking Japanese investors around the building, someone heard him saying, “We really blew you guys up, huh?” And his foot-in-mouth issues didn’t only happen in one-on-one conversations.

I have video of him telling a really cringy joke during a sales meeting. You could see at least one person covering their face in embarrassment. For three weeks, he was mysteriously gone and then came back with a beard after his “secret” facelift. I have a box of pictures from the 70s of an exotic dancer giving him a lap dance. In the conference room. Same furniture.

Unreal Zingers factsUnsplash

12. Full Body Workout

I worked for a woman as her “personal assistant/cat sitter.” She was quite rich and off the deep end nuts. She had me order a mannequin online and then paid me to take one of the legs to Nordstrom to see which suitcase to buy that would fit the dismembered mannequin body because she wanted to fly with it to Pittsburgh.

She was going to display it “as her daughter” dressed in her daughter’s clothes at that daughter’s graduation celebration. Buying the actual mannequin was a whole thing too. She kept trying to get me to order from “adult doll” websites because she didn’t understand what they were actually selling. Yeah, I left that job as fast as I could.

Weird Bosses factsUnsplash

13. Out of My Justice League

I had a boss once offer me $50 if I came in to cover a shift for him. Instead of paying me cash, he gave me a comic he claimed was worth $50. It wasn't.

Han Solo factsFlickr, Robin Parker

14. Getting in the Same Headspace

When I first interviewed for my job as a receptionist/assistant, my boss started telling me about the company's four pillars, but he could only remember three. I later found out the one he forgot was knowledge. That was when I realized that this man was not the sharpest tool in the shed. Fast forward a year later, I learn the extent of his ignorance.

He’s terrible with the English language in general and will mangle phrases and descriptions to no end. Back when we were prepping for a conference, he was on a group call and mentioned using a “golden hamster ball” for giveaways. He raved about how great it’d be spinning around while people passed it, all the while everyone on the call listened in confused silence.

At the time, I had become so good at decoding his nonsense that I knew he was referring to a gold raffle cage and sent him an image privately asking if that was what he was thinking. He constantly talks about how I can read his mind and must be psychic. Even though he still refers to a raffle cage as a "hamster ball" he’s actually a good boss. He hired me based on a gut feeling and has been decent to me ever since.

Weird Bosses factsPxHere

15. Nope, Nope, and Nope

My boss asked a Mexican employee if his new baby’s name was going to be “No Mas” during the shower we threw.

Weird Bosses factsPxHere

16. Look at What I Can Do

My old boss, who’s 70, said he invented Apple computers before Steve Jobs and that the computer he invented was more powerful than any other. He threw knives in the air and said if you could catch them, he’d give you money at a Christmas party. Once he came to work in nothing but leopard print underwear and a pink cowboy hat.

He was diagnosed with bipolar disorder but “not the bad kind.” It was the kind that “makes you super smart.” He got tipsy at work and gave some to whoever would take it. He actually needs to be institutionalized, but he’s rich, so he gets away with everything, and everyone is scared of him.

Weird Bosses factsCanva

17. Saying the Right Thing

I had a manager who tried too hard to be everybody’s best friend. He loved pep talks and thought he could raise our abysmal morale by being Mr. Positivity. It was low because were always buried in work and paid dirt. He’d crack jokes, randomly burst into song, and sneak up behind you to yell “you’re doing a great job!”

He was also, obviously, super incompetent at his job. He relied heavily on a junior colleague who basically did his whole job helping with technical work and spent days on paperwork that should have only taken an hour or two. If you had a problem, his answer was to stare at you blankly until you said "nevermind" or pat you on the back and say, “Think positive, and it’ll work itself out!”

The thing he did that I hated most was whenever people applied to work at the company, he’d print out the stack of resumes, sit at his desk, and read aloud all of the parts he found “funny.” He’d laugh at people for working at McDonald’s or any fast food places. He loved finding grammar mistakes and making fun of them. This was all done loudly, and it was an open office so you couldn’t avoid hearing it. That definitely lowered morale too.

Weird Bosses factsCanva

18. This Is How We Do It

My boss at a pizza shop made getting raises a game and handed them out for the weirdest reasons. He liked a table my friend got so much that he gave my friend a raise. Another kid was playing with a penny at the end of the night, and he kicked it into the air, and it landed in a hat someone was holding. He got a raise for it. I was listed first on the timesheet. According to him, this meant I was "becoming number one" and thus got a raise.

He had food issues and would get really offended if we didn't eat as much as him. One time, he drove an hour away during our shift to get pizza we had not tried before because it was "best in the state." People who didn’t try it were shunned that day. He bought 100 tacos from Taco Bell and had us have an eating contest for our lunch. He was so happy when someone ate 7 and was basically going to puke. He paid one guy to eat a bag of dog treats and filmed it.

After a closing shift, he got back from the casino and won $4K from playing poker. He demanded we go to the club and drink with him even though we were 18 at the time. He never trained anyone and just expected everyone to know everything and anything about our pizza place. We always had to hire and train the people while he just sat there. He loved online poker and played during our shifts. It was all too common to hear, “Can you get the register? I’m in the middle of a hand.” My friend drove past the store at 1 AM many times and saw him playing poker with all the lights on.

Unreal Zingers factsUnsplash

19. No Active Thinking

My boss and I were hired around the same time. We had to do a safety training together. We were partnered together to discuss active danger scenarios. He told me he wanted security to dress like active attackers and surprise the staff of our branch. I told him he couldn’t do that. His face was completely serious as he asked me why not.

Weird Bosses factsCanva

20. Stage No Coop

My first boss in America was a...strange man. He had an open-door policy and drank in his office. He started a small chicken farm in the back of the building and handed out live chickens to staff. One day, he had me and a co-worker try to slaughter one. All I could bear to do was nick it just a little bit and then shriek as it sprayed all three of us with blood.

He ran around the place with a wig on his head imitating me. He’d talk to Black people in a “Black” way. He would say, “wassup, shorty” to the ladies and call all the office's Black guys "Tyrone." He’d regularly fall asleep under his desk. The snoring was so loud that you could hear it in the front. Once, a client asked what the noise was, and I told her it was the plumbing.

His office is full of the weirdest things like feathers from his favorite chickens (that he had since consumed), a goat’s hoof, and a framed quote I told him a very high homeless person told me. One time, he dove head first into the wall while asleep and needed three stitches on his busted lip. He still insisted on snacking as usual. At one point, he sipped ketchup with a straw.

Even so, he’s one of the nicest bosses I’ve ever hadwell-meaning, if a bit insensitive, all the while really fascinated by other cultures. He’d buy different cuisines for us to try weekly. He gave bonuses since he knew the job didn’t pay much, which was always a nice surprise. He paid my former co-worker who had to stay home caring for her husband when he got ill. He still sends me photos of his illegal farm and recently asked me to post his cucumbers online even though I stopped working for him three years ago.

Lawyers Screwed factsPexels

21. Catch Me Nowhere Near That

I used to work for a family-owned company where my boss often had loud fights in the halls with her husband, mother, and sister who had issues with petty larceny and illicit substances. Once, for somebody’s birthday, my boss decided it'd be fun to buy an anatomically correct, male blow-up doll. She brought this doll into the office. Then she blew him up and dressed him in a construction vest since the company was a contractor. When I walked by, my boss was trying to manipulate the position of the blow-up parts and asked me if I wanted to be the “fluffer.”

Weird Bosses factsCanva

22. Extraordinary Entrance and Exciting Exit

My mom's boss was the head manager at an office in suburbia. He was then in his late 40s and invited himself to my mom's birthday party at our house once. It was just my siblings and a few family friends meeting up to hang out for the evening. He came in pastel blue shorts, a pink polo, and flip flops. He was buzzed by 9 and started yelling. He saw our neighbors who were younger guys and invited them over.

He then got into a wrestling match with one of them in our living room. He lifted him in the air and body-slammed him onto our coffee table. After he had way too many drinks, his final act was pooping his pants in our kitchen and passing out on the floor.

Stopped Caring FactsPeakpx

23. Do Your Job

He was a department head for a group of adults ranging from mid-20s to mid-60s, and in staff meetings, he said on a number of occasions that he needed to go "potty." He usually wouldn’t bother actually managing or coordinating but instead would take on some of the tech's jobs in IT like preparing new laptops for staff. Problem was, he had no idea how to do this stuff. Often, if he did something, we'd have to redo everything because he ruined the machinery.

Also on casual Fridays, he would come to work dressed in these very puffy white long sleeve shirts as if he'd just walked off the set of Pirates of Penzance. Worst of all, he accessorized his prate shirts with puka shell necklaces.

Weird Bosses factsUnsplash

24. Not a People Person

My weirdest boss was a dentist. Once, he bought a mini basketball net for the staff room. He was so excited about it that he pretended the next patient’s tooth was miraculously repaired and sent her home. He had an hour free to play alone in between the table and our bags. Another time, he hired a company that made profitable efficiency strategies. But when they were there, he spent the entire meeting interrupting them, saying how good he was and how he knew better than these guys. Still, as an exercise with the efficiency people, everybody in the team had to take a personality test. He was upset when he didn’t get the results he wanted. He made everyone wait as he took the quiz over and over until he got what he wanted.

Doctors And Patients Stories FactsPixabay

25. Little Rearranging

He decided the reason we were struggling to keep to time frames was that our checklist wasn’t right. However, he had no experience in our field of work, so he didn’t know what we actually needed, which was more staff.  But once he got it stuck in his head, and there was no talking him out of it. That's when I came up with a brilliant plan. I redid the checklist with the same layout. I just changed the order of the items. He didn't notice the change, took one look, and decided that nope, that’s not it. I used the original version and put the checkboxes on the left instead of the right. That’s all I did. It was perfect because of his idea to “fix” it.

HR interesting stories factsPixabay

26. Big Bouncing Baby

I told my boss about our pregnancy, but it was early and we weren't telling anyone since we had had a few miscarriages, so he emailed the entire agency congratulating us. After the baby, my wife had a little belly. A year or so after the baby, he congratulated her in the parking lot on being pregnant again. She wasn’t.

A year later, he congratulated me again saying he saw my wife and asked when were we due in front of all the ladies in the office. Again, she wasn’t pregnant. I once made him cry because I told him a client didn't like him and would rather deal with me. He also sat on a yoga ball and aggressively bounced on it while holding meetings with potential clients.

Weird Bosses factsCanva

27. No Rhyme or Reason

I had a boss who didn’t know how to turn on her desktop computer after a power outage. Another boss I had gave a "coupon cash prize" paid from the till straight to the customer with no questions asked. There’s supposed to be a whole process with a form to fill. Another boss ordered food from a food vendor for her and staff and charged it to the company, which was also a food vendor. Imagine owning "Jim's Hotdogs," and while doing your books, inputting expenses seeing a large bill from "Joe's Hotdogs" for food.

Weird Bosses factsPexels

28. For the Queen

I worked for a carpet store in high school for about a year and a half. I ended up dating the boss' daughter and learning that the mom/owner was literally insane. On two of the store's busiest days, she made me go to her house and power wash around 200 sq. ft. of her concrete. She was really big into boating and at one point, considered getting me and her daughter go to her house to wax her boat. She lacked any real friends as she was super into herself. So, she just tried to do the cool things her daughters did.

When her daughter bought a pair of teal Vans, she bought the exact same pair and wore them out. She received one compliment and kept repeating that one compliment for three weeks after it happened. She would inhale an entire box of marshmallow Peeps in one sitting and then complain that she had a headache from "how hard she was working."

Once, she said to an employee during an interview, “I’m not supposed to ask, but do you go to church?” She bought an inflatable kayak, brought it to work, and blew it up in her office, which always had its door open facing customers, and rocked back and forth in it. She had to visit some customers’ houses to do estimates. There, she would take Snapchats making fun of them.

Weird Bosses factsPexels

29. Active Supervisor

I had a boss who used to watch me through a gap in the glass partition between our desks. She wanted to see if I was paying attention during meetings. One day, I put a large folder to cover the gap, and she freaked out. I still laugh when I think about it.

Weird Bosses factsPexels

30. Eating Time

I used to work stocking shelves at a grocery store. Thanksgiving was coming up, and we were slammed. We were getting a massive shipment in, which was almost twice as many pallets as we’d normally get. After unloading, we're all scrambling to finish so we could all leave on time. That's when our manager called a now-infamous emergency meeting.

We all got into the back office, and he proceeded to have a 45-minute meeting about how this was a big shipment and we couldn't waste time. I thought it was a weird joke, but he genuinely thought he was giving us a pep rally.

Lacked Any Self-Awareness factsPixabay

31. A Stay with Jay

I used to work for a very reputable hotel chain up in Canada. We would get lots of kids crossing the border when pot use was allowed. My boss, Jay, became everyone’s man. He dealt his homegrown stuff to half the guests and made a big profit. He was a very “bro” guy at 45 and partied with half the kids who stayed at the hotel.

We had a whole staff meeting that consisted of a crash-course on pot and its different strains and whatnot and how if any guest asked for the “Jay Special,” Jay was to be contacted immediately. He let us get away with way too much. For example, when I was looking for an apartment, Jay told me to just live in the hotel for a while. So, I stayed there for two months for free no questions asked.

We would have this one crazy homeless lady who was always high out of her mind who would try to sneak the free coffee from the lobby. Every time Jay saw her, he would actually bodycheck her down to the floor. She would scream at him saying, “get off of me, you weirdo!” And he would say, “I’m not the weirdo. You’re the weirdo!” And they’d just go back and forth calling each other weirdo.

Weird Bosses factsPexels

32. Season Survivor

My boss decided that he wanted a pomegranate for lunch. The fact that they were out of season didn’t stop him from sending me on a quest to every single grocery store in town in search of a pomegranate.

Fruit FactsPxHere

33. Running Low

On multiple occasions, at least three, my boss ran out of gas on the way to work. He’d have to call in and let me know that he was running late because he had no gas. His car also got booted All. The. Time. He was just constantly parking in restricted areas and would get either booted or towed on a fairly consistent basis.

He routinely fell asleep at his desk like at least once a week during my 4-hour shift, and I only worked there 2-3 days a week, so presumably, it was happening constantly. Loan sharks would regularly call his office phone. If he wasn't in the office, I had to take his calls, which made for some uncomfortable exchanges. Those sharks were persistent, to say the least, and straight-up told me on multiple occasions that they knew he was dodging their calls. Fun.

Weird Bosses factsPexels

34. Felt It from the Art

I had a short-term gig working for a guy named "Art" who was a genuinely nice person but was totally obnoxious to everybody around him. Whatever thought came into his head came out of his mouth. We once had to travel to a branch location together. The company leased a 2-bedroom apartment in the branch town for HQ employees. So, for the whole 1-week trip, Art and I would be together for 24 hours a day. This was...less than desirable.

As I mentally prepared for the trip, I took solace that at least we would sit separately on the 3-hour flight. At the gate, I said, "I'll see you when we land." "Oh, we're sitting together," said Art, "I called and asked them to change things around for us." My awful week had begun.

Haunting Embarrassing Moments factsPixabay

35. Professional Mental Meddler

My deranged therapist hired me because she "didn't want me around my mother." She’d bring her ill-trained, ungroomed, often smelly dogs with her. Nobody liked them. Jobs included keeping the office neat, running to the deli to buy the dogs cheese, cleaning out a shed full of magazines, and helping her edit a book she was writing

I was 16-17 at the time. She was so awful to work for that everyone quit. She didn't fire anyone. She just made it so miserable you eventually left.

Crazy funerals factsFlickr, Roman Boed

36. Trumpeting Everything but the Truth

I worked in a small office with about 8 people. We’d been going through some not fun times as a result of not having an HR department and some harassment by one of my coworkers to another. The whole office was on edge because the boss wasn't dealing with the situation appropriately, and things were at a breaking point.

So, we all showed up to work one day, and the boss told us that we were having a staff meeting. We all went into the conference room, and he began saying, "So, I've been informed that some of you don't like working here." The silence was palpable. As we’re all caught completely off guard, he tries to talk about how to improve the office culture. Meanwhile, one of my co-workers is so stressed out that she bursts into tears and quits on the spot. It was truly the most insane meeting I've ever been in. He was later fired by the board for gross incompetence.

Quit On The Spot factsUnsplash

37. A Lot on My Mind

I worked for a family law attorney who spent almost two hours telling me about all her encounters with angels, demons, spirits, etc. She pocket-dialed me while talking to her serial cheater husband about how she could blame me for a mistake she made. She hired an office manager from the Chipotle where she liked to eat. The girl was an incompetent wreck and eventually got fired for embezzling money from the company. But it gets worse!

My boss would take naps in her office, dictate messages to relay to clients as she nodded off, then yell at me for delivering the messages, and insist she’d never said what she said. She was hours late most days and had me do the intake appointments. She’d show up part of the way through meetings and make us go over everything again.

She held a meeting to set up a 401k for me and her, and, the next time I brought it up, she called me ungrateful and told me it wasn’t happening. She would write messages with certain words in all caps like a child would. She’d spend hours a day worrying about whether her husband was cheating on her. I was sympathetic until she said she was worried about it because he told her he did it. She was crazy.

Weird Bosses factsPexels

38. Almost Got It

My boss mixes metaphors and sometimes gets lost halfway. The most recent was a mashup between "if it ain't broke don't fix it" and something about making omelettes, which came out as, "don't break an egg if...if it's working well…"

Weird Bosses factsPexels

39. A Blessing and a Curse

My boss definitely believed he had a great handle on every aspect of the store. I worked in the print marketing/graphic design department, and he’d always come around trying to give Photoshop tips and whatnot. I had a regular, real nice preacher who would come in a couple of times a month to print out little event flyers.

He always had a print-ready image, wanted x amount of quarter sheet flyers, cut, and x amount of full sheet. So, of course, I'd pull up MS Publisher, print, cut, and get him out the door in just a few minutes. Once, I was walking out going for lunch, and I saw him walking in. My manager assured me he’d take care of it.

30 minutes later, I was back, and let me tell you, I’d never seen the preacher show a hint of anger, and he was fuming. He said, "Thank God, you're back. I really need to get going, and he doesn't know what the heck he's doing." I looked on the computer and no, no he didn't.

Weird Bosses factsPexels

40. Practicing New Vocabulary

I had this Indian boss at a sandwich shop who overheard me say "that's what’s up." He asked me what that meant, and I just told him it meant "good" or "great." He kept using it over and over the next two years I was there. "I want that walk in clean like that what’s up" or "that sandwich was not that what’s up, buddy."

Disastrous Dates Facts Pxfuel

41. Trying a Scoop

I used to work at an old school gelato shop where I had a stubborn Italian boss. One summer, he fired a kid for “not being hygienic and not cleaning well” when we all knew he was uncomfortable this kid was queer. The next summer, I was the manager. My then-assistant manager and I are both queer women. In the midst of a little misunderstanding, we both came out to my boss. At one point before opening, he pulled me outside to ask me a "personal question;" if I preferred men or women. I told him women, and I'm a pretty open person and find jokes help break barriers.

So, I asked him which he preferred. He said women, "of course," and we went inside where my assistant manager was and joked with her, and I told him he's a lesbian since he preferred women. He found this absolutely hilarious and shouted out in the shop, "I GUESS I'M A LESBIAN!" He's grown more understanding ever since.

Weird Bosses factsCanva

42. Old Protocol

I worked for an old married couple in their 70s who ran the gym across the street. The wife was from Germany and super strict, and the husband was clearly losing it. He once combined bleach and ammonia to clean the hot tub and sauna room thus gassing me in the process. Every week, the wife insisted the street be swept. Almost every single time, the husband would come out midway through with a leaf blower and destroy any progress I had made.

We’d also have to regularly rescue the husband from the sauna because he would be sitting in there for far too long. I’d opened every Saturday but never got a key. I’d have to jump the fence to get in.

Friendship FactsUnsplash

43. Nailed It

I worked for a foreman who, on my first day, brought me around to the "dangerous equipment” that I’d been around since age 5 with table saws and wood and metal working gear to show me the safety features. I had to stop him twice before he hurt himself. I couldn’t stop him from getting his thigh with a nail tool though.

Weird Bosses factsPexels

44. Problems by the Husks

The general manager where I worked had a daughter with drug dependence issues, and so he hired her to give her a leg up in life...even though it was company policy not to hire relatives. Once hired, this daughter liked to fool around with the truck drivers who stayed overnight. She promptly fell in love with one, but there was one problem: He was married. He told her he would leave his wife for her, until his wife got pregnant.

The daughter then showed up to work tipsy and trashed the office. Then she recovered from her heartbreak, got married to a random guy, got bored of him and started flirting with the sales representatives. She then got pregnant with one of the production bosses who was 35 years older than her and married with 4 children. The entire time, my boss refused to do anything about his daughter.

Worst Co-Workers factsPexels

45. Big Pick-Me-Up

I had a boss sneak up behind a middle-aged female employee, pick her up, then immediately drop her down saying, "I didn't think you weighed that much!" He could not stop laughing. He was the principal. This occurred during passing period in a crowded middle school hallway.

Greatest Comebacks factsCanva

46. Priorities, People!

I had a boss who was weird in a good way. If a customer called five minutes before closing, he’d demand that I let it ring and put the message through to voicemail. He was late more often than I was. He also frequently bought us coffees. He’d always take our side in customer disputes. If a customer was hostile to us over the phone, he would call them back and get into an argument with them and tell them to order from someone else. He straight out told us that if weather conditions were bad, he didn’t care how late we were as long as we were safe. He’d tell me on random days to take a two-hour lunch.

Weird Bosses factsCanva

47. Unmerited Existence

My boss called an all-staff meeting to announce his divorce. He then instructed our receptionist to lie to his soon to be ex-wife and deny that he was in the office all the time. He was so, so incompetent. If his task was too big or complicated, he would just not do it and never ask for help or anything. He'd ignore it until the problem "went away."

Obviously, that left whatever issue to fester. I would have to constantly monitor and follow up with him to get things done that affected my job. His writing read like he used a thesaurus heavily with many superfluous words put in there to make him sound smarter. After his termination, he kept the corporate laptop and cell phone.

After several strongly worded letters, he drove back, parked on the edge of the road of a busy rural highway, and made his teenage son carry it all across the yard and parking lot. The big bosses had me coordinate his termination. They gave me his job plus my previous one. I can do both within a 40-hr week, no problem.

Weird Bosses factsCanva

48. Pick and Choose Method

My worst boss was at a big tech company. He was a network engineer that got promoted to management and had no idea what to do, which was usually fine because he would just approve vacations and let everyone do their job. The main annoyance was he was a network engineer, and I was a Windows server engineer.

Any time the customers would tell us to do something impossible or that would actively hurt them, he would leave me to defend our company’s stance. If the network team had any pushback, he would jump on and defend them and act as the point of contact he was supposed to be. He also didn't understand a lot of what I did.

He measured my productivity by whether or not I was at my desk. The network team could work from home whenever they wanted, but if I worked from home more than once in a 2-week period, he’d send emails letting me know how important it was to be in the office and ended up firing me for working from home when I was sick.

I had a project due, and I was trying to finish it but got sick. I faxed him the doctor’s note saying I was allowed off for the rest of the week, logged in, and started to work. He said since I was working, I had to be in the office. I ignored him. The next Friday, he met with me at 8 AM with HR there to escort me out.

The worst thing he did was during the football season, he’d have a team meeting the lasted 2 hours every Friday for fantasy football. If team members didn't want to play fantasy football, he said they’d have to go back to work instead of just hanging out with everybody, so I just drafted people from the Miami Dolphins.

Cuphead FactsMax Pixel

49. Past Experience

I had a boss once who spent all morning locked in his office. He asked me to come in after lunch where he showed me a handmade graph. He then proceeded to explain that this was a chart of every time he slept with someone ever in his life. "See, here it’s blank until I joined the army. Then I went overseas and paid a lady here.”

“Then they sent me to Vietnam where they only charged $2 per time. That's where you see the big jump. I was on two tours but then got hit in the face. I came back home, and you see how it just drops to almost nothing. " I was astounded.

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50. Should Be Up in the Clouds

In 2012, I was working the top end apartment market in Melbourne, Australia. My boss was in his 70s and seriously old school. Like he didn't believe in social media marketing old school. But the business world moves on and the company starts to integrate new technology. One day, the IT guy changed our data storage from an old box in the office where we worked to the cloud.

But our boss didn't want a cloud server. When he told us why, my jaw hit the floor. He didn’t want it because the wind and thunderstorms might mess it up. He was very, very serious. I would have said something during the meeting, but the look on IT guy's face was too good to disturb.

Weird Bosses factsCanva

Sources: Reddit,



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