I’ve never had ONE boss that I think was like The Office‘s Michael Scott, but I’ve definitely seen some characteristics in a few of them that made me cringe just a little bit.
And maybe if I could put all my past bosses together and pick out the most ridiculous traits of each one I’d be able to create one INCREDIBLY ANNOYING head honcho.
But these kinds of bosses really do exist and they’re out there in charge of employees all over the place!
AskReddit users went on the record with their funny boss stories.
1. Hahahaha. Wow.
“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 all the s*x he had ever had in his life.
“See, here it is blank until I joined the army. Then I went to a hooker here. Then they sent me to Vietnam where hookers only charged $2 per time. That’s where you see the big jump. I was on two tours but then got shot in the face. I came back home and you see how it just drops to almost nothing. ”
I was astounded.”
2. Oh, boy…
“My boss is certainly Michael Scott-esque.
When I first started I was essentially Pam as well since I was both receptionist and his assistant to some extent. My favorite story was back when we were prepping for a conference.
Some context, he’s terrible with the English language in general and will mangle phrases and descriptions to no end (how the turn tables…). So on a group call he kept talking about wanting a “golden hamster ball” to do giveaways with.
Was raving about how great it would be spinning around while people walked by, all the while everyone on the call was just sitting in confused silence. However by that point, I had become so good at decoding his nonsense that I knew he was referring to a gold raffle cage and sent him image privately asking if it’s what he was thinking.
To this day he still talks about the fact I can read his mind and must be psychic. And he still refers to it as a hamster ball.
All in all he’s a pretty nice guy and a solid boss. Hired me based on a gut feeling and has been decent to me ever since. I think I knew it would be a good fit when during the interview he tried to tell me about the four pillars of the company and forgot one.
Told me later it was Knowledge.”
3. Whatever you say.
“He wanted a pomegranate for lunch and they were out of season, but that didn’t stop him from sending me on a quest to every grocery store in town in search of a pomegranate.
Multiple produce guys laughed at me, but that was the easiest $13/hr I’ve ever made.”
4. Hmmmm…
“I had a redhead boss who made us all sit down and watch a training video about how we shouldn’t refer to him as a “ginger” because it is bullying.
No one had ever called him that.”
5. Peculiar.
“Had a boss who was very peculiar.
For instance, he’d open a random closet, look at the stuff inside, then go on a tirade, “look at all this! Who bought all this crap?!?!”
“Uh, you did.”
“Oh. Well somebody needs to throw it away!”
Constant stuff like this.”
6. Leave me alone.
“I had a boss that 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.
I still laugh when I think about it.”
7. Sounds about right.
“I once worked for a family company (not my family) where my boss often had loud fights with her husband, mother, and sister (an addict with a penchant for stealing) in the halls.
I have a million wonderful stories about that workplace but one that stuck out to me is this:
Once for someone’s birthday, she decided it would be fun to buy an anatomically correct, male blowup doll.
She took this doll into the office, blew him up, and dressed him in a construction vest (the company was a contractor).
When I walked by, my boss was trying to manipulate the position of the blowup d*ck, and asked me if I wanted to be the “fluffer”.”
8. Just like Michael Scott.
“I had a boss sneak up behind a middle-aged female employee and 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 of the school.
This occurred during passing period in a crowded middle school hallway.”
9. The nerve…
“My boss insisted his daughters be flower girls in my wedding.
I declined.
At the reception, he told me I was spending too much time talking to one person, and I need to work the room more.”
10. A good use of time.
“He held a meeting with our whole team less one person to discuss said person being gay.
We all knew for well over a year, and never made a deal of it.
So yes, they are out there and that is why the show is so funny to me. I can relate…”
11. Conspiracy theories.
“I literally had a boss who would stop us in the middle of our work and hold company-wide meetings talking about 9/11 truther conspiracies and chemtrails.
Mind you we were furniture-making company.
He would get so caught up in his conspiracy theories that he forgot to order wood to make furniture one month.”
12. Welcome to America!
“My first boss in America, I was 21. He was Asian-American. I had never seen the office but noted the absurdity.
He would get free potato chips from a guy in a company truck and would stuff his cheeks in the middle of telling me what to do. He always offered some.
Fired a coworker for screaming some racist stuff at me by just..yanking her out the door.
Called another coworker a cub or a baby lion because she was tiny with wild unruly hair. Would do a small mini roar whenever she was about to report for her shift or when I mentioned her name.
Ran around the place with a wig on his head imitating me.
Brought his daughter to work and give her piggy back rides in the office. Would ask me to take videos.
Would talk to black people in a “black” way. He would say wassup shorty to the ladies and what’s poppin. Called the guys Tyrone and would say shieeeeeet in his most convincing “black” voice. It was actually pretty good.
Would ask me to teach him random Arabic words so he could yell them sporadically in the middle of the day. He always got the accent right.
Had an open door policy and would do shots in his office.
Started a small chicken farm in the back of the building and would give out whole chickens to the staff. Had me and a coworker try to slaughter one one time. I couldn’t and nicked it just a little bit and shrieked, spraying all three of us with blood.
Received a visit from the city people to tell him he couldn’t keep chickens in back. He was rounding the main floor with a small basket of freshly laid eggs just as they were asking for him.
Did the chicken farm again the next summer, this time with a small garden growing squash, cucumber, corn etc to disguise the chicken coop. Happily gave out vegetables along with chicken.
Would be extremely proud of taking home a tray of his own eggs to his children. Ate two fresh eggs every morning.
Bought a wok to work to deep fry sausages in. Sometimes made lunch in the back. The entire floor would smell like food and he would round us all (3 of us) to his office to eat.
Would regularly fall asleep under his desk. The snoring was so loud you could hear it in the front. Once a client asked what that noise was and I said it was the plumbing.
Woke up after his naps looking puffy but acting as if nothing happened. Would immediately go next door for a Cherry coke.
Would constantly eat hard candy to stay awake during the day.
Ate too many edibles at a party I hosted once and passed out.
Told me to hire someone but when he saw the girl did a comical thing with his face, eyebrows raised and eyes big ( think Ken Jeong ) because she was having trouble fitting into her chair. She was a bigger girl.
Took away chairs the next day because they “encouraged us not to concentrate on the client.” The girl was a no call no show the following week.
Had a love hate relationship with a groundhog not long into his farming venture. He never caught the guy.
Once threw a cricket at me from the very opposite end of the office floor. He and another coworker kept such straight faces as I finally convinced myself the cricket flung itself at me. I watched the cameras at the end of the day only to see them do it. I’m still traumatized.
Has an office to this day full of the weirdest collection of things. A few feather from favorite chickens of his that he had since consumed all named and dated, a rabbit paw someone gave him, a goat’s hoof, a framed quote I told him told to me by a very high homeless person.. I don’t remember the rest. It’s just an odd place to go into.
Had a hard time growing a beard and would ask me what I thought of the progress of his “soup taster.”
Nicest boss I’ve ever had. Well meaning if a little racially insensitive all while being fascinated by other people’s cultures. He would buy different cuisines for us to try each week. Gave bonuses because he knew the job didn’t pay much so that was always a nice surprise. He paid my former coworker when she had to stay home all through her husband’s Covid.
Also, he loves llamas, alpacas, baby goats and when I showed him how to use Reddit he would almost always sends me an alpaca photo. I still get a photo now and then.
Also 3 years after leaving he still sends me photos of his illegal farm and recently asked me to post his cucumbers on Reddit.
Also I forgot to add that he fell into poison ivy bush once and didn’t know right away. He ran around screaming until we sat him in his office semi undressed and put medicine on his wounds. He was so miserable for days, it was hard to watch.
He dove head first into the wall when asleep once and needed to go to the doctor and get 3 stitches on his busted lip. He came to work that morning with a huge lip and kept having to explain himself all day.
We kept joking his wife was beating him up. He still insisted on snacking as usual. At one point he sipped ketchup with a straw.”
Did you ever have a boss that reminded you of Michael Scott?
If the answer is YES, then please share your stories with us in the comments.
We’d love to hear from you!
