Believe it or not, bosses like Michael Scott from The Office really do exist out there.
It seems like it would probably be a barrel of laughs, but I have a feeling that if you’re in the thick of a situation like that, it’s likely not very much fun.
Let’s all enjoy these funny stories from AskReddit users about their weird, funny, and annoying bosses.
1. The Italian Michael Scott.
“My Italian Michael Scott boss has that traditional stubbornness which he’s really allowed to display since it’s a traditional gelato shop and we’re an at-will state (US).
One summer, he fired a kid for ‘not being hygienic and not cleaning well’ when we all knew the boss was uncomfortable this kid was queer.
Next summer, I’m the manager and my then assistant manager and I are both queer women. In the midst of a mild homophobic/heretophobic (?) misunderstanding, we both came out to my boss. At one point before opening he pulls me outside to ask me a “personal question”- if I preferred having s*x with men or women.
I told him women, and I’m a pretty open person and find jokes help break barriers, so I ask him which he prefers. He says women, “of course,” and we walk back inside where my assistant manager is and joke about it with her, and I tell him he’s a lesbian since he prefers women. He finds this f*cking hilarious, and yells out in the shop
“I GUESS I’M A LESBIAN!”
He’s grown more understanding ever since. His questions are sincere, though sometimes badly phrased.
2. Five long years.
“I had one and these are just a few quick stories
He asked me how much I weighed during my interview
One time he was considering selling the company to a Japanese company and while walking them around the building he was heard saying ‘we really bombed the hell out of you, huh?’
He got on the intercom and interrupted everyone by yelling for someone to bring him the football team’s schedule
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
One time he told me to call his assistant and have her bring him a bag of coffee and his 5lb dumbbell
He had a ‘secret’ facelift. He was mysteriously gone for 3 weeks and came back with a beard.
I ended up with a box of pictures from the 70s with an exotic dancer giving him a lap dance. In the conference room. Same furniture.
One time I watched his business partner go down the pot luck line, tasting everything with the same fork. At the end of the line, he stuck his used fork into the cake. I haven’t eaten at a work buffet since.
Honestly, these are just the ones I immediately remember. It was 5 years of this.”
3. I love the part about the fence.
“My brother had two bosses at his first job that I think fit this. It was an old married couple that owned the gym across the street from us. Probably in their 70s when he started working there. The wife was from Germany and super strict, the husband was clearly losing it Some notable mentions are:
•when the husband combined bleach and ammonia to clean the hot tub and sauna room, tear gassing my brother in the process
•wife insisted the street be swept once a week, this was my brothers task. Almost every single time, the husband would come out halfway through with a leaf blower and destroy any progress my brother had made
•husband would regularly sit in the sauna for way too long and have to be rescued by brother and coworkers
•brother opened every Saturday. They never gave him a key so he would have to hop the fence to get in.”
“Yep, I had one.
Organized a thoroughly awkward award ceremony once (that we never did again).
Asked a Mexican employee if his new baby’s name was going to be “No Mas” during the shower we threw for him.
Heard me once use the phrase “economy of scale,” then used it wrong 5 minutes later in a conversation with different people.
Didn’t know the meaning behind “Black Friday” and what it meant for a company to be “in the black.”
Just like Michael Scott, only more of a d*ck.”
5. Drop your pants.
“Long ago, my 80 year old boss pulled me into his office
B: “Paul, I’ve noticed that your shirts come untucked and that looks unprofessional”
Me: I’m sorry about that Joel
B: I want you to start tucking your shirts into your underwear
B: Go ahead and and try it now.
Me: Joel, you know I have 15 women who report to me – I can’t un-do my pants in the office.
B: Sure you can. Drops pants. He is 80 and wearing Spiderman underoos…”
“I worked for a woman as her “personal assistant/ cat sitter”. She was super rich and off the deep end nuts.
She had me order a mannequin online, and then paid me to take one of the mannequin legs to Nordstrom to try and see what suitcase I could buy that would fit the dismembered mannequin body, because she wanted to fly with the mannequin to Pittsburgh to display “as her daughter”, dressed in her daughter’s clothes, at that daughter’s graduation celebration.
Buying the mannequin was a whole thing too. She kept trying to get me to order from “adult doll” websites because she didn’t get it.”
“My boss used to carry around a backpack full of hammers and if you fell sleep at your desk he started banging a hammer on your desk until you woke up and then he would autograph the hammer and give it to you as a gift.”
8. Never a good idea.
“Had a manager at my previous job that really, really tried his best to be everyone’s BFF.
He loved giving pep talks and thought he could raise our abysmal morale by being Mr. Positivity (note: morale was low because we were always buried in work and paid sh*t).
He’d crack jokes, randomly burst into song and sneak up behind you to yell “you’re doing a great job!”
Unfortunately, he was also super incompetent at his job. He relied heavily on a junior colleague for help with technical stuff (they practically did his whole job for him), and spent days working on paperwork that should really only take an hour or two.
If you had a problem, his answer was usually either to stare blankly at you until you left or to say “think positive and it’ll work itself out!”
Thing he did I hated the most: whenever people would apply 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 other fast food places. He loved finding grammar mistakes and making fun of them. If someone had a cringe-y objective statement, he’d guffaw over that too. This was all done loudly, and it was a open office so you couldn’t avoid hearing it.
That definitely lowered morale too.”
9. The real, live version.
“Worked with a genuine Michael Scott: i.e. a nice, well-meaning person who just did some absurd things.
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. No reason why kidnapping would be on anybody’s radar…
He and several of the guys randomly broke out into a push-up contest. Again. White collar office. Middle-aged dudes in khakis.
Couldn’t remember the nationality of our Hispanic colleague. Tried to “learn Spanish” to make her feel special when she returned from maternity leave. (1) What he learned was NOT Spanish, and (2) she was from Portugal. She knew like, five words of Spanish.
Disappeared for four days. No call. No email. Wouldn’t respond to any of our attempts to reach him. Finally, someone drove out to his house to make sure he was alive. He was. He’d just forgotten to tell us he was taking the week off, and then lost his phone in a lake.
There were many, many moments like these. Great boss. Genuinely cared about everyone in the company. Occasional moments of brilliance, where he really got things done.
But OMG, so many moments of ridiculousness.”
10. This happened to me once, too.
“We had an anonymous feedback program at work, and our boss was livid with the results, particularly with several comments that he frequently lost his temper in meetings and would yell at us.
The more he talked about how incorrect and unfair and hurtful these comments were, the redder and angrier he got, until he finally pounded the table and shouted, “I DO NOT! SCREAM! IN MEETINGS! OKAY?”
11. Pathetic and not funny.
“Mine had aspects of Michael Scott but the ones that are sad and pathetic and not funny. A couple examples:
he 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 he was in the office, all the time.
he was just so, so incompetent at his job. If a task was too big or complicated he would just …. Not do it. Wouldn’t ask for help or anything, he’d just move on and leave whatever issue to fester. I would have to constantly monitor and follow up with him to get things done that effected my job
his writing read like he used a thesaurus heavily. Tons of superfluous words clearly put in there to make him sound smart
when he was terminated he kept the corporate laptop and cell phone. After several strongly worded letters requesting their return, he drove back to the office, parked on the edge of the road (think busy rural highway) and made his teenage son carry it all across the yard and parking lot to deliver them
I was eventually tasked by the big bosses to coordinate his termination. They then gave me his job plus my previous one. I can do both within a 40 hr week no problem.”
12. Fun while it lasted.
“I had one for a year and it was awesome!
If he would be in the middle of a story and the phone rang he would literally say “let it go to voicemail”. If a customer called 5 min before closing he’d demand I let it ring and go to VM.
He was late more often than I was. He frequently bought us coffees. He always took our side in customer disputes and if a customer yelled at us or got abusive on 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, just that we were safe. Sometimes he would tell me on random days to take a two hour lunch ( I was salary and didn’t punch in or out). He was great! And he gave me so much free stuff.
We used to call him Micheal Scott behind his back!
Unfortunately… the owners were a bit stricter.. Myself and another coworker got fired and said boss got demoted. It was fun while it lasted.”
13. Just play along.
“I’ve had a few. One would only approve your days off if you played into her ego.
Her boring stories had to be the most fascinating thing you had ever heard. She would come into the office and spin around in a new outfit and we had to pretend it was amazing.
I had to work every weekend for months until I started playing along.”
14. Best boss ever.
“I used Michael Scott as a reference point for an old boss of mine from the moment I started working there.
He made Chewbacca noises on the regular because one of my coworkers’ names sort of vaguely sounded like Chewbacca (it didn’t), used voice to text extremely loudly in his office for no reason to send really personal messages, got really excited and wore a specific vest any time we had after-work outings scheduled.
Shouted the same like 7 references to old movies and extremely awkward hip-hop song quotes 100 times a day, and insisted on greeting all our international coworkers very loudly in their language (they all speak perfect English, of course)
Looking around for approval afterward, and then fully giggling at everyone’s French accents on conference calls. He also told me a lot about an improv show he did for a full year after it happened.
That said – he had all the good parts too. He never hesitated go to the mat for any of us whether we deserved it or not, he gave really sage business advice and great examples of how to face challenges out of absolutely nowhere, and he came to every community play I did in the 4 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 kind, helpful, and supportive.
Honestly? Probably the best boss I’ll ever have.”
Have you ever had any ridiculous bosses in your life?
If so, we want to hear your stories!
Tell us all about them in the comments!