Cringe True Stories Of Real-Life The Office-Style Bosses
From malapropisms to obliviously inappropriate comments, Steve Carell’s Michael Scott (The Office) has a faux pas for every scenario. This beloved character has long had audiences cringing even as they cried with laughter. In his quest to make his employees, in his own words, “afraid of how much they love me,” Carell’s Michael Scott would stop at nothing – delving into their personal lives and driving them into friendships with ruthless determination.
But when Reddit asked “Do bosses like Michael Scott actually exist?” the responses came flooding in. It turns out that plenty of people have worked with managers who get up to Scott-esque antics, intentionally or unintentionally. Here are 50 of the funniest, most uncomfortable and outrageous Michael Scott moments from the real world.
1. Prepared for anything
I 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…
2. Improv star
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, [and] got really excited and wore a specific vest any time we had after-work outings scheduled.
3. Fiery temper
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?”
4. Inappropriate comments
I had one and these are just a few quick stories. [1.] He asked me how much I weighed during my interview.
[2.] 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?”
5. Fruit fiend
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.
6. Team meeting
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.
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. lmao.
8. Collecting data
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 sex 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.
9. 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.
10. Titanic claims
I worked for a guy once whose least offensive conspiracy theory was that millennials are bad because women liked James Cameron’s Titanic.
Edit: To elaborate, his logic was that, because women watched and enjoyed a movie about a woman who fell in love with someone while being engaged to someone else, their children are more prone to following their hearts instead of doing what they “should.” Which is bad, I guess.
11. Nosy neighbour
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.
12. Award ceremony
Never have worked for one myself, but my dad told me a story about his boss who was giving out awards to everyone in honor of how long they’ve worked there, and he would give speeches for each person.
A woman employee received her award and he gave a speech about the story of how she came to work there. And he said, “At first I didn’t want to hire her because she was so hot.”
My dad’s not working there anymore, but I love that story because I will never not picture Michael Scott giving Pam a Dundie and saying that about her.
13. No slacking
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.
Then he would autograph the hammer and give it to you as a gift.
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… 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.
He 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.
15. Wedding guest
My ass 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.
16. Black Friday
Yep, I had one…He heard me once use the phrase “economy of scale,” then used it wrong 5 minutes later in a conversation with different people.
He 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 dick.
17. Perilous work
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.
[Another time the] 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
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. I want you to start tucking your shirts into your underwear.
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…
19. Snacking and chatting
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.
He fired a coworker for screaming some racist stuff at me by just.. yanking her out the door.
He 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.
20. The flattery game
Yes. They are everywhere. I’ve had a few. One would only approve your days off if you played into her ego. Her boring ass 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.
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.
22. Lunch party[My boss] would bring pizza and beer for lunch and try and get us to stop and party with him even though we were slammed with deadlines (our office was an open one so we would be at our desk and he’d be drinking at 2pm, playing music 3ft way from us while we try and make phone calls).
One day he came in pissed and called a meeting so one colleague put candy on the table and he stopped mid sentence in his rant because he got distracted by the shiny wrappers.
23. The company card
He went to Germany and rented a car. He didn’t know how to drive in Germany and hit 8 cars in the rental car lot. He asked me to use my company card to pay the insurance premium. I told him no.
We had so many communication problems (meaning I was a woman and he didn’t respect me) that HR recommended we have Monday morning 1:1’s. He never showed up for them. I kept record. He complained to HR that we weren’t having the meetings he wasn’t showing up to.
24. Just kidding
My previous boss loved to play this ‘joke’ where he firmly insists I’m not going to get paid because I forgot to clock in or out.
He would wait until he had me absolutely convinced and threatening to quit before he laughed and said he was just foolin’ to teach me a lesson.
25. Out of the office
Mine had aspects of Michael Scott but the ones that are sad and pathetic and not funny…
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 affected my job.
26. Party animal
My mom’s boss was the head manager at an office job in suburbia, pretty similar number of employees and function to the Office in the show. He was in his late 40’s at the time and invited himself to my mom’s birthday party at our house one year. Basically was just my siblings and and a few family friends meeting up to play cornhole and chat for a couple hours. He showed up in pastel blue shorts, a pink polo, and flip flops with a case of Natural Light.
He got hammered by like 9pm and started yelling at everyone. He saw a couple of our neighbors (younger guys) drinking next door and took the liberty to invite them over. Eventually he ended up in a wrestling match with one of the neighbors in the living room, which he finished by lifting the neighbor up in the air and body slamming him directly onto our coffee table. His final act of the evening was s***ting his pants in the kitchen and passing out on the linoleum.
27. Awkward jokes
Mine was less entertaining than Michael, but we often compared him for the following examples: He only hired people he would “have a beer with.” He was grossly under qualified to manage, but he was good at sales so got promoted.
He made really awkward, distasteful jokes/comments (e.g. asked an employee if he and his twin brother “shared” a girlfriend).
28. Sneak attack
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. This occurred during passing period in a crowded middle school hallway.
29. Protective boss
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.
Not sure how Michael Scott-ish this is, but I had a boss who was a complete f***-up. She’d get caught messing up, blame me, yell and curse at me, realize later it was her fault, and then want to take me out for a private one-on-one lunch as an apology.
After a while I just started telling her thanks, but I have plans already. Because she was too tone-deaf to realize that of course your employee doesn’t want to spend their break eating with you, after you yelled and embarrassed them in front of their colleagues for no good reason.
31. Personal comments
Yeah, and I worked for a church and he was the senior pastor. He had no filter and his own morality (which was questionable to everyone else).
He’d say things to the secretary like, “I don’t think you and your husband should be together in the upcoming pictorial directory photos since you guys are probably gonna get a divorce.” (she was fighting hard for her marriage).
32. Toilet humour
I had one former boss who was a bit odd.
He was 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’d occasionally not bother doing things like managing or coordinating and instead would take on some of the tech’s jobs (IT) like preparing new laptops for staff or other stuff which more often than not had to be redone from scratch because he f***ed something up.
In real life it’s not funny. I had a boss like that in my retail job.
He was annoying, constantly making bad jokes, and then he ramped it up when he decided he wanted to get me to quit. For the most part I just ignored him, until he started a rumor I was hooking up with an underage coworker. Then I confronted him, and he backed off.
Eventually he got fired for sexual harassment.
[My boss] told us he invented Apple computers before Steve Jobs. That the computer he invented is still to this day more powerful than any other computer.
Threw knives in the air and said if you can catch them he’ll give you money. This was apparently at a Christmas party. I wasn’t there but believe it 100%.
35. Hiring mishap
I believe every manager in the world has had a Michael Scott/David Brent moment; that is what makes it so hard to watch at times. I have had nights where I have often wondering how many I have had and how badly was I viewed as a result.
My worst I think is telling someone they got a job (in a warehouse) and then realising I had told the wrong person and having to tell the him 30 minutes later that he didn’t have a job after-all… dreadful.
36. Pampered pooches
I once had my therapist hire me because she didn’t want me around my mother. No laws broken there.
She brought her ill trained dogs with her. They also needed grooming and often smelled. No one liked her dogs.
Jobs included cleaning the office, running to the deli to buy cheese for her dogs, cleaning out a shed full of playboys, and helping her edit a book she was writing.
I was 16-17 at the time. She was so awful to work for, everyone quit. She didn’t fire anyone, just made it so miserable you eventually left.
37. Too much fun
He’s a dentist. Once, he bought a mini basketball net which he installed in the staff room.
He was so excited about it that he pretended that the tooth of his next patient miraculously repaired by itself so he sent her home and had an hour free to play alone in between the table and our bags…
38. Self-conscious Scott
I am the Michael Scott of my job. I can not believe they made me a manager.
All the dumb s*** he does, I’m like “yup, there I am”.
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.
40. Big announcement
I told [my boss] [my wife and I] were pregnant, but it was early and we weren’t telling anyone (we had had a few miscarriages), so he emailed the entire agency congratulating us.
After the baby my wife had a little belly. Nothing major, just a Pulp Fiction “pot”. A year or so after the baby was born he congratulated her in the parking lot on being pregnant again. We were not. His wife was there and was mortified.
41. Pep talk
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, almost twice as many pallets as we normally get. After we unload the truck, we’re all scrambling to get things done so we can leave on time.
Well our manager calls an emergency meeting. We all get into the back office and he proceeded to have a 45 min meeting about this is a big shipment and we can’t waste time. I thought it was a weird joke but he thought he was giving us a pep rally.
42. Weather-proof tech
I was working the top-end apartment market in Melbourne, Australia.
The boss is in his 70’s and seriously old school. Like didn’t believe in social media marketing old school.
The IT guy changed our data storage from an old box in the office we worked to a cloud.
Boss didn’t want a cloud server, because the wind and thunderstorms might mess it up.
Deadly deadly serious. I would have said something during the meeting but the look on IT guys face was too good to disturb.
43 Amateur dramatics
My boss and I got hired around the same time. We had to do a safety training together. We were partnered together to discuss active shooter scenarios.
He told me he wanted security to dress like active shooters and surprise the staff of our branch. I told him he can’t do that. He asked why.
44. Disastrous safety talk
Only boss that comes to mind, have had some really horrible ones, that fits this was a foreman that on my first day took me around to the “dangerous equipment.” To show me the safety features. All of the so called dangerous equipment I have been around since I was 5. Table saws and other wood and metal working gear..
I had to stop him twice before he hurt himself. I unfortunately was not quick enough to stop him from shooting his thigh with a nail gun!!
45. Dodging calls
Loan sharks would call [my boss’s] office phone constantly. When he wasn’t in the office, I was responsible for taking 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 stuff.
The Office came out while I was working for the worst boss I ever had and it reminded me so much of her that I couldn’t watch it at the time.
Every single time a non-Caucasian person started working there, she’d ask, “Where are you from? No, where are you really from? Where’s your family from?” And would keep going until the person named some place outside of the US.
47. A betting man
My current boss is a Michael Scott.
Once he came out to the office where all of us sit in cubicles and told us we needed to have an emergency conference. “Get up, get up everyone in the conference room this is really important let’s go.”
So we all go in, he turns off the lights and the projector turns on. On the screen is not what we expected. It was an ultrasound video of our coworkers GOLDEN RETRIEVER. Our boss wanted us to guess how many puppies we thought we saw in the ultrasound and that the person who guessed closest would win 100 dollars.
48. Fan fiction
Female version of Michael Scott. About the time Harry Potter started becoming really big she wrote a story that was pretty much an exact rip off and all but forced us read the first two chapters.
She then redecorated her office to look like a wizard room in a castle including plastic wallpaper that looked like cobblestones and fake LED candles for light.
49. Mixed metaphors
I worked for a fortune 100 company and my boss was exactly like Michael Scott. I was the only woman engineer and he called me sir all the time by accident.
His mixed metaphors were gold. Once we overheard him on the phone with another engineers and he said “I realize this is out of your element. I’m just throwing you to the wolves to see if you can swim.”
I had a boss at Subway. Granted, it’s subway, but still the district manager. One day I walk in and take inventory… I go into the fridge and there’s the box labelled “lettus”…….. like….. lettuce….. she was the one who had prepared and labelled that box the evening before.
I then continued to find labels such as “qcumbur” “cookie doe” “terreyahke” and “stake”.