35 of the Most Michael Scott-Like Bosses People Have Ever Had

Truth that’s both stranger — and worse — than fiction
35 of the Most Michael Scott-Like Bosses People Have Ever Had

Millions of Americans tuned in across seven seasons of The Office to watch Steve Carell wreck havoc on his fictional subordinates as the most comically inept boss in TV history. These Redditors, however, didn’t need to watch Michael Scott’s unhinged mismanagement to understand what it would be like to work for someone like that. 

Case in point: One of their bosses with a particular craving sent an employee out looking for pomegranates despite pomegranates being woefully out of season, while another shouted at the top of his lungs to prove a point — the point being that he doesn’t raise his voice. 

Who knew just how real fiction could be?

 6y ago It was this guy's last day with the company, and the managers brought in a cake for everyone to share. A very nice farewell gesture. Except he wasn't moving to a new city or leaving the company for a new job. Не had gotten fired. The managers literally fired this guy, then called everyone into the kitchen and said Okay, today is Steve's last day with the company, let's have some cake! Most oblivious, socially awkward, tone deaf moment imaginable. + 15K ...
FridaysOnTheFly 6y ago I handed him an aerial image I had printed. Не told me I needed to reprint it and rotate it 180. I walked to my cubicle, waited a minute, handed it back to him right side up. His reply, Perfect. 1.6K ...
Fudge-Supreme 9y ago My boss actually did organize a fun run for the whole office. The course was literally just running around the building ~20ish times until we eventually got to 5k.... it was at 7:30 on a saturday and only 7 people showed up + 2K ...
The0isaZero 9y ago 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.. + 5K ...
lolbuttlol 9 9y ago We had an office picture day. At the time, I was his sole employee. + 6K ...
steveb703 9y ago I work in the IT dept. for my company. This one day I was emptying a laptop bag and found a bunch of tampons in one of the pockets. My boss told me to go put them in the ladies room. Unbeknownst to me he followed me out of the office and into the main office floor and shouted Hey, Steveb703 where you going with those tampons?
wonderfulmeg 8y ago My old boss knew we were all stressed and overworked, so he thought that the best way to get us to relax was to have... a drum circle. In the middle of the office while we were all trying to work. Не kept trying to get people to join in, even people who were on the phone. Eventually it was just him sitting on the floor hitting bongo drums... 240 ...
OneFishySniper 8y ago My dads boss once said he would give all employees something to boost encouragement in the workplace. They all got camo baseball hats with 'GIT R DONE written on them. 121 ...
myaccount2202 8y ago Не put a fake severed head in my bottom desk drawer and watched me from the corner of the room to see if it scared me. I just looked up (in a very Jim way) and blinked a few times and then closed the drawer. The look on his face was pure defeat. Не was actually upset it didn't scare me, like that's all he thought about the night before and I completely ruined his day. + 8.8K ...
 8y ago . Edited 8y ago I work at a fortune 500 company. In the middle of an important meeting which was based around my boss, she leans over to me and whispers I'm organizing a flash mob for later this year. I want you to be a part of it + 2.5K ...
NOt_Yours . 8y ago Не told a group of his employees We, as management, have the right to mismanage. 704 ...
Safe_T_Bitch 8y ago he put a large CAUTION: SURFACE IS HOT! sticker on the denim-ed dad butt, came into my office, shook his fanny at me, and asked what I thought of his safety signage. this may sound like sexual harassment, but just like I can't imagine Michael Scott actually being a predator, I couldn't imagine my boss being one. This reminded me of when Michael wore his ladies' power suit to the office and showed off the backside. + 1.1K ...
saintexuperi e 8y ago Trying to pick the company health insurance policy so he polls the leadership team for input at an executive all-hands. CEO states that we're all young and healthy so no one needs things like dental, or optical. Half of our executive team is wearing glasses. Не moves on. + 1.8K ...
Part_of_the_Infinite 8y ago My grandfather passed away back in February. I flew back east for the funeral, and when I got back my boss was talking to me to see how everything went and touch base. The extent of the conversation was this: Boss: How was the funeral? Me: About what you'd expect from a funeral. It was a nice service. Boss: Did you see......the...body? Me: Yes. + 2.1K ...
OLD N°7 ro50 8y ago BRAND When he pages someone over the intercom he instructs them to report to the senior vice president's office instead just saying please come to Gary's office. We have like 20 people that work here. Everyone knows it's him when he starts the page. Не likes hearing his own voice and title. + 2K ...
 8y ago Boss wanted to give his tie to one of my coworkers before a meeting to look more professional. The company we were meeting with don't wear ties, our company doesn't wear ties, both companies know this. My coworker was wearing a lumberjack style shirt. So my boss wanted him to wear a formal tie with a short sleeved, lumberjack style shirt... to look more professional. + 617 ...
 8y ago Не was spelling his name over the phone to someone and when he got to the i in his name he said i, as in... um... I. + 1.9K ...
TheMcRiblsALie 8y ago Edited 8y ago My boss gave herself an award and proceeded to show it off to everyone higher up than her. Never thought this would be so popular so here's an edit to add clarification/more information: Without going into specifics, I work for a department at a college/university, and my boss who is the director of our department, also is the president of a volunteer organization that works in conjunction with higher education for our field. Any obligations for this volunteer organization are to be conducted outside of standard operating hours, yet half of my office (we're
SulliedVoice 8y ago My former boss just got a promotion and left our workplace. Не bought HIMSELF a going away full sized sheet cake, 18 X 24, 80 servings. Не cut off a small corner at his going away party and then proceeded to close the cake box and take home the other 79 servings instead of sharing any of it with anyone. Не was a really good boss and I will miss him but that was pretty typical of him too. + 5.5K ...
truman_chu 8y ago Gathered everyone in the office kitchen to demonstrate exactly how he liked his coffee made, but pitched it as if he was letting everyone in on the secret to making the perfect coffee and we'd all be thankful to him later. Не proceeds to make a completely fucking normal instant coffee in pretty much the only way it's possible to make it. 3.8K ...
itsfoine 8y ago Someone from corporate came in to teach us on racism, sexual harassment, etc. My boss thought it would be a good idea to interrupt the presentation and ask us for personal testimonies of time when we felt uncomfortable in the workplace. When no one answered she called out a coworker and asked how she felt that everyone thought she was fat and makes fun of her when she comes back with fast food every day for lunch. The coworker of mine just sat there and started to cry. My boss was like well I thought she knew
 4y ago 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 dick. 8.3K ...
holmen-2001 4y ago 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. + 13K ...
 4y ago 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 + 16K ...
harperv215 4y ago 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. + 17K ...
PAzoo42 4y ago 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. Не would get so caught up in his conspiracy theories that he forgot to order wood to make furniture one month. + 19K ...
Bolaixgirl_105 4y ago I had a boss once who spent all morning locked in his office. Не asked me to come in after lunch where he showed me a handmade graph. Не 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
lala710 4y ago Не 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.. + 22K ...
LemonsofLifee 4y ago . Edited 4y ago Не 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.
BigShoots 4y ago 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? + 36K ...
homeschoolpromqueen 4y ago 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... Не 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)
happydactyl31 4y ago I used Michael Scott as a reference point for an old boss of mine from the moment I started working there. Не 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
 4y ago 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. + 5.3K ...
outofprintluv 4y ago 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
Bolaixgirl_105 4y ago I had a boss once who spent all morning locked in his office. Не asked me to come in after lunch where he showed me a handmade graph. Не 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

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