35 Real-Life 'Michael Scott' Bosses, Called Out on Reddit | 22 Words

When you think of iconic bossesThe Office’s Michael Scott is right at the top of the list. He’s bumbling, insensitive, and at times just clueless—but his antics kept us coming back for season after season of the show!

A recent Reddit thread set out to answer the question: are there any real-life Michael Scotts? The answer, unsurprisingly, is "heck yes."

Check out these 35 people, and their crazy stories of bosses who’d put Michael to shame!

Don’t take the hint!

A few coworkers and I competed in a local Office-themed trivia contest. We came in second place, and one of the prizes was a "World's Best Boss" mug. We brought it into work and displayed it proudly like a trophy in one of our offices. My boss, who was not involved in the contest, has never seen 'The Office,' is not friends with or well-liked by any of us, (and is a huge idiot) saw the mug in someone else's office and just took it. None of us could figure out where it had gone until we saw her drinking out of it. -MyHandsAlwaysHurt

That car ride was less than ideal!

As a blizzard approached, he offered to drive home anybody who needed a ride because he'd just bought a new "badass" Hummer H2 that "could drive through anything." An hour later, he and three of my coworkers are sitting in his new SUV in a snow drift on the side of the road, waiting for the wife of one of them to pick them up. -Smiling_Mister_J

Valiant attempt, but Subway is on every other street.

Every year representatives from my old company would attend the International Bridge Conference in Pittsburgh. The first year I went, my boss got me all hyped because there was a restaurant in Pittsburgh and it was his tradition to go to every year when he was there for the conference. He kept saying how exciting it was that he could introduce me to the tradition, so I figured it had to be some awesome unknown local gem or at the very least a Pittsburgh icon like Primanti Bros. It was the Subway across from the convention center. -Gumburcules


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. He 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. -bird-ghost

If this boss wanted to be included, he had a strange way of showing it!

We work in digital marketing. He stalks our coworkers on social media and brings up their posts at weird times. We’ll be in a meeting, and he’ll bring up someone’s weekend plans from a month ago, in front of everyone. Most of the time he’s not even friends with these people. It’s so awkward and cringey. -TurbulentJello What other Michael-isms have people found out in the wild? Find out on the next page!

Now this is just gross.

Literally just last week, our boss decided a "fun activity" during our hands-on meeting was to challenge someone to see if they could eat a handful of dead crickets faster than him. -blueeyesredlipstick

Just goes to show: if you treat your work like garbage, janitors will too!

My one boss, an absolute nightmare of a human, carried all of his paperwork around in a black trash bag. And he was rich, like filthy rich. He inherited his father's contracting company and during the boom of the early 2000's made a ton of money. But he said he didn't trust briefcases... yeah, I know. So one night he left his trash case in an office and a cleaning woman threw it out. All contracts, building specs, whatever, gone. -Theres_A_FAP_4_That

This boss didn’t really get “professional."

My boss took us to a Farmer's Market for an office lunch outing, and when me and my two coworkers walked over to his table after having browsed and eaten, he told his attorney friend he was with, "They don't like to be too far from daddy." -carbcat

A swing and a miss with this barbecue.

We grill out for lunch occasionally, and when we told our new boss this, he got all excited and insisted on providing the meat. Great, except they were the nastiest freezer-burnt turkey brats I’ve ever seen. I think he just cleaned out his freezer. Everyone was wrapping them in napkins and throwing them out when he turned his back. I mean turkey brats are bad enough but, yeesh! -kev_61483

Nobody wins if the boss can’t win, apparently.

Boss canceled work for the afternoon so their team could all play a new board game they bought. Called it a ‘team building exercise.’ Then when they started losing, started berating and yelling at junior employees for not 'playing fair' or 'being too competitive.’ -PM_ME_UR_Definitions You won't believe the crazy things these Redditors' bosses have done on the next page!

Are we sure Michael Scott isn’t a real person?

This is one of the most Michael things here because it hits all the checkmarks:
  • Being excited about a new thing he got
  • Wildly overestimating the impressiveness of said thing
  • Trying to get his employees to like him by doing an unnecessary, unhelpful, but ultimately nice thing
  • Assuming the employees are in need of his help in the first place
  • The whole thing blows up in his face, of course
  • Winds up getting bailed out by someone he probably was embarrassed to accept help from - not just his employee, but the employee's wife.

In your car on a highway is a really bad place to show off.

I had a boss who got a promotion to senior manager. The very next day he pulled into the parking lot with a BMW 1-Series. No one on my team even knew they made a 1 series (cheapest possible BMW/badge car). He gets out wearing a BMW polo and a white BMW hat. He offered to take me to lunch in it. He jumps on the highway, adjusts his BMW hat and says to me, "I don't exactly do 60 in this thing!" does a little triumphant laughter and starts going 80. There was a cop on the bridge above us. We were immediately pulled over. I will never forget the look of defeat on his face. -BasicAlgebrah

Were these candles from ‘Serenity by Jan’?

My boss put candles in his dishwasher to clean them and they ended up melting and distributing a thin layer of wax over everything. -frangoon1984

Isn’t this theft?

He was approved to buy a furniture set for out new office waiting room he bought one then took it home and brought his old living room furniture for the office to use. Then when they shut that office down a year later, he took his old furniture back instead of letting them take it to the new office location. -offhandaxe

Now that’s a Napoleon complex!

My boss makes me walk 2 meters behind him because I'm tall and he's short. -holybull Keep reading the strange and hilarious things Michael Scott-esque bosses have done on the next page!


Let us have most of the day off to go watch ‘The Hobbit’ as a team building exercise. Another good one, When Bin Laden was killed, he kept asking one of our Muslim coworkers, who was from Sudan, if she knew him. -FAHRENHEIT_311

One boss dined and dashed on her own employees.

After a successful project, the owner of the company invited everyone out to lunch (about 12 employees) at a nearby restaurant by the office. Little did she know, the place was very expensive, so she bounces early before the check comes, stating that she had a client call. She gives us money to pay for her meal and takes off, leaving the rest of us to figure out the check. It also turns out she didn't give us enough money to pay for her portion of the check, so someone had to throw in a few extra bucks to cover that. -Ricetaco

Managerial style: awkward high-fives.

He followed customers around and gave them high fives on their purchasing choices. If we closed the store, we wouldn't get out for 2 hours after close. When I eventually learned how to close, I could get out within 20 minutes. My belief was he was married to a real Jan, and he didn't want to go home. -mattcruise

When staff appreciation turns into staff demoralization:

Mandatory Staff Appreciation Day. It fell on my day off, and I had to come in, to participate in the team-building activities that were scheduled. It went from 7 am to 7 pm, which was longer than a normal shift. That was my only day off that week. -1YearWonder

Sometimes you’ve just gotta be the fanciest person in the room.

Wore a tuxedo at work lunch to give out superlative type rewards. The lunch was at a local sports bar. He had never seen 'The Office.' -Chosen_Fighter As you can see, Michael Scotts aren't that uncommon. See more wacky examples on the next page!

You keep using that word. I don’t think it means what you think it means!

My boss would confuse the word fillet and fellate. I about lost it a few times when he came up and said: "If we don't get [project] done by the deadline they're going to fellate us in the next meeting!" -Risin247

Don’t leave this guy by himself!

Made someone come with him to get his shoes shined because he wanted someone to talk to. Except, we all wore sneakers, so the lucky guy got just to stand there and wait while he got his shoeshine. -Hrekires

Both of these examples are pretty big “don’ts."

It's either the time he talked about his divorce to a couple trying to rent tuxedos from us. Or the time when an African American couple walked in, he switched from the normal greeting, "welcome to tuxedo store" to "What's up brother." -madethisforoneremark

And this is how to fail at business!

We were very close to getting a very big client in an Asian country. We ended up losing the client because he did his racist Asian impression (very similar to Michael Scott's "Ping") to the guy over the phone without realizing that the guy was Asian himself. -Salad_Fries

Sounds like someone needs a dictionary!

There is a very large list of words that he always mispronounces. We actually have a notebook where we record his pronunciation of these words as well as a variety of super weird (boss's name)-isms that he likes to use. -Salad_Fries Not only do these bosses do similar things; sometimes, the show parallels life almost exactly. On the next page, see how!

Letting down schoolchildren: the Michael Scott way.

Not my boss, but a guy created a few scholarships at the university I was at, and then something weird happened like they were supposed to be 4-year deals, but he only had the money for 1 year. Anyways, when it happened, I remembered someone saying he ‘Scott's Tots’-ed them. -billbapapa

Pretty sure this should be reported to HR.

Ranked all 7 of us in order of his most favorite to least favorite. -garrybibb

Well, that’s one way to say goodbye to an employee.

On my last day at a sucky catering job, my boss gave me an ultimatum: work the rest of the night or record me embarrassingly doing the Dougie and post it on Snapchat. The shortest shift I ever worked. -Arizonias

They say ‘life imitates art.’

We legitimately had to lay off 4 people last year, and management decided to wait until the day before the Halloween office party to do it. No joke. It was like the Halloween episode in real life. -Amedais

Are we sure this isn’t just a summary of The Office, Season 5?

My supervisor left to start his own software company. They sub leased their office from my employer. When the company failed, my employer hired him back along with several of his employees. -CrabbyBlueberry The next few slides put the icing on the cake! Keep reading to see what totally Michael Scott-like things these real bosses did!

This boss just didn’t seem to know HOW to work.

She would do almost no work at all. She would come into our offices and bother us while we were working talking about how bored she was and how we should redecorate our offices. Any work she got, she would just forward the emails to someone and never even read them herself. Then she would decide often how we needed to change the furniture in her office, move things around, paint a wall in her office. She would call meetings 3 times a day to talk about nonsense, and they would go for about an hour each time on nothing. -Economy_Cactus

Is it an understatement to say this was bad funeral etiquette?

Was at a funeral for a co-worker's husband (who I was good friends with as well) and my boss came along for support. He had bought a large floral arrangement for it and spent most of the service nudging me on the shoulder and pointing to it in an "Eh? See that? Niiiice right?" fashion. He later went on to brag that he ordered the largest arrangement of everyone in attendance. -Goran1693

It’s important for managers to be eagle-eyed!

I handed him an aerial image I had printed. He 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." -FridaysOnTheFly

How petty can one person be?

This is a story from my brother. He works at a credit union and one morning around 10 am his boss walks out of his office asking if anyone wants the other half he cut off of this huge bran muffin. Everyone there said they were fine and the boss went back into his office. Later, around 12, an employee comes in for her shift with a box full of doughnuts to share with the office. Everyone came up and took one thanking the employee for bringing in the treat. The boss was visibly mad that everyone went for the doughnuts and no one wanted half of his bran muffin. He was just a big grump for the rest of the day. -puntini

This is not why Human Resources was invented.

HR mandated "personal development" course. They did them every year, and they always centered around not discriminating in some way (based on gender, age, religion, etc.). Well one year, they had a new lady in charge of it. The topic was "invisible" disabilities. Basically, some form of disability which is not visually apparent (OCD, ADD, developmental disorders, etc.).  The task we had was to write down a list of "challenges" a person with the disability might face in everyday life. Then we had to act out a scene showing how these challenges would affect them. We asked her to clarify, and it became apparent she was literally asking us to stereotype disabled people and mock their daily lives. That HR lady was not present for any of the future rounds of "training." -anormalgeek Like this story? Share with other The Office fans, and see which real-life Michael Scott moments make them laugh the loudest!