15 Crazy Stories of People Working With Bosses Like Michael Scott

There’s no question that Michael Scott (Steve Carell) is one the most beloved characters in the history of cinema and television. Although his antics on The Office are ridiculously hilarious, Michael Scott, at times, could be bumbling, insensitive, and at times just clueless.

As a result, some of his antics got a bit out of hand and and drove people crazy. Michael Scott also made everyone else at Dunder Mifflin cringe over his lack of poor social skills. 

In my professional life, I have yet to encounter or work for a boss like Michael Scott. A ton of other people have and are sharing their stories of what it was like working for real-life Michael Scott like bosses online. 


Now, with all of that being said, here are 15 Crazy Stories of People Working With Bosses Like Michael Scott:

1. Michael Scott Boss Story #1 – The Grocery Store Quest for a Pomegranate:

“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.”

-Redditor LemonsofLifee


2. Michael Scott Boss Story #2 – The One With The Unnecessary Sensitivity Training:

“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.”

-Redditor ResepctFar


15 Crazy Stories of People Working With Bosses Like Michael Scott

3. Michael Scott Boss Story #3 – The Most Michael Scott-esque Boss You Will Ever Hear About:

“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.”

-Redditor Happydactyl31

4. Michael Scott Boss Story #4 – The Actual Gay Witch Hunt:

“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.”


-Redditor Lala710

5. Michael Scott Boss Story #5 – The Results of The Anonymous Feedback Program:

“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?””


-Redditor BigShoots

15 Crazy Stories of People Working With Bosses Like Michael Scott

6. Michael Scott Boss Story #6 – What My Boss Did at My Wedding:

“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.”


-Redditor Holmen-2001

7. Michael Scott Boss Story #7 – The Inappropriate Joke:

“During an unplanned fire drill, he made a joke about the possibility of an active shooter. It made everyone very uncomfortable.”

-Redditor PresidentZuko


15 Crazy Stories of People Working With Bosses Like Michael Scott

8. Michael Scott Boss Story #8 – The Hallway Incident:

“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.”

-Redditor Jezebellrae


9. Michael Scott Boss Story #9 – The Many Incidents:

“He used to delay meetings as they started to make someone go to his office to get candy to share with everyone.

He found out a woman in the office had a weave and then asked every black woman in the office if her hair was “fake”.

He was suspended with pay for getting drunk at the holiday party and grabbing ass.



10. Michael Scott Boss Story #10 – The Boss Threw a Hissy Fit Because No One Wanted His Half of a Bran Muffin:

“This is a story from my brother. He works at a credit union and one morning around 10 his boss walks out of his office asking if anyone wants the other half he cut off of this huge bran muffin he had for breakfast. 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 his half of his bran muffin. He was just a big grump for the rest of the day.”

-Redditor Puntini


15 Crazy Stories of People Working With Bosses Like Michael Scott

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11. Michael Scott Boss Story #11 – Just Like Michael Scott, but More of a D***:

“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***.”

-Redditor Mackenziefox55


15 Crazy Stories of People Working With Bosses Like Michael Scott

12. Michael Scott Boss Story #12 – We All Saw Way More Than We Needed To:

“CEO of our company Skyped into a meeting, but accidentally hit his laptop screen and aimed the camera down revealing he was Skyping in with the classic ‘no pants’ style. It was like a real life sitcom moment.” 

-Redditor Jorgwalther


13. Michael Scott Boss Story #13 – The Backpack Full of Hammers:

“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.”

-Redditor Supersecretsecretary

14. Michael Scott Boss Story #14 – He was So Random:

“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.”


-Redditor Startinearly

15. Michael Scott Boss Story #15 – The Super Unprofessional Moment:

“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.””

-An Anonymous Redditor 


Have you personally ever had to work with a Michael Scott-esque boss in your career so far? If the answer is yes, share with us in the comments section your Michael Scott Boss Stories down below!

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