30 People Share The Most 'Michael Scott' Thing Their Boss Has Ever Done. That's What She Said!

Everybody wants to have a boss with a sense of humor, but what about when they take things just a little too far, say the wrong thing, and just make things intensely awkward?

Well, you might just have a Michael Scott on your hands...

Here are 30 real life Michael Scotts and their office adventures.

Many thanks the two Reddit users who posed this question. You can check out more answers from the sources at the end of this article!

1/30. We had an office picture day. At the time, I was his sole employee.


2/30. 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."


3/30. He 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.

He was actually upset it didn't scare me, like that's all he thought about the night before and I completely ruined his day.


4/30. In a meeting, he zoned out and was staring out the window. Someone asked what we should do for the new hire's initiation lunch, and he mindlessly said "take her to a field and leave here there." It reminded me of how Michael talked about Toby.


5/30. My boss absolutely IS Michael. His name is Malcolm, he looks the same and I'm always calling him Michael by mistake. I am essentially his Pam. He's the director of the company, single guy likes sports cars and only socializes with people who he knows through work. Confirmed when a) I do his christmas cards for him and b) have to constantly avoid meetings that turn into lunches that turn into nights out with just him and my significant other.

He eats at restaurants every night and brags about the loyalty discount he gets at the curry house on the top of my street. He's constantly calling me into his office to watch funny youtube videos from about five years ago.

For christmas I bought him a jar of sweets which he keeps on his desk and I'm expected to keep it constantly refilled. If I really wanna keep him...sweet...I fill it with old 60's sweets to make him nostalgic and he's amused for days.


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6/30. My last boss before I left corporate America nearly 20 years ago had to be the basis for Michael Scott. The most Michael Scott thing he'd do was to cop a German accent anytime he was speaking to our German clients on the phone. He didn't speak a single word of German, so he compensated by trying to sound like a German speaking English.

So many times, I struggled to keep from laughing in the middle of conference calls.


7/30. Boss would always shout out the same thing as he walked out for his lunch break

'Off to the strippers!'

After weeks of joking about going to the club to check, a few of us finally decided to. He was there. Having lunch. Adjacent breasts.


8/30. My boss is basically the female version of Michael Scott.

She hollered at me to come into her office the other day to help her understand what was said in a voice mail reply. Of course I agreed because voice mails are hard to understand.

The whole message plays and they left a website at the end. My manager says she can't figure out if they had some .com or .con

She has a tendency to hide her name tag and go watch sports out in the lobby.


9/30. He was teaching me how to enter data on the computer and said "1 is for male, 0 is for female". Then, using his pen to sketch in the air, he said "I remember it because men have a 1" (poked pen back and forth) "and women have .... a .... " (pen goes round in a small circle where he was just poking the air).

It was really weird and awkward the way he did it. Not to mention, there's no need for a system to remember that.


10/30. I really love my boss. But he does this thing sometimes where he'll go in for a high five and when you reciprocate he grabs your hand like a hand hug or something and just makes eye contact and smiles for a few seconds (too long).

Finally he ends it with an "Alright!" and walks away.


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11/30. 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.."


12/30. To boost morale, he put out a "Smile Box." It was a cardboard box filled with 100 one-dollar bills. People were allowed to take a dollar, but they had to stand there and smile for 60 seconds. He believed this would make people happier.

The box was empty in a matter of hours. Everyone was still miserable. The box disappeared the next day.


13/30. Mid-level manager. Had eyes for the shy clerk girl. At a company wide conference, in front of the maybe 250 fellow employees, starts his presentation with "They say that when you make a presentation in front of a lot of people, you should imagine your audience naked." Looks directly at the girl... "Thank you shy-clerk-girl".

You can imagine the crushed look on her face and the reaction of the audience, half chuckling, half gasping and a prolonged awkward silence.


14/30. Nothing really crazy, but I had a boss that had everyone introduce themselves before a meeting by stating their name, their position and where they were on 9/11.

After 30 people, it got really depressing.


15/30. The whole company was required to participate in a 2 day "Respect in the Workplace" seminar. I was 6 months pregnant at the time. I showed up on the morning of the first day and my supervisor commented to the entire room, which included our directors, my employees and the seminar leader, that I was getting so big that I should be seated at my own table.

I almost turned around and went home.


16/30. My boss got a smartphone about six months ago, to replace an ancient flip phone. The day after he got it, he came to me to learn how to use it, and that became my job for the next week. Complete disregard for what he had to do, what I had to do, it was just all about him learning his smartphone to the point where he was blowing off meetings and making excuses so I didn't have to attend mine.

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The following week, he comes to me because he discovered free online dating apps...


17/30. He bought a hammock and hung it inside his office.


18/30. My former boss just got a promotion and left our workplace. He bought HIMSELF a going away full sized sheet cake, 18" x 24" - 80 servings. He 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.

He was a really good boss and I will miss him, but that was pretty typical of him too.


19/30. My former boss never had me do any 'work' related work. I have booked him dancing lessons, drove around the state looking for soup that didn't exist, created schedules for the basketball team he coached, shopped for ridiculous things for him etc.

It was a GREAT job to have during college but I didn't learn a damn thing. He also would tell me to tell clients he was at meetings but really he was at sporting events or some other fun thing.

The man never worked.


20/30. A bunch of years ago, I worked at a Petsmart that had a very Michael Scott-esque GM. In the middle of our shift one day, he calls all the staff up to the front door of the store where the floor mat has worked its way out into the path of the automatic doors and is keeping them from closing.

Standing on the mat, he looks at us and very seriously says, "We have a problem, guys."

"I've been here since we opened this morning and this is the fourth time that this floor mat has moved out into the path of the door. Now does anybody know what this means?"

Nobody pipes up for this because it's clearly bait for him to tell someone that they're wrong.

"This means that we have more people leaving the store than we have coming in."


"The reason that we have more people leaving the store than we have coming in is because we're not providing the best customer service. Once we start doing that, we'll have more people coming in than leaving. Now I want you guys to put on your best customer service and by closing tonight, I want to see this floor mat against the back wall of the store."



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21/30. 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 and proceeded to point out all the office gossip and what everyone felt about each other.


22/30. 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.

He proceeds to make a completely normal instant coffee in pretty much the only way it's possible to make it.


23/30. Called me and my coworker down to her office with a "Come to my office now, it's important" message.

We get there, ask what it's about.

Her: "We need to discuss our Halloween group costume"

It was February 16th....


24/30. I work in the IT department 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 Steve, where you going with those tampons?"


25/30. He 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."


26/30. 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.

He looked so defeated for the rest of the day.


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27/30. -Constantly called full staff meetings to watch motivational videos but was too cheap to pay for the full thing so it was mostly ads for speakers.

-Encouraged us to treat ourselves (like she did) with a pool (paid for by borrowing from her 401K), which she says was to save her marriage.

-Photoshopped copyrighted images to make promotional materials for a major, non-work related event she put on after being told it wasn't legal.

Photoshopping it made it legal, she said.

-Wrote a book about her family and promoted it across the office after sending out an email that no one was allowed to promote any kind of products or fundraisers at work.


28/30. I had a boss that always messed up cliche phrases. For instance, he would say TGYF! and not even on Friday. My favorite when he would give someone a little tip or pointer and then say "Just a little FYI for ya".


29/30. My boss gave herself an award and proceeded to show it off to everyone higher up than her.


30/30. 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."


Sources 1 & 2.

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