What's the Most "Michael Scott" Thing Your Boss has Ever Done?

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Hired a consultant to come in and see who wasn't functioning in the company, after a week of interviews with the consultant the problem was pointed out to be the boss, consultant didn't come back.

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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.

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The following week, he comes to me because he discovered free online dating apps, and asked if there was a "setting where fat chicks couldn't message" him.

Edit: Just remembered this one, too.

Same company, different boss. I was sitting in on a conference call with a client and were discussing a print request. My boss started in on the pitch for different colored paper, but said "I don't know if you know this or not, but we're one of the few sites that still utilize colored people."

Dead silence for a solid minute, and I had to leave the room because I was laughing so hard.

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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.

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That does actually sound like something Michael Scott would've done.

I used to work at a hotel/convention center. My boss was super awkward and nerdy and nice to the core. Mr. Nice-guy. Unfortunately that meant most people walked all over him. This had a real effect on him over the years - and eventually he became sort of sullen and reserved. Anyway - late one night me and 4 or 5 guys were setting up this enormous banquet room when Mr. NiceGuy and his assistant manager (we'll call him Dwight) pop in the room, walk over to the stage, fiddle with something up their for a bit, then dip back out of the room without saying a word. I remember thinking it was odd, but didn't care enough to investigate.
Had I investigated, I would've found out that they'd turned the volume on the sound system all the way up and then swiped one of the wireless microphones. Then they took that mic into the office and set it down next to the computer speakers Then Dwight came back into the room in a rush, ran back up to the stage area and turned off all the lights in the room - for a moment it was pitch black, and then this VERY loud music came booming over the speakers. I din't recognize it right away, but it was Stone Cold Steve Austin's song that played whenever he'd enter the arena or whatever. Then Dwight flipped on this AV system which was had a function that'd swirl various spotlights around for a moment then suddenly focus them all on the 2 big doors at the end of the room (this typically used when wedding parties enter the room during a reception.) When the lights hit the doors, Mr. NiceGuy swung them both open and stormed in the room, much like Stone Cold would've - with more confidence and gusto and bad-arse-ness than any of us in attendance though he was even remotely capable of. In that moment he fricking was Steve Austin. When the song ended this great grin spread over his face - it was the look of having just lived out a life-long dream. We were so taken aback and amazed by the whole thing that we were just frozen, and then Dwight got mad and told us all to clap for him, and Mr. NiceGuy's face dropped and he told Dwight that he'd ruined it - then walked out, and Dwight ran after him.

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So great that I think it is fake

Definitely fake and seems like it might have been on the show.

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Hired a consultant to come in and see who wasn't functioning in the company, after a week of interviews with the consultant the problem was pointed out to be the boss, consultant didn't come back.

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I worked for a company that had a similar experience. My boss was an a-hole of epic proportions. Made a huge deal about how this company was going to come in and tell us all the things we were doing wrong, and how great things were. Its all we heard about for months. Company came, did interviews, looked at all kinds of stuff. We had to fill out several surveys and questionnaires. Then, that was the end. Never heard any more. Never spoke about it again.

In the process of business, we found a copy of the report. It basically said that the owner was an absentee owner, the Ops manager (my boss) was a tyrant and a major impediment to efficiency. Short time later, ops manager was fired for embezzling money.

When I first graduated law school and was working at a firm, they had just required everyone to have a smart phone. There was a meeting for which everyone was told to bring their phones because they were going to teach everyone how to use them (this was mainly for the older attorneys). This one partner who was probably 75 years old is late to the meeting, and he yells for his assistant to come into his office. He couldn't figure out how to unplug his phone and bring it to the meeting, he was actually trying to unplug everything from his desk phone and bring it to the smart phone meeting.

My boss overuses the word, "Conscientious" and always in the wrong context. I think he means "Conscious" or "cognizant" but he's so damn sensitive I'm afraid to correct him.

example: We have to be conscientious of the fact that costumers maybe entering our building at any time so we must dress accordingly.

Example (2): We have to be conscientious that is a live wire.

My boss told introduced the new member of the team and said he hated him b.c he was tall and how tall people sucked. The boss was a midget.

One time he went off on how you can't hire anyone in france, and he would fire anyone who hired someone in france b.c then we couldn't fire that person.

I had another boss tell us about the time he took mushrooms. It was interesting to say the least and everyone in the office had their jaw dropped.