'[He] would gather admin staff... and show them funny YouTube clips': 30+ People whose silly bosses have the whole office facepalming

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Remy Millisky • Writer and Editor
Nov 7, 2023 11:00 AM EST

Not every boss is serious and hard-working—some are so goofy, they barely get any work done at all. Much like the lovably cringe Michael Scott, the boss from "The Office," these people had bosses who seemed to want to do anything other than work. Instead of leading a team, they'd rather try to be everyone's BFF. They want to be known as the "cool boss," but in reality, their employees are probably mocking them behind their backs for trying too hard to be liked. It's one thing to try and establish a professional relationship with your colleagues, but it's a whole different story when the boss keeps to organize staff happy hours or team building exercises to try and get the team to become actual friends (not work friends).

These people shared the "most Michael Scott thing your boss has ever done." There are some great stories included below, from bosses who wanted to organize fun runs, to others who are insistent on being hip with the latest slang. At least these workplaces are entertaining places to be at, even if very little actual work is getting done. Up next, these bakers gave one star to some recipes because of their own substitutions, like the person who decided to make carrot cake without carrots, and instead adding kale. 

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  • 01
    What is the most Michael Scott thing your boss has ever done?
    via u/rileytp
  • 02
    TheOisaZero 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.."
    via u/The0isaZero
  • 03
    lolb lol. We had an office picture day. At the time, I was his sole employee.
    via u/lolb***lol
  • 04
    Fudge-Supreme 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
    via u/Fudge-Supreme
  • 05
    Peanut ButterSoda I had this Indian boss at a sandwich shop that overheard me say "that's whatsup". He asked me what it means and I just told him it meant "good" or "great". He kept using it over and over the next two years I was there. "I want that walk in clean like that whats up" or "That sandwich was not that whats up, buddy".
    via u/Peanut ButterSoda
  • 06
    amaster09 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.... Edit: Image: http://imgur.com/Jm8pG i6 I'm King Triton. My boss is Ursula. Coworkers are Ariel and Sebastian. And our "Flounder" is a pug statue wrapped in yellow construction paper.
    via u/amaster09
  • 07

    This is quite the Halloween group costume!

    5538
    via u/amaster09

    Those massive googly eyes are utterly hilarious. 

  • 08
    noobmama I was the receptionist, and she tried to start a rumour that I was in a torrid affair with the IT man. We're married... Edit: fine. IT guy. I'm married to the IT guy. Better?
    via u/noobmama
  • 09
    PM_ME_YOUR_BOO_URNS. He bought a hammock and hung it inside his office
    via u/PM_ME_YOUR_BOO_URNS
  • 10
    KTBoo 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.
    via u/KTBoo
  • 11
    darkwingduckles 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.
    via u/darkwingduckles
  • 12
    Edit: this post picked up more steam so I will add more stories. Also, yes to the guy that noticed when I said "hollered". And we have a guest lobby that they can watch TV in. Most of the time we deal with new people so none will recognize her. The other day she just left work and was gone for an hour. She called me back and asked me to help her find her keys. I can't make this up yall. She drove all the way down back to work and realized she left her keys in the ignition. She always has me veri
    via u/darkwingduckles
  • 13
    spriteburn My boss acts noticeably more macho in front of ladies. He likes to bark orders at me in their presence, but not in a condescending way. I play along, he's a great guy and really looks out for me.
    via u/spriteburn
  • 14
    BasicAlgebrah 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
    via u/BasicAlgebrah
  • 15
    whiskey_smoke Middle of the work day, would gather the admin staff around and show them a funny youtube clip he found.
    via u/whiskey_smoke
  • 16
    lobster_liberator I closed the door in my office and he walked in dead serious and said, "We have an open door policy here, so you'll have to keep this door open.."
    via u/lobster_liberator
  • 17
    hightreason 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".
    via u/hightreason
  • 18
    oh__what My boss intercepted some emails between a couple of coworkers in which they were referring to him as "the fun s ker" (he totally is). For a few weeks after that, he was noticeably mopey, and any time he came over to our corner for something, he'd say something like, "don't mind me, just the fun sker coming around to s k the fun from your day." Of course he sounded just like a distraught Michael when he said s like that.
    via u/oh__what
  • 19
    One day, we all get called into the conference room. He's got a scoreboard drawn up on the whiteboard, and an old trophy he'd bought from a thrift store (with the engraved placard from the previous owner's MANURE SHOVELING CONTEST WIN still attached!!). He'd orchestrated a Harry Potter trivia contest for all of us, despite his total lack of knowledge on the subject, because he knew it was something his employees would enjoy. It was awesome, save for the fact that any time it became especially ob
    via u/oh__what
  • 20
    shout, "I'M REALLY REDEEMING MYSELF FOR FUN SCKING!," which would make things uncomfortable for a few seconds before play resumed. One of my coworkers has the trophy in her cubicle now.
    via u/oh__what
  • 21
    denimb 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 socialises 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 SO. He eats at restaurants every night and brags about the loyalty
    via u/denimb****
  • 22
    constantly calling me into his office to watch funny youtube videos from about 5 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 60s sweets to make him nostalgic and he's amused for days.
    via u/denimb****
  • 23
    **Edit:**So much love for Mich...Malcolm! I will pass this on to him, I'm sure he'll find it very funny. Also, thank you for the gold! 5 years of trying to get it by myself and in the end it goes to the boss, typical! :P Also, you might all be amused to know that I just came off a phone call with him. He called to ask me to send a file to a client, and stayed on the phone for 47 minutes narrating the traffic and all the cars that were on the road.
    via u/denimb****
  • 24
    TWANG BANG TWANGnBANG My last boss before I punched out of 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. ETA: He had no idea he was doing it, which is
    via u/TWANGnBANG
  • 25
    A new push for customer service: the Customer Service Initiative. (CSI) The whole place went from totally sterile to absolutely clustered with posters, props, and just downright weird sayings. "Don't flee the crime scene without your proper closing!" "The criminal always returns to the scene of the crime - as long as they were greeted with a smile."
    via r/AskReddit
  • 26
    There were dozens of them. It was weird. Like, uncomfortable weird. Our "CSI" became a metric that was 1/5 of our overall performance every month. It had a special grade sheet with a pun-filled checklist measuring customer service effort. Did we "search for clues" that they might need further help? Were you able to "dust for fingerprints" in order to pull up their account? This s affected our pay big time. While the bottom line was understandable, I despised sitting down with my boss and, in a v
    via r/AskReddit
  • 27
    I worked there through months of this before finally quitting (for unrelated reasons). I talked to a friend from work about a year later to find out it was still happening. All because CSI.
    via r/AskReddit
  • 28
    ambulation I used to show up early to work because of the bus schedule. One day I got there a lot earlier than normal and it was my boss' lunch hour. We chatted for a minute about what needed to be done that day. We got on the subject of cheeses somehow and how Costco has a "wall o'cheese". He asked me to go for a quick road trip after chatting a bit more. I had time so I figured "What the h Why not?" We got in his truck and he drove me to Costco. He led me to the wall o'cheese and told me "I wa
    via u/ambulation
  • 29
    first i though he was joking, but he insisted and looked so sincere. I chose a little block of Havarti. He told me to get the big one... So I got a $50 block of Havarti as a reward for working hard. The other staff didn't believe me until they asked him about it. Awesome gesture. I love cheese. It just wasn't something I expected from my department store boss.
    via u/ambulation
  • 30
    Hhonkers 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
    via u/Hhonkers
  • 31
    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 b
    via u/Hhonkers
  • 32
    Steve Austin's song that played whenever he'd enter the arena or whatever. Then Dwight turned on this AV light system which had a function that'd swirl various spotlights around for a moment and then suddenly focus them all on the 2 big doors at the end of the room (this was typically used when wedding parties enter the room during a reception). When the lights hit the doors, Mr. Nice Guy swung them both open and stormed in the room, much like Stone Cold would've - big powerful stride and a seri
    via u/Hhonkers
  • 33
    and bad-a-ness than any of us in attendance though he was even remotely capable of. In that moment he f was Steve Austin. When the song ended this amazingly great grin spread over his face - it was the look of having just lived out a life-long dream, and done it well. 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 Dwi
    via u/Hhonkers
  • 34
    DEMENTED_FRESH Deleted the 'SUBJECT' column from his emails and ask me to make it reappear. Every. Single. Day.
    via u/DEMENTED_FRESH
  • 35
    cfenton23 When I send him e- mails, he prints them out and writes his replies on the paper and hands them to me.
    via u/cfenton23
  • 36
    RowbbyTheSheeth He flies his RC Helicopter around the warehouse to scare the birds and stop them s on the floor. He also covered our forklifts with so many LEDs it looks like we're driving Christmas trees.
    via u/RowbbyTheSheeth
  • 37
    Nigelwithdabrie My last boss fancied himself a seriously good Christian and a doer of good deeds. He's neither. He came up with the idea for our firm to donate money to local Christian charities during live broadcasts so everyone would know that he's the greatest guy ever. Being a cheap b he only wanted to pony up a hundred or so bucks for the good cause, but he wanted to present it to the charity in the form of an oversized check. For a
    via u/Nigelwithdabrie
  • 38
    week he had half the office looking to buy the cheapest oversize check they could find. When someone informed him that the checks would be as much if not more than what he was donating and suggested he increase his amount, he just cancelled the whole initiative instead.
    via u/Nigelwithdabrie
  • 39
    girlxgenius I just started working for a new place part time, more as an independent person so my 'boss' is really that in name only. I witnessed this org's equivalent of the 'perfect storm': pay agreements and pay checks had to be signed. They were all set up in 2 folders. Watching the finance admin hound him all day while he did everything possible to dodge the responsibility was absolutely amazing and horrible. Real life Michael Scott.
    via u/girlxgenius
  • 40
    [deleted] -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. -Came in the day after Obama was elected with state voting numbers, read a dummies guide synopsis of how the electoral college works, then said how our state almost voted the wrong way (Democrat), and tha
    via u/[deleted]
  • 41
    -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. -Got caught hiding pay scale information that should have been public in a full staff meeting with the corporate executive board, and then fought to keep it hidden in front of everyone. -Consistently told us a million dollars isn't a lot of money. (CONTEXT: Not company money, but personal wealth)
    via u/[deleted]
  • 42
    -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.
    via u/[deleted]
  • 43
    Ciubhran My former boss was a trucker that read Steve Jobs auto-biography and decided he wanted to form an IT company. When the product I built was ready to be sold, we invited some clients to an evening meet 'n greet to show off our product. After the presentation, one of the clients asked what protocol we used for our VPN tunnel... Our boss, not knowing anything about IT, was growing tired of not being able to chime in on any questions, but now he felt this was a question for him!
    via u/Ciubhran
  • 44
    So he quickly raised his voice, with a smile on his face: "We support PDF and Excel!" The room went silent for a good five, ten seconds.
    via u/Ciubhran
  • 45
    o facepizza Do you remember the Christmas episode where they're supposed to do Secret Santa but Michael changes it to White Elephant? And Phyllis knitted that potholder for Michael and he hates it and pretends to brag about the craftsmanship just to get rid of it? That exact thing happened at my office. We had a white elephant party and my boss opened a knitted scarf and gloves that I could tell were homemade. I also knew that there was one woman in our department who knits a lot and ALWAYS brin
    via u/facepizza
  • 46
    Anyhow, apparently my boss wasn't interested in these items, so first he made some backhanded insulting comment about them. But then he took the opposite approach - praising their stylish colors, etc. I looked at the woman who I knew had made the scarf and gloves and could tell her feelings were getting hurt and I just couldn't stand it. When it came to my turn I stole them from him and put them on for the rest of the party. I wish this weren't a true story, but it is.
    via u/facepizza
  • 47
    'When I send him emails, he prints them out and writes his replies on the paper and hands them to me'
    via Olga Serjantu on Unsplash

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