‘He asked me how much I weighed during my interview’: Employees Share Most Entertaining Boss Stories

Author image for Eleonora Bader
Eleonora Bader
Apr 9, 2024 12:00 PM EDT

The clock strikes 5, and you zoom out of the office. You don't even look back when your boss yells out sheepishly, 'Wait, are you leaving?'.

Yes, you're leaving! Right this instant, actually. Every day in the office feels like stepping into a weird, alternate dimension. The fluorescent lights flicker ominously as you shuffle past coworkers, half expecting your awkward boss to greet you dressed in royal garments. He is quite the character. Some might compare him to Michael Scott from the Office.

Your typical workday begins with a strong dose of coffee, necessary to brace yourself for whatever oddities lie ahead. Once settled at your desk, you can hear the faint strains of accordion music drifting from your boss's office. Who knows why? You have long since given up trying to decipher his eccentricities.

You aren't alone… many people have weird bosses. Scroll down for a hilarious thread about the most entertaining boss stories by employees who could barely stand to handle them. Then check out this thread about employees quitting on their first day.

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  • 01
    Employees Share Most Entertaining Stories About Bosses
    via Canva
  • 02
    Do bosses like Michael Scott actually exist? And if you work/ed for one, what's your craziest story?
    via u/u/Supersmaaashley
  • 03
    outofprintluv⚫ My boss is certainly Michael Scott-esque. When I first started I was essentially Pam as well since I was both receptionist and his assistant to some extent. My favorite story was back when we were prepping for a conference. Some context, he's terrible with the English language in general and will mangle phrases and descriptions to no end (how the turn tables...). So on a group call he kept talking about wanting a "golden hamster ball" to do giveaways with. Was raving about how gre
    via u/outofprintluv
  • 04
    nonsense that I knew he was referring to a gold raffle cage and sent him image privately asking if it's what he was thinking. To this day he still talks about the fact I can read his mind and must be psychic. And he still refers to it as a hamster ball. All in all he's a pretty nice guy and a solid boss. Hired me based on a gut feeling and has been decent to me ever since. I think I knew it would be a good fit when during the interview he tried to tell me about the four pillars of the company an
    via u/outofprintluv
  • 05
    LemonsofLifee ⚫ 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. EDIT: wow this blew up, rather than replying to each of you I'll say it here -no I did not find a pomegranate, and when I came back he was eating subway and he seemed to have forgot he'd even sent me. -maybe I could have gone
    via u/LemonsofLifee
  • 06
    [deleted]. 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. 5.3k Share
    via u/deleted
  • 07
    happydactyl31 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 a
    via u/happydactyl31
  • 08
    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 k
    via u/happydactyl31
  • 09
    startinearly 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 c_p?!?!" - "Uh, you did". "Oh. Well somebody needs to throw it away!" Constant stuff like this. 2.0k Share ..
    via u/startinearly
  • 10
    harperv215 I had a boss that used to watch me through a gap in the glass partition between our desks. She wanted to see if I was paying attention during meetings. One day, I put a large folder to cover the gap and she freaked. I still laugh when I think about it. 17.1k Share darkbro66 This sounds way more like Dwight but still hilarious 7.8k Share
    via u/harperv215, u/darkbro66
  • 11
    [deleted] Never have worked for one myself, but my dad told me a story about his boss who was giving out awards to everyone in honor of how long they've worked there, and he would give speeches for each person. A woman employee received her award and he gave a speech about the story of how she came to work there. And he said, "At first I didn't want to hire her because she was so hot.' My dad's not working there anymore, but I love that story because I will never not picture Michael Scott giving
    via u/deleted
  • 12
    holmen-2001. My 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. 13.3k Share lvmcson. ??? Was he referring to your new spouse?? 5.1k Share
    via u/holmen-2001, u/lvmcson
  • 13
    lala 710. 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.. 21.6k Share
    via u/lala710
  • 14
    Two_for_joy I had one and these are just a few quick stories • he asked me how much I weighed during my interview • one time he was considering selling the company to a Japanese company and while walking them around the building he was heard saying 'we really bc ed the hell out of you, huh?' • he got on the intercom and interrupted everyone by yelling for someone to bring him the football team's schedule • I have video of him telling a really cringy joke during a sales meeting. You could see at
    via u/Two_for_joy
  • 15
    • one time he told me to call his assistant and have her bring him a bag of coffee and his 5lb dumbbell • he had a 'secret' facelift. He was mysteriously gone for 3 weeks and came back with a beard. • I ended up with a box of pictures from the 70s with an exotic dancer giving him a I dance. In the conference room. Same furniture. • One time I watched his business partner go down the pot luck line, tasting everything with the same fork. At the end of the line, he stuck his used fork into the cake
    via u/Two_for_joy
  • 16
    [deleted] 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 ck. 8.3k Share
    via u/deleted
  • 17
    paulfromatlanta. Long ago, my 80 year old boss pulled me into his office B: "Paul, I've noticed that your shirts come untucked and that looks unprofessional" Me: I'm sorry about that Joel B: I want you to start tucking your shirts into your underwear Me: Uhhh... B: Go ahead and and try it now. Me: Joel, you know I have 15 women who report to me - I can't un-do my pants in the office. B: Sure you can. Drops pants. He is 80 and wearing Spiderman underoos...
    via u/paulfromatlanta
  • 18
    [deleted] 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 15.8k Share lala 710 To be fair to your boss, is falling asleep at work common? 8.1k Share
    via u/deleted, u/lala710
  • 19
    [deleted] ⚫ Had a manager at my previous job that really, really tried his best to be everyone's BFF. He loved giving pep talks and thought he could raise our abysmal morale by being Mr. Positivity (note: morale was low because we were always buried in work and paid s). He'd crack jokes, randomly burst into song and sneak up behind you to yell "you're doing a great job!" Unfortunately, he was also super incompetent at his job. He relied heavily on a junior colleague for help with technical stuff
    via u/deleted
  • 20
    Thing he did I hated the most: whenever people would apply to work at the company, he'd print out the stack of resumes, sit at his desk and read aloud all of the parts he found "funny." He'd laugh at people for working at McDonald's or other fast food places. He loved finding grammar mistakes and making fun of them. If someone had a cringe-y objective statement, he'd guffaw over that too. This was all done loudly, and it was a open office so you couldn't avoid hearing it. That definitely lowered
    via u/deleted
  • 21
    homeschoolpromqueen Worked with a genuine Michael Scott: i.e. a nice, well-meaning person who just did some absurd things. We had kid. 'not be kid ping drills one day, where we learned how to ped'. Notably, this was a regular, boring office in >ing would be a regular, boring suburb. No reason why kic on anybody's radar... He and several of the guys randomly broke out into a push-up contest. Again. White collar office. Middle-aged dudes in khakis.
    via u/homeschoolpromqueen
  • 22
    Couldn't remember the nationality of our Hispanic colleague. Tried to "learn Spanish" to make her feel special when she returned from maternity leave. (1) What he learned was NOT Spanish, and (2) she was from Portugal. She knew like, five words of Spanish. Disappeared for four days. No call. No email. Wouldn't respond to any of our attempts to reach him. Finally, someone drove out to his house to make sure he was alive. He was. He'd just forgotten to tell us he was taking the week off, and then
    via u/homeschoolpromqueen
  • 23
    BigShoots 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?" 36.1k Share
    via u/BigShoots
  • 24
    jamminatorr Mine had aspects of Michael Scott but the ones that are sad and pathetic and not funny. A couple examples: • he called an all staff meeting to announce his divorce. He then instructed our receptionist to lie to his soon to be ex wife and deny he was in the office, all the time. • he was just so, so incompetent at his job. If a task was too big or complicated he would just .... Not do it. Wouldn't ask for help or anything, he'd just move on and leave whatever issue to fester. I would
    via u/jamminatorr
  • 25
    • when he was terminated he kept the corporate laptop and cell phone. After several strongly worded letters requesting their return, he drove back to the office, parked on the edge of the road (think busy rural highway) and made his teenage son carry it all across the yard and parking lot to deliver them I was eventually tasked by the big bosses to coordinate his termination. They then gave me his job plus my previous one. I can do both within a 40 hr week no problem. 1.4k Share
    via u/jamminatorr
  • 26
    No_Higgins Yes. They are everywhere. I've had a few. One would only approve your days off if you played into her ego. Her boring stories had to be the most fascinating thing you had ever heard. She would come into the office and spin around in a new outfit and we had to pretend it was amazing. I had to work every weekend for months until I started playing along. 2.8k Share
    via u/No_Higgins

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