Everyone remembers The Office, and the show’s all-too-relatable characters, especially Michael Scott, the boss everyone loved to hate. Unfortunately, living with such a boss is common, as these Redditors know. Keep reading to hear some workplace stories of people who had to deal with real-life Michael Scott bosses. Sometimes, reality is worse than TV.
1. Playing The Pied Piper
We had mice. Bossman was terrified of mice and a total skinflint who didn’t want to pay for an exterminator. His big idea—I kid you not—was to give me cotton to put in my ears and an air horn. He then opened the back door, closed all other doors in the little shop, and I had to attempt to herd mice out of the store with an air horn, with cotton balls sticking out of my ears.
I wish I was joking.
I tried to explain why it wouldn’t work, but he essentially told me not to worry my pretty little head over it, and that was my entire afternoon. It was the most ridiculous thing I’ve ever done at a job ever before and ever since.
2. He Couldn’t Get His Fax Straight
One time, my boss came to my desk and handed me a piece of paper while saying, “Can you fax this to me”? I said, “You want me to fax the piece of paper that is in your hand to you”?
He replied, “Yeah”. Still confused, I said, “This sheet of paper that you’re holding right now, you want me to fax this to you”? He said, “Uhhh yeah, so I can e-mail it [to] somebody”.
I said, “Ohhhhh, SCAN. You want me to SCAN the paper and send it to you”. He looked at me like I was an idiot and said, “Yes”!
3. Parting Party
It was this guy’s last day with the company, and the managers brought in a cake for everyone to share.
A very nice farewell gesture, except he wasn’t moving to a new city or leaving the company for a new job. He had gotten fired. The managers literally fired this guy, then called everyone into the kitchen and said, “Okay, today is Steve’s last day with the company; let’s have some cake”! Most oblivious, socially awkward, tone-deaf moment imaginable.
4. Stuck With The Bill
After a successful project, the owner of the company invited everyone out to lunch—about 12 employees—at a nearby restaurant by the office. Little did she know the place was very expensive. So she bounced early before the check came, stating that she had a client call.
She gives us money to pay for her meal and takes off, leaving the rest of us to figure out the check. All of us just sat there in shock.
It also turns out she didn’t give us enough money to pay for her portion of the check, so someone had to throw in a few extra bucks to cover that.
5. The Pain Of Mr. Positivity
I 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. Morale was low because we were always buried in work and paid terribly. He’d crack jokes, randomly burst into song, and sneak up behind you to yell, “You’re doing a great job”! But it gets worse.
Unfortunately, he was also super incompetent at his job. He relied heavily on a junior colleague for help with technical stuff—they practically did his whole job for him—and spent days working on paperwork that should really only take an hour or two. If you had a problem, his answer was usually either to stare blankly at you until you left or to say, “Think positive, and it’ll work itself out”!
The thing he did I hated the most was 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 cringy objective statement, he’d guffaw over that too. This was all done loudly, and it was an open office, so you couldn’t avoid hearing it. That definitely lowered morale too.
6. Beamer Bonehead
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—a 128i. No one on my team even knew they made a 1-series, the cheapest possible BMW/badge car.
He got 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”!
He does a little triumphant laughter and starts going 80. But karma got him instantly. There was an officer on the bridge above us. We were immediately pulled over. I will never forget the look of defeat on his face.
7. Flipped Off
We had a particularly demanding client, and a couple of the project managers were having trouble keeping him pleased. After hearing them complain, Larry—the boss—pulled out his flip phone and said, “Let’s call him right now”, and put him on speakerphone. After making a show of being the “tough guy” and putting him in his place, he got in the last word, flipped the phone closed, and put it in his shirt pocket.
He proudly told the room, “You see, that’s how you handle a [jerk]”. But he’d made a hilarious mistake. From his pocket, we heard, “I’m still here, Sir”! Larry fumbled for his phone while stammering, hung it up correctly, and dismissed us.
8. Dodgy Deal
He cooked us lunch. This was at a mattress store. It was meant to be a reward/incentive because he was “a [freakin’] good cook”. He would cook us “the best meal youse have ever eaten”.
He built it up all week. We did not have the facilities for cooking, so he cooked us chicken burgers on a vertical grill. Dodgy, pub-grade chicken burgers that only the dodgiest pub would ever sell as like their Tuesday $5 lunch special.
Later, when he was out of the store—because he was always out of the store—we were out in the back all chatting, and we just sort of looked at each other. I said, “We…we only ate that out of sympathy, right”?
9. What A Kick-Off!
The first morning of the summer camp I worked at, our camp director brought the campers—first through third graders—to the basketball court. He gave a fun speech while bouncing a kickball around to start the camp.
He ended it with, “Alright guys, let’s have a great summer”, and punted the kickball (accidentally) straight into a first grader’s face, who fell to the ground and started crying very loudly.
10. Not Worth The Hype
I had a boss who kept talking about this restaurant.
He was going to take us to this “amazing” place he had discovered. We’re in North Austin, and one day he loads us all in his car and drives us to Lakeway. It took about an hour to drive there from the office to eat at this “amazing” restaurant. The whole time he’s telling us that he’s going to help us order because it’s super trendy, and we wouldn’t understand the menu.
We get to the place—it’s Thundercloud, the local equivalent of Subway. I straight-up thought he was joking, but no. Not only that, but there is a Thundercloud location less than a mile from the office.
He was so crestfallen when we weren’t totally impressed by his amazing trendy sandwich place. If he was a nice guy, we totally would have pretended it was awesome to spare his feelings, but he wasn’t.
He was a holy terror of a human being.
11. Begging For Radio Silence
I worked for a radio station once, and we were hiring a new employee to do sales. Pretty much all of the afternoon, we were supposed to do job interviews to find a new salesperson.
I was the sales manager and in the interviews with me was the general manager. He was this big giant man—huge—sweaty—sloppy—super weird—and uncouth.
I had gone over all the interview rules with him before, like stop asking how old people are—it’s not allowed. He was doing better, and then all of a sudden, this particular afternoon, he just went “forget it all”. He asked a lady if she was married, how long she was married for, and if they had kids or if they were “Trying, heh, heh”.
He asked a guy which branch of the service he was in and why he rented an apartment, “Why are you poor or something”? When he asked a lady if she was a lesbian, I just sat there aghast.
It was one of the most uncomfortable Michael Scott-ish moments I have ever been a part of in my life.
12. The CEO Was N-U-T-S
We had an all-hands meeting where the CEO of a small company—50-ish employees—announced that he had just fired the CFO for “embezzlement”. We all knew he was full of beans, and he fired the CFO because she disagreed with a decision.
Anyhow, right after he announced this, he offered $100 as a “morale booster” to anyone who could sing the entire Tigger song from Winnie the Pooh.
So, one brave girl gets up and starts singing the whole song.
She gets to the last line and messes up one word. The CEO says that it doesn’t count, pockets his own $100 bill, then proceeds to sing—and dance to—the whole song while we stand there—watching him—mouths agape. When he finishes striking a maniacal pose with, “…And I’m the only ONE”, we are all eerily silent.
It was physical painful.
He then straightens up, unbuttons his suit jacket, and shows us the lyrics to the song have been embroidered on the inner lining. I’m 40 years old and have been working as a professional for 22 years.
I’ve seen some stuff, but I’ve never seen anything remotely as crazy as this, and I pray that I never do again. He’d also come in while we were trying to work and challenge us to plank and squat contests.
No one ever took him up on the offer, but he’d still plank and squat just the same. Hard to focus on coding when the guy who signs your paycheck is three feet away from you, covered in sweat, grunting, and groaning like he’s in labor.
After firing the CFO, he took it upon himself to handle all hirings and firings. We found out that this usually meant that he would Facebook creep the candidates and only bring in women of a certain “caliber”.
He rarely hired men unless they were on the development team, like me.
He was very into cycling and would often wear only his cycling outfit the entire day. Coupled with his lack of understanding of personal space, this resulted in highly awkward situations. We once walked past his office when he was conducting one of his “hot girl” interviews, only to see him on the ground, doing push-ups in front of her.
He highly encouraged us to join the gym, offering to let us wear our workout clothing if we exercised at lunch, but then he would give us men a hard time about it. It was clear he only had the policy to see the girls wear skimpy clothes, which they never did.
He would bring in a masseuse every few weeks. It was a male masseuse, so typically only women would sign up for it.
Once, a female colleague canceled and offered her spot to me instead.
When I got to the conference room that doubled as the massage parlor/changing area, I noticed that there was an active webcam hidden in a plant. The dude was a major perv. At first, he was kind of entertaining, but the dude was just noticeably off his nut.
13. This Boss Was The King Of Cringe
I had a Michael Scott boss; 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 bombed the [heck] out of you, huh”? Another time, he got on the intercom and interrupted everyone by yelling for someone to bring him the football team’s schedule.
I have a video of him telling a really cringy joke during a sales meeting.
You could see at least one person covering their face in embarrassment. Once, he told me to call his assistant and have her bring him a bag of coffee and his 5 lb dumbbell. He was mysteriously gone for three weeks and came back with a beard; he had a “secret” facelift.
I found a box of pictures from the 70s with an exotic dancer giving him a lap dance.
It took place in the conference room—same furniture. One time, I watched his business partner go down the buffet line, tasting everything with the same fork. At the end of the line, he stuck his used fork into the cake.
I wanted to be sick. I haven’t eaten at a work buffet since.
One time he got new patio furniture and sent the guys from the shipping department to put it together at his house; orders did not go out that day.
He also had a huge closet where he’d hoard random stuff. He was a total pack rat, and his wife didn’t let him keep junk at home. I was looking for something one day and found a box labeled “watches with dead batteries”. He saved an entire box of watches that he knew didn’t work and also knew how to fix them, but instead, he just kept them in a box.
14. He Was Beyond Words
For a solid three months last winter, every time a female in the office would wear boots, he would say that they reminded him of Gestapo boots.
He would then march in a circle around the office with a Gestapo salute, high step, and screaming gibberish. This was typically followed by him giggling, thinking he was funny, while everyone in the office would cringe and/or try to ignore him.
Then, we were very close to getting a very big client in an Asian country. We ended up losing the client because he did his Asian impression—very similar to Michael Scott’s “Ping”—to the guy over the phone without realizing that the guy was Asian himself. There was also a very large list of words that he always mispronounced.
We actually have a notebook where we record his pronunciation of these words as well as a variety of super weird “isms” that he likes to use.
15. A Malicious Michael Scott
She told me I could take a day off when I was dealing with some severe insomnia problems, then came running into my office five minutes later to say too many people had the day off already.
It was two people whose jobs didn’t overlap with mine. It turns out it was because she wanted to take a half day and didn’t want the place to look unstaffed. However, she took the day off when multiple other people were out and left us with just two people out of six.
She has also brought her soymilk maker into the office and kept talking about it. She used the lunch room toaster oven to make cakes, but not for us. She also just last week started telling people all about her UTI, in particular in front of the brand new employee, who was, at that moment, being introduced to her.
She would buy food for her daughters using the company credit card when she was supposed to be out shopping for things for the company.
She asked a co-worker to try not to schedule her mother’s funeral anywhere within the three-week span that she would be taking her vacation because that wouldn’t be convenient.
She said it somewhat—but not completely—jokingly and brought it up more than once. I could go on. She’s like the more malicious version of Michael Scott you see in the earliest episodes.
16. Derailed Development Day
HR mandated a “personal development” course. They did them every year, and they always centered around not discriminating in some way based on gender, age, religion, etc. Well, one year, they had a new lady in charge of it.
The topic was “invisible” disabilities. Basically, some form of disability that is not visually apparent—OCD, ADD, developmental disorders, etc.
The task we had was to write down a list of “challenges” a person with the disability might face in everyday life.
Then we had to act out a scene showing how these challenges would affect them. We asked her to clarify, and it became apparent she was literally asking us to stereotype disabled people and basically mock their daily lives.
That HR lady was not present for any of the future rounds of “training”.
17. Do Not Touch The Do-nut!
My co-worker was one of four women working for a 10-person architecture firm that was struggling. Everyone was called in for an early meeting before work, and when they all showed up, there were a ton of cakes and coffee, and donuts.
Their boss instructed them not to touch any of it and that he needed to have some brief one-on-one meetings first.
He calls in one woman. Five minutes later, she comes out with a look of disbelief.
Then the same thing happened to my co-worker. The whole firing of all the women isn’t necessarily a Michael Scott thing.
However, the fact that the boss of a struggling company bought a massive spread, laid it all out, and told nobody to touch anything, then immediately fired four employees feels tone-deaf in a very Michael Scott way.
18. The Redecorating Rambler
She would do almost no work at all. She would come into our offices and bother us while we were working, talking about how bored she was and how we should redecorate our offices.
For any work she got, she would just forward the emails to someone and never even read them herself. Then she would often decide how we needed to change the furniture in her office, move things around, and paint a wall in her office.
She would call meetings three times a day to talk about nonsense, and they would go on for about an hour each time on nothing.
19. Mooching Manager
I organized a meal for my team on a holiday, and each member pitched in $10 for a total of $50.
I, being their supervisor/leader, pitched in another $50 for a total of $100. My wife and I prepared the meal—BBQ ribs, corn on the cob, and a salad. It was a lot of food for a small team.
The boss was informed of the plans with plenty of time. He had confirmed participation and even told me he’d help out with the cost. He showed up, ate, took some home, and never pitched in.
20. Knowledge Is Everything
My boss is certainly Michael Scott-esque. When I first started, I was essentially Pam since I was both receptionist and his assistant to some extent. My favorite story was back when we were prepping for a conference.
For some context, he’s terrible with the English language in general and will mangle phrases and descriptions to no end.
So on a group call, he kept talking about wanting a “golden hamster ball” to do giveaways with. He was raving about how great it would be spinning around while people walked by.
All the while, everyone on the call was just sitting in confused silence. However, by that point, I had become so good at decoding his nonsense that I knew he was referring to a gold raffle cage.
I sent him an image privately, asking if it was 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. He 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 and forgot one.
He told me later it was “knowledge”.
21. No Respect For The Deceased
I came in on a typical Monday morning and found out my co-worker, Chris, was out because his father had passed away over the weekend. My boss came up to me and asked, “Did you get that contract from Chris”?
I told him that I had not. My boss paused and then looked at my office phone. Before I could tell him not to, he picked up the phone and called him.
He then put it on speakerphone and proceeded to ask him a bunch of questions that could have waited.
Chris dutifully answered everything my boss needed to know, but you could hear the “this is the last thing I should have to deal with right now” in his voice. It was then that I decided I needed to find another job.
22. Pat, The Unprofessional Pain
I work with a guy named Pat. He was actually assigned to my engineering team until a few months ago. Pat is a pain in the neck. If you ask him to solve a complex problem, he’ll make an exhaustively detailed plan that is tens of pages long, outlining the entire problem space, detailing possible solutions, etc.
Then, he will execute that plan and solve the problem.
But if you ask him to do something simple that should only take a couple of hours, he’ll take the exact same approach. He only knows how to make things complicated, then solve them.
He’s also arrogant and not shy to tell people when he thinks they are stupid. In fact, he did so on a video call with some colleagues at another site.
When I immediately stopped him and told him to either talk to people like a professional or leave the room.
He told me that I was full of it and stormed out. Then, Pat went back to his desk and typed out a very long letter to our boss and the VP of our company, accusing me of being a “world-class idiot” and a liar.
Fortunately, I had witnesses on the other end of the call who supported my simple writeup saying that Pat had lost his temper and couldn’t act professionally.
My boss, who is named Michael, didn’t want to fire Pat even though the VP said, “Fire him” because he didn’t “want to hurt Pat’s feelings”.
What about my feelings and the feelings of everyone else who works in this office and our partner sites?
23. No Brains And No Brawn
We started a startup a few years ago with an idea and found a few investors, one of which was the rich father of the guy who I went to school with and graduated with.
Obviously, he became our “VP” because of his dad and also because, according to himself, “He cannot work in a company unless he is in charge, and he cannot take orders from a boss”.
At that time, I did not watch The Office, but when I watched it for the first time, I was surprised at how Michael Scott resembled him. One morning I was in his office when one of the employees—five employees total—got to the office late, maybe at 9:45 or something.
As she walked in, he asked her why she was late, and she replied with some excuse and walked away.
He turned to me and said, “Did you see that? She thinks that she is smarter than me.
Someone needs to tell her that if she was smarter than me, SHE would be running this company, not me”. I just sat there in awkward silence.
Then, he arranged office soccer with a bunch of people from school.
During the game, he was totally a Michael Scott. He was out of shape and barely could run and sucked at soccer, but he would yell at employees for not running enough and not passing the ball to him, and he would get really mad if someone used good soccer skills on him.
He would occasionally use the phrase, “Guys, remember, you are very valuable to this company. In this company, I am the brain, and you are the muscles”. One time we were having lunch with other co-workers, and I was having a salad.
He told me, “I have noticed you are having salad every day these days. What’s up”? I replied, “Well, I haven’t been able to go to the gym in the past few weeks, and I have been sitting at my desk all day.
“I gotta watch my calories.
Otherwise, I’ll gain weight”. He said, “You must have some genetic problem. I have never gone to a gym, and I have been sitting all day, every day, at my desk in the past eight years, and I am fine”. I am not a muscular jock or anything, but I regularly exercise, and I am relatively fit.
He, on the other hand, is known for being overweight. Everybody at the table was shocked at this conversation.
24. Inappropriate Ignoramus
One of my co-workers is Black and loves chocolate. He was talking to the boss one day and mentioned something along the lines of wishing he had some chocolate right now.
The boss said, “Who needs that when we got some milk chocolate right here”, referring to my co-worker. Another time, it was the Friday before a long weekend, and I was getting ready to head out.
He comes up to me and asks me what I’m up to. I said not too much, hoping for a relaxing weekend. He then makes a jerking motion with his hands and goes, “Make sure you don’t [do] too much relaxing, eh”? One of my co-workers was having an argument with her boyfriend and was telling me about it.
He walks by and listens in on the conversation and goes, “Uh-oh. I know someone who’s not getting laid tonight”!
We went to a work event, and one of the team-building exercises was that you and your colleagues were stuck on a desert island with specific items, and you had to figure out how to use them to survive together.
At the end of the exercise, when it came time for us to describe our strategies, he referred to one of the groups that had one girl and five guys in it.
He said, “And these guys have one woman and a bunch of dudes…I think we all know what that means”!
He was not a bad guy by any means, and he’s generally fairly nice and considerate, just really tone-deaf and inappropriate sometimes.
25. Singing For Dollars
He offered to give everyone in the office a $100 bill but said the new receptionist had to sing in front of the entire company or nobody would get paid.
She was mortified but complied, and he went around handing out $100 bills. He then told everyone they had to post pictures of the money on Facebook and tell everyone he was the best boss, and he’d check Facebook to make sure they did.
This was one of many awful things he did.
26. Playing The Blame Game
I was assistant manager at a one-hour photo lab. We were next to a strip mall with a sandwich place in it. A Mac Tools guy ate there every day, but his truck didn’t fit in the parking lot, so he would park in the back of ours.
One day, the store manager decided she didn’t like him doing that and made me go to the restaurant to tell him to move his truck while he was eating lunch! I couldn’t believe what I was hearing.
I said no, and she said I’d be fired if I didn’t. So, I went over there and told him the store manager said he needed to move his truck. I told him I was really sorry and I felt horrible.
He said he wanted to talk to her. I really couldn’t wait to see him yell at her. We walked into the lab, and I went back and told her he wanted to have a word.
She told him she never had a problem with it, that I was the one who was mad, and that I was trying to blame it on her.
27. Never A Dull Moment
I worked with a genuine Michael Scott.
He was a nice, well-meaning person who just did some absurd things. We had abduction drills one day, where we learned how to “not be abducted”. To note, this was a regular, boring office in a regular, boring suburb.
There was no reason why abduction would be on anybody’s radar. He and several of the guys would randomly break out into a push-up contest. Again, it was a white-collar office with middle-aged dudes in khakis.
He couldn’t remember the nationality of our Hispanic colleague. He tried to “learn Spanish” to make her feel special when she returned from maternity leave. What he learned was NOT Spanish, and she was from Portugal.
She knew, like, five words of Spanish. Then, he disappeared for four days—no call—no email. He wouldn’t respond to any of our attempts to reach him. We all started to get really scared.
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 lost his phone in a lake. There were many, many moments like these.
He was a great boss and genuinely cared about everyone in the company. There were occasional moments of brilliance where he really got things done, but OMG, so many moments of ridiculousness.
28. The Book Of Moron
I used to work for a Broadway theater producer, and we were in a meeting about the ADA, the act that requires places of business to accommodate the disabled.
Like Michael Scott, our VP had come into his position through no merits of his own and had no idea what he was doing, let alone how to run a meeting. So he starts us off with, “Okay, so we’re going to go around, and I want us all to share if we know someone who’s disabled”.
It was just like when Ed Truck passed, and he was asking people to share stories of loved ones passing. As people are awkwardly sharing, our boss is completely detached from the touchiness of the subject.
Every time someone would talk about their crippled granny or terminally ill cousin, he’s like, “This is good! Really getting the juices flowing here”!
One of the senior managers said, “Well [boss], as you know, my uncle had Parkinson’s”, to which my boss replied, “Oh great!
Was he in a wheelchair”? Then we watch the office industrial the ADA puts out, specifically the scene of wheelchair-bound customers. As it finishes and we’re talking, the next chapter starts up on the projector.
It’s little people. Our boss stopped the meeting and was like, “OOH MIDGETS, WE HAVE TO WATCH”. So then we watched little people. It was not a productive meeting.
29. How Is She Allowed To Act Like That?
I work with handicapped and elderly people.
I am the face-to-face, and my boss is scheduling and programming. She has yelled at stroke victims because she can’t understand them, hung up on elderly persons who can’t understand what she’s saying, and refused access to people who cannot pay full price for the service because she thinks they’re lying.
We are a non-profit and receive multiple donations and bursaries to assist financially needy people.
She asks casual drivers to work for free and won’t fire anyone; just never calls them. She is astonishingly inept and is the first point of contact for anyone using our service. Many people don’t understand it’s not me on the phone, so that’s always fun when she’s been a jerk.
She has a physical handicap herself, so her lack of compassion for the people we assist is really disappointing.
She hung up on a woman who didn’t speak English as her first language because she couldn’t understand her, and the woman was understandably upset. She answers to a board of senior citizens in a small town, and they are all just so impressed by her because she uses a cane.
Hence, they make allowances for completely inappropriate behavior that I would be dismissed for in a heartbeat.
30. Someone 86 This Guy!
All the time, he would claim that the back was Vegas, meaning whatever happened there stayed there.
He used that to justify his incredibly childish behavior, like sleeping on the job, throwing a tantrum when he actually had to work, pawning all his work off onto others, or letting his favorite get out of her duties as well.
He also started leaving early, giving an excuse every time.
However, he eventually stopped giving excuses and would just leave. Then when the branch president came downstairs one day and asked where he was, we all told him.
He called him and made him come back to the office with 45 minutes left in the day. He pouted for weeks after that about how it wasn’t fair that he had to stay late when in fact, he was staying his normal working hours since the branch closed at 5 PM.
31. Where’s The Beef?
A co-worker asked me for some help with a personal errand. It was close to our break time, so we went out and got it done on our breaks. On the way back to the office, we hit the drive-thru, and he bought me lunch.
We get back to the office with our burgers. The boss looks up and goes, “Where’s mine”? We apologize and say we didn’t think to bring one back for her. We then sit at our desks and eat our lunch.
The next day, at around the same time, the boss disappears for a bit. She was about to do the cringiest thing I’ve ever seen. She comes back with a bag from the same fast food place we went to the day before, sits at her desk, and starts eating a burger.
She occasionally yells out, “BOY, OH BOY! THIS IS SUCH A DELICIOUS BURGER! AND I ONLY GOT ONE FOR ME! CUZ WE’RE SELFISH LIKE THAT AROUND HERE, AREN’T WE”? My co-worker just looked at me and said, “Is she seriously having a revenge burger”? Yes, yes, she was.
32. Running Late? Running To Eat!
My boss was really hungry and ordered a pizza moments before a very important video conference call with a client. Instead of waiting to eat the pizza after the meeting, she asked me to pretend that she was “running late for the meeting” while she actually just sat on the opposite side of the table, out of view from the camera, and ate an entire large Domino’s pizza.
By the time she was done, she frantically motioned to me that she had “arrived at the meeting”, and I had to introduce her into the conference call, pretending like I hadn’t just watched her aggressively eat an entire pizza for 30 minutes on the other side of the table.
33. He Didn’t Know His Output From His Input
I was working as a developer and performance engineer, and we had to stress test our software.
This involved running tests that generated result files in a not-very-user-friendly format. So we manually had to go through them, manually compiling the results and then publishing the results on the network. While my boss was on vacation, I took it upon myself to create a piece of software that took the raw performance files as input and generated the final report as HTML.
The team seemed to really like it, and when my boss got back from vacation, he asked what I had been working on, and I told him about the utility. He wasn’t happy that I had “wasted my time on non-performance related things”.
A couple of hours after our little talk, he IM’d me that the utility didn’t work, saying, “It just fails”. It turned out he was feeding it the output HTML files.
34. Not Jivin’ With This Jerk
We had a mandatory staff appreciation day.
We were encouraged to come in on our day off with the promise of getting paid for the party. They talked up how it was a 1970s theme, and it was going to be a lot of fun with games and such.
My boss convinced me to grow out my sideburns and disco it up. For starters, I walked into work, and the idiot 20-somethings I worked with were all dressed as hippies—no disco anything—all hippies.
Then my boss was there—the two of us the only ones looking remotely disco—and he commenced with the festivities. First, we did a PowerPoint presentation.
Then he began karaoke, for which he had pre-selected the songs AND the participants. I wish I was joking. Then, he told us all to line up and collect one ice cream sandwich each and return to work.
Everyone was disappointed that day, and I learned that I was Dwight in that office.
35. Cringy Christmas Caroling
At the office Christmas party of about 100 people, we had a 10-minute video of the management team dressed in Christmas sweaters in front of a winter background, singing songs to the tune of popular Christmas carols.
There were a half dozen songs where the lyrics were some inside joke about the company that very few people outside of them knew; none of them were singers.
It was 10 minutes of uncomfortable chuckles while everyone hoped that this was the last song.
Most of the office gatherings were high on the cringe scale, but this was the peak. Much like Michael, my boss always meant well, but awkward and uncomfortable was his gift. This was all years before The Office. I sometimes thought that some of the office party scenes were sourced from actual events I witnessed.
36. Tater Tot Turmoil
We all went out to eat on company time to celebrate an employee getting a promotion, and we were going to just split the bill. My boss gets the idea that he wants to buy $30 worth of tater tots separately.
He kept going on about how this place had the best tater tots, yadda, yadda. So they barely even get touched because everyone got fries with their lunch, and he is visibly angry.
The check came, and someone started to split it when the boss wasn’t paying attention, and we worked out that everyone owed 21 bucks. When he realized this, he started freaking out and yelling because he was supposed to pay an extra 30 extra bucks, and it was his gift to everyone, and nobody but him should be responsible for the tater tots.
It just kept getting more and more awkward.
All the money was already gathered, though, so we just wanted to pay and leave. He makes everyone take their money back. After all that, he realized he didn’t have enough cash on him, and the place didn’t have an ATM.
So he ends up only paying an extra $11. We have to collect the now $20 back from everyone. We walked out and never spoke of it again.
37. The Big Lie
He told a very large client that we had 200 subject matter experts to assist us in developing the material they contracted for.
There were five of us in the company, two of us straight out of college, and zero subject matter experts. Surprise, surprise, the client wasn’t happy with what we gave them, tried not to pay, and then settled for about 30% of the amount, which happily was enough to make payroll current—it was late—and then I quit.
The same boss also threatened to murder his ex-wife and—unrelated—believe it or not—had armed federal marshals come looking for him on the one day he was having a bender and wasn’t in the office.
38. Playing Politics
In true Michael Scott fashion, my boss, who was the owner of a small business, did the most cringe-worthy but well-intentioned thing when interviewing a candidate for an open position.
“Because of the current political climate”, my boss was worried about hiring a white supremacist or someone who hates all immigrants, etc., so he decided to throw a curveball into the interviewing process to vet out any individuals who might have different political opinions than him.
His “plan” was the most insane thing I’ve ever heard.
He was at the tail end of interviewing this poor, innocent guy just looking for a job when he suddenly said, “Well, it’s been a pleasure meeting you, and I look forward to speaking with you again, but I have to go because I’m gonna be late for this rally”.
The interviewee said, “Oh, really? Okay. What rally are you going to”?
“Oh, I’m just heading over to the white power rally downtown. We’re meeting today to lobby for getting rid of all the foreigners in our city”.
To which the interviewee replied, “Ah. okay. Well, it was nice meeting you”! He didn’t get the job, and my boss still wonders why we’re having such difficulty hiring a replacement.
39. A Deluded Don Draper
I had a boss at a privately-owned marketing firm who was obsessed with Mad Men. She wanted to be the female Don Draper.
She had a business blog and would write extensively about how she was a woman on the rise in a man’s world. The problem was marketing is a fast-changing world, and she was not adapting to the game.
She had terrible management skills and had no idea how to bill for work, but she always maintained that she was the next “big thing” in the business world.
We had maybe three clients. It was still a pretty fun gig because she encouraged us to have a 2 PM happy hour at our desks, and it was my job to surround her blog posts with images of drink glasses and martinis.
She continually asked me to make our work “go viral” and was always really pleased when I said that I did. She had so many delusions of grandeur, it was like watching Threat Level Midnight live every day, but “the business” is still going strong thanks to old family money.
40. He Was The Best And The Worst
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 coworker’s names sort of vaguely sounded like Chewbacca—it didn’t. He used voice-to-text extremely loudly in his office for no reason and to send really personal messages.
He got really excited and wore a specific vest any time we had after-work outings scheduled, shouted the same seven references to old movies and extremely awkward hip-hop song quotes 100 times a day, and insisted on greeting all of our international co-workers very loudly in their “native” language. Meanwhile, they all spoke perfect English.
Of course, then he would look around for approval afterward.
He would fully giggle 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 to 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.
He also came to every community play I did in the four years I worked for him, 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, more helpful, and more supportive. He was, honestly, probably the best boss I’ll ever have.
41. He Was A Total Hack
In 2010, my boss discovered Google Earth.
He spent the better part of a week trying to find a way to incorporate Google Earth into our day-to-day operations even though there was no feasible reason why. Then he kept missing the automated verification call because the number he used on Google went straight to voicemail.
Another time, he discovered hard drive partitions and spent the entire weekend setting up a new drive for every letter of the alphabet. Then Monday rolled around, and no one could find any of their crucial files on the server.
42. He Bucked All Conventions
I was at a convention with my boss, and a well-dressed businesswoman came by our booth to talk about our products and see if they would be a good fit for her store. My boss proceeded to ask her how much she was going to buy before she even learned about the products, and when she could not give him an answer, after his consistent insistence, she walked away.
As she made her way away from our booth, my boss proceeded to yell after her—in a packed convention—that she needed to go get her husband to come back and make a decision for her. I wanted to crawl into a hole.
43. A Star Was Not Born
The boss wrote a screenplay.
He “hired” us—the staff—to be in the “sample tape” that he’d send to “Hollywood”. We refused. He instead acted out scenes on his iPhone on a tripod. He and I then spent an entire 8-hour day taking “headshots” of him, so he could include them in his package to Hollywood because “they won’t even look at your stuff without a headshot”.
He wore a black turtleneck and a man bun. He then penned a letter to a “big Hollywood producer” in which he explained that he was an up-and-coming filmmaker who had experience producing movies—he didn’t—and that because he’d had said experience under his belt, he was hoping to be entered into the Producers Guild of America, because that’s how you “network”.
They declined, and the letter was outstanding.
44. This Cowboy Thought He Was A Ladies Man
My first job out of college was for a Michael Scott-type of guy. For starters, any time he would order lunch for the office, it would be sandwich platters or something for everyone and a salad for the 300+ pound woman in the office.
Also, when hosting any events, he would “strategically” invite only the attractive workers along. He also wore a huge cowboy hat when partying, despite being a city boy.
The couple times I golfed with the guy, he constantly thought the cart girls were falling in love with him, saying things like, “You’d better talk to her next time she’s around. I can’t have my wife finding her number”.
He would get real “urban” with any person of color who was hired or came through the office, both in the way he talked and asking them if they liked Obama or LeBron.
He would hook potential employees by saying the position was for a supervisor or team lead position and then essentially say in the second interview that it was actually a coordinator or telemarketer role.
We were on a work trip, and he talked over and over about this great local bar that he goes to every time he’s in the city.
It ended up being Howl at the Moon.
He had friends back home who told him to go there this particular year due solely to there being a hot bartender there. She did her thing and flirted with him the first night, and he went back there all three nights we were in town.
On the last night, he invited her to Vegas for his guy’s trip.
He went as far as to buy her ticket on his phone in front of her. He was 52, and she was probably 22.
He went to the bathroom after, and she asked me if he was serious or joking, then wondered how I could work for him. The list could go on and on.
45. Some Overly Personal Moments
My old boss had so very many Michael Scott moments.
There’s the time he grabbed my hand, saw the stamp on the back of it from the club the night before, and lectured me that I shouldn’t be going to clubs. I should be going to either the gym, the grocery store or the laundromat because that’s where I would meet a boyfriend; I was very freshly out of a long-term relationship.
There’s the time he gave me grief for never wearing a dress, which made me a lot like Rosie the Riveter, saying perhaps I’m a lesbian. I’m an upholsterer. All of my work clothes are torn up, and every day, I go home covered in dust and glue.
One time he won $200 on a scratch ticket and, in a fit of giddiness, swept me off my feet and hugged me.
He once said, “I’m not [prejudiced], but I deal with a lot of Kenyans at the flea market, and they’re just the worst”, and “This one guy was asking $50 for this painting, but I Jewed him down to $30”. I come from Jewish heritage, and he knows it.
And then there’s the time his wife made him sell his camper, and he texted me about it all night because he was so sad and didn’t have anyone else to talk to.
46. Don’t Get Me Started Up
At a special meeting designed to teach employees inventory management, the boss made us stand up from our seats, played the song “Start Me Up” by the Rolling Stones, and told us to walk around the table. When the music stopped, we had to sit down in the chair closest to us, just like musical chairs.
He played all 3:33 minutes of the song as we all walked around awkwardly, expecting him to randomly stop the song and not wait for it to finish.
To make it cringier, there was a class clown-type of guy who was walking around the table, except in the opposite direction because he thought it was funny.
And when we all sat down at the end of the song, the boss said, “LOOK UNDER YOUR SEATS”! And the class clown ended up with a gift card, much to the dislike of the boss.
47. The Guffaw That Lasted A Lifetime
I used to work in a computer store. The owner was a good guy, smart and sociable, but from time to time, had a socially handicapped moment. The best one happened when I wasn’t working there, though. A customer came in to buy a computer; they were a little girthy but not obese.
The owner was covering the floor and started to pitch a laptop when he noticed the customer’s belly.
He said, “Oh, you’re having a baby? When is it due? Mind if I feel”? Without waiting for permission, he puts out his hands and starts feeling the customer’s belly, and starts making baby noises. The customer was apparently frozen in shock as one of the salesmen came over to whisper in my boss’s ear, “Um, that’s a guy”.
My boss turned bright red and ran out of the room into his office.
48. He Threw Us A Curveball
We are a medium-sized company in a business that is dominated by two huge companies. We had a meeting where we had to present products to arguably the largest distributor in the world. My boss is at that meeting, as is my co-worker who is presenting.
We were in a big boardroom with major players there, and it was a big deal for us. My boss was on his laptop during the meeting.
Not a huge deal, I guess—but it was way worse than I thought. Mid-sentence, and out of nowhere, my boss kinda yelled, “Yes”! My co-worker stopped and immediately asked, “You have something to say”? In the most friendly way possible, my boss replied, “No, sorry. Manny just slid safely into 3rd”. He was watching the Red Sox game.
49. This Is Not A Drill!
They had a company-wide fire drill where they had all employees vacate the building, which was standard. It got strange as the normal ten-minute disruption turned into an ungodly amount of time in the summer heat.
Emergency services came and went. But it was all a messed-up ruse. Someone walked up with a bullhorn in front of the hundreds of employees and announced, “Layoffs will be happening today”.
“You’re probably wondering what is going to happen to me, which is a great question. You will find out very soon.
Just scan your security card to get back in the building. If your key card won’t validate, then you have been let go, and on the other side of the building, a box will either be waiting for you or is en route with your belongings. The details of your individual termination will be in the box”.
There was no previous warning or discussion with middle managers about who should be let go.
Morale and productivity dropped swiftly as they let go of high performers as well as underperformers in the same fell swoop.
50. Dave The Milk Man
I had a boss, Dave, who was head of sales, and he was notorious for taking people’s food out of the fridge or off their desks to eat right in front of them.
He was also always late for meetings. Well, one day, we were sitting in an all-managers meeting, and Dave came in late as usual with his always-present cup of coffee and sat down.
There was a small lull in the meeting, and Dave looked across the table at Katy, who just had a baby, and said, “Katy, I hope you don’t mind, but I used the rest of your milk in the fridge”.
Katy turned pale and looked at him with the most embarrassed and angry look: “That’s my milk I have been pumping for my baby”. Dave just sat there, looked her square in the eye, and without breaking his gaze, sipped his coffee the rest of the meeting.