He Was So Inappropriate, Even Though He Usually Meant Well
“This was at a previous job. 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. My boss replied, ‘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. My boss came up to me and asked me what I’m up to. I said not too much, hoping for a relaxing weekend. He then made a jerking off motion with his hands and went, ‘Make sure you don’t too much relaxing, eh?’
One of my co-workers was having a fight with her boyfriend and was telling me about it. My boss walked by and listened in on the conversation and went, ‘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 are stuck on a desert island with specific items and you have 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 and said, ‘These guys have one woman and a bunch of dudes…I think we all know what that means!’
He was a character. Usually well-intentioned, but really tone-deaf and inappropriate sometimes. “
The Cruel Way They Handled Layoffs
“They had a company-wide fire drill where they had all employees vacate the building. Standard procedure.
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.
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. On the other side of the building, a box will either be waiting for you or is in 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 underperforms in the same foul swoop.”
They Should Have Called HR A Long Time Ago
“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, 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).
How about the time he won $200 on a scratch ticket and in a fit of giddiness swept me off my feet and hugged me.
One time he said, ‘I’m not rude, but I deal with a lot of Kenyans at the flea market and they’re just the worst.’
Another time he said, ‘…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. This one was tough because he really did mean well and was genuinely sad, but…geez.”
She Figured Her Relationship Exempted Her From Criticism
“My boss was married to a black man, so maybe she thought she could get away with saying some of the things she said.
One day we were in a meeting (I was the assistant and had to do all the typing) and I misspelled the word forty as ‘fourty.’ My boss looks at it and says something along the lines of, ‘You spelled it like fowty, you know like the drink fowty.’
Being polite, I was like, ‘Yeah, haha,’ not thinking much of it.
She then said, ‘Yeah, he gets it, he’s been hanging out with da brudahs.’
We were the HR department.”
This Probably Wasn’t What Corporate Had In Mind For The HR Presentation
“Someone from corporate came in to teach us about harassment. 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.”
It’s Difficult To Understand How Anyone Could Work For Him
“My first job out of college was for a Michael Scott type of guy. For starters, any time he would order lunch in 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 only ‘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 black person that was hired or came through the office, both in the way he talked and asking 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 that 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. The last night he invited her to Vegas for his guys trip. He went as far as to buy her ticket on his phone in front of her. He was 52 and she 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.”
“It Was Like Watching A Car Crash In Slow Motion”
“I worked a very corporate job at a branch of a big corporation. One February morning, we had a branch-wide meeting. All 45 people crammed into a conference room so the branch manager could talk to us about what just came down from corporate.
The topic was ‘Celebrating Diversity.’ Instead of quickly going through the Powerpoint that corporate provided, he decided to ‘wing it.’
He told all the white people in the room to find someone a ‘few shades darker’ and to ask them about their culture. He said, ‘It’s easy- just do like me: Hey Dwayne what’s your culture like? What do your people like to do?’
It was like watching a car crash in slow motion.”
His “Urban” Relations Could Stand Improvement
“I had a job selling furniture. My boss was a tall lanky character. He was a white guy that had a head for sales but had some real disconnects when it came to other cultures. The conversation began when he walked up to a group of us and looked at the big black guy (named Rory) in the group and went, ‘You know, I’ve been taking some online college classes and one of the electives I’m taking is urban American culture.’ By his description, it was a study of how black culture developed from the slaves to the diverse group we have now. Rory rolled his eyes and I could tell he was peeved (my manager had a bad habit of laying the bullcrap on extra thick).
I looked at Rory and said, ‘Come on man, let go move some tables.’
My manager said, ‘What’s that about Aesop’s Fables?’
Before I could get out what I actually said, Rory said, with a confused look on his face, ‘What are those?’
I quickly tried to explain that they were short stories with a moral tied into them mainly for kids but as I was getting this out, my manager went on this full lesson about what they are. ‘Picture this Rory. A dog is waking in the forest with a big bone in his mouth. He goes to a lake with a massive bridge across it. As he’s crossing the bridge, he notices another dog below him with a bone in his mouth. He really wanted that bone too. When he stopped, the other dog stopped. He looked down over the side of the bridge and the other dog looked back at him. At that point, he attempted to scare the other dog away to get his bone – he barked! But in the process, he lost his own bone and realized the other dog was just a reflection. That’s why you must always be thankful for what you have and not to be jealous of others.’
Rory had zoned out at this point. The poor guy was so confused on how we got from moving tables to this long story so he just looked at my manager and went… ‘What?!’
It was at this point that my manager said something I’ll never forget: ‘Ah, I see you don’t understand but thanks to my studies, I’ll put it in a way you can understand: Picture this – Little Ray Ray is walking down the streets of the New York with his favorite chicken wing in his hand…’
My eyes got huge and I clapped my hands and said, ‘Woah! Good story but we have to work. Come on Rory!’ As I’m pulling Rory away from the conversation, my manager went, ‘Wait, what are you doing?’
To which I replied, ‘Saving your job. Don’t go there, sir.’ And then continued to walk Rory to the opposite side of the store.”
This Obnoxious Boss Finally Got Served Some Karmic Justice
“I use to work for this real peach of a man. And by peach, I mean pervy geriatric. Not only was he constantly doling out uncomfortable shoulder massages to all of our female temps but his voice was like the embodiment of a dolphin from New England getting punched in the nuts. Anyway, the whole office kind of took him as a joke because he thought he was a hot shot, but in reality, he was hardly capable of doing anything substantial. He always talked down to his employees even though we did 90% of his job for him.
So, one day our company issued new phones to all of the full-time employees. My boss was freaking elated. He’d come in early that day just to be the first to activate the new phone he’d been on the committee to pick out. He was already bragging about all the differences in this phone compared to the old ones and how he’d been the one to push for this model for its durability. The more he talked, the more I could see the people in the office wanting to simply mess with him. My other boss finally got fed up listening to his nasally accent and said, ‘Okay, if it’s so great why don’t we go drop it off the porch outside.’
My boss immediately backpedaled, ‘Well, it’s durable but I shouldn’t try to damage it.’ But the whole office kept pushing him, saying stuff that would really get under his skin because it was so easy to do. He started turning red in the face and sputtering over his words calling us all pricks – the works.
Eventually, he caved and we all followed him out to the porch. Now is probably a good time to mention we work in labor and our office is surrounded by semi trucks and other equipment. He held the phone out over the railing and dropped it. We were all hoping it would break or something. But it landed safely after its 6ft drop. We were all standing there, kind of disappointed and my boss was feeling as smug as ever. He turned around and started to lecture us. ‘This is what you get for being children. I was right the whole time and you all owe me an apology.’
He took a step to go retrieve his phone and just as we were all starting to disband, a forklift RUSHED by and ran over his brand new phone. He just lost it! He stumbled over his words, ‘Look what you guys made me do!’ My whole department just started cracking up. All of us were dying of laughter at my boss’s stupidity. He was red in the face with his smashed phone in his hands. He was running after the driver like they were going to stop.
It was glorious.”
He Thought He Was Funny, While Everyone Else Tried To Ignore Him
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 ‘Hitler boots.’ He would then march in a circle around the office with a Nazi salute, high step, and screaming jibberish. This was typically followed by him giggling, thinking he was funny while everyone in the office would cringe and/or try to ignore him.
We were very close to getting a very big client in an Asian country. We ended up losing the client because he did his problematic Asian impression (very similar to Michael Scott’s ‘Ping’) to the guy over the phone without realizing that the guy was Asian himself.
There is a very large list of words that he always mispronounces. We actually have a notebook where we record his pronunciation of these words as well as a variety of super weird (boss’s name)-isms that he likes to use.”
Jobs With Bosses Like This Aren’t Worth Sticking Around For
“We were having 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 it 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. Yeah. So, one brave girl got up and started singing the whole song. She got to the last line and messed up one word. The CEO said that it doesn’t count, pockets his own $100 bill, then proceeded to sing (and dance to) the whole song while we stood there, watching him, mouths agape. When he finished, striking a maniacal pose with, ‘…and I’m the only ONE,’ we were all eerily silent. He then straightened up, unbuttoned his suit jacket, and showed us the lyrics to the song had 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.
Some other crazy things he did were:
He’d come in while we were trying to work and challenge us to planking and squatting contests. No one ever took him up on the offer, but he’d still plank and squat just the same. It’s 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 dev 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.
When I first started working, he was kind of entertaining, just noticeably off his nut. But usually, he’d make up for his crazy behavior by doing nice things. After he fired the CFO, he – as well as the company, itself – started getting really unstable. I discovered that the company had a huge software licensing issue and when I let him know, he publicly humiliated me. Full-on screaming at me, talking baby talk, scolding me like a bad dog. All this right in front of all of my colleagues. I should note that I did not approach him to discuss the licensing problems in front of everyone. He asked me what I was working on as I was writing up the report. I tried to be discrete about it, but he kept probing until I had no choice but to tell him everything I’d discovered.
I started looking for a new job right away. From what I understand, things got much worse after I left.”
He Set The Gold Standard For All Workplace Fumbles
“I used to work in a computer store, the owner is a good guy, smart and sociable, but from time to time has 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 little girthy, but not obese. The owner was covering the floor and started to pitch a laptop when he notices the customer’s belly. ‘Oh, you’re having a baby? When is it due? Mind if I feel?’ Without waiting for permission, he put out his hands and started feeling the customer’s belly and started making baby noises. The customer was apparently frozen in shock as one of the salesmen quickly came over to whisper in my boss’s ear, ‘Um, that’s a guy.’
The boss turned bright red and ran out of the room into his office.
Now, this became the legend of the workplace, the gold standard fumble that all fumbles would be compared against. If you messed up, it didn’t matter because it wasn’t as bad as the time the boss thought a male customer was a pregnant lady. Even his wife would come in and get digs on him for it.”
Everything He Does Is Cringy
“My boss is so weird.
He regularly asks me and my coworkers to set him up on dates. He holds ‘meetings’ and by meetings, it’s him going through his OkCupid and Tinder profiles so we can help ‘judge’ the girls.
If he’s on the phone with someone and doesn’t wish to continue the conversation, he will make a weird comment like, ‘I gotta go, but let’s talk later when you’re in my basement after I kidnap you.’
If you’re eating lunch, he’ll stand behind you and stare at your food until you offer him some, which he will then reach onto your plate and start touching all your food to find the ‘perfect fry.’
He will answer any and all questions in an Arnold Schwarzenegger impression.
One time my boss and I attended the same wedding and were placed at the same table. He told me not to think of him as my boss, but as my ‘party buddy.’ He also said he just wants us to, and I’m quoting directly, ‘Let loose, maybe get wasted, dance, heck, we could even shoot up dope together!’
There are a thousand more things he does that are so cringy and I could go on and on.”
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