30 Redditors Share Their Real Horrible Boss Stories

By Sana Ahmad - December 11, 2019

It is a given that we all want an employee friendly work space and an amazing work culture, isn’t it? Having said that, all of us would agree that one of the most important requirement for the above is to have an understanding and motivating supervisor, boss or manager. It is next level amazing when your boss is not only the one who you report to and take orders from but also that person who acts as your mentor and a friend, who has your back, guides you in the right direction, wants you to move up the work hierarchy ladder and genuinely cares about you!!

While many are lucky enough to actually get a gem of a boss, some of us are just not (and what option do you have but to deal with it at least until you give up and QUIT)… Well, they do say, life is a roller coaster ride and you can’t have it all!! So!!

From instances of the supervisor or manager being a creep, or where they orchestrated power plays, to those where he/she was outright incompetent and just not fit for the part, the list is quite long. Read on to find out ‘the horrible boss’ experiences shared by some of our Redditors…

The One Who Refused To Sanction Leave For Visiting Dying Grandma

Credits: Quickmeme

“I had a boss who refused to let me take an “unplanned vacation” to see my grandma on her deathbed. I quit on the spot.

It was strange because up until that incident, she was really cool and laid back. But when I asked for the weekend off to go visit my dying grandmother, she snapped and lectured me about how I needed to “plan” my “vacation” better.” (ostentia)

Professor Who Never Accepted Late Assignments

Credits: Makeameme

“I had a professor in my last semester who didn’t do makeups, redo’s or take late assignments for ANY reason. Literally any. Toward the end of the year there was a guy who had been in the hospital for a lot of the semester, with notes and all that jazz, who had otherwise carried perfect grades the rest of his time in school (so he said, didn’t know the guy, just overheard this conversation with the prof). The prof said “I told you in the beginning, and I wrote in big bold letters in the syllabus, NO LATE ASSIGNMENTS FOR ANY REASON”. Ironically, if you attended and turned in stuff on time, he was also one of the easiest graders I’ve taken as well. Big classes, he just didn’t give a crap.

Extra info: Dude ran a million dollar business and wasn’t teaching for the money, so he’s a great business person and extremely knowledgeable, but a total Satan when on his wrong side.” (titanicpuppies)

District Manager Who Fired Without A Cause

Credits: Imgflip

“Long, long ago, I was fired from my job as an assistant manager at a convenience store by the district manager who hated me. I applied for unemployment insurance, and the company said I wasn’t eligible, because I’d been fired for cause. (I wasn’t, but that was a matter the review board had to decide.) We showed up for the review, and I was prepared to explain how my direct boss had decided to leave keys to the inner safe in the outer safe area overnight, which had resulted in more than $100 going missing, which was the reason they gave ME for firing me. Mind you, this wasn’t even my error, but I was the person on duty when it was discovered. Instead, the district manager tried to say I falsified paperwork. Uh…okay. I settled in to hear her tale of woe. Then she proceeded to show how I’d “padded paperwork” to hide missing money. Uh…no. I showed them that my manager had accidentally put $50 extra into the bank the week before the incident they fired me for, so I made a note of that on the paperwork for the day she made the error and then made a note of it on the day I was doing paperwork for, the day that showed the $50 missing. The panel of reviewers asked my district manager how I SHOULD have noted it, and she went off into some incomprehensible and highly illegal (did I mention one of my degrees is in Accounting?) way of “subtracting” the amount from the numbers in a way that would under-report income. I got as far as “But that–” when one of the panel members shushed me. They informed her that what she was trying to tell me to do was illegal, and they would be informing the local tax office, in case they wanted to perform an audit on the company, thanks to idiot DM here. Oh, and yes…I was eligible for my unemployment money. Win win win, and the look on the DM’s face? Classic. I wish I had a photograph!” (CaptainOnBoard)

CIO Who Did Not Acknowledge Her Mistake

Credits: Imgflip

“I once worked at a company where the CIO (Chief Information Officer) sideswiped a woman’s car as she pulled into a parking space. The woman who had the car that got hit got out and stood beside her car to see what damage was done.

The CIO got out of her Mercedes and brushed right past the woman without so much as speaking to her. Completely ignored her and walked away. Even with witnesses.

The woman that had her car damaged had to go to the HR department and the company cut her a check for damages (the actual business paid for it – not the CIO, she got away scot free without ever admitting anything or paying anything).” (lets_start_a_cult)

Boss Who Got Fired Because Of Her Behavior

Credits: Imgflip

“I had a boss that absolutely hated me. After realizing she wasn’t qualified for the position and had already slept with two different guys at the company, I came to the conclusion she was a joke and to just be dismissed.

I never paid much attention to her and when she’d show up at my building once every blue moon I kind of just ignored her. I was busy and didn’t have time to play her games.

She wrote me up for being late on three separate occasions. 1 min late, 3 min late and 6 min late. I lived an hour from work and had to deal with traffic, I left my house 2 hours early most days to account for this. But when there’s a wreck, there’s not much you can do as the freeway is backed up and side roads are clogged. Each time I got stuck in traffic I called to let her know.

Still wrote me up in hopes to eventually fire me. So I started leaving the house crazy early, I’d get in super early and leave early. She haaaated it.

Eventually her behavior got her fired and people till this day remember her and laugh at what a horrible person she was. I also had that write up removed from my file as it was recognized that she was treating many of her employees unfairly.” (RedditInBed)

When The Supervisor Made It Awkward

Credits: Quickmeme

“My supervisor at this nonprofit was maybe a couple years older than me, and for the six months I worked there, never bothered to set me up with my own computer. I’d work in the mornings and she tended to show up around lunch time, so she told me I could use hers, which was pretty annoying in and of itself. But more often than not she’d come in about an hour before I was scheduled to leave, and stand over me, eating her lunch, as I worked at her desk. I’d say things like, “Oh I’ll go find somewhere else to work” and she’d say no no you’re fine. And continue to stand over me as I sat at her desk.

She was also the Director of Marketing, and for about two weeks she had me walk around the city and put up flyers in various cafes/buildings for this class we were hosting. Two weeks later she’s frustrated that no one’s signed up. As the Director of Marketing, you should have some sort of better strategy than putting up flyers in coffee shops…” (retrouvailles26)

Vice President Who Acted Like An Angry Teenager

Credits: Makeameme

“The vice president told me I was being disrespectful during a conversation. I asked how and she told me that I “knew what I was doing”. I asked again, stating that I had asked because I didn’t actually know and was told she didn’t have time for me because I “know what you’re doing and I don’t have time for this.”

You’re the vice president, not a 15 year old angry at her boyfriend *edit- Vice president of our company.” (thatskyguy)

Crazy For A Boss

Credits: Quickmeme

“I was fresh out of the military and got a tech sales job. Easy enough work, but finding/screening clients was a pain due to having a semi-strict territory rule.

After 6 months there I managed to turn a 1 off sale into a meeting with the CIO of a Fortune 500 company. My client asked to speak with our CEO just to meet and greet, but would deal with me direct afterwards.

I set the meeting at my CEO’s office to make it convenient for both execs. As soon as it hit the calendar my CEO calls me direct asking me why I was booking him for a meeting (allowed) with an exec (allowed) at a location outside my area (special cases only).

I explained the situation to him and he told me to talk with my manager. In the time it took me to walk down the hall, he canceled the meeting, took the account, scheduled me for remediation, and gave the account to someone with ~1 week on the job and his manager.

The CIO took offense to this and never bought with them (HUGE BUDGET) and it started my process of leaving that company.

Edit: their budget was over 1 month gross revenue for the company.” (Armigedon)


The One Who Was Racist

Credits: Imgflip

“My first boss managed a gas station. He was good in most ways–efficient, fair, disciplined, ran a tight ship. Just one drawback.

He was racist. I don’t mean that he was insufficiently outraged by Dukes of Hazard re-runs. I mean that he used the N-word often and loudly. He resurrected other racist words that would have sent Bull Connor running for a thesaurus.

The truck driver who delivered our tankers of fuel every week was a black man, and they almost came to blows over this.

His comeuppance finally came when the corporate office hired a new third level supervisor who was a young black man out of business school. That boss just could not take orders from a black man.

When he quit, he trashed the office and tore up every floppy (it was the 80’s) disk in the office so we couldn’t do our accounting for a few days.” (gnujack)

Boss Who Hated Children

Credits: Flickr

“I worked at a Boys and Girls Club where the boss HATED children. Hated them. There are too many stories to pick just one here, so I’ll sum her up with a story of how the kids saw her.

I was washing dishes after cooking classes with the same tiny little 7 year old (the smallest, most adorable girl at this place… so sweet with huge eyes that made her look like a Pixar character) when the second-in-command boss walked by and coughed. The little girl looked up at me and said, “He’s sick.” I responded with “I know, isn’t that sad?” To which she replied, with the darkest, most ominous voice I’d ever heard from this angel child, “… I wish Ms. Boss Lady would get sick…” (90_beeetch)

Horrible Experience At Walmart

Credits: Memecreator

“I used to work at Walmart and I had 3 people I had regular contact with that were in a higher position and were technically my boss.

I’ve always said that it was the worst place I’ve ever worked, because of how thoroughly they want to mess up their employees out of what they work for. I was hired as a temporary employee that they said I would be able to become a full-time employee once I got past 6 months.

I worked 3rd shift and spent my entire nights stocking the grocery aisles. It was 10-7am minus a half hour for lunch and 2 unpaid 15 min breaks so I got a 8 hr schedule. Half the time after my shift my supervisor would come to me and go “Hey we don’t have any cart guys scheduled to come in soon, mine going out and getting every cart from the parking lot and bring it up to the return?” Of course I say yes because it’s not really a question so much as a “Do this or do it after an argument.” If you’ve ever seen those lots they aren’t small, and I didn’t get to use the little machine that lets you push 50 carts at a time, I had to settle for 10-20 that threatened to ram any cars parked in my way. Doing this took me about an hour to do.

Then once pay time came around my supervisor would come up and say “Hey I noticed you’re going to be in overtime soon, I need you to take an extra 30 min on your lunch.” or “Hey come in an hour later tonight so you don’t get overtime.” I had to carpool with my mom since we both worked there and she already came at 9 for work. Half the time they’d tell me just to clock in any way and double my lunch again. Even when the store was cleared to pay out overtime my Manager was given actual bonuses that he would get for denying overtime to the employees, even around black Friday and Christmas. We got min. wage and he was a salary position who came in for an hour at the beginning of 1st shift and another at the end of it.

Then finally, around Christmas they had me scheduled off and I had told my supervisors how glad I was because my brother, sister-in-law and niece were in town and we were going to get dinner and see a movie. I didn’t have my phone and the next day when I came to work I got fussed at for not coming in because they decided they needed me to work last minute. (Even when they stated that during holidays they wouldn’t do last minute changes so as not to inconvenience us with our families.)

Oh and once the 6 months were up they laid me off because tax season was coming around and if they kept the temps they would have to pay more. When it was over they offered another temporary position with the “promise” of full time after 6 months.” (tatsuedoa)

When The Executive Board Was Not Nice

Credits: Makeameme

“My story is pretty tame.

I work at a museum. The board president basically  me out on the phone before a big seasonal event, saying that she heard from other people that I was not giving 100% dedication to my job. That I needed to step my game up or face some serious consequences. Everyone was pretty stressed due to the event and I was pretty pissed. I emailed her after the conversation, because it came completely out of left field. I had never had anyone complain about how I did my job. Tourists, the executive director (my direct boss), or even the president and the rest of the executive board. No one had complained before. So I asked her who it was that had a problem.

Turns out, no one had said a word to her about the job I was doing. She hadn’t “heard” from anyone. She just listed a bunch of her own grievances about what I was doing (wearing a costume to work on Halloween, not labeling some artifacts she had brought in that had zero historical value, keeping my bike out of sight in the office, trivial things). I told her that she could just tell me that she was unhappy with these things as they happened, especially seeing as I was never told not to do these things, rather than cuss me out on the phone months later. I lost a lot of respect for her that day, but I was still employed. So I counted my blessings.

Also, I found out that the executive director and the president were paying me $1.25 less than they originally agreed to. When I first got the job two years ago, they gave me a job description with the original pay listed on it. Naively, I didn’t make a copy of it. When I started the job, my paycheck was much less than I thought it would be, and I was given another job description with the lower pay on it. I didn’t make a fuss, because I was hard up for money, and I needed the job. Plus, the museum was kinda doing some shady stuff. Additionally, I was an idiot who had no backbone at the time.

Anyway, something went down earlier this year. My boss and the entire executive board stepped down from their positions, and I found my original job description with the original pay. Needless to say, I’m now getting paid what I was supposed to, plus back pay.

Working here used to be a nightmare. But the new executive board is pretty nice.” (SoulCommodore)

Screaming Lady Becomes The New Supervisor

Credits: Quickmeme

“Several years back I started a new job and was told the office would re-organize in the New Year and my position maybe shuffled to a new work group. A month later we’re busy running a major year-end event and things are going crazy. Everything requires total coordination across multiple divisions and came to a grinding halt with a lady in my office. She hadn’t prepared adequately and the entire process was hours behind schedule, causing huge problems. She proceeded to have a melt down and walked around the office screaming at people. Guess who became my new supervisor?” (shrimpcreole)

Bosses Who Were Not Nice To The Clients

Credits: Pinterest

At my last job at a marketing company, our President and Owner went on an hour long tirade to a client, basically calling them “stupid’, “ungrateful”, “idiots”, along with a bunch of swears. It started because the client, a dentist, presented my boss with some ideas that came from her receptionist.

Just the standard advertising suggestions (bench signs, radio ads) that the layperson would know, but nothing so bad that someone deserves to get ridiculed and harassed over.” (bucaqe)

The One Who Always Argued To Assert Superiority

Credits: Imgflip

I had a boss who would try to turn every single interaction into an argument or confrontation. I would be at work, going about my business, doing the same thing I do every day, and he would come around and our interactions would go something like this:

Him: I want you to do it this way

Me: That’s how I’m doing it, that’s how I’ve always done it.

Him: Don’t argue with me, just do what I’m telling to do!

Me: But I…


My only course of action around this guy was to act dumb and make him feel like he was a wise old sage because he had been in this business longer than me. Sometimes 30 years of experience just means that you’ve sucked at your job for 30 years.

Oh, and during my last review with him, he wanted to know why we weren’t better friends.” (DrWhoisOverRated)

The Super Creepy And Inappropriate One

Credits: Memegenerator

My boss is an absolute HR nightmare. First of all, he’s the CEO of the company and thinks he can get away with anything because his brother is the company lawyer and his other brother is the HR manager. He is SUPER inappropriate. Like makes awful sexual comments to me all the time. In the beginning he used to hug me ALL THE TIME. When I told him that I wasn’t much of a hugger, he said “well, we will have to change that.” Creepy. He also told me all about his first sexual experience (with a co-worker!), and said that women should be more sexually aggressive in the workplace. Urm, whert? Needless to say, I’m nope-ing the hell out of here real soon. Putting in my two weeks on Monday.” (kennie_leigh)

The Kind Of Outright Idiotic One

Credits: Memeshappen

 Not so much horrible as outright idiotic. I used to work at an ice cream stand in a pretty popular tourist spot. Boss was a nice guy, friendly, accommodating, etc, but not necessarily the brightest bulb on the tree. Clearly his first year running the place.

Dude would order the same quantity of EVERYTHING. Like, just went down the order sheet going 5, 5, 5, 5. Doesn’t matter how fast we run out of vanilla or how few people ordered the weird flavors; we got 5 tubs of each a week. Nuts come in tiny pouches and sprinkles huge bags? Doesn’t matter, you get 5 each. Cones are boxes of 24 and cups bags of 50? BIATCH DID I STUTTER WHEN I ORDERED 5?

It was spectacular how quickly we ran out of certain things and how massive our stockpiles were of other stuff. And it took him until August to figure this out and let us “advise” his orders, since we couldn’t do it ourselves.” (swaggatracin)

The Wealthy And Insane Ones

Credits: Makeameme

“I’m a personal assistant and have worked for some very wealthy and insane people . . . Wealth-management CEO & his Russian bride: He would tell me everyday of the new jewelry and sports cars he was buying his wife. Literally, everyday she got a gift that cost over $50k! He spent more on her daily than I would make working for him in one year. Russian bride when I had to help her would never look at me, or even speak to me unless she had no choice. She would just make hand gestures or the maid would “translate” her glares to me.” (TheLifeofDime)

The Biggest Cheapskate Ever

Credits: Makeameme

My first job was working fast food for the biggest cheapskate ever. This was over ten years ago, so I am kinda fuzzy on specifics, but he would regularly schedule me for more hours than I was legally allowed to work, paid less than minimum wage due to a loophole, and refused to turn the ac on, even in the lobby, to save money.

One day, I was scheduled for a shift that he knew I was not available for, (I relied on my parents for rides so I couldn’t work week days,) so I spent the night before at a friend’s house who lived close enough for me to walk. It was raining heavily that day so after walking twenty minutes to work I was drenched. I pulled the door handle and the building was locked. No signs on the door, just locked. I call my boss and he says, “You don’t have to work today, we are closed for business.” I say, “Am I working tomorrow?” “No, we are closed for good.”

He was afraid people would mess up their last shifts and steal product if they knew we were closing, so he just didn’t mention anything. One of the managers was his own brother, and he didn’t even bother to tell the guy that he would be unemployed and needed to find a new job.” (drfattyphd)

The One Who Isn’t There When Needed

Credits: Memegenerator

I’m in the Navy, and have actually had good luck with my supervisors. Even the one I’m about to talk about isn’t terrible. It’s just that he’s never around. Ever. Whenever you need him, he’s not in the office, not in the building, and his car is gone. He has all these pet peeves and rules that aren’t really necessary. When you make the decision to go against his “ways”, sure enough, he’s right there, and demanding answers as to why things aren’t being ran like he expects.” (1800fullytorqued)

The Not So Understanding Supervisor

Credits: Memecrunch

“One day I got a flat tire on the bridge driving to work. At the time I was carpooling with 3 other guys. All 4 of us were late, the other 3 told me their supervisor let them start an hour late and go home an hour later than usual so they wouldn’t get a point on their record. I ask my supervisor and what does he tell me?

“We aren’t allowed to do that, plus you didn’t give us enough notification.” I kid you not this idiotic bagel actually said I didn’t give enough time notice of the flat tire.


The Supervisor Who Underestimated His Employees’ Worth

Credits: Quickmeme

“This will be quick:                       

I worked for a retail store, I’d been there for close to three years, I asked my supervisor for the possibility of a promotion, the supervisor laughed at me, told me I had bad attitude. I left that job the next day. Fast forward 5 years and… said supervisor was a greeter at Walmart while I now work for the State.” (ImNotYourGuyPal)

Nepotism At It’s Best

Credits: Imgflip

“My girlfriend was just fired recently by an idiotic boss.

She used to work at an independent restaurant. When the old owners were there she was fine, but when the new owners took over all hell broke loose. He immediately hired his cousin and gave her all of my girlfriend’s hours. According to the other girls working there she did nothing in her first few days of being there. Because she was related to the boss she acted like the boss despite everyone having superiority on her.

The new owner started to really stress out my girlfriend by telling her she wasn’t working hard enough and everything she did was wrong. It got to the point she burst out into tears because he wouldn’t stop. The second owner saw her crying and sent her home. Later in the day when she called into work she asked for her hours for the next week. The first owner told her she was fired for leaving work and according to him she was taking advantage of his generosity. When asked what he was talking about he wouldn’t give any examples. He also said the other girls she worked with were complaining and when asked again what they were saying he wouldn’t give an answer.

All in all she was fired due to nepotism and following orders.” (SteroidSandwich)

The Manager Who Messed Things Up

Credits: Mememaker

I worked at a mall bookstore when I was in college and the manager was, kindly put, a moron. She would enter payroll wrong, couldn’t make a schedule and while I do really think she WANTED to be nice she just didn’t have the brains that God gives your average rock. So jump to the release of Harry Potter and the Goblet of Fire, about 3 months prior to release we had a pre-order signup sheet. Obviously there was some insane demand for this book and the list was about 4 pages long. So a couple weeks or so before release we had to actually place our order and she counts up our pre-orders and asks me how many more past that we should order, I tell her at least double, maybe triple the number of preorders as the company was going to have a midnight release party for the book. About is time I had to take some time off as I was in school and had a major project that needed my full attention so I come back 2 days before the release party, and the pre-order sheet is still out, and it’s now 9 pages long. I bring this up to her and ask how many extra copies she ordered. “I decided do just double the preorders, why?” I hand her the sheet, the deer in headlights look was priceless, she was going to be short about 20 books for the release party. That’s when I told her I wasn’t going to be able to work the release party.” (JustABitEvil)

The One Who Was Dilbert’s Human Counterpart

Credits: Twitter

“For those who know Dilbert’s “pointy-hair” boss in the Dilbert comic strip, my boss is his human counterpart.

He hears nothing of what you’re actually saying, even when he takes you aside and asks for input (which is rare). Even after a discussion, 5 minutes later he doesn’t remember a word you said, no matter how important the subject.

He is the personification of the “Peter Principle” – namely, he’s been promoted to his level of incompetence. Everyone who works with me agrees, in full. Yet, he makes the big bucks …” (Back2Bach)

The One Who Planted Hidden Cameras

Credits: Imgflip

“I worked for a small independent company, running the little office doing admin, accounting etc. Hated the boss, as he was an egomaniac and probable psycho, but got on with the job. However, unbeknownst to me he’d decided to plant a hidden camera disguised as a movement sensor, perfectly placed to watch me. He told me off for doing a crossword while he was out of the office; I had a snoop round, found it and quit.” ([deleted])

Uncle Turned Out To Be A Horrible Boss

Credits: Memeshappen

“I worked alongside my uncle in a betting shop for almost 2 and half years, and I ended up hating him. He would try anything just to make it look like he was in charge. He once made a cashier count all of the betting slips in the shop (there were approx 7500), and made her re-count them because he didn’t believe there were that many. He referred to himself as his colleagues’ “employer” which caused a stir; he was a manager at a crappy retail store and not the employer of anything. He felt the need to sign everything “THE BOSS”. And he was a constant one-upper; I have an English degree but you’d be damned if he didn’t know more than me about the pronunciations of Middle English words, Shakespeare, grammar, EVERYTHING- he just had to try to be cleverer than you in an attempt to seem like he was above you.” (Jurasheep)

Executive Director Who Orchestrated Power Plays

Credits: Pinterest

I once worked for a small nonprofit with a terrible Executive Director–she enjoyed pitting all the senior staff against one another by making up stories about things people had said, promising three people the same promotion, and generally orchestrating power plays. Staff turnover, as you might imagine, was super rapid (and not just among the senior staff), but the board of directors never caught on that anything was amiss because the rotation policy was built in such a way that board members rotated off every two years. The whole experience was hideous and nearly drove me out of the nonprofit field.” (justaskosh)

The One Who Couldn’t Change Flat Tires Properly

Credits: Pinterest

“I used to be an archaeology technician and my crew chief (an evangelical Christian that believes the earth is 6,000 years old) was driving us out to a site. The previous day we had a flat tire and he changed it.

So fast forward to the next day, I’m sound asleep in the truck, when I get tapped on my shoulder. My boss stopped on the side of the road and was standing next to me outside and said, “Don’t move, the wheel may fall off.” The idiot forgot to tighten the lug nuts and the wheel came loose and was just rolling on the axel as we were barreling down the road at 80mph. I may have died that day…” (zZINCc)

The Terrible Employer

Credits: Memeshappen

“I worked for this guy at an ice cream store. He kept cutting my hours for arbitrary reasons, so I got another job and put in my two weeks notice. Halfway through my two weeks notice, I got the flu, and tried to call in. He told me if I didn’t show up I would be fired. So I showed up, and he told me I wasn’t being “cheerful enough” for the customers. So I looked at him, said nothing, grabbed my bag, and walked out the door. At which point he followed me and threatened to call my new job and tell them I was a terrible employee. I called his bluff, and then called my new job to give them a heads up. They said “We don’t care, you’re already hired. Feel better, we’ll see you Monday.” (invisible_23)