The 11 Worst Boss Stories We’ve Ever Heard
Twenty years ago, Office Space appeared in theaters, and the American workforce collectively cringed in recognition. We did, at least. Who among us hasn’t had a bad boss like Bill Lumbergh? In fact, half of all employees have quit a job because of a poor boss.1
So to celebrate Office Space’s anniversary, we rounded up the best stories about bad bosses—and trust us, we found some doozies. If you could just read them and then share your own stories in the comments below, that would be great. M’kay?
Your best worst boss stories
1. The work/family collision
“One night, he and I got into a big argument (I think over politics?), and we both stormed off to bed. The next morning, I got ready for work, prepping myself for an awful commute. But he never showed up. When I texted him, he responded that he couldn’t let me come into work because it reflected poorly on his business having an employee who couldn’t keep their room clean (there were literally two pairs of shoes on my floor). I should consider myself suspended without pay until such a time that I could clean my room to his satisfaction.
“I ended up thoroughly enjoying a week off of work (during which time I did zero cleaning) until finally my mom explained that if I didn’t have a job, my dad would be paying for 100% of my living expenses. Also he couldn’t actually suspend an employee because their room wasn’t clean or something, I dunno.”
2. The stripped-down interaction
3. The unsympathetic administrator
4. The underhanded exec
“He was particularly bad at managing the company we worked for, which he was the CEO of. By consistently overpaying what was basically a mafia of account managers and by underpaying writers, devs, SEOs, etc., he ensured that there was a race to the bottom of talent. People who were any good left for a better, less toxic work environment. People who were fresh out of college or prison stayed because that’s all they could do. (This was 2009. Not the best time to be looking for a job.)
“Something I found out later was that this boss was also scamming our customers by telling them that the sites we ‘sold’ them were actually theirs, although our company retained ownership of the domain. I’m pretty sure this is fraud. When bad decision-making eventually led to the company running out of money, we didn’t find out until our paychecks started bouncing. Instead of being up-front about it, the boss told us all that he’d just secured a round of investors and that we’d be reimbursed on bounced paychecks.
“That was a lie. The office was closed up and all the furniture was sold the next week. There was no official announcement, and some of my coworkers who hadn’t quit already found out when they went to work on Monday and the building was locked up.
“They still owe me about $800 in bounced paychecks. I’m one of the lucky ones, as some were owed more.
“This boss moved immediately to California and couldn’t be found. Pretty sure he was afraid of lawsuits from both his clients, who he scammed on purpose, and his employees, half he scammed on purpose and half because of extreme carelessness.”
5. The literal drill sergeant
6. The too-casual conference call
7. The ballad-belting boss
8. The backseat composers
“First, they didn’t give me a full copy of the film. Ever tried writing music for a movie you’ve seen only once on a laptop in a dark room? It is not a fun experience. You have to guess and hope the music hits the right moment. But hey, they asked me to write music without looking at the film—then criticized me for not hitting the dramatic points. My fault, I guess. To make things worse, there were three directors working on this film and each had a different taste in music. Trying to combine solo acoustic piano, industrial synthwave techno, and Wagnerian opera themes into a 10-minute short was not only difficult but completely impossible in terms of satisfying any one out of the three directors.
“During all the feedback sessions, I received interesting critiques. I can easily take negative criticism, but telling me that the ‘correct way’ to write for a piano is to just keep to an octave (for you non-music folk out there, basically think a measly eight-note span) is beyond absurd.
“If you thought that was weird, try appeasing demands to write music for a 45-second scene as ‘a battle between acoustic piano and electronic music, where it seems the electronic music at first is winning, but the underdog piano fights back and wins—transitioning into the next scene.’ Funny how after I was fired, the next hired composer was asked to write a single note drone underneath.
“In the end, I’m glad I cut ties with them.”
9. The confusing communicator
“One of the most memorable moments I have of just how screwed up my job was happened after I wrote a story about a book fair the local library put on. (Real compelling news, I know.) The librarians hosted a bunch of games for the children, one of which was a game where they’d try to throw a hula hoop around a bookend.
“After writing the story and submitting it to my editor, I got an email back requesting a certain photo to go with the story.
“But let me back up for a second and explain how my editor sent emails. The subject line would include all of the contents of the email. That’s right, when you opened the email you’d find nothing else inside.
“So my inbox dings and here pops up this email with the subject line: ‘Send me the photo of the hula hoop flying child.’ Word for word. I will never forget my train of thought as I tried to puzzle out just what the heck a ‘hula hoop flying child’ was.
“Eventually I figured it out, but that will always be one memory that never goes away with time.”
10. The sexist supervisor
11. The locked-in leader
An abundance of bad bosses
While some of these stories definitely horrified us, we were even more horrified when we found out how many people have bad boss stories to share. One boss bottling their own urine is upsetting, sure, but knowing that almost everyone has suffered under a bad boss? That’s downright depressing.
No wonder Office Space found such a following.
Did you have a memorable bad boss? Tell us about them in the comments below!
1. Bloomberg, “Americans Can't Stand Their Bosses, and Bosses Admit They're Phoning It in”
2. CNN, “Film Flops Flourish on DVD, VHS”