The 10 Worst (Real-Life) Bosses – Could You Cope?

The 10 Worst (Real-Life) Bosses – Could You Cope?

Dwight from the office getting mad gifA couple of weeks ago, we re-posted one of our favourite blogs: 10 Types of Horrible Bosses and the response we received was fantastic (and slightly overwhelming).

It seems that many of you have suffered the wrath of a terrible boss – some even make Miranda Priestly (The Devil Wears Prada, you know) look like a complete pussycat.

From miserable moaners, to downright monsters, a boss can get it wrong in so many ways…

So this week, we’ve been looking through your responses, as well as scouring the internet to pull together a countdown of the top 10 worst (real-life) bosses for your Friday Funny.

If you think you can beat these… then we really do pity you!

10. #karmasabitch

effie trinket in the hunger games with quote : I just LOVE that.If you’ve ever been made redundant, witnessed redundancies or (goodness forbid) had to break the bad news to others, you’ll know how harrowing it is for everyone involved.

Well, almost everyone.

Coming in at Number 10, we’ve got Alejandro Rhett, (ex) vice president of fashion brand J Crew.

Just hours after making 175 staff members redundant, this truly horrible boss was caught bragging on Instagram, with ‘funny’ photos and hashtags such as #hungergames and #maytheoddsbeeverinyourfavour.

Karma soon came and bit Alejandro on the arse though, as he was sacked shortly after the incident; the odds were clearly not in his favour.

You can read the whole horrible story over on The Independent’s website.

9. Dic(k)tation.

woman putting her head in her hands with quote #fmlTranscribing isn’t exactly the most fun job in the world anyway… but it really doesn’t help if you have a horrible and slightly stupid boss who has no common sense.

Johnny Walker from Pennsylvania tells Reader’s digest about a ridiculous situation he witnessed at work as his boss’s assistant was transcribing a letter from an audio file.

“My boss’s assistant… suddenly let go with a string of expletives, words I’d never realized were in her vocabulary. “Is everything all right?” I asked.

Steaming, she rewound her digital dictation device a few seconds and let me listen to what she had heard my boss saying, “No, no, forget all of that. [Pause] ‘Dear sir …’” 

How idiotic can one be? It would have taken just 5 seconds to say ‘oh fast-forward to 23 minutes because I start all over again there.’

(Or just do your own typing next time)!

8. Caught on Camera.

The next horrible boss to make it into our hall of fame is the (anonymous) Panera Bread Manager who punched his employee (twice).

Onlookers filmed the entire dreadful attack, which shows the victim attacking the manager just moments before he retaliates with 2 brutal punches.

Warning: This video is not pretty (and definitely not for the faint-hearted).


Not surprisingly, both members of staff were sacked.

Read the full story at

7. The “Serious” Talk.

woman looking confused and disgustedYou just HAVE to feel for this poor, poor employee…

‘Today, my boss called me in to have a serious talk. The “serious talk” was him asking me to notify him of my menstrual cycle ahead of time so he can “avoid that sh*t”.’ Anonymous.

Her boss has managed to cover the three most undesirable of qualities of a manager.

Inappropriate…check. Offensive…check. Sexist…check.

Whoever you are, get the hell out of there!

6. Setting A Model Example.

Naomi campbell with caption: I will kill youUnless you’ve been living under a rock, you’ll know who Naomi Campbell is. Supermodel, fashion icon, businesswoman… absolutely terrifying boss.

Over the years, a great number of stories have been revealed about her abusive behaviour towards employees, from housekeepers to drug counsellors and her weapon of choice is famously a mobile phone, hurled across the room.

She is certainly a force to be reckoned with, yet surprisingly, she’s only ever been found guilty of assault once.

That’s the power of fame, I suppose.

Discover more about Naomi’s Horrible Boss bio from this TIME article.

5. Power Trip.

This (anonymous) horrible business owner certainly let power go to his head…

Britney spears looking awkward and embarrassed“…He pushed staff members up against walls, threw chairs across the room and once punched both fists into an employee’s homemade birthday cake. 

Staff had to hide numerous affairs from his wife, were forced to work weekends with no overtime pay and he used to send these weird emails about how terrible we were at our job, copying in the rest of the office.

Once, he even put together a presentation, detailing the failures, mistakes and errors ‘of the month’ with print-out examples, naming and shaming the culprits!  Anonymous.

No wonder this poor employee wished to remain anonymous!

If any of this sounds familiar – it’s time to start looking for a new job.

4. Stir Crazy.

drawings of a village - with cranes

khunaspix at

Rocking up at number 4, we’ve got George Pullman… the genius who decided that the best way to get his employees engaged, motivated and loyal was to build them a ‘company town’ to live in.

That all sounds above board, right?

Unfortunately, power (also) went to George’s head and he reigned ruthlessly, making up his own rules and controlling all of the town’s profits.

Rent (which was automatically deducted from everyone’s salary) was increased, yet wages were decreased, leaving most employees with just a pittance to feed their families.

Even if you ignore all of that – would you really want to live in a town surrounded by your colleagues?

3. Bad Teachers.

Teachers are supposed to know better!

Unfortunately, it appears they don’t… as this poor newbie teacher found out.

ryan from the american office with caption 'bitch' gif“I’d just started a new school and was getting on really well, but all of a sudden one lesson, the kids started playing up. When I told them off, they called me ‘mental’ and asked if ‘the voices were telling me to do it’.

It was so random that I knew that something was up, so I had a chat with one of the kids who told me that my boss – the head of department – had spent the entire previous lesson badmouthing me to the entire class.

Apparently I was ‘mental’ and a ‘skitzo’ which she explained as a “disease” where you hear voices and change your mind all of the time. She told them a number of other really weird things and to this day, I have no idea why. I left pretty soon after that.”  Anonymous.

Teachers are supposed to be setting a great example for their students, not belittling and badmouthing mental health (and/or co-workers)!

2. A Formidable FBI Director.

FBI agent cartoonIf you wanted to be a truly horrible boss… then becoming director of the FBI is pretty clever isn’t it really?

You can pretty much get away with anything and no one can ever tell! Genius.

J Edgar Hoover, described by The Telegraph as ‘corrupt, venal, egomaniacal, drunk, paranoid…’ and as a monster who “waged war on homosexuals, black people and communists” by The Guardian, did just that.

Among his weird and horrible rules as a boss, Hoover forbade the consumption of coffee after 8.15am and insisted that all his employees were “on-call” 24 hours a day, should he need them to fulfill menial tasks like mowing his lawn or scraping up animal faeces on his patio.

So fearful was their leader, that when Hoover once wrote ‘WATCH THE BORDERS’ on a piece of paper (referencing the lack of margin-space) they all panicked and tightened security at the Canadian and Mexican borders.

Put it this way… Hoover had them scared.

1. The Winner! (Or should I say, loser?)

Woman holding her nose

marcolm at

Richard Beckman… how on earth did you get away with this?

The Conde Nast executive was accused of assaulting two female staff members, Emily Jahncke Davis and Carol Matthews because they refused to kiss, during an office party.

Beckman, who clearly got a little bit overexcited, attempted to push their heads together and in the process, broke Matthews’ nose. Ouch.

Immature and violent… what a lovely combination!?

Strangely ‘Mad-dog’ Beckman has gone on to bigger and better things and is now working for Vanity Fair… hopefully he’ll have settled down a little since the incident though.

The Important Stuff.

Hopefully, these horrible boss stories will make you feel just a little bit better about your current workplace…

If you think you’ve got a story to top them; let us know in the comment section below or drop us an email (and please accept my sincere sympathies)!

You also might want to take a read of our recent post – 10 Ways to Deal With Bully Bosses – you really shouldn’t (and don’t) have to bear the brunt of their inadequacies!

Recruiter Pro Tip for Employers.

If you’re feeling a uneasy with this post, then perhaps YOU are a little bit guilty of being a bad boss? (Click Here to find out for sure).

Being a horrible boss is a HUGE mistake.

Your staff will become disengaged and disloyal, they certainly won’t care about the business and did you know that your bad behaviour could actually make them ill?

Would you like more advice? Check out this blog about the 3 most fatal mistakes you could be making as a manager.

If you enjoyed this post and want to discover some more horrible bosses, then check out this article by Business Insider.

It seems like there are thousands of horrible bosses out there, lurking in the shadows… and the best way to deal with them? Naming and shaming.

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BK Max 187
BK Max 187
3 years ago

Most of my bosses have been pretty shitty, except for a few. I got fired over some f***ing b******* in my time. It just goes to show that some people never grow up, even when you put them in charge of a team.