5 bosses you never want to be: True tales of monster managers

Phil Kendall

Mar 2022 ⋅ 7 min read

Business man with with open collar and white coffee cup his hand.

From a lack of engagement, to poor company culture and unexpected life events, there are plenty of reasons why an employee might hand in their notice.

Scroll through the countless threads and conversations on sites like Reddit and LinkedIn however, and you might notice one other big reason why some people find themselves dusting off their C.V.: their boss.

Where great bosses motivate, support, and inspire their staff, nightmare bosses leave their employees praying for a blizzard or a city-wide power outage during the lead-up to their shift.

Curious to know whether managers like these really existed, we put out a request across our various social media networks, asking people to get in touch with their own true tales of horrible bosses.

The responses were eye-opening to say the least.

From dressing gown-clad directors to spirit-crushing CEOs, there’s an anecdote — and perhaps a cautionary tale — here for everyone who's ever held a management role.

So strap yourself in, brace for a major dose of ‘cringe’, and prepare to meet five bosses that you never, ever want to be.

Out of courtesy to our contributors and to protect their identities, all of the names, roles, and locations in the following accounts have been changed.

1. Absent Alan

“I once worked for a guy who ticked pretty much every box on the Horrible Bosses checksheet,“ wrote ‘Sara’, a former marketer from the North of England.

“This guy was a total narcissist who cared more about immediate increases to his personal wealth than building anything meaningful and long-term – I later found out that he would often ditch a business he’d started, and all its staff, the moment it showed any sign of struggling.”

To make matters worse, this particular monster boss apparently took a very “hands-off” approach to management.

“He only turned up to work when he felt like it,” Sara continues. “Sometimes we wouldn’t see him in the office for days or weeks on end, then he’d burst in, usually yelling at someone about something.”

“You never knew when he was going to snap, so everyone would always be walking on eggshells around him.”

To make matters worse, Sara’s boss also took a pretty lax approach to things like paying tax and compensating his staff…

“He barely paid any of us the minimum wage, regardless of roles or experience. There were also no payslips to speak of, and I later found out that he hadn’t told HMRC about half of the company’s employees, including me.”

“He was the kind of guy who’d do well on The Apprentice;” Sara concludes, “he’d charm Lord Sugar, but the minute he faced any sort of real-world scrutiny he’d crumble and start blaming everyone else for the failure of the task.”

2. Chaotic Christine

“Probably my worst boss ever was when I worked at a sandwich shop during university,” writes ‘Ed’, who is now a secondary school teacher.

“We'd spent at least 10 minutes during my interview talking about my uni course and the fact that I could only manage 8-12 hours a week, but when I got my first rota I found that my boss had scheduled me to work nearly 30 hours a week.

“When I called her up thinking it must have been a mistake, she told me that, if I couldn’t work the shifts I’d been given, I had to find someone who could cover for me. This was my responsibility, she said, and not hers."

Not only did Ed find himself with a tonne of shifts to contend with, there seemed to be very little rhyme or reason to his rota.

I never once had the same shift pattern weeks in a row,” he writes. “One week, I’d be down to work Monday, Tuesday, Wednesday; the next I’d be in for the whole weekend, plus a weekday evening.

“Once, she even had me go in at 4 o’clock on a Saturday for a two-hour shift. It was impossible to organise anything in my private life.”

Sadly, even after all his hard work and his ever-changing schedule, Ed was rarely compensated correctly.

“My pay was almost never right; sometimes whole shifts’ worth of pay were nowhere to be seen.

“We had no way of recording if we’d stayed late or covered a shift for someone else, so we had to rely on the manager remembering so we got paid properly. This rarely if ever happened.”

Close-up of woman screaming with long hair covering one side of her face

3. Spirit-Crushing Steven

“A few years ago, when I was working for a company whose head office was in New York, I got invited to a managers’ conference,” writes former retail manager ‘Janine’.

“They had all these guest speakers and managers who were giving presentations on how to manage your team and how to get the most out of your staff, and by the end of it we were all feeling pretty buzzed and excited.”

Sadly, the motivational moments then came to an abrupt end.

“One of the big bosses — not my direct line manager, but an important VP at the company — took to the stage right before the end of the event,” Janine continues.

“He then spent what felt like an hour berating us, telling us that the company was losing money year after year and that we should all be ashamed of ourselves.”

“We knew things hadn’t been great for a while, but my team and I had been giving blood, sweat and tears trying to claw some money back for the company, and this manager had put the blame squarely on us. It was horrible.”

But he wasn’t done yet.

“By far the worst part of his speech was when he said, to a stunned silence, that none of us should be sleeping at night because of how bad the sales figures were.

“It’s fair to say my commitment to the company died that afternoon,” Janine concludes.

4. Intimidating Ian

“At the very start of my career, I found myself working for a company that was established in the 1960s,” writes ‘John’, now a copywriter in Nottingham.

“The guy in charge, who we were all told to address as ‘Sir’ or ‘The Chairman of the Company’, and never by name, had been there since the business was established, and it showed: he had a reserved parking space right next to the front door, his own private ‘quarters’ upstairs, and the only type of feedback he believed in was the negative kind.

“The whole place was kind of stuck in a time warp,” he added.

“One day, I was summoned to his office to show him some trade magazines that contained reviews of our products, which he always insisted on seeing.“

“After flicking through the first of the trade mags, he glared at me and asked me why I hadn’t bothered to mark the pages that the product reviews were on,” John continues.

“Just as I was explaining that we’d run out of Post-It notes, one of the sales team knocked and entered the room. This was really bad timing for him because — and I don’t know why, because he was a salesman — it was his job to keep the office stationery cupboard stocked.

“The Chairman demanded to know why we didn’t have any Post-It notes, then threw one of the magazines across the room,” John writes.

“It turns out, the other guy had actually ordered the Post-Its but there’d been a delay with the delivery. But before he even open his mouth to say this, The Chairman shouted, quite loudly and with a lot of spit, ‘Go and stand in that corner, you stupid, silly boy while I finish with… what’s your name again?’”

Bearded man sleeping in bed with stripy white sheets.

5. Lazy Lewis

Our final monster boss comes courtesy of ‘Will’, whose first employer was an early advocate of working from home, albeit not in the way that most of us would prefer…

“My old boss one day told me and another member of staff that we’d ‘probably’ be moving from our office in Sheffield to Doncaster. This meant an extra half an hour of driving for me every morning, so I wasn’t exactly thrilled, but as I was still pretty junior at that point in my career I didn’t make a fuss.”

“Our boss had toyed with the idea of moving offices a few times before, so we didn’t think it would actually happen, but two weeks later we turned up for work and half of the office had been packed into boxes and we were told we needed to get out ‘ASAP’.”

Keen to stay on their boss’ good side, Will and his coworker got busy packing boxes. But it was then that they realised something…

“It turned out that we were not only helping to move office, but also helping our boss move out of his current flat into a new one — we ended up packing all his stuff away while we should really have been working.”

Things really took a turn for the surreal, however, when the team arrived at their new headquarters.

“The new ‘office’ was actually one of the spare bedrooms in his new flat,” Will explains, “which was a converted church surrounded by a creepy old graveyard.”

“A few days after the move, my closest colleague handed in his notice. This resulted in him and our boss yelling at each other for most of an afternoon, barely three feet away from me in this bedroom-slash-office, while I sat there pretending I couldn’t hear anything.”

“I somehow hung on for another three months, but the situation only got more and more bizarre. I’d often turn up for work to find that my boss was out ‘networking' and it was now my job to answer phone calls and do all the work singlehanded.”

Then came the final straw.

“One day in early December, he asked me to come in two hours early, which meant walking through a pitch-black graveyard, to get a head start on a big project we’d landed.

“I got in, walked to the spare bedroom and sat down, only to hear the sound of running water coming from upstairs. Five minutes later, my boss walks down wearing only his brown fluffy dressing gown and VERY tight underwear.”

“I’d already started writing my notice by the time his belly made an appearance from inside his robe.”

Have a nightmare boss story of your own? We’d love to hear it! Tag us on Facebook, Twitter, or LinkedIn.