Ah, the noble CEO.
Perched high atop their ivory tower, gazing down upon the masses with a benevolent smile and a crisp, freshly pressed suit.
But every so often, a CEO decides they’d like to venture down to the real world - to brush shoulders with the common folk and prove they’re just like the rest of us.
It’s a noble effort, truly.
But much like trying to teach a cat to fetch, it often ends in chaos, confusion, and the distinct feeling that someone, somewhere, has made a terrible mistake.
So, in honour of those brave leaders who dared to (awkwardly) mingle with the masses, here are some of the funniest times a CEO tried to be ‘one of the people’ - and it backfired spectacularly.
1. The CEO Who Tried to Make Coffee
It’s a simple task for most of us, but when you’re used to having an assistant cater to your every caffeine need, the humble coffee maker can seem like a Rubik’s Cube wrapped in a Sudoku puzzle.
One ambitious CEO decided to surprise the team by personally brewing the morning coffee.
Unfortunately, they’d never actually used a coffee maker before.
The result? Half the office was promptly evacuated due to the smoke alarms being triggered by a mysterious, ominously burnt smell.
Turns out, you’re not supposed to add the coffee grounds directly into the water reservoir.
2. The CEO Who Tried Casual Fridays
We all love a good Casual Friday - a chance to swap the suit for something a little more relaxed.
But when one CEO showed up in what can only be described as a “Hawaiian Dad on Holiday” ensemble, complete with neon shorts and flip-flops, it raised more than a few eyebrows.
And by eyebrows, I mean HR complaints.
Casual? Certainly.
Appropriate for a board meeting with investors? Not so much.
3. The CEO Who Joined the Company Sports Team
Ah, the company sports team - a bastion of camaraderie, teamwork, and mild corporate coercion.
One CEO decided to get involved, joining the weekly football match with gusto.
Unfortunately, their enthusiasm far outpaced their athletic ability.
After an impressive attempt to header the ball resulted in a collision with a goalpost (and a broken nose), they decided to stick to safer pursuits.
Like foosball.
4. The CEO Who Hosted a Town Hall Q&A
In an effort to bridge the gap between the corner office and the cubicles, one CEO scheduled an open Q&A session with employees.
It started well enough. Until one employee asked:
“What do you actually do all day?”
After a flustered attempt to explain the intricacies of high-level strategy and decision-making, the CEO inadvertently admitted:
“Honestly, a lot of meetings and emails.”
The room erupted in laughter, and the CEO learned a valuable lesson: honesty is the best policy, but maybe not that much honesty.
5. The CEO Who Tried to Use Public Transport
In a bid to reduce the company’s carbon footprint, one environmentally conscious CEO decided to take the train to work.
Things were going well until they realised they didn’t actually know how to purchase a ticket.
After mistakenly buying a child’s fare and getting stuck in the automatic barriers, they finally arrived at the office an hour late - slightly frazzled but with a newfound respect for the daily commute.
6. The CEO Who Tried to Make Lunch
In an effort to show they were just like their employees, one CEO decided to join the team in the break room for lunch.
With a flourish, they unveiled a homemade salad—only to discover they’d forgotten the dressing and accidentally used tofu instead of mozzarella.
The result was a bland, chewy concoction that was politely described as:
“Interesting…”
The CEO’s attempt to bond over a shared meal turned into a group outing for emergency takeaway.
7. The CEO Who Tried to Relate to Millennials
In an attempt to connect with the younger workforce, one well-meaning CEO sprinkled a recent presentation with millennial slang and memes.
Unfortunately, phrases like “on fleek” and “lit” were past their sell-by date, and their attempt to dab mid-presentation resulted in a minor shoulder injury.
The effort was appreciated, but the execution left everyone cringing harder than a back-to-back marathon of The Office.
8. The CEO Who Tried to Join the Christmas Party
Ah, the office Christmas party - a minefield of awkward small talk, questionable dance moves, and regret.
One enthusiastic CEO decided to let loose and join the fun on the dance floor.
Unfortunately, their ambitious rendition of a breakdance move led to a collision with the DJ booth, cutting the music short and bringing the party to an abrupt and clumsy halt.
It was the stuff of legend.
And a video that resurfaced every year without fail.
Need to Recruit a CEO with People Skills?
If reading this has made you reconsider your own leadership style, we can help.
At Coburg Banks, we don’t just find leaders - we find leaders who know how to actually engage with their employees without causing a minor disaster.
So, if you’re looking for someone who can balance being “one of the people” with maintaining dignity, get in touch.
We promise not to make you dance.
