Business bloopers – funny moments on the job

While running a business is a serious endeavour, there are plenty of lighter moments when dealing with customers, suppliers and employees. Here are some of our favourites…

Strange bedfellows

“When starting out my business with my business partner, I spent months unsuccessfully trying to win over a big client.

“However, my business partner then gave it a shot, and signed the client up after just one meeting. Shocked and intrigued, I emailed my partner and joked 'What did you do to get him on board – take him to bed?'.

“It wasn’t until after I hit send that I realised I had sent it to the client!Smiley faces

“After the initial heart attack, I was surprised to see the client’s response, which went along the lines of ‘I’m so glad to see you wanted my business so badly – look forward to working with you’.”

Web designer

First line of defence

“Back when I opened my first studio, I was sleeping in the business, and I remember one time we had a break-in.

“The funny thing was I went and confronted these two burglars [and] when they saw me, they were obviously quite startled.

“Their first response was: ‘Are they your pyjamas?’.

“I laughed and said ‘Yes, now get out’. They left and everything was just fine.”

Personal trainer

I object to Mondays

“The best [sickie] excuse I ever heard was that a woman couldn’t come in on Monday because she’d been to a dinner party on Saturday night, and the dinner party was being filmed for a television show.

“At the dinner party, she had had a little bit too much to drink and said some things that were recorded.

“She thought about it the next day and couldn’t come in on Monday because she had to see her lawyer!”

Architectural designer

Picture tells a thousand words

“I have employees based in several countries around the globe. At one point, one of my Asia-based employees pre-emptively requested he be allowed a week of sick leave.

“However, when I reminded him that a medical certificate was required for all extended periods of sick leave, as per the company’s policy, he instead produced detailed photos. His ailment? Haemorrhoids.

“Incidentally, he no longer works for the company.”

Software developer

Cone of silence

“[For one client, I was asked to install] a cone of silence, like in Get Smart, and I actually did it.

“I built it, I designed it. It did move up and down.

“I don’t know why [they wanted it] … it was a financial services business, and they wanted this cone of silence for one of their meeting rooms, and they wanted it operable, they wanted it to work!”

Office designer 

Head above the rest

“Customers are quite funny. We used to sell frozen chicken necks, and one time a customer brought it all back and said 'I can't feed this to my dog, there is a head attached to the neck!'.

“We didn't have the heart to tell her that, in fact, ‘Where do you think chicken necks come from? And the head is actually the more nutritional part of what you're feeding your dog anyway!’.

“So we just gave her back her money and smiled.”

Pet supplies retailer

Do you have a funny experience to share? Want to vent about something weird and wacky you came across recently? Email us at This email address is being protected from spambots. You need JavaScript enabled to view it.!

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