More Business Horror Stories from the How I Failed in Business Community (Vol. 2)

Vol. 1 clearly hit a nerve.

The response to our first collection of listener-submitted business horror stories was... a lot. Apparently the How I Failed in Business community has been sitting on a quite extraordinary amount of professional humiliation, and once we gave them an outlet, the floodgates opened.

We received stories involving wrong invoices sent to the wrong companies, clients turning up to meetings on the wrong continent, auto-correct failures in crucial pitch documents, and one unforgettable tale involving a fire alarm, a boardroom presentation, and a PowerPoint slide that was definitely not supposed to be visible to external visitors.

We cannot publish them all. But we can publish these. Once again, all names and identifying details have been changed — but the chaos is entirely, painfully real.

"I accidentally got paid £14,000 by a complete stranger"

A freelance consultant — let's call her Rachel — sent an invoice to a new client. Standard stuff. Except that in her haste, she entered the wrong company name and sent it to an entirely different business that had a very similar name and happened to be registered on the same invoicing platform.

The wrong company paid it. Immediately. Without a word of query.

Rachel only noticed when her actual client chased the invoice two weeks later. She was sitting on £14,000 that did not belong to her, paid by a company she had never heard of, who seemingly had not noticed they had paid someone they had never worked with for services they had never received.

She spent a deeply awkward afternoon explaining the situation to a very confused accounts manager at the wrong company, refunding the payment, and then sending the correct invoice to the correct client.

'The strangest part,' she says, 'was that the wrong company just said 'no problem' and that was it. No follow-up. No questions. I genuinely wonder if they ever figured out what they had originally thought they were paying for.'

"My auto-correct changed a crucial word in our pitch document"

A creative agency director had spent two weeks preparing a pitch document for the most significant contract his company had ever pursued. It was detailed, polished, and — as far as he was aware when he emailed it across — completely perfect.

The potential client called the next day to say they loved the proposal but had one question about page seven, where the agency had apparently described their approach as 'pubic relations' rather than 'public relations.'

Auto-correct had silently made the change at some point between final draft and PDF, and nobody on the team had caught it during the review.

'They were very gracious about it,' he says. 'They said it showed we were human. We got the contract. But I have proofread every document in a printed-out, physical copy on an actual desk ever since. Every. Single. One.'

"I gave an entire keynote speech to the wrong conference"

This one is so specific in its disaster that we almost did not believe it. Almost.

A business consultant — let's call him Marcus — had been booked to give a keynote at a conference in a large hotel. He arrived, registered at the desk, found the main hall, set up his slides, and delivered his full forty-minute presentation on digital transformation in the financial services sector to an audience of about eighty people who listened very politely.

At the end, a woman in the front row raised her hand and asked, very gently, whether his talk was perhaps intended for a different event.

There were two conferences running simultaneously in the same hotel. Marcus had walked into the wrong one. His actual audience was in the adjacent suite, where a very different speaker had apparently been explaining digital transformation in financial services to people who were expecting a talk about sustainable packaging in the food industry.

'The organiser of the conference I actually spoke at was lovely about it,' Marcus says. 'He said it was by far the most interesting keynote they had ever had at their packaging summit. I did not know whether to be flattered or horrified.' Both, Marcus. Both.

"I quit live on a video call — then realised it was being recorded for training"

A senior manager — let's call her Diane — had reached the end of her tether with a particular role and decided, after months of deliberation, to resign. She had prepared what she felt was a dignified, professional resignation delivered via video call with her line manager.

She said her piece. Her manager thanked her for her honesty, wished her well, and the call ended.

Diane then received an email from the company's training department, with a link to a recording of the call, notifying her that as per the agreement she had signed when joining the company, some management calls were recorded for professional development purposes and asking whether she consented to this one being used.

'I had completely forgotten I'd signed that form,' she says. 'My resignation speech — which I had written, rehearsed, and delivered with what I thought was enormous dignity — is now apparently available to watch as part of an onboarding module called Difficult Conversations.'

She consented. 'I thought about it and decided if even one manager handles a resignation better because of what I said, that's not the worst legacy I could leave.'

Want to know more?

Still got a story that tops these? We are running out of superlatives but we refuse to stop collecting. Send your submission (anonymous or otherwise) to us at www.howifailedinbusiness.co.uk.

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