Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).
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This story is still one I tell people all the time. I don’t know why, but I find it absolutely hilarious. A long time ago, maybe fifteen years ago, I was in my mid 20’s and working in sales. I had another friend who was a fast-talker and really personable, and I always thought he would be great at sales too.
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He was working pretty crappy jobs at the time in restaurants and kitchens and maybe had a bit of a drinking problem. But I tried to give him some advice and told him he could do well, he just needed to get his foot in the door somewhere. 
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He took my advice and found a job doing telemarketing fund-raising for one of those firefighter charity things. I’m not exactly sure how it works but basically his job was to call people and ask them to donate money, which I honestly thought he would be amazing at. I even acted as a reference for him, and he ended up getting the job. 
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On his first day there, he got on the phone in the morning, then called me about an hour later thanking me for helping him get the job. He said it was better than working in a kitchen and he was excited to see how well he could do. I told him to call me if he needed any help or advice. 
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That same day, around 1pm, he called me back. He was whispering into the phone and I could barely hear him. He told me that he’d left for lunch and that he wasn’t going back to the office. But since he didn’t have a license and had gotten dropped off there by his girlfriend (who he didn’t want to tell that he was quitting), he needed somebody to pick him up. 
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I had a lot of flexibility at my company and I found the whole thing amusing, so I agreed to go get him. Here’s the funniest part: for some reason, he was hiding in the woods behind the building. He had gone to lunch and then hid in the woods behind the parking lot until I could pick him up. I was dying laughing at the whole thing. He’s actually in sales for a furniture liquidator now and does quite well. I guess that first job wasn’t meant to be.  
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Anonymous             Location withheld 
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This happened at my first corporate sales job and is the biggest lesson I’ve ever gotten in doing research beforehand, as well as thinking before I speak.
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I was an AE at an agency and our main client base was FMCG companies (P&G, Johnson & Johnson, Unilever, etc.). We provided a variety of services and we tried to visit prospects on-site for introduction meetings as much as possible. One time we went to visit Conagra Brands, my coworkers' account, and I attended as support because I had more experience.
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We arrived at the office to meet the prospect. She was a really nice lady and we were walking to an office to pitch our services. On the way, I spotted a painting on the wall that looked very familiar. Out loud I said, "Cool, is that the KFC man?" to which she replied "No, that's Orville Redenbacher." One of the biggest brands that Conagra owns.
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The meeting still went okay and there didn't end up being a fit, so nothing really came of it. But I'm sure my comment didn't help at all...
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Anonymous             Location withheld 
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This actually happened to my wife, not to me, but it's still one of my favorite stories. She is a director at a public relations company and has been in that industry for close to twenty years. She pretty much runs the place at this point, the only ones above her are the company owners, and they rely on her to do a lot of day to day operations.
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During the end of the first year of the pandemic, she was looking to switch project management software providers, so she had one of her employees set up a few demos. She (my wife) was going to personally sit in on the demos since a big part of what she does at work is make sure all accounts and projects are being managed correctly. 
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The demo was with a young sales rep at this software company, and it was taking place over zoom. If I’m remembering correctly, the rep was working from home – from her bedroom or something like that. She introduced herself to my wife and her two employees, then started asking them some questions, going through discovery. 
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Well she had only been on the call for less than ten minutes when she paused in the middle of speaking, looked at something in the corner of the screen and let out a blood-curdling scream. Then she jumped out of her seat, and the next thing my wife knew, the sales rep’s computer tumbled over a bunch of times while she screamed like a maniac in the background, then the video disconnected. 
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My wife and her employees were horrified and were discussing whether they should call the cops when they got an email from the rep who apologized profusely and said there was a giant spider that had landed on her keyboard in the middle of the presentation. The poor sales rep was so embarrassed about what happened that she actually suggested that she pass my wife’s account to somebody else. Her company ended up buying from another vendor, but not because of the spider incident. Still one of my favorite stories to tell. 
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Anonymous             Location withheld