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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I had this customer who was coming up for a contract renewal in a few months. I had a good relationship with the guy, and he even gave me a heads up that his boss had him talking to some of our competitors just to see what was out there and if they could save some money.

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Well, I was out at a restaurant one night with a prospective client and saw the guy at a table at the other end of the restaurant with (who I assumed) was his wife. My dinner meeting was going well, and it was going on the company card, so I decided I would pick up my existing client's dinner bill personally to try to get some good will.

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I told the waiter, who left and came back to my table to let me know that the bill would be $600. Apparently, the guy had ordered two bottles of really expensive wine. I was shocked but tried to hide it. I couldn't back out in front of the prospective client I was with so I nonchalantly said it was fine and paid the bill.  My existing client left first, and came over to introduce me to his wife and thanked me for picking up the tab saying that it wasn't necessary but he really appreciated it.

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Well, you can probably guess what happened next. He of course ended up not renewing the contract, saying that his boss decided they wanted to go with a different vendor. I did end up closing the prospective client I was with, so, in my eyes, it was basically a wash. I've bumped into other clients at restaurants since then, now I just buy them a round of drinks. 

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Anonymous       Atlanta 

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This is a story that happened to me earlier in my career but actually taught me a valuable lesson about being thorough before sending out emails. I was selling marketing services for a small company. Our sales team was about 15 people total. It was a very "sales bro" environment, but it was fun.

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So our company ended up buying these expensive contact lists for us to do mass cold email outreach. I got my list, which was 1,000 emails. I went ahead and wrote out my pitch for the email sequence and built out the campaign in our software. It was some really crappy outreach software that was hard to use and I never really got the hang of. Well, I messed up the [First_Name] dynamic template and ended up sending out the emails to the entire list with the 'Hey John' placeholder to every prospect. I didn't want to tell my manager, but I told one of my coworkers about the screw up over beers that evening.

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My coworker ended up telling the entire team and people kept saying, "Hey John,' to me every time they saw me the next few days. We had our standard end-of-the-week all hands sales meeting, and at the end of the meeting, my sales manager put my email up on the screen of the conference room for everyone else to laugh at as a lesson for why everyone needed to double check emails before hitting send. The sales manager called me up and presented me with a custom t-shirt they had made that said "Hey John" on it. Everyone in the room started laughing as they made me put the shirt on as punishment and wear it for the rest of the day. Eventually, the "Hey John" stopped and I ended up staying at the company for two more years. But I triple check every email I send now.

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Anonymous       Location withheld 

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I had just started out in sales. I was selling solar, knocking on doors. I was in an unassuming neighborhood in the suburbs and this guy said he was thinking about getting solar and invited me in to chat. It was a raised ranch house so I walked up a small flight of stairs to his living room and the place was FULL of taxidermied animals. But it wasn't like deer heads or anything he hunted; it was cats, dogs, rabbits, and mice all over the floor and on the side tables. It was really weird.

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Anyway, I went into my pitch and the guy seemed to be listening but he kept darting his eyes around the room looking at the animals like he wanted me to look at them too. I handed him some of the materials that had different package options. He looked at them, then looked at one of the stuffed cats on the ground and said, "What do you think Clyde?" I sat there confused for a second and then the guy started bursting out laughing like the stuffed cat told him a joke or something. At this point I was really creeped out, the hairs on the back of my neck were literally standing up. I wanted to get out of there immediately, but somewhere in my mind I was hoping maybe this guy would actually buy so I suggested we go outside so we could look at his roof and talk over options. He said he changed his mind and actually wasn't interested. I don't know what that guy thought that cat told him, but I was thankful just to get out of there.

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Anonymous       Location withheld