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).
I was selling design services for a small firm that mostly worked with other startups. I was in the final stages selling a full website redesign project that was worth $20k. The prospect came inbound and had seen some of our work before and wanted to hire us. He was the founder of the company, so he was a decision maker, but he was also price sensitive; investing $20k into design was a big jump for him. I sent over the contract for signature and he emailed me back asking if he could pay with a credit card instead of our standard payment terms of ACH or wire. I assume he asked because he wanted to earn points on his business credit card. I went to my boss (the CEO) and told him the deal would be locked in if we let the customer pay by credit card. The credit card fee came out to about $600, but my boss didn't want to eat it. Again, we were a small business, so I understood where he was coming from. He said we'd accept the credit card payment but the client would have to cover the fee. I emailed the prospect to let him know. He balked at it. He started talking about how much money he was already spending with us and that he wasn't going to spend another $600 just to use his preferred payment method. I forwarded the email to my CEO and he reversed course. He emailed the prospect himself on the email thread and apologized, telling him we'd be happy to cover the fee. The prospect emailed us back and said he was no longer interested and didn't want to work with a company that was going to nickel and dime him over every little thing. He actually walked over the credit card fee. Lesson learned. Salespeople — just eat the fee and close the deal!
Anonymous Location withheld
—
This was by far the most awkward interaction I've had with a prospect in all my years of selling. I was working on a deal that I had a really good feeling about. The prospect was my internal champion and was convincing the CFO to pull the trigger. I had built some rapport with him about baseball since we were both born and raised in the area and were huge fans of our city's MLB team. They were in the playoff for the first time in over a decade, so I got approval from my boss to take him to a game.
So we're at the game, it's an elimination game and we needed to win this one or the season would have been over. We were enjoying ourselves — the guy was super into it, maybe too into it. He kept standing up screaming after every big play and was swearing at the umpire if he didn't like the call. As the game was winding down and it became apparent that our team was going to lose, he started getting really quiet and was just slumped down in his seat. I could tell he was really upset.
The game ended, our team lost. The guy just looked broken. I didn't want to end our night out with a bad vibe, so I convinced him that we should get one more beer at the bar down the street. He agreed. We sat at the bar and ordered. I tried to lighten the mood and change the subject but the guy just started quietly sulking on the bar stool while I was talking. He was practically crying. I patted him on the back because I didn't know what else to do but he pulled away, got up and with tears in his eyes and said, "I'm sorry I just have to go home," and he left.
I figured the best thing to do was never to talk about the game or what happened after, so I waited a few days and followed up over email and kept it strictly business. I ended up closing the deal (thankfully) but that was the first (and hopefully the last) time I saw a grown man weep over a sports team.
Anonymous Location withheld
—
I'm sure every salesperson has a story about some friendly hazing on the job going a bit too far. This is mine. I was selling financial services early in my career, way back in the 90s. We had a fun little ritual that we'd do to new hires. When a new rep came in and missed their quota for the first month, the sales team would pitch in and send a giant flower arrangement to their desk with a card that said "Sorry for your loss." Most people took the joke and just moved on with their day.
Well, one time we had a new rep and he missed his quota the first month. It was not surprising since it was his first sales job. We were all sitting in the office. We knew the flower delivery was coming in the afternoon so everyone was patiently waiting. The flowers were delivered to the guy while he was sitting at his desk. We were waiting for him to look around so we could all start laughing, but instead, the guy dropped his head on his desk and started sobbing. Nobody was laughing. We all just looked on, feeling sorry for the guy. Apparently his girlfriend (who he lived with) had left him two days earlier but he hadn't said anything to anyone about it. The guy went to the bathroom to compose himself, and I went in to apologize and told him it was just a joke and that we did it to all the new reps. Needless to say, after that incident, we decided to put the kibosh on our little flower prank.
Anonymous Location withheld
