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 sell enterprise software, usually big multi-year agreements, which means there's a lot of wine & dining with decision makers (golf outings, box seats at sporting events, etc.) One of my customers, who I check in with every quarter and had known for a few years, told me that he was going to be down in my neck of the woods in Florida for vacation. I'm big into deep sea fishing, so I invited him to bring his two young sons and come fishing with me on my boat one afternoon. Surprisingly, he took me up on it.
So, the day arrives. It's a great day—clear sky, the sun is shining. His kids were really excited. Well, we got out there and for 3 hours, we did not get one single bite. The sun was beating down on us. His kids were getting tired and cranky. My customer wasn't pissed or anything but he was clearly not having a good time. He asked if we could go back to shore and call it a day. I told him we would, but convinced him to just wait 20 more minutes while I drove us over to one last spot I knew usually had fish. I zipped us over to the other spot and we finally got a bite. The kids were yelling with excitement. I started reeling it in and could tell it was a big one. But I wanted to let one of the kids catch it. I kept reeling and got it close enough to the boat and gave the pole to one of the kids so he could finish it. As soon as I gave him the pole, the fish ripped it out of his hands and it went flying into the water and the fish got away. The kid started crying and I decided that was my cue to call it a day. I drove us back to shore and apologized to my customer. He was very cool about it and it didn't affect our relationship, but that was the last time I ever took a client out on the boat.
Anonymous Location withheld
—
This isn't necessarily a sales fail, but more of an example of my childhood friend making a bad decision. I sell kitchen remodels. This friend of mine wanted to remodel his kitchen (well, really, his wife did). I went over there one night to chat about what they wanted and to give them a quote. His wife pulled out these really rough designs that she had made herself. They were just sketches and weren't usable from a professional standpoint. She had this idea for an absolutely horrible polka-dotted backsplash with giant red dots, and when I saw it, I couldn't help but burst out laughing. She immediately looked pissed, so I composed myself and showed her some other nicer, more contemporary backsplash options.
I left and my friend got back to me 2 weeks later. He gave me an awkward call saying that he appreciated me giving them a discount but that they were going with a different company. I could tell by his tone that it was his wife's decision and it was probably because I had laughed at her design. I always felt like she hadn't liked me that much anyway, so this kind of confirmed it. When the remodel was completed, they threw a party to show off the new kitchen. I walked in and saw a polka dot backsplash. It looked much different than her original design, but it still looked pretty bad. I didn't want to cause any more trouble, so I lied and told them how great everything came out.
Anonymous Location withheld
—
This one's a lesson. I used to work selling equipment to ports and harbours back in the day when I was young and green. I landed a meeting with the Assistant Procurement Manager for a large European port on the back of successfully selling to a sister operation of theirs. So I drove several hours for this meeting, was greeted by this guy in reception, and was led by him into what I thought was going to be his little office. But instead, he led me into a conference room where they had the port CEO, the maintenance manager, their marine contractor etc etc — about 10 people in total.
I then got asked if I had a presentation to share with them, which I didn't because I'd rocked up with a brochure and a notepad to speak to one lower-level guy and then maybe, just maybe, get into a meeting like this a few months down the line if all went well. But it turned out to actually be that meeting...
I riffed through it as best I could, got a few nods here and there along the way, but realised I hadn't done the opportunity justice. And then on the way out the door I saw one of my competitors sitting in reception and it suddenly clicked that I'd been involved in a beauty pageant without even realising it. I didn't get the business, but since then, I always qualify who's going to be in the room and what the agenda looks like before I confirm a meeting so I can prepare properly, which has served me well.
Anonymous United Kingdom
