Sales Fails: "I made a joke while selling a car and the prospect walked out on me"

Andrew Lever/

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).

At a previous company, I had been assigned to work on an account with a large public company to partner on construction projects. When it came to my 'trade' and 'division,' I ran point for 3 years and got us deep into the account where we were negotiating and partnering with them for exclusive deals. They really had no idea what they were doing, and being a veteran in the industry, I walked them through every painful step so they could become a well oiled player in the market as a prime contractor and financier. 

So... we bid numerous projects with a school district and won. My sales counterpart with our partner company actually went in after we won some of the sites, and negotiated to get 30% more of the sites than we were going to be awarded. All was good, they were happy with us and I was partnered with a great sales counterpart. It was a great match. Despite my company realizing they mis-bid the project and giving price increases, I was able to maintain trust and rapport and keep things going cordially. 

Then my boss in all his wisdom decided to go meet with my sales counterpart in the partner company without me to 'schmooze' at a 'higher level.' During this shmooze session, he proceeded to tell my counterpart that I said that no one on their team knew what they were doing. Unbeknownst to me, I now had none of their team responding to calls or emails until I got a call from my counterpart who then proceeded to tell me that he told his whole team I was talking shit about them. My boss completely killed this account that took me 2-3 years to build trust and rapport with, and took more than 6-figures of commission out of my pocket for projects we were working on together. 

It was a really messed up situation — my boss basically shrugged and said 'oops.' Our group lost millions of dollars in revenue. My boss ended up being promoted in the organization and I eventually left when I raised other ethical issues. Anyhow, never let your boss talk to the customer if you can avoid it, unless they are seasoned salespeople and know what NOT to say.

Anonymous             San Diego, CA    

I work in car sales and have enough Sales Fails and other hilarious stories to fill a book. But the one that comes to mind happened a few years ago and still makes me laugh when I think about it. 

I like to joke with customers, and most of the time it works. I’m not a high-pressure salesman, and I don’t take myself too seriously. I’ve found that being playful can surprise people a bit because when they step on a car lot, a lot of them are expecting to be pressured and cajoled into buying. I don’t do that, and it’s worked for me over a long and illustrious career. 

One day, a woman came in with her husband to look for a used truck. They were friendly but maybe a bit on the quiet side. It was a weekday so we weren’t very busy. I showed them a truck the husband had spotted from the street, but when they found out it was RWD, they asked to see some other options. 

I guided them to a nice-looking Silverado we’d just taken in on trade. The husband seemed to like it and was looking at it very carefully. He was in the cabin, but the wife was walking around the exterior. When she got to the tailgate, she stopped and said, “excuse me.” I walked over, knowing exactly what she was going to say.

She pointed to the right side of the tailgate, where there was a pretty deep scratch running vertically all the way to the top of it. “What is this?” she asked, as if she had never seen a scratch before. “Well ma’am,” I said, trying not to smile. “That’s actually a designer scratch. People pay extra for that.” 

And that, my friends, was all she wrote. The woman glared at me, then immediately called to her husband and said, “Let’s go. I don’t think this business is interested in making a sale today.” I’m sure everybody reading will say how unprofessional I am and that I cost myself a deal, and they’re right. But this was the rare occasion when being a bit playful and silly backfired. It actually usually works!  

Anonymous             Location Withheld    

This happened to me at an old job but I'll never forget it. I was selling software to SMBs. I had spent three weeks working with a prospect who was finally ready to buy. He was really annoying throughout the entire process and kept saying he was looking for “a partner he could trust.” No matter how many times I tried to reassure him, he kept saying this. 

Anyway, I finally emailed him the paperwork. It was the new standard template we had been using for the last few weeks. But it turns out that the page numbers at the bottom of the paperwork were wrong. The last page always said 'Page 8 of 9'. There was no page 9. I hadn't noticed it and no one had said anything before.

As soon as I emailed him the paperwork, he emailed me back and asked where the 9th page was. I was surprised and apologized profusely, telling him it was a mistake and it was a new proposal template our company just started using and that I would send him an updated document ASAP. He got all flustered and emailed me back saying that he doesn't do business with shady people. I never heard from him again; he completely ghosted me. 

It was an honest mistake, but he really thought I was trying to pull something over on him. I talked to legal and got it fixed the next day. I still can't believe I lost a deal over something so silly, but now I ALWAYS check the page numbers on proposals before sending them out.

Anonymous             Location Withheld   

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