The following nine stories come from various sources, most notably Dan Seidman's classic book The Death of 20th Century Selling: 50 Hilarious Sales Blunders and How You Can Profit From Them.
I've retold all nine stories in the first person, which is how most of them were originally related to me.
1. The Strip Tease
I discovered that my pen had leaked onto my shirt just as I stepped out of my car at a customer site, late for an important meeting. Cursing, I tore off the stained shirt, threw it in the bushes, and replaced it with one from my suitcase. When I got to the meeting, turns out the waiting customers had seen the whole thing through the conference room window and my stained shirt was in plain view on the bush outside.
2. Mr. Helpful
I brought a marketing manager to a customer meeting, expecting a presentation on a new set of products. Instead, what I got was a presentation the consisted of reasons why the product couldn't be built based upon the inability of the marketing group to decide on what kind of product we should be building.
3. The Volcano
I took my sales manager with me on a sales call to answer any question that I couldn't answer. However, rather than staying in the background, he kept interrupting and eventually got into a screaming match with the customer. After the meeting ended (disastrously), the manager said that he still expected me to make quota that quarter.
4. Mr. Helpful, Part 2
I brought along one of our engineers to answer technical questions but every time I was about to close the sale, the engineer, trying to be helpful, would pipe in with: "Or we could also do it this other way..." thereby reopening the discussion. The third time this happened, I could see that the client was getting annoyed, so I ended the meeting without closing the sale.
5. The Conflict
I proposed the next step in my sales proposal, but there was something about the idea that surfaced an internal issue and the customers began fighting among themselves. The discussion quickly spiraled out of control until, finally, a couple of them stormed out of the room. Guess who got blamed for the conflict?
6. Dead Ringer
I was chatting with the customer about television shows. Since we were both from the Midwest, it turned out we both liked Drew Carey. I said, "Gee, it's amazing that guy could be so popular given that he's so ugly. Then I remembered what I should have noticed earlier--that the customer looked like Drew Carey.
7. Mistaken Identity
I was meeting with a customer for the first time in his office and spotted a photo of him with his arm around sports personality John Madden. Looking for something to break the ice, I asked: "How did you ever get your picture taken with John Madden?" The customer replied: "That's my wife."
8. Smoking Gun
I was using the restroom on the ground floor of a tall office building prior to an appointment with a new potential customer on the eighth floor. A guy comes in the restroom with a burning cigarette, so I have him the stink-eye and asked him, not too politely, to put out the cigarette. Guess who the meeting was with?
9. Colorful Mistake
I was going on a sales call with a colleague and on the way we stopped at a 7-11 and, for some reason, we decided to order Slurpees. We finished the drinks off just as we entered the building. When we sat down with the customers and began to speak, we realized that my tongue was bright blue and my colleague's tongue was bright green.