(reading time: 5 minutes)

Sales is an exciting profession. Most current and former salespeople can point to quite a few situations they’ve been through or witnessed in their careers that make for crazy stories. Because of the fast-paced nature of the business and the fact that you regularly deal with so many different people, fascinating and bizarre things tend to happen.

This is especially true when it comes to closing deals. We wanted to hear some of the craziest things salespeople have ever done to close a deal, so we asked the Sales Humor audience on Facebook to share their craziest close stories. And we’ve picked the ten craziest ones for you. If you have any stories of your own that can top these, leave a reply below!

(Editor’s Note: these answers have been edited for grammar and clarity, and we have withheld the names to protect the innocent (or guilty) parties.)

1. Duck Catcher

“I was told that if I could catch a duck in some woman’s garden, then she would sign up, so i became professional duck catcher…It only took me like 2 seconds.”

2. Take Your Best Shot

“I used to sell military spec cell phones (Nextel). I would tell contractors that if they can break the phone in one shot they would get it for free. (This is back when phones cost three grand!)…. But if it makes a phone call after you take your best shot, you have to buy 10. It always worked. I had a few people back out, but it was always good fun and always resulted in getting the deal. I also used to drive 16 penny nails with the phone.”

3. Operation Vacuum Drop

“I was selling Kirby vacuums and a wife was purchasing the unit without her husband. She wanted to keep the sale a secret from him. So she signed the paper work and asked us to take the unit with us and to come back at 9pm when she knew he’d be asleep. I called her on the way back to her home and she said that he’s still awake, and is there any way you can hide it in the bushes in front of the house? So I said for sure we can. We pull up and the way their home is set up, the couch was backed up against their front window, so his back was towards us. We put the shampooer in the bushes and he peeked out of the window. We ducked into the bushes to wait for him to turn back around and ran back to get the vacuum. As we were approaching the house again he got up and not knowing where he went we threw the vacuum into the bushes and took off! I never heard from them at all or anything!”

4. The Pink Ride

“A couple of years ago our store all wore pink Harley Davidson shirts for breast cancer awareness and I was pretty new to the company. I was working with an older gentleman who wanted to buy a Trike. He wanted to test ride it but didn’t have his license, so my boss told me to meet him at the back door. I rode the trike over there and picked him up! I drove him around on it and he came back and loved it! He came back and bought the trike! I’m pretty sure that my boss still has a picture of me with him on the back and wearing a bright pink shirt! Got the sale though!”

5. The Promise

“I was talking to a prospect over the phone, pulling out all the stops to get him to commit and he was convinced I was pulling his leg in order to get him in the door. So I asked him “What can I say to prove to you that this is the real deal?” He proceeded to say, “There is probably no way to convince me you’re not lying. I’ve been burned by people lying to me to get me in the door in the past.” I replied, “If it turns out I am lying to you, Mike, you can come into my office and punch me right in the face!” In less than 1 minute he pulled out his wallet and gave me his credit card number to give his a deposit. I had another salesman come in to my office after I hung up the phone and say to me “I really thought you had no chance of getting him to commit. That you can punch me right in the face line had me laughing pretty hard.” Sometimes the craziest things actually work!”

6. Sandal Blackmail

“I had a customer that was interested in a car on our lot. He wasn’t ready to make a decision, wanted me to hold the car, but wasn’t committed enough to put money down to hold the car. I was a little frustrated because I had spent so much time with him. I placed a bag on the counter and stapled what paperwork I had on it, opened it, and told him “I’ll hold the car for a couple days if you place your sandals in the bag. I will hold them as collateral.” To this day, I don’t know how I said that with a straight face. The look of confusion on his face will never be forgotten. I really just wanted to see if he’d walk out of the dealership barefoot after burning 2 hours of my time. Well, he did and two days later he returned and rolled off the lot with that car.”

7. Whatever it takes

“While working a cell phone sales job at a call center, I had a minor heart attack in the middle of a call, closed the sale, and went to the bathroom, was in there almost 2 hours, passed out…”

8. The Terminator

“I cyber stalked a prospect and over a period of months I sent him an escalating series of emails/voicemails that were Terminator themed, pretending to be him from the future. In the future the technology that his company was standardized on was destroyed when lizard men invaded and his company’s stores color scheme was the only color scheme that was invisible to the lizard men. So if he standardized on our technology now we would have the advantage in the future. Because in the future he was the sole leader of the resistance and he was trying desperately to get a message back.

I even went so far as to include sound effects in the voicemails. It was a huge hit because he was a huge nerd like me and loved Terminator. When we connected he had moved in the company and was no longer the IT decision maker but promised to get me a list of the current IT decision makers. He then went dark and I proceeded to hit him with a series of Fast and the Furious voicemails where I was Paul Walker’s character in every movie and I needed the list of IT decision makers in order to solve the plot of the movie and to get Dominic Torreto to trust me, I had to get the list… we ended up becoming friends and the reason he went dark was because he left his company. To the day, we still chat.”

I recorded most of the Vmails here:


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About the Author Ken Kupchik

Ken Kupchik is the creator of Sales Humor and the author of the funniest sales book ever written, The Sales Survival Handbook, which you can order on Amazon.com. Connect with him on LinkedIn.

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