The Worst Sales Horror Stories

The thought of working in sales can be scary. Fear of rejection, fear of uncertainty, and fear of prospecting keeps many people out of sales jobs, and quickly weeds out many of those brave enough to try. 

For those who choose to make sales their profession, overcoming their fears doesn't mean that they don't have terrifying moments. We asked reps to share their worst horror stories, and picked the most mortifying ones below. The names have been withheld to protect the innocent, as well as the guilty...

Legal Troubles
"I was signing a contract with a law firm and the principal decided to bring in all of the interns and junior associates to pick apart the sales contract, ask what every single sentence meant, and then had them cross out our verbiage and manually rewrite clauses, asking me to initial each one as they went along. My worst nightmare."

The Wet Close
"I sell hot tubs. While showing a client a filled, working spa, I reached over to adjust some settings and went in head first into the hot tub. Without missing a beat, I looked up and said, "And that's how you don't get in!" Needless to say, I think they bought the unit from me out of pity when I continued to make the sale in my soaking wet clothes." 

Foot in Mouth
"When I was pregnant and selling, I went to help a couple who just walked in and opened with "Awww, how far along are you? I'm 6 months!" The wife's response; " I'M NOT PREGNANT!!" I walked away and got them another salesman. 😐"

Fur-ballin'
"I tried to impress one of my first ever home visit customers by building rapport with the whole family. The little daughter was playing in the next room with a ball and when it rolled towards me, I playfully kicked it back to her. As the kids started screaming, I was quickly told to get out of the house and forget the sale. 

I'd never seen a hamster ball before, how was I to know?!"

Who Let the Birds Out?
"I was talking to a new lead on the phone, arranging a deal, when suddenly, I hear a single big 'SKWAK!' followed by a chorus of skwaking and flapping. I hear him shout 'Oh sh*t!! The birds are out!' Then, the line goes dead and I never hear from him again. It's not really a sales horror story but I've been waiting for an opportunity to tell it."

The Great Escape
"I went in to sell a uniform contract and didn't know we were suing the owner for breaking his contact a few years before. He chased me with a tire iron and threw it at my car as I drove away!"

Bad Timing 
"On my very first solo outside sales call, I knew nothing about my product and I was nervous as hell. I told myself, "What's the worst that could happen?" and walked in the door. A sobbing lady darts past me, carrying a box and an envelope. The entire firm was in the process of being laid off or relocated, while I was standing there with brochures and a box of donuts. It was a proper welcome to the Oil & Gas industry."

Little Old Lady from Pasadena
"I've been a professional car salesman at the same dealer for almost 5 years, and I've seen a lot. The strangest was a sweet, but senile, old lady named Virginia. 

She drove up in a silver 2001 Lincoln Town Car. She said that demons had possessed that car and 'the man in the radio' had told her to buy a new one. I was a little perplexed, but I agreed to show her a (new at the time) 2011 Lincoln Town Car in silver. She immediately fell in love with it and said she wanted to test drive it.

I felt a little awkward about the whole thing but nevertheless, I asked her for her driver's license. It was current and valid, so I got the keys. She started the car, drove it across the parking lot, and stopped when she saw her current 2001 TC sitting in the parking lot and says "Hey! There's a silver one! Can we drive that one?"

Now I'm really confused. I remind her that the car she is now pointing to is her car, and we are test driving a new silver one. She says "Oh, ok. We'll drive that one when we get back."

Now I'm feeling really uncomfortable so I ask her to stay stopped for a moment. I call my sales manager and explain to him what's going on. In typical manager style, he tells me to proceed with the drive, if I think there's a chance she'll buy, but not to leave the general area or go on any freeways. We leave the lot and pull up to a busy intersection. While we are waiting for a green light she starts asking me if this car has any bad demons. I chuckle a little bit but say absolutely not, it's a brand new car.

The light turns green, and we proceed down a busy main road at about 20 mph (Speed Limit 45). She won't go any faster. Cars are flying around us blaring their horns. I tell her to ignore them and focus on driving at a safe speed. She gets to about 30 mph.
We are cruising along at 30 mph (while still annoying all of the traffic around us) when she suddenly, for no reason, slams on the brakes. Luckily, there were no cars behind us because there surely would have been a collision.


I politely ask her to pull over to the side of the road. She asks me why and I tell her that there are some feature I want to show her. She pulls off the road. We both get out, and I jump in the driver's side seat and say "Ok Virginia, I'm going to show you some cool stuff,  hop in, I'll drive." As I drive us back to the dealership, I start pointing out the ride, the radio, the steering, all while she's being very quiet.

I pull up at the dealership, walk her inside and then tell my sales manager what went on. He admits that it seems very strange and comes out to talk to her. When he walks out, she tells him that she wants to buy the car which of course is music to his ears. He looks at me and says, "What's the big deal? Sell her the car."


At this point, I simply don't feel right about it. I ask her if she is absolutely sure that she wants to buy a brand new car today. She says "Yes, I'd love to. Do you have any silver Town Cars?" I explain that we just got back from a test drive in a silver Town Car. She doesn't believe me and wants to see a new silver Town Car.

I called the police and explained that she seemed very confused and probably should not be driving. They came down to the dealership to meet her, and that's when we found out that she had gone missing from an institute not too far away. They had no idea how she got the 2001 Town Car. It was reported stolen by a family in town with no relation to her!"





Vidya is the head of marketing for AppMesh, the makers of SalesMesh. Prior to joining AppMesh, she worked for Salesforce. Her favorite sales movie is Tommy Boy.

SalesMesh is the personal CRM/sales app that works the way you sell. Automatically track customer interactions, notes, schedule follow-ups, collaborate with your network, sync to and from Salesforce all from your iPhone and iPad -- even when you're offline. Learn more here.
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