Sales Fails: "I photoshopped my sales manager's head on someone else's body... and he saw it"

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).

“My biggest sales fail ever was when I worked at a big telecom company (you’d know it) in a huge call center. We had inbound and outbound sales reps there as well as customer service on one giant floor. 

My sales manager was this guy who was pretty short. He was probably just over five feet tall. And he took himself really seriously. He had apparently switched careers a few years earlier, and had quit whatever he was doing (I think it was law but I can’t remember) and was trying to work his way up in the company, so he was all business all the time. He wasn’t a bad guy, but he just didn’t really build any relationships with any of us reps.  

Me and a few of the other guys used to email funny pictures back and forth. This was before memes were called memes, and before we had interoffice messaging software. One day, someone had sent over a funny photo of a little kid playing basketball against a full-grown man, and the kid was crossing up the adult, but the two people’s faces were photoshopped as celebrities (I forget which ones). 

I figured this picture was ripe for remaking, so I edited a photo of my sales manager’s face onto the kid’s body, and a photo of one of our tall coworker’s faces onto the adult. I sent it off to three other people and sat back and waited for a response. An hour later, one of the guys I sent it to comes over to my desk, and he’s totally stone-faced. He whispers to me that the manager was walking by when he opened the email and stopped and saw it. He said he tried to close the window but the manager asked him to pull it back up and when he saw it asked who had sent it to him, and clearly saw that it had been me. 

But here’s the weirdest part of the whole situation: I never heard another word about it. The manager never pulled me aside, never sent an email, and never changed the way he behaved towards me. He just continued on as if nothing had happened, no better and no worse. I ended up leaving that company but he’s still there and it looks like he’s a regional VP now.” 

Anonymous, 38               Location withheld  

“I used to sell tutoring services for a company that focused on high-end clientele – basically, the children of very rich people who wanted to make sure their kids weren’t falling behind their peers. I didn’t have the job for long, less than nine months, since there was literally no career advancement whatsoever. The two owners made a ton of money and paid us just enough not to leave (which obviously didn’t work in my case).

One day, I was talking to a guy who I think worked in finance, and he was interested in signing up his son for our program. Our pricing was flexible on the upside, which meant that we could charge more (assuming we could close the deal) in order to earn a bigger commission. I knew this guy was loaded, so I quoted him a price at the higher end of the scale. 

Apparently, though, he really liked negotiating, so we went back and forth for a while, where he tried to get me to come down on the price. I think it was more of a game for him than anything else, but he was aggressive about it, responding via email with short paragraphs justifying a lower price. 

Finally, I told him this was the lowest we could go, and that I really hoped we could earn his business. He responded to send the contract over, and I sent him what I thought was the contract with the correct price. But in my hurry, I’d sent him a contract for another client, who literally bought the same exact package for ten percent less a few weeks earlier. I caught it less than ten minutes later, and resent the right contract and told him to disregard the other email, but he had already opened and viewed the other contract. 

He responded to my email and said that he appreciated my time, but that he couldn’t do business with a “dishonest broker.” Cost myself a few thousand bucks by being too hasty. Now I always, always double-check the contract! 

Anonymous, 27               New York  

A while back I was selling big enterprise tech contracts for customized software projects. I had been talking to this prospect that was referred to me by another customer. It was a whale of a deal. They were super excited during the first call. Decision maker, budget approved, had an immediate need for our services. It was a home run. After the second call he asked me to send over a contract, so I sent over our standard agreement.

He didn’t answer for over a week, which isn’t unusual, but seemed odd for this guy who was so excited about getting started right away. So I sent a follow up email and he immediately messaged me back, but the tone was entirely different. He had flipped his negotiator switch on and was super combative and started asking for a bunch of considerations and special agreements in the contract, some of which were completely absurd. 

For instance, he wanted to have the legal ability to audit any internal communications regarding his project at his request, meaning our internal chat logs. He also requested the personal phone number of our CTO  as well as the project manager who would be in charge of his implementation, so he could contact them at all hours of the day, and said that this was because he traveled so much that he needed someone who would be available. 

I ended up spending so much time going back and forth playing telephone between him, our legal team, and my sales manager trying to get the deal done that I missed my quota for the month because this guy had me running around like a madman.

I ended up closing the deal three months later, but this guy made me miss my quota for the first time in over 8 months.

Anonymous               Location withheld  

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