Sales Fails: I accepted an indecent proposal from a prospect -- even though I closed the deal, I still regret 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).

“Not sure if this is really a sales fail but about ten years ago, I worked for a large mortgage company doing inside sales. I was trying to get promoted to sales manager, and was busting my ass. One day, our regional Vice President came in for a meeting with the branch manager. This was a guy that everybody was deathly afraid of even though he was literally five feet tall, no joke. 

Anyways, they were meeting behind closed doors, then one of the managers popped out and called me over and asked me if I could go pick up lunch for them since we didn’t have a secretary or assistant in the office. Of course I said yes, then took their order, and the regional asked for a chicken salad wrap with no onions, adding that he definitely didn’t want onions in his wrap. The branch manager hands me a few twenties and I go pick up the food up the street, stressing to the cashier that I don’t want onions in the wrap. I head back and give the managers the food and they close the door again. Within a few minutes, I got an instant message from the branch manager telling me the wrap had onions and the regional manager refused to eat it and declined an offer for another one. 

When he was leaving that night, the regional gave me a blank stare as he walked by my desk. A few weeks later, I lost out on the team manager position to another guy. Can’t help thinking it was because of the onions, but who knows.” 

Anonymous, 41        Calabasas, CA

“This might not be a Sales Fail per se, but it happened when I was working in sales. I had an inside sales job in my early 20’s. It was basically a call center with about twenty to thirty of us, mostly guys, sitting in an open office. There was a lot of ball-busting, but generally, most of us got along pretty well. 

There was this one guy who worked with us, and it was his first sales job, but he was an absolute pathological liar. He would tell these grandiose stories about how his family owned manufacturing plants in Italy, and how he was descended from royalty (seriously). He would lie about little things too. For instance, he had a Movado watch, which was just a regular Movado (I was into watches back then), but when he showed it to me, he said it was a limited edition and one of only twenty-five released in the states. He was a nice guy overall, but there was definitely something going on with him. 

Anyway, one night we were working pretty late, but we were kind of just sitting around and bullshitting instead of working. It was me, the guy who was a pathological liar, and another guy who sat near us all sitting at our desks talking. The one who was a liar started telling us this elaborate story about how he was a majority owner in a commercial real estate business in New Jersey (mind you, we were basically entry-level inside sales reps at this time) and how they were looking to purchase a skyscraper in Manhattan. 

So I sent a message to the other guy who was part of the conversation through the company chat, and said something like “Man, this guy is so full of shit.” Well, as you can guess, I accidentally sent it to the pathological liar, who saw it pop up on his screen. His face turned super red and he looked at me, so I tried to play it off and say that I was talking about a prospect that I’d been chasing. I’m not sure if he bought it but he didn’t give me a hard time or anything. But after that, I don’t remember him telling me any other stories, even though he was still nice to me. We’re still friends on Facebook – I think he does actually own a small jewelry business now.” 

Anonymous, 36    New Jersey  

“I work for an ad agency now, but in my early 20’s, before going back to school, I spent a year in car sales, selling Nissans. A few months into the job, a guy came in to look at a truck. From what I remember, he was in his mid 40’s, pretty soft-spoken, and really, nice. 

Anyway, he didn’t buy on the first day, and he was definitely one of those people who did a lot of research before agreeing to anything – not a clipboard guy or anything, but probably had a spreadsheet somewhere on his computer. So he called me a few times to ask questions, before finally agreeing to come in to test drive a base-level Frontier.

So he makes an appointment and comes in, but then starts looking at a fully-loaded Frontier that we had parked near the entrance. I figure there’s no way he’s going to buy it, but when we get to my desk, he looks at me and makes an offer. He says that if I agree to go on a date with him, he’ll not only buy that day, but he’ll buy the fully-loaded truck (bigger commission in this case). 

In retrospect, I should never have agreed to do it, and if it happened today, I would absolutely say no, and would call it out as completely inappropriate, but I was young and dumb, and was still making plenty of mistakes in my life, so I agreed to go on a date with this guy who was twenty years older than me. He ended up taking me to dinner at a really nice restaurant, and had a nice conversation, but I definitely wasn’t interested in anything romantic with him. 

At the end of the night, I gave him one of those hugs where you stick your butt out so you don’t get too close. But he was nice about everything and didn’t try to bother me again. So I guess since he bought the truck, it’s not exactly a Sales Fail, but I definitely look back on it and cringe.” 

Anonymous, 30    Arizona

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