Sales Fails: "I made a joke about a prospect's favorite sports team and he kicked me out of his office"

Roman Samborskyi/

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I still laugh about this one. Pre-Covid, I used to work in outside sales as a vendor in a pretty specific industry. One time, I was nearing the end of my day, and I had time for one last drop-in before businesses started tying things up for the day. I decided to stop at a one-man shop where I'd been before, knowing we'd had a decent conversation about our MLB teams' rivalry last time I was in and that maybe this time he'd have an opportunity to send some business my way.

When I dropped in, he was on the phone, but he recognized me and waved me in while he finished up his call. Once he was done, we started talking about his family, how his kids were doing, etc., and, since it was near the end of the MLB season, we started talking about how playoffs were shaping up. 

This guy knew his team wasn't going to the playoffs (and that my team was) and started to randomly get REALLY agitated. I never once bragged about my own team or said anything bad about his team or anything, but he apparently took his team's bad season personally. At one point, he accused fans of my team of not being able to read. I said, "Excuse me?" And he followed up with, "Well it's obvious, since you clearly couldn't read the 'No soliciting' sign on my door. You can get the f$*! out of my office," and ripped up my business card on his desk.

As soon as I left, I called our local office and told them to blacklist his business in our CRM, so none of our AEs would have to deal with his attitude. I spent the whole drive home on the phone with a coworker in another territory laughing about the whole incident. Four years later, I'm pretty sure this guy went out of business anyway, so it wasn't much of a lost cause.

Anonymous             St. Louis, MO   

My very first day in sales was my most memorable Sales Fail. I still remember it like it was yesterday. It was early 2001, I was 23 years old, just starting out in sales after college working for a wine and beer distributor. I was on my first day in the field, learning my new route of grocery and package stores, while shadowing the rep that was getting promoted. When we arrived at our biggest account, as we got out of the car, he said, "If he asks, DO NOT tell the buyer you’re a rookie." This was the most important account I was inheriting, which had a lot of experienced competitor reps. The buyer was brutal to reps with no experience, and just tough to sell to in general. 

Well, we walk in and do our introductions in his office, and the first thing he asks me:

Buyer: "Did you work for another distributor before this job?"

Me: "Yes"

Buyer: "In this area?"

Me: "No, in Kansas."

I totally made that up on the fly. I have no idea why I said Kansas, but I wasn't about to let him know that it was my first day in sales! The incumbent rep I was with looked at me like he had just seen a ghost. I somehow got through that first encounter without the buyer digging into my shady answer. 

I proceeded to race home after work, then jump on my dial-up internet to find and research wine/beer distributors in Kansas for the next couple of hours to cover all my bases, in case he asked me for more details the next time we met! I’ve never felt more sick to my stomach. Luckily, it never came up again, and I did very well on the account for the next couple of years. 

To this day, I still can't believe I told him I worked for a distributor in Kansas *facepalm*

Anonymous             Atlanta, GA   


Back in the early 2000s, I was part owner of a mobile electronics company. Basically, we installed all sorts of electronics into cars and trucks. Stereos, alarms, remote car starters, navigation systems, etc. Back then, it was a pretty good business before cars started putting in all that stuff standard. 

One day, this young woman came in with an older guy. She couldn’t have been older than twenty, but he was well in his forties or older. He basically told her to pick out anything she wanted, and that he’d be the one paying for it. She was driving a new Honda Civic, but he talked her into the top of the line speakers, full navigation system, the works. It was obvious he was trying to impress her. 

So he put down the deposit for all the work, which literally cost over 7k. It was way over-the-top, but we weren’t going to talk him out of it. We installed everything, and had the car for almost a week. When it came time to pick it up, she showed up at our shop and was in tears. She told us that she had gotten in a huge fight with the guy, and that he refused to pay for anything else. 

My business partner, who owned the majority of the business, was super pissed, and he wouldn’t budge or give this girl a break. So we basically refused to give her her vehicle back until she could come up with some money. She ended up bringing us a few grand and we agreed to release the vehicle to her, but she still owed us another 3 or 4 thousand. 

We spent the next two months basically hounding her to pay what she owed, and tried to get ahold of the guy too, who apparently ended up being some sort of scam artist. Finally, when my business partner threatened to have her car repossessed, she showed up at the shop with her father, who was (rightly) incredibly pissed off, and he paid off her balance. Still the wildest sale I’ve ever made. 

Anonymous             Location withheld 

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