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).

‍

About fourteen years ago, I was a year or two out of college and was looking for a new sales job. My friend worked for a regional telecom company that sold phone and internet services to small businesses. It was an outside sales role. I met with the manager for the first round of the interview and for the second round, I was supposed to go out prospecting with one of their reps to see how everything worked.

He and I met at the office and drove to a small downtown where we knocked on some doors. I wasn’t crazy about the job or product but I needed money so I was thinking I would take the job if they offered it to me. For lunch, we went to a diner and I ordered a bunch of heavy, greasy breakfast food like pancakes and sausage and things like that.    

‍

After lunch, he wanted to stop by his house, which was not far from the town and the office. When we got there, we hung out in the living room for a little while. I think the only reason he was comfortable having me there was because I was friends with his coworker (the one who got me the interview). Well, I had eaten so much food that after sitting on his recliner for a while, I started to doze off and fell asleep. 

‍

For some reason, he didn’t want to wake me up and he went back out prospecting for the afternoon without me. I called him when I woke up and he said to just hang out until he got back. He picked me up and we went back to the office. A few days later, I got a call from the manager who said he didn’t have any open positions at this time but that he’d get back in touch when something opened up. There’s no doubt in my mind that the other guy told him I fell asleep in the middle of the workday. But all he had to do was wake me up! Anyway, I found another job and I’m still in sales. 

‍

Anonymous      Location withheld 

‍

—

‍

Love this column, I've got a funny one that happened to me a few years back. I worked for a pro sports team doing ticket sales. I sold season ticket packages, so I was often selling to the same people who buy tickets every year so I got to know some of the diehards who were long-time season ticket holders. 

‍

I was having a good year, we were pretty much sold out before the season started. One morning I got a push notification to my phone from ESPN - our star player got traded in a deal for some supporting cast type players and draft picks. I could feel the impending doom floating over me as I read the article. Then the emails started flowing in. People who had already paid for their season tickets started asking to cancel. One big time corporate guy who had a company box suite for the last 4 years called me up and started ranting about how he wasn't going to take his clients to see "a bunch of bums have a losing season." I tried to talk him down but he was pretty adamant. He said he would keep the box, but wanted a 50% discount. 

‍

We were in full crisis mode. I talked to our GM of ticket sales and he let me do a 10% discount for the guy and my other unhappy clients. Some of them stayed but the corporate guy stuck to his guns and didn't renew his box suite. As the season started the box was still empty. My boss ended up giving me clearance to sell the box at a 50% discount as it was just sitting there making no money. I called the corporate guy to let him know, but he didn't want it because the team started the season with a pretty bad losing record. I did end up selling the box to another company, at the 50% discount, but they didn't renew it for the next season. I ended up struggling to sell box suites for the next few seasons and eventually left and got out of the ticket selling game.

‍

Anonymous      Location withheld 

‍

—

‍

Here is the story of how I lost the biggest deal of my life. I can look back on it now and laugh, but at the time, I was miserable. It was going to be a life-changing amount of money for me and when it collapsed, I felt like a loser who had failed at one of their big shots in life. 

‍

This was close to fifteen years ago, when I was still a young-ish pup. The deal in question was a very big contract which would have paid me over $200k in one shot. At that point in my life, I had never made more than just over $100k in a year, so this would be my chance to pay off my student loans, buy a house, and basically do all the things I’d been dreaming about for years. 

‍

It also blew up in the worst way possible, at the last minute. We had literally sent over the contracts to sign and I traveled to the company’s headquarters to make sure I was there to answer any final questions and that everything would go off without a hitch. When I got there, they kept me in the waiting room for hours, which made me start to think that something was wrong.

‍

Eventually, they sent some random person who I’d never met before into the room to talk to me. The executive who I had been dealing with wouldn’t even answer my calls. The person they sent was like a robot. He looked at me with dead eyes and said that unfortunately, there had been a last-minute change of plans and that they were going to “delay” signing the contract. Of course, this gave me hope, but I would soon find out the only reason he put it that way was to get me out of there with as little drama as possible. 

‍

In reality, some high up executive had vetoed the deal at the last minute, probably to save money, even though we had a good product. The worst part of how everything went down was the lack of transparency, and the fact that nobody had the guts to just tell me they were pulling the plug. But it was a learning experience in itself too. I know that if I got through that and got back on the horse, I can do it again and again if I have to. I still remember how my heart sank though. What an awful feeling.    

‍

Anonymous      Location withheld