Sales Fails: Fancy dinners don't close deals.

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 cost me a $400k deal and a commission check that would have made my entire year. To this day, whenever I think about this deal, I get a sinking feeling in my stomach. This happened just a few years ago, when I was working for a SaaS company that was trying to go from SMB (small and mid-sized businesses) to enterprise. They were willing to invest in order to do that. I had never sold to any Fortune 500 companies before, so I felt a bit like a fish out of water. 

I ended up getting this qualified lead from a contact at a pretty big regional firm that was in the same state as us. The guy and I went back and forth about our software a bit, then my sales manager, who was also new to enterprise, told me to take the guy out to dinner and spend a few bucks (for which I’d be reimbursed), and try to make him feel important. 

I was kind of excited because I was going to have an expensive dinner on the company’s dime. The dinner went well, and the guy said he was looping his supervisor in on the deal, and that they would have an answer for us within a few weeks. 

A few weeks went by, and I had stayed in touch with the guy, but it felt like he was kind of stringing me along. Finally, I asked him to tell me if they couldn’t do the deal, that it was fine, and that I just wanted to know. He responded that he would be in my area later that week and asked if I wanted to meet him at a (different this time) restaurant. I said yes, got permission from my manager to cover it, and went to meet him after work that week.

Dinner was good, he seemed upbeat, and when we got to talking about business, he said, “I have great news… we got the approval and should be able to sign next week.” At that point, I was on cloud nine. I ordered another round of drinks and he and I talked about everything except business for another hour or so. That night I drove home in super high spirits. 

The next day I emailed him additional details and paperwork to get things rolling. He didn’t respond. Then he didn’t respond to my emails or calls for the next few days. Early the following week, I called him again, then emailed him (obviously I was worried by this point). Almost immediately I got an automatic response from his email address saying he was no longer with the company and instructions for getting in touch with somebody else. I had to start from scratch with the new point of contact, who talked to me for three weeks before politely declining to move forward.” 

Anonymous             California      

“Reading this newsletter reminds me of something that happened to me last year. I was (and still am) working remotely, using a home-office setup in one of our bedrooms. I have two screens set up at my desk, one for work, one for personal stuff, so that I can go look at non-work things when I have downtime throughout the day.

I was pitching a prospect when this happened. It was our first time meeting with each other, and we were doing a video call. He was an engineering manager, and I had done a presentation for someone who worked for him already and they had liked our product (software) and made the introduction. 

So the call was going fine. The prospect really wasn’t super responsive to my attempts to build rapport, but that’s not uncommon in my field – it’s usually all business. So I was about halfway through my presentation, and I had accidentally moved my cursor over to my non-work screen to get it out of the video chat. But I needed the cursor because I wanted to turn off my screen share. 

Unfortunately, my other screen had a paused video that was of a prank, and when I went to grab it, I unpaused the video right in the middle of three super loud maniacal screams. When it happened, I got super nervous and it took me a few seconds to shut the video off again.

Normally, a prospect would probably have found this amusing, but I don’t know if this guy was already having a bad day or what, but once I turned the video off he started to look around, then he mumbled something that I couldn’t make out and dropped out of the call. I actually couldn’t believe it. I tried calling him back, emailing him, and emailing the first guy I’d spoken to. Not a single one of them responded to my messages. Sales Fail! 

Anonymous             Location withheld    

“My first sales job was selling newspaper subscriptions over the phone. It was a lot of cold-calling, and a lot of getting hung-up on, but surprisingly, we used to close a pretty good amount of deals since this was before the internet and newspapers and magazines were a big thing back then. 

One day, I was calling a list of people who used to be subscribers but had canceled their subscription. We had a special offer pitch for them to get them to come back. I reached this guy who picked up the phone and said he would renew the subscription, but said that it was his office number and to call his house and his wife would handle it (he said he would let her know). He said: “Just call and ask for Jessica.” 

So I did what he told me, called the home number and asked for Jessica. The woman who picked up the phone was silent for like ten full seconds before she started screaming, “Who is this?! Who is this?!” I told her who it was and that her husband had told me to call. She said something like “Don’t you ever, EVER call here again, you son of a bitch,” and hung up. 

I chalked it up to some weird prank and didn’t think about it again until I got a call transferred to me. It was the guy I had originally talked to calling me back to scream at me too. He asked how the hell I knew the name Jessica and what right did I have to go intruding in their lives. So I told him that HE was the one who’d given me that name. Then he calmed down and said, “Listen son, I don’t know how old you are, but my advice is to never, ever get married.” Then he hung up and I never heard from either one of them again. 

Anonymous             Location withheld        

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