Sales Fails: I tried to engage with a prospect's social media account. It backfired spectacularly.

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).

“This happened a year ago. I was working B2B SaaS sales -- marketing software. My sales manager had always encouraged us to engage with our prospects on social media, so when I was working a seventy-seat deal, trying to land a large auto insurance broker, I followed their Facebook and LinkedIn pages and began interacting with them. In one post, they shared a picture of one of their employees standing in front of a hospital with the caption, “Congratulations to [employee’s name] for completing his last round of cancer treatment.” So I clicked the “care” reaction on Facebook and went about my day. Later that afternoon, my sales manager called me into his office; He looked like he’d seen a ghost. It turns out, I had accidentally clicked the “laugh” reaction and left it up. I sent them an apology email right away. Needless to say, we didn’t get the deal.” 

Embarrassed, 34      Rolling Meadows, IL 


“I have been in the mortgage industry for almost two decades. A few years back, a woman called in who wanted to do a cash-out refinance of her home. She and her husband were pulling out almost forty grand, and the money was going to remodel a bathroom and pay off about twenty thousand dollars in credit card debt. She was really easy-going and fun to talk to. She would joke about playing a ton of scratch tickets and talked about how she always used a nickel to scratch, and that you should never use any other coin. 

“Anyway, the process went well. She sent us all the docs we needed, and her appraisal came back right on target. Finally, it was time for the closing. We had her come into the office to do the paperwork. I decided to sit in with her, her husband, and the attorneys since she was my customer. She was really friendly but looked different than I expected (people always look different than they sound over the phone) but her husband wasn’t super friendly. I don’t think he trusted mortgage companies (this was after 2008). 

“So they were both signing the paperwork, and everything was going fine until they got to the page that showed the breakdown of where the cash-out was going. We, as the lender, were going to pay off the credit card debt directly, so everything was spelled out in the document. Her husband takes one look at it and says, “What’s this?” and she says, “Honey, just sign it. Just sign it. Don’t make a scene.” It becomes obvious that he had no idea that his wife had racked up all this credit card debt. She asked us to give them a minute, so we left and listened to them screaming at each other from outside the room. Finally, she called us back in and they signed the paperwork. The husband didn’t make a single peep the rest of the time, and left the second he was done signing. She apologized on her way out and looked like she was going to cry. I never heard from her again.” 

Anonymous, 46   Connecticut 


“Early in my career, I was selling insurance -- inside sales, phone job. One month, when I happened to be struggling, this older guy called in. He was super talkative and was telling me about life in Vegas back in the fifties, and how you could make so much money in real estate. So we start talking about how many residential apartment buildings he owns and how he wants to switch all the policies over, and even about changing out his life insurance plan, and I’m thinking I’m about to make my whole quarter off this deal, so I’m thrilled. I spent four hours on the phone with him, convinced I’m gonna close it. 

We finished the call, but I didn’t hear back from him the next day like we planned. So I called the number he gave me a bunch of times with no answer. Eventually, I figured out which number he had actually called me from and called THAT one. Turns out, the number was to a nursing home and the poor guy suffered from advanced dementia and somehow got ahold of a phone line and started dialing out. Needless to say, it did not close.“

Anonymous, 44  Littleton, CO

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