Sales Fails: I made fun of a prospect's handwriting. It did NOT go over well.

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“Years ago, when I first got into sales, I was working for a heavy equipment manufacturer. A guy who I had only spoken to on the phone came in and brought in some paperwork I’d sent him to fill out. He was friendly enough and we were bantering a little bit about the neighborhood our building was in (it was in a bad area), and he was making jokes about it, so when I looked at his paperwork and saw the handwriting, I made a joke about how bad it was, comparing it to a doctor’s scribbles. All of a sudden, he stiffened up, looked me right in the eye and responded, “I have Parkinson’s.” I’ve never wanted to crawl in a hole as badly in my life. I couldn’t apologize enough. He said it was ok, but for the rest of his time there, it was all business.” 

Anonymous, 46      Dallas, TX


“I’m in SaaS sales, and we mostly sell to other SaaS companies. One day I got a call from a prospect (a CMO) I’d been working with who told me he was still really interested, he just wanted to hear the entire pitch again from start to finish. So I went through everything in detail, then he started asking really specific questions, and started digging real deep. This went on for literally hours, then finally I sent him the contract via DocuSign and asked if I could walk him through the signing process on the phone. All of a sudden, he bursts out laughing and hangs up on me, then refuses to answer my calls. A half hour later, I get an email response to the contract with just four question marks. We go back and forth by email for a few minutes before it becomes clear that the CMO had never called me and that he had no interest in moving forward. Totally bizarre. A few weeks later I found out that one of our sales reps who had been fired was calling the sales team and pranking them to try to get back at the managers who’d fired him. He even ordered three dozen pizzas to the office. They had legal send him a cease and desist letter before it finally stopped. I still felt like an idiot.”

Anonymous, 33   New York, NY 


After spending three years selling for a Fortune 500, I took a chance and joined a SAAS startup, hoping I could end up leading a sales team, and that my stock options would eventually make me rich. The CEO of the company was a hard-charging former telecom exec, who referred to himself as a “serial entrepreneur” and he was pretty aggressive about trying to land big deals even though we were super early-stage and didn’t really have product-market fit yet. Anyway, I managed to get us in the door of the U.S. division of a global conglomerate, and the CEO and I were presenting to the division director, a VP, and their staff, when the Director asked if our software could do something that it definitely couldn’t do, and (as far as I knew) would never be able to do. I started to answer, but my CEO cut me off, looked the Director right in the eye and said, “absolutely.” We got a commitment that day based on the made-up feature. 

Fast forward a week later, and the VP of Engineering pulls me aside and asks me why I told the CEO we’d be able to ship that feature. He told me that it was literally impossible and that he was being put in a bad position because of me. I tried defending myself by telling him what happened, but the drama spiraled out of control and I ended up getting let go less than a month later because of it. What I later found out was that the CEO was using the commitment from the Conglomerate to close our next round of funding, so he would have done and said anything just to ensure he could raise more money. Eventually, the company ended up going under, but I saw on LinkedIn that the lying CEO just raised money for another venture. I’m sure he’s lying to his investors about that one too. 

Anonymous, 42   Austin, TX

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