Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration,

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I used to sell cars at a good-sized Chevy dealer. Our sales manager was obsessed with "follow-up culture" and required us to make 50-100 calls a day to people who'd visited the showroom or past customers. One summer, I was working through my call list and reached a guy, let's call him Marshall, who had a test-drive several months earlier. He didn’t answer my first five calls over two weeks, so I left a few voicemails asking about his car search.

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Apparently, after my third call, Marshall had phoned the dealership demanding to be removed from our call list. Whoever answered had told him they'd handle it but never updated the system. So I kept calling, completely unaware. Two days after my fifth call, I arrived at work to find Marshall standing across the street with a massive homemade sign reading: "[My dealership name] AND SALESMAN [My name] VIOLATE FEDERAL LAW BY IGNORING DO NOT CALL REQUESTS."

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My sales manager panicked and sent me out to apologize. Marshall calmly told me he planned to stand there every day until we "learned to respect the law." Our general manager eventually had to personally apologize and offered him $500 in "inconvenience compensation," which Marshall declined, saying, "This isn't about money." He continued his one-man protest for five straight days—one day per call. 

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Anonymous       Location withheld   

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I used to work at a high-end bike shop. One day, a customer came in looking for a racing bike, saying he was a serious road cyclist. I showed him several of our premium models —carbon fiber frames, the works. After narrowing it down to two bikes, he wanted to test ride both. I led him to our back lot where we do demonstrations, away from any traffic or parked cars. Before handing over the first bike, I grabbed a helmet from our rack. He brushed me off saying he didn't need the helmet, emphasizing his years of experience. I had to insist it was a non-negotiable store policy for insurance and safety reasons. He reluctantly put it on, clearly annoyed.

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He mounted the bike and started riding smooth circles around the lot, getting a feel for the handling and gearing. Everything looked perfect, then he decided to test the brakes. Instead of gradually applying the rear brake like an experienced cyclist would, he grabbed the front brake lever hard. The bike stopped instantly and he went flying over the handlebars and landed on his head.  I ran over to help him up; he was clearly embarrassed. The bike's paint got scratched when it hit the asphalt behind him and the helmet had a crack down the middle. When he saw the damage, he started apologizing and promised he'd pay for the helmet and whatever damage there was to the bike. We went inside and I rang him up at the counter for the helmet and told him I'd call him about the damage to the bike. He agreed, apologized again, and basically ran out of the store — still embarrassed. He didn't even thank me for saving his life by forcing him to wear the helmet.

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Anonymous       Location withheld   
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I'd been working on a deal to supply custom office furniture to a growing marketing agency for about six weeks. After several promising calls, I had a great conversation with their owner about delivery timelines and budget approval. She seemed genuinely excited about moving forward.

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I took thorough notes during the call but wanted to make sure my follow-up email was perfectly crafted so I decided to use ChatGPT to help structure my thoughts into a professional email, copying my notes and asking it to write a follow-up. The response looked great, so I quickly copied and pasted it into my email client, gave it a quick skim, and hit send. For the next three days, radio silence—unusual since she'd been very responsive throughout our conversations.

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I reviewed our email thread and discovered my fatal mistake. At the bottom of my follow-up email was ChatGPT's response: "This email effectively summarizes your discussion points while maintaining a professional tone and clear next steps. The structure moves logically from recap to value proposition to call-to-action. Is there anything else you'd like me to help you with regarding this client communication?"

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When I sent a follow-up asking about next steps, she responded explaining that she was disappointed I was using AI to write communications and couldn't even proofread properly. She said if I couldn't take time to write a genuine email, she didn't trust me to handle their furniture order carefully. The deal was dead, and I learned an expensive lesson about always double-checking before hitting send.

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Anonymous       Location withheld