Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration,
I was wrapping up a three-day trip in Dallas, trying to close a deal with a manufacturing company. The meeting was supposed to end at 2PM, giving me plenty of time to return my rental car and catch my 6:30PM flight home. Except, the decision maker showed up an hour and a half late. By the time we finished, it was 4PM and I was starting to panic about my flight.
I should've had plenty of time to find gas on the way to the airport, but of course, there was an accident that turned the highway into a parking lot. I sat there watching my flight time get closer, doing mental math about whether I could still make it if I stopped for gas.
Every exit I passed, I kept thinking about how much time it would cost to refuel. Find the station, pump the gas, get back on the highway. At least 10-15 minutes. Missing my flight meant another hotel night and rebooking. I returned the car on fumes at 5:30 PM and sprinted to catch my flight. Two weeks later, the charge posted: $156 for fuel service. It was on the company card, so I just hoped that no one ever brought it up.
My manager called into his office IMMEDIATELY, pulled up Google Maps, and showed me six gas stations between the client meeting and the airport. I explained that the client was late to the meeting and I made a game time decision to make sure I caught my flight. He still wasn't happy about it. He told me that if I didn't close the deal, I'd have to pay for it out of my own pocket. Well, guess what? The deal didn’t close. What a waste!
Anonymous Location Withheld
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I had an intro call scheduled with a new prospect at 1 PM. I'd been in back-to-back meetings all morning and was starving, so I ordered Uber Eats timed to arrive at 12:30. Plenty of time to eat before the call. Except it didn't show up until 12:58.
I grabbed the bag, set my burrito bowl just off-camera, and joined the video call with my stomach growling. The guy had his camera turned off so I decided to turn mine off as well. 10 minutes in, I realized this guy had zero budget and no decision-making authority.
The guy was rambling about his business, so I muted myself to take a huge bite. Then he asked me a direct question. I frantically tried to chew and swallow, unmuted, and attempted to answer with a half-full mouth. I said. "Sorry, had something in my throat." This happened four more times throughout the call.
Every time I tried to wrap up, he'd launch into another story about his previous vendors or ask about stuff we don't even offer. I'm pretty sure he noticed because he asked if I had another meeting coming up. I lied and said yes, hoping he'd wrap it up. Instead, he started talking faster, trying to cram in more questions.
The call finally ended after 45 minutes. The guy thanked me for my time and said he'd "think about it" (which means never). My burrito bowl was room temperature and soggy. I scarfed down the rest of the bowl in 10 minutes before I had to hop on another call. I've never been so frustrated eating lunch in my life.
Anonymous Location Withheld
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I sell marketing automation software to SMBs. I had landed an in-person meeting with a director of a mid-sized retail chain. I showed up prepared. Deck was polished with specialized case studies for his industry and I'd done my research on their current tech stack. I showed up and met the guy in his small office. I was immediately shook. He had the most impressive unibrow I'd ever seen in person. It was like a caterpillar had set up permanent residence across his forehead. I kept trying not to stare, but my eyes kept drifting up there.
The guy seemed interested as I walked through the platform, asking good questions about integrations and reporting capabilities. But honestly, I was having trouble focusing.
About fifteen minutes in, he paused and looked at me. "You keep staring at my eyebrow," he said flatly. I felt my face go hot. I started stammering some excuse, but he cut me off and told me it was fine, that people noticed it all the time. Then he leaned back in his chair and started explaining how the unibrow made him powerful. How it was his signature. His brand. He talked about how it showed he didn't conform to society's arbitrary grooming standards, how it made him memorable in a sea of forgettable people.
I just sat there nodding, convinced this was some rehearsed bit he did with every salesperson to throw them off their game. But he kept going, getting more philosophical about it, talking about disruption and authenticity. I completely lost control of the meeting. When I finally left, I sat in my car in the parking lot for a solid five minutes, just staring at the steering wheel. He never returned my follow-up emails.
Anonymous Location Withheld
