
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 to me earlier in my career, when I was young and dumb. I was selling enterprise software and had been working on my biggest deal of the year with the CEO of a logistics company. I was relatively new to sales and wanted to "look the part," so I bought a fake Rolex from some website for $200. It looked pretty convincing to me, and I figured it would help me fit in with high-level executives.
I met with the prospect in-person for the first time after a few calls. The meeting was going incredibly well, and he seemed ready to move forward. As we were wrapping up, he glanced at my wrist and his eyes lit up. “Is that a Submariner? Beautiful piece,” he said enthusiastically. “I’m actually a bit of a watch collector myself. Mind if I take a look?”
My stomach dropped, but I couldn’t refuse without seeming weird. I reluctantly slipped off the fake Rolex and handed it over, hoping he wouldn’t look too closely. He immediately flipped it over to examine the back, and his expression changed instantly. He frowned, handed it back to me, and dryly said "very nice." I could tell he realized it was fake but was too nice to say anything.
We finished the meeting on a good note, he gave me a verbal commitment and I ended up closing the deal a few weeks later. I eventually bought a real Submariner.
Anonymous Location Withheld
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I sell IT managed services and was working at my company's booth at an industry conference. There was a casual lunch buffet on site. I grabbed a chicken Caesar wrap from the buffet and was standing near some high-top tables, trying to eat quickly since I wanted to get back to the booth (I was down bad and really needed to get some warm prospects from this event).
Halfway through the wrap, a big piece got lodged in my throat. I couldn't breathe or swallow - it was completely stuck. I started panicking, hitting my own chest trying to dislodge it, but nothing was working. My face was turning red and I was making weird choking noises.
A woman at the next table rushed over to help with the Heimlich maneuver. The problem was, she was maybe 5'2" and I'm 6'5" - she couldn't get the right angle or leverage. She was jumping up trying to reach around my diaphragm while I'm hunched over, still choking.
Getting desperate I stumbled to the nearest high-top table and started ramming my stomach against the edge, using my full body weight. After three hard hits, the wrap chunk finally shot out of my mouth and flew across the room like a projectile.
The entire room had stopped eating to watch my performance. Dead silence, then scattered applause. When I returned to my booth after lunch, people kept coming up to me asking if I was okay, and then laughing about my "dramatic lunch presentation," but hey - they remembered me. I guess the whole embarrassing situation made me more approachable, I got some great leads that ended up converting down the road and hit my quota for the quarter.
Anonymous Location Withheld
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We were at our annual sales conference in Vegas, and my colleague (who had become a good friend) was going through a brutal breakup. His girlfriend of two years had dumped him over text just days before the trip, and he was putting on a brave face but clearly struggling.
The conference went well during the day. He even crushed his presentation and got compliments from our VP. I thought the trip was helping him move on.
Then came the after-party at the karaoke bar. He started drinking heavily, which wasn’t like him at work events. I should have intervened, but he’d been through hell and I figured he deserved to blow off steam. Plus, most of our big clients had already left.
Around 10 PM, karaoke started with the usual conference crowd doing safe songs. Then he stumbled up to the DJ booth, flipped through the songbook and picked Someone Like You by Adele.
He started off fine, decent voice and everything. But thirty seconds in, his voice began cracking. By the first chorus, his eyes were watery. The whole bar was starting to notice, including our VP and several clients who were still there.
Then he hit the emotional bridge and completely lost it. Full-on sobbing while trying to sing about missing someone. But instead of stopping, he powered through the entire four-minute song, crying into the microphone in front of 200 industry professionals.
When he finished, he wiped his eyes and said, “Sorry guys, rough week,” then disappeared into the bathroom.
Anonymous Location Withheld