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I was mid-deal with a prospect who ran a manufacturing plant (I sell logistics software). I’d been working on the deal for a couple of months, and the guy finally agreed to meet in person to talk details over lunch. He picked the place. Barbecue. I didn’t think twice about it. I was just happy to be out of email and into the real world.
He knew everyone that worked there, he was a regular and took the lead ordering. He ordered ribs. Full rack and some sides.
That’s when I remembered something important about myself: I’m a notoriously messy eater. I like to be clean. I over-napkin. I’m the guy who uses ten napkins for a sandwich. But it was too late. The food was already on the table.
I tried to pace myself, but the sauce was everywhere. Fingers, plate, table. I kept reaching for napkins on instinct. By the halfway point, I had built a small, greasy pile beside my tray. Somehow this guy, apparently a professional rib-eater, had barely made a mess.
The server came by to ask if he we needed anything else, and the prospect looked at the napkins, smiled, and said, “Can you bring my friend a wet nap, and maybe a bib” and started cracking up. I laughed along, but was super embarrassed. He was nice about it after and didn’t bring it up again.
I ended up closing the deal, but learned a valuable lesson about making sure to be conscious about what I order when taking prospects out to eat.
Anonymous Location Witheld
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I was giving a demo to a startup I’d been working for a few weeks. They were small but serious, the kind of company that moved fast and liked to remind you of it. My point of contact mentioned that their founder might sit in on the call but probably wouldn’t participate. I said that was fine.
The call started normally. I shared my screen and got into the deck. About ten minutes in, I noticed an extra Zoom tile with no camera had joined. No one introduced them, but I assumed it was the founder. I figured since he was just there to listen and didn't say anything, I'd just keep it moving. The rest of the call went fine, my POC seemed excited, the founder didn't say anything.
After the call, I sent my usual follow-up to my contact. An hour later my manager forwarded me an email that was forwarded to him by our CEO. It was from the founder of the company I was pitching.
It detailed a bunch of notes about what he thought was wrong with our product and our pitch. Specifically he called me out for being "amateurish." At the end of the email he said he'd be willing to buy, but not from me, and wanted a crazy discount (it was something close to 70%).
I was stunned. I called my manager immediately to explain myself. He calmed me down and let me know that the CEO didn't care and he didn't care—they both thought the founder guy was a jerk and wouldn't work with him.
Naturally, I followed the startup closely after that, praying for their downfall. I was finally vindicated last year when I found out they went out of business.
Anonymous Location Withheld
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This happened during my first week at a SaaS company that sold analytics software to retail brands.
One of the more experienced reps told me he wanted to throw me a bone. He knew someone at a target account who could help move things along. He called them a champion and said I should definitely take the meeting.
The introduction came through email, and I treated it like gold. I booked time right away and spent the night before the call over-preparing. On the demo, everything felt easy. They were friendly, engaged, and asked thoughtful questions. They told me the product was interesting and nodded along throughout the pitch. I hung up feeling like I had momentum.
Over the next couple of weeks, we kept in touch. They replied quickly. Always positive. Always encouraging. Eventually, I asked if it made sense to bring in their manager or someone from procurement. That's when the responses stopped. I followed up two more times but still nothing. I was discouraged and decided to bring it up to the rep on my team who made the intro. He burst out laughing.
Apparently my point of contact at the other company was one of his frat brothers and they were playing a joke on me.... seeing how long they could string me along. I was pretty furious that this guy was actually wasting my time that could be spent on actual opportunities. I didn't say anything because I was afraid of the repercussions. I still think about it to this day.... and wish I did give him an earful....
Anonymous Location Withheld
