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This isn’t exactly a fail but it’s one of my best stories from my time working in sales. About a decade ago (I am old), I was an Account Executive for a regional commercial accounting firm. We handled accounting and other financial functions for large and mid-sized companies. It was a pretty good job although there wasn’t much room for advancement in sales.
One day, I went with my sales manager to a client’s office for an initial consultation. They were some sort of technology company, and had a big boring office in an office park. They showed us around the office then brought us into a conference room. There were about a half-dozen people from their company in the meeting. We were in suits and they were dressed more casually.
There was a pitcher of water on the conference room table, so I poured myself a glass. Then we all engaged in a bit of small talk for a while. They were pretty laid back and somewhat looser than the other companies we typically dealt with. I remember thinking that I would love to work for a company with that kind of culture someday.
As we were talking, there was one guy who was very funny. I don’t remember what his position was but he had a head of curly hair and a thick mustache and a deadpan delivery. They were telling us about a firm they’d tried before us, and that the firm had promised them the world but had ended up being a complete nightmare. As they were explaining this, the guy with the curly hair made his voice very high-pitched and pretended he was from the other firm and said, “We’ll give you nothing, and you’re gonna love it, you pieces of crap.”
When I heard this, I completely lost it. But the problem was I had just taken a huge sip of water, and it came flying out of my mouth in a giant half-spray, half-mist. The entire table in front of me was covered in water. And even though everybody stopped and looked at me, I couldn’t stop laughing because the curly haired guy just looked at me with a grin on his face. I apologized profusely and cleaned everything up. But I was completely red-faced through the rest of the meeting.
Anonymous Location withheld
This isn’t exactly a Sales Fail, but it might be my best sales story ever. About ten years ago, I was working as an AE for a large company. This was long before remote work, so we were always in the office doing a combination of inbound and outbound prospecting. I wouldn’t exactly call it a boiler room environment, but it wasn’t too far off from that.
Our branch manager was a hard-charging young guy who had dropped out of college to climb the corporate ladder. He was in his mid-20s but was already super successful. He was also an arrogant hard-ass. He watched everybody like a hawk and when he talked about himself, it was always in really glowing terms, as if he was a narcissist.
I did not have a great relationship with this manager. In fact, I wanted to leave the company because I couldn’t stand how toxic he made the environment for everybody else. Not everyone felt this way, though, and I think most people really only cared about how much money they were making. I am a millennial, and was the youngest rep there, so maybe that’s why I cared about the culture more than others did.
Things seemed to be coming to a head, and I was probably weeks away from quitting. Then, one night, I went to a local restaurant with one of my friends. I lived in the same town where the office was located, but the manager did not. I was enjoying a drink when I looked over and saw my manager in a booth with one of the girls who worked on our sales support staff. They were looking into each other’s eyes and holding hands across the table.
But here’s the kicker: the sales manager was married to somebody else. When they saw me, they both turned bright red. Then he came over and put his hand on my shoulder and started talking to me as if we were best friends. It was the most bizarre experience, since he had been like a drill instructor to me up until that point.
After that happened, everything changed. It was as if there was an unspoken agreement between us that I would keep my mouth shut about what I saw, and in exchange, he would treat me better at work, which he did. I stayed there for another few months but then left when I got a better job somewhere else. Last I heard, he was a VP for a well-known software company, and still married to the same woman.
Anonymous Location withheld
I was working for a small HVAC company a few years ago. It was my first sales job, and I was basically learning the ropes and trying to get some experience before trying to move to a more established role at a bigger company. The company’s owner was this really serious guy who didn’t give people too many chances and was known for firing people quickly. He was nice enough to me, but he also seemed like he couldn’t care less about anything except how many deals I closed.
One day, I was at a young couple’s house writing up a quote. The job was more complicated than the ones I was used to because of the way their house was built. That week, the technician who normally helped answer my questions was on vacation, so I didn’t want to call him. Instead, I went out to my truck and called the owner of the company and described the issue and asked how he wanted me to price it out.
For some reason, he got extremely angry. His response was essentially, “Why are you bothering me with this, it’s something you should already understand.” Well, I was tired and hungry and had sat in traffic to get to the couple’s house, so I put the phone on mute while he was talking and said, “Great leadership, %&*#-face.”
Well, the phone was not on mute, and he heard me say it. He stopped and said, “What the hell did you just say to me?” I told him I didn’t say anything and that it was my radio on in the background. He told me he wanted to see me in the office first thing in the morning. I wrote up the quote the way he explained, and the next day, met him at the office, ready to get fired. He showed up and very calmly told me if I ever said anything like that to him again, I’d get fired for cause and wouldn’t be able to collect unemployment. But he didn’t even write me up. I stayed there for another few months then got an inside sales job. To this day, it’s still my best sales story ever.
Anonymous Location withheld