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Years ago, I was a rep/account manager for an app development company. We built apps for businesses and entrepreneurs, nothing below $50k. This was around the time that apps really started taking off, so we were staying busy and making great money.

I got introduced to a prospect company through somebody I had previously worked with. They were a web startup that was going to expand into a physical product that worked in conjunction with an app, and they were looking to hire our company to develop the web and mobile technology. It was potentially a massive deal, and we were working hard to try to win the business.

The company was based in Chicago, so we had planned to go out there and do our presentation in person. I went along with my manager, one of the company owners, and two other people who worked with us. We got a nice hotel the night before and had dinner and were all having a good time.

One of the people at the company we were pitching knew we were in town and invited us out for drinks. He was a manager there and met up with us along with a few of his friends who didn’t work for the company. The night started to get crazier and crazier as we went from nightclub to nightclub. At some point, the people from my company went back to the hotel, but I decided to stay out.

I drank a ton, and honestly don’t remember much of the night. What I do remember is waking up the next morning at a random apartment in Chicago at 10 am with over thirty missed calls and texts and emails from my team. The pitch meeting was supposed to start at 10, so I was already late. I hurried to the company’s office still wearing the clothes from the night before and looking like death. By the time I got there, they were already mostly done presenting and I just sat in the corner with my mouth shut feeling like a complete idiot.

My company won the deal, and they paid me my commission, but I was never again invited on any company business trips. My saving grace was that the deal closed, but if it hadn’t, I’m 95% sure I would have gotten fired. I definitely don’t drink like that anymore now that I’m older.    

Anonymous      Location withheld 

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My biggest Sales Fail is 100% my fault. Years ago, I used to sell furniture for a company that did a lot of advertising (still does) in the Northeast. I made really good money at the time, but since then, I’ve left retail and now work in B2B sales. 

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I had a couple come in to look at a bunch of furniture, including a couch, a bedroom set, and a desk. They didn’t buy anything but they took notes and I honestly didn’t think I’d hear from them again. Well, a week or two later, the husband called me and wanted to place a really big order. I was pumped. 

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When we got to the desk, there were two size options. He wanted the shorter desk because there was a spot in their new house where a window frame or something like that would get in the way of the bigger desk and they wanted it up against the wall. 

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I gave him the size of the smaller option. He asked me multiple times to confirm. “Are you sure that’s the size?” he said, because he went to the manufacturer’s catalog and was seeing something different. I was measuring the desk with a tape measure and I said yes multiple times. Finally, I kind of raised my voice a little and said, “Look, I’m literally staring at the desk right now. It’s the right size.” He apologized and said okay and placed the order.

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The day of the delivery, I got a call from the customer. The desk he had ordered was bigger than the size I’d given him and did not fit. Turns out, I was measuring the completely wrong desk when I was on the phone with him. He was livid. He said he had taken a day off from work to take delivery and I had wasted his time. And since the desk didn’t fit, he no longer wanted the dressers that (sort of) matched. He ended up returning everything except the couch. Sales Fail! 

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Anonymous      Location withheld 

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A few years ago, I had an important pitch meeting with a potential client. This was an in-person meeting, and it was essentially us (small team) giving them (directors and support staff) an in-person presentation to get it over the finish line. I had sourced the deal and was the point of contact for both sides.

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The weekend before, I had gone hiking with my girlfriend. I’m athletic, but not a super outdoorsy person, so I maybe wasn’t as well-prepared as I should have been. I wore shorts and short sleeves, even though we went deep into the brush. When we got back, she checked me for ticks and actually did find one which we got rid of. Needless to say, I wasn’t thrilled. 

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So the morning of the meeting, I noticed that my ankles and the side of my neck were itchy. And the more I scratched, the worse it got. By the time we were all in the conference room, it was starting to become unbearable. I kept trying to fight it, but the more I tried to ignore it, the worse it felt. I would ignore it until it got so bad that I would jerk my body toward the itch to try to make it stop.

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Well, I just happened to be sitting next to the most important decision-maker from the company. At first, he didn’t seem to notice, but after a while, every time I went to scratch myself, he would look at me, and kind of hold his gaze for a long time. It seemed that both of us were more concerned with my itching than with the sales presentation. I was miserable the whole time. 

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We broke for lunch, and when we came back, the guy sat in a completely different seat as far away from me as possible. Nobody else sat next to me, so I was basically all by myself at the end of the table, scratching myself like a crazy person. Thankfully, I had a good team and we were prepared and the presentation went off without a hitch. 

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Fast forward a few days later. The company told us they were going with another vendor. They talked about budget and fit, but I am convinced that they passed on us because I was scratching myself like a crazy person during the meeting. Oh, and if you haven’t guessed, I got really bad poison ivy all over me. My girlfriend and I never went hiking again. Sales Fail! 

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Anonymous      Location withheld