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).
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“I sell card machines for a leading UK independent sales organization. One of my customers referred a friend who specialized in canine hydrotherapy. After some calculations we established we could save her some money when compared to her current provider, as well as an equipment upgrade. 
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Buoyed by this impending success, I asked for her driver's license to begin the application process. It featured a charming photograph of my prospect complete with an amazing bouffant of curly hair. She was currently sporting a much shorter bleach blonde cropped hairdo. I commented: "Well you've certainly had a trim!"
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She replied: "Well... cancer will do that to you."
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Thankfully she was three months into remission and took my comment in the spirit it was meant, but to say my heart sank is an understatement.”
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Anonymous, 37      England, UK
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“I used to work for an outbound call center, and our manager was an activity-obsessed type of guy. Basically, he was a stickler for tracking activity, and even if you were closing deals, if you didn’t hit your required activity numbers, he’d come after you.
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There was this one guy we worked with who was a bit older. After he started, it was pretty clear within a few weeks that he wouldn’t fit in with the rest of the team – he was more “independent” minded and didn’t like the rigid activity requirements, etc. 
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One of our daily requirements was to hit 100 outbound calls, no matter what. Even if you were busy closing deals, you still had to hit that number, so most of us would schedule time throughout the day to make sure we got there. Some people would do it first thing in the morning, some would do it at night etc. It was good-intentioned, but not something that was really effective (at least from our perspective). Nevertheless, we all did what we had to do.
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Then one day, I saw that this guy (the older one) had been called into the conference room, and since the room was made of glass, we could see him gesturing wildly with his hands, while our general manager and his sales managers sat calmly across from him, their arms crossed. After about fifteen minutes, the guy came out, grabbed his jacket and a few things out of his desk, and walked out without saying a word to anyone, including me who sat across from him. 
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So later that day, our manager calls us all into a meeting and explains (in his passive-aggressive way) that this guy had been calling Home Depot and his own home office every single day in order to hit his required call numbers. The meeting was a warning shot to the rest of us not to even think about making fake calls. (Little did he know that everyone had their own ways to get around this, we just weren’t as blatant as this guy).
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A few weeks later, the guy who got fired called my cell phone and told me that what the company was doing was illegal and that he wanted to file a class-action lawsuit against them or something. I basically told him I’d get back to him and never did. Not sure whatever happened to him, but the whole situation was bizarre.” 
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Anonymous, 40         Massachusetts 
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“The funniest thing that’s ever happened to me in sales happened at a corporate training in 2006. I had just started working for a national bank, and they flew all the new hires out to a suburb of Chicago for a week-long training. 
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I flew out with another guy who started at the same time as me at my branch, but we didn’t really know each other. Anyway, he was a bit odd. He was friendly and nice enough and everything, but it just felt like something was “off” about him. I remember he was really big into conspiracy theories. 
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Anyway, a few days into the training, we were in a conference room with about 15 other trainees, eating catered lunch from Panera or something like that. A woman who was there took a bite from a sandwich and didn’t like it, so she left it on her plate. All of a sudden, the guy who I had come to training with says, “Are you gonna finish that?” and picks it up and starts eating it. People started giggling, but it was not a huge deal or anything. 
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The next day, we were all in a classroom, sitting at desks, and they passed out lunch, which came with a pre-wrapped cookie. The lights were dimmed because we were watching a training video. At the end of the video, the lights come on, and I hear someone shouting in the back of the room: “What the hell? Why did you eat my cookie?”
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It turns out, the guy I came to training with had eaten his own cookie, then stole the cookie of the guy who sat next to him, who wasn’t having it. It was a really awkward scene, and the guy who had his cookie stolen would not let it go. Still one of the funniest things that I’ve ever seen happen – sometimes I wonder where the cookie thief is today.” 
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Anonymous      Location withheld