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’ve been in car sales for a long time and have seen almost everything. One story that sticks out in my mind is about a cosigner. This happened a few years after the 2008 crash so it probably was around 2010 or something like that. 
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We had a customer come in, a younger guy who was super friendly. I think he worked as a bartender or something in the restaurant business. He picked out a car (I think it was a Honda Civic) but his credit was jacked up – really bad, and we couldn’t get him qualified for financing. 
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So he calls his good friend down, who is in law school in some other state but happens to be in town for summer break. I don’t think this guy knew his friend was going to ask him to cosign on the loan. At first he said no, but this guy begged, pleaded, charmed, joked, and kept pestering and pestering until finally, the law school guy made him swear on his mother’s life that he would make payments, and agreed to cosign (the law student had perfect credit). 
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So the guy drives off in his new car and everyone is happy. Fast forward about a year and I get a call transferred to me, and it’s this law student who is screaming and freaking out that he was trying to get a pre-qualification letter so he and his fiance could start looking for a house, but now they can’t use his income from his new job because his credit is absolutely destroyed. 
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It turns out that the guy he cosigned for made like two payments on the car and then stopped paying until it got repoed. The law guy was so upset, especially because he was such a buttoned-up guy and clearly would never have missed a payment on anything. It was one of the most uncomfortable calls I’ve ever had to be on, but in my defense, I never pushed the guy to cosign. His friend did all the pushing for him. The last thing he said to me on the phone was a swear – he screamed it and hung up. 
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Anonymous, 43                  Louisiana     
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“I used to work at a call center in the mortgage industry. It was a combination of inbound and outbound prospecting, so we were expected to make a lot of outbound dials every day, even though our branch manager didn’t (usually) count calls or have a specific amount of calls that he wanted us to make every day.
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Anyway, I sat next to this guy who absolutely hated the outbound side of things. He used to complain that he didn’t want to bother people, and that if they wanted to refinance, they could call in and do it. He only said this privately to me, of course, and he actually did close deals, but they were from inbound calls that we got, so he basically was able to fly under the radar because he was pretty smart and had a high close rate from inbound leads.
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One day though, the branch manager decided to look at the volume of outbound calls we were making. Most people were averaging around seventy or eighty per day, but the guy who sat next to me was at like seven. In any case, the manager called him out in front of everyone, and said that he wanted the guy to call people until they said yes or no, no exceptions. 
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This guy was really pissed, but he knew he had to start making calls or this manager (who was pretty ruthless) would definitely fire him to make an example out of him, so he started making calls. When he finally got someone on the phone, I could hear him talking to them, and going back and forth a bit, because it sounded like the person was frustrated that they were being bothered at home by a telemarketing call.
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But the guy who sat next to me wouldn’t give an inch, and finally, he said, “I’m going to keep calling you every single day until you either tell me yes or no, so which one is it gonna be?” The person hung up, but about twenty minutes later, the branch manager came out of his office and said that he’d just got a call from an angry customer, who said they were being harassed by a sales rep, and repeated what he’d told them (“I’m gonna keep calling you every single day, etc.”) But not only was the manager not upset, he went up to the guy who sat next to me, put out his hand for a high-five, and said, “Nice job! That’s how you do it.”
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That’s the kind of environment we worked in back then – those guys all thought they were in the movie Boiler Room. In any case, the guy who sat next to me quit a few weeks later. Last I heard, he sells for Oracle, and apparently does really well.  
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Anonymous          Somewhere in New England  
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“Funniest thing that’s ever happened to me in sales was when I was a sales support rep for a big online retailer about four years ago. We weren’t “first line” reps, we were basically a hybrid sales/customer-support role. People browsing the company’s website would call in or email and ask questions that each of us would handle, and for every sales we processed, it would count towards a monthly bonus above a certain level.
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Anyway, this guy called in with some questions about an item, and my company was big on customer support, so we were trained to ask questions and be really conversational. So I was being very engaging, and somehow we got on the topic of boots and I told the guy that I had bought these boots from Austin, TX that I really like, and he started asking a ton of questions about the boots. Pretty strange, but not THAT weird. 
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After I finally got him back on track and answered his questions, he asked me to email him some information and he’d probably buy, which is pretty normal, so I sent off an email to him. He responded about a half hour later, and said thanks, and then asked me to send him some pictures of the boots I had bought (which I had told him I was wearing). I didn’t think anything of it, just thought he was genuinely curious about the boots, so I sent him a pic of the boots and asked if he wanted me to process the order.
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He responded that he wanted to see a few more pics of the boots and asked if I could find a mirror so that he could see them from a different angle. Now I was getting suspicious, and I took a while to respond, but then HE replied again directly to the email with the boots pics with “nice.” lol. 
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At that point I realized that this person very clearly had a foot fixation or something else that was extremely weird, so I responded with something like, “Would you like me to go ahead and process this order for you, to which he took a while to respond. Finally I got a message from him that just said, “Thanks.” Ugh!  
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Anonymous, 34         Nevada