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).
A few years ago, I was working for a company that put on in-office events for mid-size and large corporations. I don’t want to go into too much detail because it might become obvious about which company it was. I was an Account Executive who was responsible for sourcing deals and closing new business.
Things were a bit slow because of the summer months, so the company decided to do something it had never done before: offer a limited time discount for anybody who booked us to come in. This promotion was designed to get a bunch of people off the fence and get more commitments so we would be on track to hit our number. But there was one caveat: once the offer expired, we would not honor the discounted pricing.
I had a prospect who I had been going back and forth with for a while, and when the offer became official, I reached out to them and explained in detail that they could basically get the same package we had been discussing, but only if they signed and gave us a deposit before the end of the following week.
The prospect, a mid-level manager who was always friendly but generally seemed bored by his job and maybe life in general, told me the pricing adjustment was really compelling and that he would get back to me as soon as he discussed it with his team. At this point, I reiterated that the offer was only for a limited time, and that management would not extend past the promotion date. He told me he understood.
Over the next week and a half, I checked in via email and voicemail, reminding him the offer was for a limited time only, so you can probably guess what happened. He called me the Monday after the offer expired and told me he was ready to move forward on the discounted pricing. I took it to management and they refused to honor the pricing, which I can’t say I blamed them for since it was very clear it was only for a limited time. The prospect didn’t end up moving forward with us at all. Sales Fail!
Anonymous Location withheld
–
When I was in my 20’s, I got a sales job through a friend of mine who had previously worked for a company that sold janitorial supplies to small businesses like restaurants and gas stations. The friend had previously worked there and got me an interview with the owner, who was an older guy who had started and run the business for decades.
After I started, however, the older guy wasn’t around for the day-to-day. Instead, his daughter, who was this really nice woman in her late 30s or early 40s, was taking over the business. She had this enormous boyfriend who looked like a WWE wrestler who was always with her, but he didn’t really give directions or anything, he was kind of just there. Also, they had a brand new Cadillac Escalade on huge rims that they always drove around.
My first few months at the company were fine. The coworkers had been there for a while and it was a pretty laid-back and supportive environment. It was only in my third month that things got weird. One day, I got a call from my bank saying that a check I had recently deposited had bounced. I was surprised and called the boss lady, who told me they had had payroll issues in the previous week and that everything would be sorted out shortly.
Well, this happened two more times, before, finally, one of my coworkers called me and explained what was happening. Apparently, the woman who was taking over the business had been taking out every single dollar she could so she could finance her and her boyfriend’s lifestyle. She had met him on a website for prisoners and had flown him up north from Florida after he was released and they were living the high life with company funds.
I ended up getting laid off along with most of the staff and the company was temporarily shut down. Apparently, the father (the guy who owned it) never fully gave up legal control, and he ended up selling the company to someone else in the year after everything fell apart. It would’ve been a great sales job if it had been real, but it was all a mess.
Anonymous Location withheld
–
I used to sell home improvement services for a pretty big regional contractor. This was my first sales job, so I hadn’t learned some of the “lessons” one learns after spending enough time working in sales. We had good inbound lead flow, and we did a lot of prospecting from networking events and things like that.
A friend of mine found out where I was working and reached out to me. We weren’t super close, but we had been friends for quite a long time. I was excited to have sourced my own deal and was going to make a higher commission rate on it than if it had been a deal that came in through from one of our mailers.
He had just bought a house and needed a bunch of new windows, which was basically our bread and butter. I quoted him out and he agreed and gave us a nice deposit. Everything was going well and I was convinced that since I knew him, he would be an easy client and one I wouldn’t have to worry about at all.
Well, as it turns out, this became one of my most pain in the ass deals I’d ever worked. His wife, who I had met a handful of times, became the point person for the job, and basically treated me and the company as if we were her servants. She changed the color of the windows and hardware at least three times, then, when the windows finally came in, she actually refused to let us install some of them because she claimed they weren’t what she ordered.
To make things worse, she had her husband calling me all the time to complain about what was happening. He would sigh after I picked up the phone and practically beg me to just make the changes because she “was going to kill” him if he couldn’t make it work. It was the most stressful deal I’d ever worked on until that point because I actually cared about his friendship and didn’t want to tell him off like I probably would have if it had been anyone else.
We ended up getting everything done but by the end of the job, his wife pretty much hated me (for no good reason) and our friendship was never the same after that. After this happened, I pretty much stayed away from selling to friends and family. It almost always gets weird and usually isn’t worth the money or the trouble.
Anonymous Location withheld
