Sales Fails: "My sales manager tried to help me close a deal. He got into an argument with the prospect instead"


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My biggest Sales Fail was actually a double fail. A while back, I was selling mechanical testing systems. Our customers ranged from food manufacturers to companies that made eyewear and everything in between. 

I was working on a really promising deal one week, and was actually pretty pumped about how that year was going, so I was feeling confident. On this particular deal, we were going head to head with one of our main competitors, which was a bit unusual. In any case, I was pretty confident we would win because we were better and (usually) cheaper.

The prospect was really friendly and had a good sense of humor. I remember distinctly that it was a Friday. Well, after going back and forth over email, on that day, he finally decided on the exact piece of equipment he wanted and told me to send over a proposal with our best and final price. I was getting ready to go to NYC with my girlfriend that night, so I put everything together and hit send. 

Well, unfortunately, I forgot to include the most important part: the price! I sent the proposal and took off to meet her at the bus station (we took one of those discounted buses into the city). I was feeling good. Then I got an email from the prospect, and all he said was, “So does this mean the equipment is free?” I was distracted and talking to my girl, and I just thought he was kidding, so I just responded with “LOL.”  

Unfortunately, it didn’t go any further than that. I completely ignored my email over the weekend and on Monday, when I checked and realized my error, the prospect said he understood but that he’d already committed to the competitor. Dumbest mistake I’ve ever made in sales. 

Anonymous             Location withheld 

I have been in the mortgage business for close to fifteen years. Currently, I’m a branch manager at a regional lender, but about seven years ago, I was working as a Loan Originator for a bigger company. It was a decent job. I mostly handled refinances, and not a lot of purchases.

One day, I got a great inbound lead for a refinance. The woman was friendly, she had a lot of equity in her house, and she had a pretty high rate compared to what we were offering. She wanted to pull some cash out to pay off other debts and do some home improvements, and even after the cash out, we were still lowering her payment by close to a hundred bucks a month.

Everything was going well. She filled out her application, paid the application fee, and sent in her income and asset documentation as needed. I ordered the appraisal and sat back. I always loved having “solid” deals like this in the pipeline. They were the ones you didn’t have to worry about, unlike seventy percent of your other deals, which were always complicated in one way or another. 

Well, a week and a half went by, and her appraisal came back. It was fine, there were no issues. But a few days before I got the appraisal, I had a message from her asking me to call her back. When I did, she told me she wanted to cancel the loan. I asked her why, and she told me it was because her dog – who she said was an excellent judge of character – didn’t like the appraiser, and that she had to go with her gut on this one. 

I begged and pleaded with her to be reasonable but she wouldn’t budge. So I lost a deal because the woman’s dog didn’t vibe with the guy doing the appraisal. Still makes me angry.  

Anonymous             Location withheld 

This happened to me early in my sales career, and honestly, I think I am still scarred by it. I was just a green sales rep, a year or two out of college, working for a consulting firm that was pivoting into creating its own software. Basically, we helped companies implement software, but then decided to launch our own since the recurring revenue was much better than relying on billable hours. 

A few months after I started, my sales manager left, and was replaced by a new sales manager. I did not have a ton of experience, so I wasn’t sure yet what a good manager was as opposed to a bad one, but I didn’t really get a good feeling about the new guy. Nevertheless, I stayed busy, plugging away and hitting the phones as only a young, naive, recent grad could. 

I somehow got a great potential customer on the hook. I think it was actually an inbound lead, but I can’t remember. They were a small-ish company, but they were interested in our new software, which, at that time, was what management was trying to push. My sales manager wanted to get involved with the deal, so when I scheduled an in-person meeting (they were in our state), he said he would accompany me, along with one of our engineers, just in case.

For the meeting, we went to their office. Everybody went into the conference room. Their management team was there. I went through the short presentation, and then we got into Q and A. Until then, everything had gone fine. They were friendly, we were professional, etc. I did most of the talking in the beginning since I owned the relationship. 

Well, when they started asking questions, my sales manager took over. And within about ten minutes, he got into an argument with somebody from their team. The argument wasn’t even about our software – they were arguing about a third party software that we often implemented. I don’t know who was right or wrong, but I remember just sitting there and wondering why the hell my sales manager was arguing with the people who had wanted to buy something from us. 

I tried to interject to smooth things over, but everybody in the room must have sensed how new I was because they basically just ignored me. The argument went on for about ten to fifteen minutes, and after that, it was super awkward in the room. Needless to say, we did not get the deal. My manager played it off like he didn’t care, and that they were a bad prospect and we were better off without them. But he was just trying to justify his own stupidity. It was a good deal, but he blew it with his own ego. 

Anonymous             Rolling Meadows, IL

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