Sales Fails: "I brought our CTO to a sales meeting and he completely blew it"

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“My biggest sales fail wasn’t even my fault. A few years back, I was an AE for a fairly new tech startup. We had literally less than twenty employees, and I was probably the most experienced seller except the CEO.

About a year into my time there, I was working a medium-sized deal with another tech company which I had sourced. They were within 2 hours drive, so the CEO suggested that I go out there in person for the sales presentation (this was before Covid) and bring our head of engineering along so that he could answer any technical questions that might come up. 

Our head of engineering was actually a pretty outgoing guy for an engineer, so I wasn’t worried about him. Everything was going great. I made the sales presentation to four managers and executives at their office, and we answered all their questions, including technical questions which were mostly from their CTO. 

Once we had covered everything, their CTO said that everything looked good and that they were going to go ahead and do the deal. I was pumped. And so was my head of engineering, who started getting super excited and talking fast about everything we had on the horizon. Well while he was having his verbal diarrhea, he also mentioned that we were working on some bug fixes (facepalm) and I could practically see the buyers’ eyebrows going up. 

I tried to get him to stop talking but there was no real polite way to do it, especially considering he was in a higher position within our company than I was. We finally got out of there, but I had a feeling that something had changed. A few days later, they told us they didn’t have the budget. Let this be a lesson: once you close the deal, shut your mouth and stop talking!  

Anonymous             Location withheld

“About seven years ago, I was selling telecom for a very big-name company. We were in the B2B division in an inside call center, and were fielding inbound calls and web leads from businesses in areas where we were looking to expand. 

I was only a month or two out of training, and to be completely honest, I wasn’t sure that I was going to stay at the company long-term. I didn’t like the huge corporate atmosphere, and was used to working for smaller companies, but I really needed a job at that point. I had actually gotten the job because the guy who cut my hair also cut one of the sales manager’s hair, and he put us in touch with each other. 

So I got a new lead. I can’t remember if it came from the web or if it was an inbound phone call. But it was a great lead that was going to basically get me to my monthly quota off that one deal alone. I forget the details but the person owned multiple buildings and was basically ready to go after their area had been surveyed properly. Again, I wasn’t super excited or anything since I didn’t know whether I was going to stay at the company, but it was nice to get the deal and know that I was gonna make some money. 

So we started the paperwork, and everything seemed to be going fine. Then, a day or two later, my sales manager (a different person than the one who’d gotten me the job), asked me to come to his desk. He asked how I’d gotten the lead, and after I answered, he told me that the lead belonged to another rep who was in a different building and had apparently been working the deal for months. 

He called the rep and his manager to try to figure out what happened, and the sales rep started insulting me and saying I was a scumbag who was trying to steal his lead, when it was very obviously in Salesforce under his name. I definitely remembered searching for it, and my sales manager (to his credit) searched the same lead in the same way it had come in, and because of the way it had been entered into the system, it didn’t come up when he searched for it either. 

So my manager reassured me that I wasn’t in any trouble, but that the lead belonged to the other rep and I wouldn’t be able to get any credit for it. The other sales rep was still whining about it even after they told him he would get the deal. It was a totally innocent mistake, but I got insulted and cursed out for it. The funny thing was that I honestly didn’t care much. I left a few weeks later and rejoined my old company.”

Anonymous             New Hampshire          

“I remember my biggest Sales Fail like it was yesterday, probably because it happened not so long ago. I worked (and still work) for a seventy-person sales team. We are the entire sales team for our company, which advertises strictly online. We call both inbound and outbound leads. 

At the beginning of the year, I was working a deal. The prospect was qualified but kept putting off the decision. My month wasn’t looking great, and he was the hottest deal I had going, so I racked my brain for all the sales tips I could remember in order to get the deal over the finish line, and decided I would make him an offer he couldn’t refuse. 

I called him and left him a message. When he called me back, I said that we were doing a limited time company-wide sale that would end on the last day of the month, and that he could get the discount but only if he signed ASAP. He listened calmly, then said he would call his wife and call me right back. 

Well, little did I know that instead of calling his wife, he called my company back through the main phone number instead of my direct line, and asked about our limited time sale. The rep who answered told him that we weren’t running any sort of promotions at the moment. 

A few hours later, I got an email from the prospect which said that he can’t do business with someone who he can’t trust, even if he was going to save a few more bucks with me. I tried to reason with him but he wouldn’t respond to any of my emails or calls. The worst part was that I didn’t hit my goal that month because I was so focused on his deal that I neglected to prospect for something better. Sales Fail!”  

Anonymous             Location withheld        

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