Sales Fails: "I took a prospect golfing and he embarrassed me at my own club"

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I sell commercial real-estate for a successful regional firm (we’re a big fish in a small pond). It’s a relationship-based business, and involves a lot of networking and nurturing relationships. Usually, this means taking people out to nice dinners or, in some cases, to play golf at my club.

A few years back, I invited one of my clients out for a round of golf. He brought a friend of his from out of town who is a successful residential investor who was looking to dip his toe into the commercial world. 

We got to the course, and it was a beautiful afternoon. The guy was nice enough, and we talked a bit throughout the round about what types of stuff he was looking for etc. Everything was going fine. But a few times during the round he was chopping up the fairway on his shots and wasn’t filling the divots. I decided not to say anything, even though the course rules (and common etiquette) is to fill the divots.

We finished the round and headed over to the clubhouse for a late lunch. The service was a little slow and the guy was complaining. At this point, I was annoyed with the guy but I cracked a joke to try and keep everything fun and friendly. A few minutes later, our drinks still hadn't arrived, so the guy called over a waiter and started giving him a hard time. I knew the waiter so I was embarrassed and tried to defuse the situation but the guy kept harping on him. 

Finally, I was fed up with the guy being disrespectful and making me look bad at my own club, so I just said to the guy, “If you don't like it here, you’re welcome to leave.” The guy got even more pissed, got up, and walked out. My client who brought him realized the guy was out of line and apologized, so that relationship was fine, but, needless to say, I didn't end up working with the jerk who left.

Anonymous      Location withheld 

I work inside sales in what I guess would be called financial services. We sell to consumers and have to discuss people’s incomes and personal finances in order to get them approved. Rarely does this become an issue.


A few months ago, I got an inbound lead. It was a middle-aged guy who was no different from our typical customer. He was friendly and conversational, telling me about his kids and his hobbies, the usual stuff.


We eventually got into a conversation about finances. This is part of our application process. When I asked his salary, he told me (it was in the low six figures), and mentioned that he’d just received a pretty big raise. As I normally would, I said, “Congratulations. That’s really awesome.”


After I said that, he responded with, “Is it though? Inflation eats up most of it and my payments eat up the rest. I don’t think it’s awesome at all.” Then he completely changed and started being super rude to me. He sounded distracted and was giving one-word answers, after being cheerful and conversational the other times we spoke.


Finally, after another ten minutes or so, he said, “Actually, I don’t think I want to do this. Don’t call me again,” and hung up the phone. I don’t know if there was something wrong with this guy, but I’ve never had someone change on a dime that quickly. I still don’t think I did anything wrong.


Anonymous      Location withheld 

The most embarrassing thing that’s ever happened to me in sales happened in 2006, when I was in the mortgage industry. I worked for a broker and we were churning out a ton of loans. 

I was working on a refinance for a couple that lived in somewhat of a rural area about an hour from our office. They had gathered up all of their paperwork, but they didn’t have a fax machine and I offered to go out there and go over everything and pick it up while having them sign something. 

I hadn’t been feeling well that morning, and on the drive over, I started sweating and was just feeling tightness in my stomach, but I figured I’d just get there and get in and out. Well, when I arrived, these people were incredibly nice and I could tell they didn’t have guests very frequently because the wife had put out snacks on nice plates and different drinks so I would be comfortable. 

I sat there talking with them for a while, going over everything, but my stomach was getting worse and worse, and finally I just asked if I could use their bathroom. They said of course, no problem. 

I kid you not, I was in their bathroom for close to an hour getting sick. Every now and then, the woman would come to the door and ask if I needed anything and was I sure. It was absolutely brutal. But I explained that I must have had a stomach bug, and the deal closed as planned. Still, it was the most miserable few hours of my life. I’ll never forget it. 

Anonymous      Location withheld 

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