Worst Sales Call, Highly Valuable Lesson

I started my career in as a technical guy in a large organization’s support team. Over my time with the company I switched jobs a few times, but somehow ended up getting moved into a sales job as a Client Executive. It came as a surprise, but I would be managing clients I had been working with for the past 2 years as a Customer Success Manager and this would jut mean I got paid for additional sales. It was during this early time in my sales career that I learned an extremely valuable lesson that the most important thing you can do as a sales guy is listen, verify, then pitch. Understanding a customers vision and priority is not easy and sometimes you think you have all the answers, but they end up being all wrong. This blog is a story is of a blown deal by me that taught me to shut up and listen when working with a client.

I had just been promoted to a Client Executive role and there was zero opportunities in the pipeline. I was optimistic though because my clients I had been working with as part of my previous support & services role. I knew there were opportunities in my clients, there was budget, and I had a relationship, what could go wrong? One of my largest clients had a project underway that fit perfectly into my products capabilities. I had an engineer that worked full time on-site and he knew all the players and details around the project. I had worked for a couple of years with all of the influencers and had a friend/client relationship with the CISO. This was going to be a $3m sale and get me President’s club and accelerators in one hit.

I started working the deal by gathering all the information I could. I talked with all my contacts that were running the project, I talked to my engineer onsite, the CISO, and anyone else who would share with me project details, pains, and concerns. Our team had a meeting scheduled with the CIO who was the decision maker to discuss the project business details and how my company might fit in. It was in this meeting that I make the sales blunder of a century and I did it in front of my brand new boss as well.

After all my research I came up with the perfect proposal and the perfect business case to go with it. I was going into this meeting with the CIO with 100% confidence I would not only make the sale, but I would close it in this meeting. I was going to get commitment to buy, because I was prepared with all the right information and the right pitch. The meeting started off fine with the CIO introducing what they were looking for, challenges they were facing, and his priorities. Yeah, Yeah, let’s get to the point here was running in my mind. The whole time preparing what I was going to say and how I was going to position our company. Finally, there was an opening that allowed me to say something. I articulated the perfect story about how we could help this company with efficiency and provide a huge ROI. By the way, as a side note we could do this and we were a perfect fit. When I finished, without hesitation, the CIO continued talking, seemingly dismissing everything I had said. Frustrated, I figured he just did not understand my point so I started to reformulate how to position this in my mind to take a second run at the story. Shortly after the first attempt a second one presented itself. I re-told the story in a different way to the CIO and again he continued on without even a glance my way. Really frustrated now I was not sure what was going on here. Again, I started to think about how I might tell the story a different way to help him understand why our solution was the perfect fit. Yep, you guessed it, once again I got an opportunity for input and I went after the value proposition with direct and concise wording. Surely this would get his attention and put this to bed.

Wrong! The CIO stopped, physically turned toward me and said: “I heard you the first two times, you obviously are not hearing me. Please do not say another word in this meeting because I have no interest in what you are saying!”

Ouch! I guess you can imagine that we did not win the deal. I was completely embarrassed and probably should be thankful my boss did not fire me on the spot. See the CIO was the type that believed he was the smartest one in the room. Anything being implemented had to be because he thought of it and the plan was his. All my insights and research were correct, we were a perfect fit for what they needed, but I missed the biggest element of the sale, the CIO personality.

My interruptions and assertions that our solution was going to solve all of his problems were offensive to him. It was like I was saying your organization is broken and I am going to fix it for you. When selling to someone with a huge ego, not the best approach. Questions, praise, and conversation steering was what was needed. I needed to feed into the CIO’s ego and let him come up with the solution that we were the perfect fit. Had I listened the my value proposition and vision did not align with his. He had not shared what his priorities were with his reports, so all the research I did caused me to miss the mark. Not paying complete attention to what he was saying in the meeting and asking probing questions made my interruptions annoying to him. The most important thing you can do in sales is understand the person behind whom you are trying to sell to. The second is to really listen when they speak so you can articulate your proposal in a meaningful way to them.

I want to be clear that all my previous research and effort was the right thing to do, but not tailoring my approach to the CIO was the mistake. Make sure you are listening all the time, taking notes on key points, and truly understanding what matters most to your prospect. What matters to the CIO is different to what matters to the CISO or the Senior Administrator. Adapt your messaging to your audience and always adapt it to the highest decision maker in the room. What I mean is if the CIO is there his vision and priorities are the focus. If you are meeting one on one with the Sr Admin then his are priorities are the focus. You get the point.

I hope that my most embarrassing sales call might help others not make the same mistake as I did. Good hunting to all of you out there.

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