One of the most important things I discovered early in my sales career was getting the hidden messages and concerns behind prospects' questions. I was selling technology at the time. During one call, my prospect peppered us with detailed questions about our system's capabilities. Unfortunately, we couldn't do a lot of what he wanted, and I felt the opportunity slipping away.
So, I decided to speak up and said, "Tom, why are you asking me all these questions?" He proceeded to tell me what he wanted to accomplish with the computer system and explained that he wanted to make sure we had the capacity to do it. Well, we absolute could do it, but we did it in a way that was different from how he was used to doing it. When I explained how we could help him, he was blown away, and I got his business.
From that day forward, I changed my approach. Whenever I felt a prospect's questions were being used to evaluate something I offered, I would ask, "What are you hoping to accomplish?" And, whenever I was asked a question that didn't make sense to me, I would question the question.