One of the most interesting things I've discovered early in my sales career was the importance of questioning my prospect's questions. I was selling technology at the time. Now I'm not a real tech guru myself, so I had my sales support guy with me. My prospect was peppering us detailed questions about our system's capabilities. Unfortunately, we couldn't do a lot of what he wanted. I felt the opportunity slipping away.
So I finally spoke up and said, "Tom, why are you asking us all these questions?" He proceeded to tell us what he wanted to accomplish and that he wanted to make sure we had the capacity to do it. Well, here's the deal. We absolute could do it -- but we did it differently that he'd ever thought about. When we explained how we could help him, he was blown away -- and we got the business.
From that day forward, I changed. Whenever I felt my prospect's questions were being used to evaluate something, I'd ask: "What are you hoping to accomplish?" And, whenever, I heard a question that didn't make sense to me, I questioned the question: "Why are you asking that?"
It's amazing what you'll find out when you ask. And, if you don't ask, it's amazing what you can lose.