Nicolas Cole explains that good sales questions aren't about sounding smart. They're about finding out what actually failed before, what the prospect really needs to fix, and who decides. Ask to learn, not to impress.
Chapters
You're not asking questions for the sake of asking questions. You are asking questions so that you genuinely understand their problem and what they care about. The goal is not how do I ask the perfect question? The goal is whatever the client situation is, you are asking questions to make sure that you understand what their biggest problem is, to make sure that you understand the things that they've tried in the past that didn't work, to make sure that you understand the things that they care about when making this decision. Your goal is to make sure that you're like, I want to know that I'm speaking to the right things. So what information do you need from them to make sure that you're speaking to the right things?