As a sales keynote speaker, I often ask audiences, "What keeps you up at night when it comes to sales?"

So often, sales people are losing sales because they never get to the heart of the challenge that the prospect is facing. Most sales interactions involve only a very surface-level conversation about how and where the prospect is hurting. However, in today's market, that is the primary goal of a sales person--to understand the core challenges a prospect is facing. Once the sales person understands the challenges on a deep level, then suggesting a solution is the next logical step.

That is why my favorite question is: "What keeps you up at night when it comes to [fill in blank with what you do]?"

Here are some examples:

• "What keeps you up at night when it comes to your branding?"
• "What operational challenges are keeping you up at night?"
• "What about your website is keeping you up at night?"

This question is so beautiful because it cuts right through all of the fluff and gets a prospect talking about what is frustrating enough to bring home after hours. This is a true indicator of whether something is meaningful to a prospect. Remember, if a prospect is not hurting, then he is not going to be qualified. The other aspect to this question that makes it so powerful is that it is personal. Often times, business challenges are not personal, but issues that keep a person up at night are always personal. By asking that question, you are cutting right through to the personal. What other questions do you ask your prospects to understand their challenges? Please share below.