Asking these “new-connections” questions is an article for another day. But there is one question that you can start working into your discovery conversations now.

It was inspired by a talk given by author and journalist Krista Tippett at Google in 2019. Rather than asking the “What’s important about _____ to you?” question or the “What’s your earliest memory of ____?” question, you make a subtle but meaningful twist by actually combining those two questions.

Let’s say you’re exploring your client’s beliefs and biases around money in an effort to bring forth a new aha. You could ask something along these lines: “Mary, can you share with me the very first time when the word ‘money’ meant something to you?” Or make a slight twist to that by asking, “Joe, what’s your earliest memory of when you started to understand what money means to you?”

These types of questions will be most effective when you preface them by explaining the context behind why you are asking them. And asking them early in your conversation creates a shared understanding that is a solid base on which to build upon.

Conducting 400 podcast conversations doesn’t make me a great podcaster if all I did was do one podcast 400 times. Rather, it’s the cumulative effect of tweaking, of trying new things, of learning what works and what doesn’t, and then practicing and aspiring toward mastering those skills.

Likewise, becoming a better listener so you can cultivate deeper insights and connections with your clients is an ongoing practice with many layers. Yet it’s one well worth pursuing.

Steve Sanduski, CFP, is the founder of Belay Advisor; the CEO of ROL Advisor, a discovery process technology system; a New York Times bestselling author; host of the Between Now and Success podcast and a financial advisor business coach.

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