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3 High-Value Questions that Turn into Valuable Conversations

by Bill Cates

A high-value question is one that brings value to either the person asking the question or the person being asked. For you, the advisor, the more context you have about a prospect or client, the more you are able to help them.

Sometimes the value is perceived by the prospect or client in the form of learning something new and/or opening up their awareness and thinking to a new concept.

And while new awareness and new thinking are important, the true value comes when one or both parties begin to take new actions.

In my interviews with top advisors for my podcast and presentations to groups, I almost always pick up new high-value questions or am reminded of tried-and-true questions.

Here are 3 high-value questions that can turn into valuable conversations (in no specific order):

NOTE: The request for 3 answers with each question is intentional. Sometimes the most important answer is their first answer, with no hesitation. However, sometimes their third answer to the question is most significant – after they’ve thought more deeply. All answers should be treated with equal importance until you gain further understanding. Feel free to adjust the wording of these questions to fit your style and the situation.


What are the top 3 items on your bucket list – 3 things you would regret not doing, being, or having?

Lester Matlock (Top Advisor Podcast – Episode #3) has used this bucket list question to bring tremendous value to his clients. Sometimes he helps them set aside the money. Sometimes he makes introductions or just keeps their dream and wishes alive.

You may already ask your clients about some of their wishes and dreams. Do you take it to the next level? Do you keep those items alive in your meetings and do you provide whatever support you can to make those dreams and wishes come true?


What are 3 things your current advisor doesn’t know about your goals, dreams & legacy?

This is a bit of an edgy question, so timing is everything. If a prospect has reached out to you, you might ask this question early on in your conversation. If you’ve initiated contact, you may want to wait a bit longer. Experiment for yourself.

What’s neat about this question is that just asking the question might help a prospect decide he/she is working with the wrong advisor; maybe because their current advisor never asked the question or didn’t keep the conversation going throughout the relationship.


When you worry or grow concerned about your finances, what are 3 things that tend to come up?

The most common reason a prospect will give you some of their precious time and attention is because there’s a gap between where they are and where they want to be with regard to one or more parts of their financial life, such as needing more saving discipline or wanting to pay less in taxes.

In addition to this financial gap, there’s usually an emotional gap, such as a lack of clarity or lack of confidence (they usually go hand in hand).

Now it’s our turn.

What are your favorite high-value questions? Let’s all learn from each other. My direct email is:

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