Mastering the Art of Great Questions for Meaningful Growth

For nearly seven years, I've been hosting a podcast, and throughout this journey, I've experimented with multiple formats—from having a co-host to going solo and inviting guests.

Although the names and formats may have changed, my goal remained constant: to connect with as many people as possible.

Initially, I believed launching a podcast would be a straightforward ticket to widespread recognition.

As would be expected, that didn’t end up being the case early on.

I soon realized that, like the early 2000s fallacy of "launch a website, and customers will come," much more effort was required.

The real breakthrough came when I understood the more profound value of asking great questions.

Listening to renowned podcasters like Tim Ferris and Andrew Huberman inspired this lesson. I learned that the essence of a captivating podcast lies in the art of questioning.

At first, I took the skill of asking questions for granted. However, I soon discovered that it's a craft that can be honed and perfected, leading to richer and more meaningful conversations.

Being adept at asking questions is about more than curiosity. It's about being genuinely present in the conversation.

We've all seen interviews in which the host runs through a list of questions mechanically without engaging with the responses. This approach often misses the opportunity for deeper insights and connections.

Great questions are shaped by context, tone, and a profound understanding of the subject.

One powerful lesson came from William Rosenberg, the founder of Dunkin' Donuts, who once said:

"Though I dropped out of school in the eighth grade to help support my family, over the years I learned a key lesson, as did other entrepreneurs like me: We know we don't know.

That's why we're always asking questions, seeking answers.

Sometimes people who hold a lot of degrees think they know everything. If they think they know everything, they stop growing. They're not open to new ideas."

Rosenberg's insight emphasizes that success stems from a perpetual curiosity and a willingness to learn and adapt.

In wealth management, this translates to continually asking questions to understand clients better and serve them more effectively.

Success rarely comes from the first attempt; it is refined through questioning, learning, and iteration.

The culture we grow up in often discourages questions, valuing answers over inquiry.

This mindset is ingrained in our education system, where teachers are seen as the ultimate source of knowledge, and students are rewarded for correct answers rather than insightful questions.

As we progress in our careers, there's an unwritten expectation that higher positions come with all the answers. Yet, the reality is that the more experienced and senior we become, the more questions we should ask.

Rewiring our approach to value questioning over simply having answers can lead to exceptional returns.

To become great questioners, we must cultivate natural curiosity and remain present during conversations.

I invest significant time researching my guests and their areas of expertise for my podcast. This preparation allows me to ask informed and engaging questions, leading to richer discussions.

The words we use to frame our questions also matter.

I’ve found that starting questions with "what" and "how" tends to elicit more detailed and thoughtful responses than "why," which can sometimes make people defensive.

Focusing on emotions—asking what someone thinks, feels, believes, or wants—invites more profound and more personal answers. There is no right or wrong answer when talking about your emotions. These questions make respondents feel more comfortable and less judged, encouraging them to share more openly.

In our industry, understanding our clients goes beyond the initial questionnaire. It's about delving into their worries, purposes, experiences, desires, and aspirations. Effective questioning transforms the advisor-client relationship.

In our role, the client expects us to get to a plan of action or a solution. Thus, questioning is just one aspect of the conversation.

A practical approach I've used is the funnel methodology: starting with broad, open-ended questions to gather comprehensive information, then probing for more details on specific topics, and finally summarizing and confirming the understanding with closed questions. This method ensures we capture the full scope of the client’s needs and perspectives before formulating an action plan.

Asking great questions fosters a deeper understanding and a stronger connection.

When clients feel heard and valued, their trust in us as advisors grows. This connection is crucial in our industry, where the decisions we help our clients make significantly impact their financial futures.

In our profession, we have the unique opportunity to learn from the diverse experiences of our clients.

Every interaction is a chance to expand our knowledge and improve our service. By mastering the art of questioning, we can uncover the nuances of each client's situation and tailor our advice to meet their specific needs.

Ultimately, our goal is to impact our clients' lives positively.

By being genuinely curious, present, and skilled in asking great questions, we can build the deep, meaningful relationships necessary to achieve this goal. This approach benefits our clients and enriches our professional journey, making us better advisors and more empathetic individuals.