Why Most Advisors Fail to Connect With Clients

The best advisors aren’t just great with money—they’re great with people. In this episode, I sit down with Brendan Frazier, host of The Human Side of Money, to dig into a game-changing truth: advice alone doesn’t drive action. Connection does.

Brendan unpacks the psychology behind why clients often don’t follow advice and what top advisors do differently to earn trust, spark motivation, and influence behavior. From mindset shifts to science-backed strategies, this conversation is a masterclass in the human side of advising—and how it’s often the missing piece in a thriving practice.

Three Insights From This Week's Episode

• Deliver advice in a way that drives action. It’s not just what you say—it’s how you say it. Brendan shares how advisors can borrow from doctors to improve follow-through by focusing on communication, not just recommendations.
• Use your clients’ words to build deeper trust. Instead of defaulting to praise or reassurance, reflect on what you hear. Brendan unpacks how small shifts—like repeating their language or resetting between meetings—can dramatically improve connection and clarity.
• Ask “Why now?” in every first meeting. This one simple question reveals the emotional reason a client is sitting in front of you. Brendan explains how it uncovers urgency, builds empathy, and sets the foundation for meaningful planning.

“We think people just want the answer, the solution, but they really want to feel heard and understood before they’re actually willing to follow through and do it.”  – Brendan Frazier

Doing Business and Doing Life.

In this week's episode, I sit down with behavioral finance expert Brendan Frazier to talk about the human side of financial advice—specifically, how to create the kind of connection with your prospects and clients that a spreadsheet never could.

We dig into the best questions to ask in appointments—the ones that build real trust and help you focus on the aspirational side of what every retiree wants out of their retirement.

For the comedy fans out there, we even referenced a little-known skit by the late comedian Mitch Hedberg, where he talks about a radio interview and gets asked the simple but profound question, “Who are you?”

Brendan shares some of his favorite connection-building questions to use in your appointment process. And on that note, I also wanted to resurface a set of questions I’ve talked about before with behavioral finance expert Daniel Crosby. These came from a 1997 study by psychologist Dr. Arthur Aron—better known as the “36 Questions to Fall in Love.”

Fun fact: Cosmopolitan even tested these questions out, published the full list, and reported a few surprising results.

Below, I’ve pulled out some of my favorites that you might consider trying in your next appointment.

• What would constitute a “perfect” day for you?
• If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
• What in your life do you feel most grateful for?
• Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
• Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

Reflection Question: What small shift could I make in my next client conversation to build deeper connection?