Listen to this week’s episode

Episode 159

On this week’s episode of Next Mile, I sit down with Melissa Caro, Founder of My Retirement Network. For the past decade, Melissa has studied real advisor conversations to understand what communication behaviors build stronger client relationships. Today, she helps advisory firms close the client language gap through digital learning, live coaching, conversation analysis, and AI-powered insights that turn real client meetings into learning opportunities.

We discuss why the best financial advice starts with the right conversation. We explore why wealth management is a people business first, how to make discovery meetings feel less like data collection and more like meaningful conversations, and how advisors can use AI and technology to create more room for human connection.

Key Takeaways

• Put the relationship before the financial plan. The strongest advisors know that trust and engagement come first, and then use their technical knowledge to support the relationship.

• Turn data gathering into a conversation. Instead of treating discovery as an intake form, use open-ended questions and genuine curiosity to uncover what actually matters to clients. 

• Don't rush past the important moments. A simple answer—like a client's expected retirement date—can open the door to deeper conversations about identity, fears, goals, and expectations. Those insights can make the financial plan feel collaborative rather than prescriptive. 

• Use technology to become more present, not less. AI can remove administrative work such as note-taking, but advisors need to retrain themselves to use that extra capacity for deeper client engagement. 

Quotes

"The real elite advisors know that you need to engage with people, build trust, and build those relationships first." ~ Melissa Caro

"What makes a great associate isn't necessarily the same as the characteristics you translate into what makes a great lead advisor." ~ Melissa Caro

"You can turn anything that is considered a hard data point into a soft data point if you just ask open-ended questions. That's where the moment is—that's where your gold is." ~ Melissa Carro

Links

• Melissa Caro on LinkedIn

• My Retirement Network

• Julie Littlechild on LinkedIn

• Pink Floyd - The Dark Side Of The Moon

• The StorySelling Method

• On the Shortness of Life

Connect with our hosts

• Milemarker.co

• Kyle on LinkedIn

• Jud on LinkedIn

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Kyle Van Pelt