Tuesday Email: The soft skills needed to help someone identify their purpose

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

My notepad sat untouched on the conference table, three bullet points waiting to be delivered.

Seventy-five minutes into the client meeting, I still hadn't said a word.

I kept waiting for my dad to transition—to mention the portfolio returns I'd calculated, to discuss the rebalancing strategy I'd prepared, to reference any of the technical analysis I'd spent hours perfecting.

My CFP and CFA credentials felt like expensive weights in my pocket.

Instead, my dad asked about the client's daughter's college decision. Then about his father's health. Then about whether he still felt anxious when the market dipped, or if that had changed since we last talked about his Depression-era parents.

When the meeting ended, the client shook my dad's hand and said, "I always leave here feeling lighter."

Not smarter. Not more informed. Lighter.

I looked down at my pristine notes and realized I'd been preparing for the wrong meeting entirely.

Here's the uncomfortable truth our industry doesn't want to admit: we've been training advisors backwards.

We pile on certifications and technical credentials because they're measurable, testable, and quantifiable.

A CFA charter proves you understand portfolio theory.

A CFP designation proves you know the tax code.

But neither proves you can do the one thing that actually matters in this business—make someone feel understood.

My dad founded our firm with street smarts and an uncanny ability to make people feel like his best friend after one conversation. No fancy designations. No technical wizardry.

Just connection.

That firm now serves over 6,000 families and employs more than 100 people.

Meanwhile, I spent my first three years trying to "prove" I belonged by collecting credentials.

I thought technical excellence was the price of admission to the family business. I was wrong about what mattered. Here's what I learned in that 75-minute meeting: money isn't actually about money.

It's about worry.

It's about feeling foreign and lost in a world of financial jargon.

It's about wanting someone to simply say, "I see you, I understand what keeps you up at night, and I'm looking out for you."

When someone trusts you—truly trusts you—they don't need to see the quarterly performance report to feel confident.

They don't need you to explain the Sharpe ratio. They need to know that you know them.

This is the shift happening in our industry that most advisors are missing.

As technology automates the technical work, our jobs are becoming less about calculation and more about connection.

Less about having answers and more about asking the right questions.

Less about being the expert fixer and more about being the guide.

So here's what I'm asking: What if our confidence in our technical skills is actually hurting us?

What if the hours we spend pursuing another designation were better spent learning to sit in silence after asking a difficult question? What if instead of preparing talking points, we prepared to listen so deeply that our clients surprise themselves with what they reveal?

The advisors who thrive in the next decade won't be the ones with the most letters after their names. They'll be the ones who mastered something far harder to measure: the ability to make someone feel lighter when they leave the room.

My dad never earned a CFP. But he built something more valuable—a practice where clients stayed not because of returns, but because someone finally understood what their money really meant to them.

That 75-minute meeting was the most important education I received in this business.

Not because it taught me what to do, but because it taught me what actually matters. The technical skills still have their place. But they're the baseline, not the differentiator.

Connection is the skill that transforms a transaction into a relationship, a client into a referral source, a meeting about money into a conversation about what makes life meaningful.

We aren't in the investment management business. We're in the business of helping people carry the weight of their financial lives a little more lightly.

That's what my dad understood.

And that's what I finally learned to see.

The best is ahead!

-Matt