Key Takeaways

• Leading discovery conversations with curiosity rather than fear can help financial advisors better understand what matters most to their clients. 

• Harvard research found that people who ask more questions, especially follow-up questions, are better liked by the people they’re talking with.

• Forward-looking discovery questions still address risk, but they’re framed around what clients want rather than what they fear.

• The Passport Package™ (patent pending) gives curiosity a repeatable structure: clients rate 8 core mindsets from 1 to 12, so the gap between where they are and where they want to be shows advisors where to start.

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Advisor prospects can take weeks, if not months, to close sometimes, which naturally leads to some antsy-ness on the advisors’ part. As you’re thinking about how to shorten that sales cycle, one option has always been to create urgency. 

Many of us were taught that urgency moves people. Reminding them of risks like market drops, health changes, and life’s unexpected curveballs is easy to point to. Fear motivates people to act, and it can work.

I’ve learned that approach isn’t for me. Maybe you know it’s not for you, either. Fear is just one way to help someone take a next step, but in my experience, it isn’t what builds lasting client relationships. 

Why Advisors May Hesitate to Raise the Alarm

Surface acting is what researchers who study emotional labor call displaying emotions you don’t truly feel. A large body of research links surface acting to exhaustion and burnout.

Plenty of advisors talk about risk because they truly care about protecting their clients. But when an advisor feels pressure to create urgency that doesn’t come naturally, those conversations can start to feel forced. That’s surface acting, and over time, it can wear you down.

So if a fear-led conversation feels off to you, it might point to a different approach, one that fits and lets you do your best work while growing your practice. 

That approach is curiosity.

Why Lead with Curiosity?

Across three studies of real conversations, a team of Harvard researchers found that people who asked more questions (especially follow-up questions) were better liked by those they were talking with.

Questions signal responsiveness: that you’re listening, you understand, and you care. 

Think about what that could mean for a discovery meeting. A new client could say that their goal is to retire comfortably. But what does “comfortably” mean to them? It takes a second, third, and more questions to find out.

At that point, you understand what your client wants and can advise them better, and they’ve seen you care enough to understand them as individuals. That’s trust.

Questions That Point Ahead

Many financial advisor discovery meeting questions focus on what a client wants to protect against. Forward-looking questions focus on what they want to build toward. I’ve found that questions like these open the door:

• When you picture your life five years from now, what’s in it that isn’t there today?
• If work became optional, what’s the first thing you’d make more time for?
• Who do you want to take care of most, and what does taking care of them look like to you?
• What would help you feel ready if something unexpected came up?
• What are you already proud of in how you handle money?
• What would make our work together feel like a true partnership?

You still cover risks like readiness, protecting your loved ones, and care later in life; they’re just framed as what the client wants rather than what they fear.

Giving Curiosity a Structure

Maybe you love the idea of asking those questions in your discovery meetings, but you already feel there’s not enough time to cover what’s on your agenda to begin with. Remembering new questions that are supposed to domino into more questions seems impractical at best.

We built The Passport Package™ (patent pending) to give curiosity structure, something you can repeat and scale along with your firm. It includes two assessments: Your Expansion Passport® for clients who are still building wealth, and Your Walkaway Passport® for those preparing for their next chapter.

Each assessment covers 8 core mindsets, including Readiness, Foundation, Wellness, and Partnership. Clients rate where they are now on a scale of 1 to 12, and where they want to be.

A client at an 8 who wants to be at a 12 is telling you where their energy and focus are.

What the Results Can Reveal

One advisor I work with was certain philanthropy would be his high-net-worth client’s top priority. When the results came back, Purpose wasn’t where their focus was at all. What mattered more to them was Longevity, and what would happen if something happened to them.

The advisor never would have guessed it, given their wealth. But because the assessment asked the question privately, from the comfort of home, the client answered honestly.

Suddenly, he had a surprising and much stronger place to start with that client. 

The Passport Package™ (patent pending) isn’t meant to replace your discovery process, but to support it by bringing the same kind of structure to the human side that you already bring to the financial side.

Why Clients Stay With Their Advisors

Vanguard research found that emotional elements, like trust and a personal connection with an advisor, made up about 40% of the value investors placed on financial advice. With traditional financial advisors, much of that value centered on the relationship itself.

That certainly tracks with what I lived in my own practice. Over the years, about 98% of our clients stayed with us, including through the loss of a partner and as wealth passed to the next generation.

I don’t credit any one technique for that record, but I do know every meeting started with questions and curiosity. 

Growth That Feels Like You

If fear-based selling has never quite felt like you, you don’t have to do it anyway. Curious, forward-looking questions do the same work of moving a client toward a decision. 

But because the conversation starts with what your clients want, they usually walk away feeling understood. That feeling is often what keeps them coming back.

Curious where your clients would rate themselves? Book a short walkthrough of The Passport Package™ and see the assessment from their end.

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Frequently Asked Questions (FAQs)

Q: Can I use forward-looking questions without the assessment?

A: Sure. The questions work on their own, but the assessment adds structure that makes them a repeatable, scalable part of your process with every client.

Q: What if a client wants to start with risk?

A: Following their lead works well here. Curiosity means starting where the client is, and some clients feel most at ease when you tackle concerns first.

Q: Will asking more questions make my meetings longer?

A: Not necessarily. Because clients complete the assessment ahead of time, you can enter the meeting with a clearer understanding of their priorities and focus your questions accordingly.

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