In a world full of data, projections, and performance reports, it can be easy for financial advisors to default to numbers. But what truly sets advisors apart is in the questions they ask.

Today’s most effective financial professionals aren’t just managing assets. They’re building trust, fostering emotional connection, and helping clients align their wealth with their values. To do this, you have to go deeper. And that starts with asking powerful questions.

Whether you’re onboarding a new client or preparing for an annual review, the right question can shift the entire conversation and relationship. It can build clarity, reveal priorities, and show your clients that you care about more than just the numbers.

Here are five powerful, human-first questions that can transform your client conversations – plus how they align with key client mindsets within The Passport Package™.

1. What are you most passionate about pursuing or learning outside of your work?

This question opens the door to your client’s passions and interests. It’s a chance to step outside the financial box and learn about the things that energize and inspire them.

Understanding what brings your clients joy can help you create plans that support their lifestyle in more personal and fulfilling ways. Whether it’s learning a new language, exploring creative hobbies, or investing in travel, this question uncovers the goals that numbers alone can’t capture.

Relevant Mindsets: Purpose Mindset, Accumulation Mindset

2. What routines or habits help you feel grounded and secure in your daily life?

This question brings out the foundational habits that help clients feel safe, stable, and in control – things like daily routines, morning rituals, or financial habits that give them stability.

When you understand how your clients anchor themselves in day-to-day life, you can build strategies that support and protect those anchors. You’re not just helping them accumulate wealth, you’re helping them sustain a life that feels steady and rooted.

Relevant Mindsets: Foundation Mindset, Readiness Mindset

3. How do you prioritize your mental and physical health, and what new habits would you like to develop?

Health and wealth go hand-in-hand. Clients who aren’t taking care of their physical and emotional wellbeing may not be able to fully enjoy the financial future they’re working so hard to build.

This question gently invites clients to reflect on their wellbeing and the role it plays in their long-term planning. It also helps you identify areas where additional support may be needed, whether that’s adjusting financial goals to include wellness resources or simply starting a more empathetic conversation.

Relevant Mindsets: Wellness Mindset, Longevity Mindset

Also check out our blog Wellness and Wealth: Why And How Financial Advisors Should Prioritize Client Health in Planning for more on this.

4. How do you like to celebrate your achievements, big or small?

This question helps you understand what motivates your clients, how they mark progress, and what makes them feel accomplished.

Celebrating wins – especially the small ones – can build momentum and engagement. When you learn how your clients recognize success, you can create milestones in your planning process that mirror what matters to them.

Relevant Mindsets: Accumulation Mindset, Walkaway Mindset

5. When you think about your future, what possibilities excite you the most?

This is the dreaming question. It shifts your client’s mindset from fear or stress to excitement and hope. It invites them to imagine the life they want, not just what they’re trying to avoid.

This question can open the door to discussions around retirement, career transitions, lifestyle design, philanthropy, or even legacy planning. When you know what lights them up about the future, you can build a plan that leads them there.

Relevant Mindsets: Purpose Mindset, Longevity Mindset, Income Mindset

When to Ask These Questions

Timing is everything when it comes to meaningful client conversations. Here’s when these questions work best:

• Initial Client Meetings: Start relationships with depth and purpose right from the beginning.
• Annual Reviews: Use these questions to reflect on growth and reset goals.
• Life Transitions: Bring these into the conversation during major changes like career shifts, retirement planning, or family milestones.
• Quiet Periods: If a client has been unresponsive or disengaged, the right question can reignite the connection.

Bookmark this blog! Because these aren’t one-and-done questions, they’re ongoing tools that can guide planning at every stage.

How to Ask These Questions (Without Making It Awkward)

The delivery matters just as much as the question itself. Here’s how to integrate these questions into your process naturally:

• Frame it as a conversation, not a checklist: Let clients know you’re asking because you care about what really matters to them.
• Start with one or two: You don’t need to ask them all at once. Choose one that fits the moment.
• Create space for reflection: Ask the question, then pause. Let clients think and respond in their own words.
• Use tools to make it consistent: This is where The Passport Package™ can help.

The Passport Package™ includes two client-facing assessments that are designed to ask powerful, human-first questions – like the ones above – in a way that feels seamless, personalized, and thoughtful.

Best of all? It’s completely white-labeled to your firm, making you the trusted source of these insights. You’ll receive data-rich reports that highlight key client mindsets and give you a starting point for the kind of conversations that deepen relationships and inspire action.

Whether you use these questions on your own or as part of The Passport Package™ process, the key is to make them part of how you show up, not just once, but over time.

How The Passport Package™ Provides Powerful Questions that Align with Key Client Mindsets:

These five questions are just a starting point. When you begin to understand your client’s mindset – how they think, feel, and make decisions about money – you can deliver advice that truly resonates.

That’s exactly why The Passport Package™ was created.

The Passport Package™ is a scalable, repeatable process that helps financial advisors uncover 11 distinct client mindsets:

• Readiness Mindset: How prepared are they for change?
• Caring Mindset: Who matters most to them?
• Foundation Mindset: What routines give them security?
• Wellness Mindset: How do they support their health?
• Resource Mindset: How do they manage time, energy, and skills?
• Accumulation Mindset: What drives them to build?
• Walkaway Mindset: What’s next when they step away?
• Longevity Mindset: What does independence look like as they age?
• Income Mindset: What brings financial security?
• Purpose Mindset: What brings meaning?
• Partnership Mindset: Works to build trust between you and your clients? 

When you integrate these mindsets into your discovery and review process, you gain a deeper understanding of your clients’ lives, not just their finances.

And that changes everything.

Bringing It All Together

If you’re looking to strengthen your client relationships, start by asking questions that go beyond the numbers.

Because at the end of the day, it’s about helping your clients create lives that feel whole, secure, and purpose-driven.

Ready to deepen your conversations and uncover what really matters to your clients?

Start with these questions. Then take it further with The Passport Package™.

Want to learn more: Book a free 15-minute demo of The Passport Package™ with a member of our team today!