Sometimes the most revealing insights into a client’s situation come not from portfolio analysis or performance metrics but from a well-placed, probing question.
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Yet in early discussions with prospects or onboarding calls, it can be difficult for advisors to find a path into a deeper conversation, one that goes beyond numbers to illuminate the fuller picture.
And for clients, especially those new to an advisory relationship, opening up about what they want, both from their advisors and for their financial futures, can be challenging. As a result, advisors might have to act as detectives, uncovering the difference between a client’s stated goals and their true reality.
The information they surface often has little to do with markets but rather things like family obligations, hidden financial fears and unconscious biases.
Before looking at investments or doing any planning, Gloria S. Garcia Cisneros, a wealth manager with the RIA LourdMurray in Los Angeles, likes to pose questions that probe around money behaviors — often subconscious and ingrained from childhood.
“Things like scarcity, fear, oversaving, overspending, avoidance,” she said, adding that uncovering these internalized patterns can help clients understand that their finances are about more than math.
She also asks what a client’s life would look like if everything goes “right” for them financially.
“Most clients define goals in abstract terms — retirement, wealth, freedom — but struggle to articulate what they’re actually building toward,” she said. The answers to this question help her translate vague goals into concrete planning.
But what might be the “most powerful question” in her arsenal, Garcia Cisneros said, is beautiful in its simplicity: “Anything else?”
The open-ended query allows clients to expand as much as they want, which helps them process, add color and go deeper.
“The biggest breakthroughs rarely come from better spreadsheets, they come from better questions that help clients feel seen, not just analyzed,” she said.
With that in mind, we asked advisors across the country: What question has led to your most surprising or revealing client insight?
Reframing legacy, beyond lineage
Jay Zigmont, founder and CEO of Childfree Wealth in Nashville, Tennessee:
“I work with the 25% of the U.S. that is child-free. When you don’t have a legacy based on lineage, it can be hard to focus your life and financial plan. My favorite question is: ‘What does the second line of your obituary say?’
“The first line of your obituary is usually your name, age, and location. The second line says something like, ‘Father of three leaves behind Jack, Joe and John ….’ As child-free people, that won’t be our second line. For us, our second line talks about the impact we had on the world and what matters to us. My second line probably says something like ‘Loving Husband, World Traveler, Author and Innovator.’ It isn’t written in stone yet, but it gives focus that then can be planned around.”
The one word that says it all
Vered Frank, founder of StackWealth in New York City:
“I used to ask a series of questions to understand a client’s relationship with money. The typical ones like, What does money mean to you? What’s your earliest memory of money?
“Important questions. But more often than not, people would freeze, overthink or give me the answer they thought I wanted.
“So I stripped it back to one: What’s the first word that comes to mind when you think about money? Don’t edit yourself. Just say it.
“You’d be surprised what comes up. Security. Freedom. Fear. Shame. Guilt.
“And sometimes: Greed. Cheap. Desperate. Words that reveal not just what they want money to bring them, but how they see the people who have it. Or don’t.
“That one word always kicks off a powerful conversation. They hear themselves say it, and suddenly they want to know where it came from.
“What reveals itself naturally is a wealth of everything I need to truly know how to work with them.”
Facing the reality of parental care
Chad Holmes, founder of Formula Wealth in Fairhope, Alabama:
“One question I come back to often is: ‘What role do you think you’ll realistically play in your parents’ financial life over the next five to 10 years?’ It sounds simple, but it opens a door most planning conversations ignore.
“Clients start to think beyond inheritance and into responsibility. Will they step in with power of attorney? Will they need to supplement care? Is there a long-term care gap hiding in plain sight? And just as important: Are they counting on an inheritance that may quietly be shrinking?
“I typically ask this when clients are in their 50s or early 60s. It reframes planning from ‘What will I get?’ to ‘What might I need to give?’
“The answers often reshape everything from cash flow planning to investment risk to estate strategy. We’re no longer planning for one couple, but two.”
What dream free time reveals
Samantha Mockford, associate wealth advisor at Citrine Capital in San Francisco:
“Kiersten Peshek, a wealth advisor at my firm, asks clients how they would spend three extra hours in the day. They clarify that these are good hours — in this hypothetical, they are not tired from a full day, the chores are done, the kids are content, etc.
“Clients often list ‘retirement’ as a very vague goal, but homing in on how they would spend a few free hours each day reveals how they actually want to spend their time if they had the freedom to choose. Some would pursue hobbies; some would spend unhurried time with family; some would continue working on enjoyable side projects. Surprise — many people would continue working out of enjoyment instead of necessity, and we plan accordingly!”
The importance of past advisor experiences
Joon Um, certified financial planner and enrolled agent at Secure Tax & Accounting in Beverly Hills, California:
“One question I often ask is: ‘Have you worked with an advisor before, and what did you like or not like about that experience?’ It’s a simple, more personal question, but it usually opens up a much more honest conversation.
“Clients will share what actually mattered to them — communication, responsiveness, trust or feeling understood — not just performance or results. As a tax advisor/CFP, it helps us understand what kind of relationship they’re really looking for, not just what they say they want on paper. It also reveals frustrations or gaps from past experiences that we can address early. We’ve found that long-term relationships come down to fit, and this question helps set that foundation from the start.”
Letting clients speak their minds
Todd Calamita, founder of Calamita Wealth Management in Charlotte, North Carolina:
“It might sound simple, but the question I started using about five years ago with prospects was ‘What’s on your mind?’
“The best part about this question is that it’s wide open, and it instantly triggers for the prospect to share exactly what’s on their mind and what their specific concern was that led them to speaking with a financial advisor. Most of the time it’s around a specific fear. I think of it now as ‘magical,’ but it ends up being so revealing without a lot of back-and-forth of the typical financial advisor questions.”
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