“Parlor-Trick Questions” Advisors Ask to Sound Deep

By Jean-Luc Bourdon

Comedian Chloe Radcliffe nails it. In her set, she makes fun of the kind of pseudo-profound questions that some financial advisors also like to ask.

“What would you do if you didn’t have to worry about money?”

She adds, exasperated, “What are we talking about? I hate those questions.”

Then comes the follow-up cliché:

“What would you do if you knew you were going to die tomorrow?”

Radcliffe’s R-rated answers aren’t fit for a family audience, but her summary line is perfect: “I’d do something that’s going to make me really need to be dead tomorrow.”

It’s funny—and spot on. Those kinds of questions are what I call parlor tricks. They seem deep but are really conversation shortcuts. Instead of building understanding through trust, they try to force it out of you with a clever-sounding prompt.

Why These Questions Make Me Cringe

I’ve always disliked them because they confuse imagining an experience with actually having one, which can obviously be very different. Such questions sound like invitations to meaning, but they’re really just invitations to speculate.

Many years ago, I ended up in an emergency room with a doctor who thought my time might be short. I’d always imagined that, if I were facing death, I’d party all night, live it up, and max my credit cards. Faced with reality, all I wanted was to finish my last college classes and clean up my affairs so I wouldn’t leave a mess. My top goal was to die a college graduate. Who could have guessed? Not me!

Maybe the reason I recovered was to tell you that those “imagine the unimaginable” questions are bunk.

It’s Not Just Me — Psychology Backs It Up

Harvard psychologist Daniel Gilbert, author of Stumbling on Happiness, has shown that humans are terrible at imagining what will actually make us happy. He and others have studied what’s called affective forecasting—our ability to predict how we’ll feel in the future. The verdict: we’re consistently wrong.

Gilbert contrasts two mental strategies:

• Simulation – imagining ourselves in a future situation, and predicting how we’ll feel.
• Surrogation – learning from how other real people in similar situations actually felt.

It turns out we’d do better with surrogation, but most of us prefer to trust our own imagination. We tell ourselves, I’m different; other people wouldn’t feel the way I would. But research shows we’re not that different. We’re just bad at imagining future emotions in context.

So when an advisor asks, “If money weren’t an issue, what would you do?”, the client is being asked to simulate. It’s an exercise in fantasy, not planning. What people imagine on Tuesday afternoon in an office is a poor predictor of what they’ll actually want when things get real.

Why Clients Might Dislike Parlor-Trick Questions

A survey of prospective financial planning clients suggests that advisors with supposedly “deep” questions drive them away. There are several reasons why that might be the case. First, it can feel invasive or manipulative, as if the advisor is picking your brain and planting a hook.

Worse, the questions demand instant vulnerability without earning trust. They make the client feel like they’re failing the test if they don’t have a ready, inspiring answer.

It may also be that some prospective clients simply don’t want their financial advisor to act like a life coach or therapist. They’re looking for financial guidance, not psychological excavation, and they can reject the attempt outright.

My wife recently fired her chiropractor because he suddenly started playing psychologist by asking about past emotional states and if she ever felt vulnerable. She only wanted a spine adjustment. The same thing can happen in financial planning: when a client comes in for financial guidance and ends up in an unanticipated therapy session, the relationship might be over then and there.

An effective advisor doesn’t squeeze disclosure out of a client. They create enough psychological safety that the client chooses to open up.

What Actually Works

Real connection doesn’t come from trick questions. It comes from truly caring, empathy, and respect.

Here’s what helps:

1. Build safety before depth
    Start with questions that are easy to answer truthfully. Show respect for limits. People share more when they feel safe, not probed. Permission, purpose, and orientation help here. Explain the reason for the question so it doesn’t feel random or intrusive. Ask for permission before going deeper—like knocking on a door instead of barging in. For example: “Longevity is an important part of every financial plan. For that reason, may I ask about your health? If it doesn’t feel relevant, just let me know and we’ll skip it.” That framing turns what could feel like discomfort into an invitation. It signals respect, caring, and collaboration.

2. Ask concrete, not cosmic
    Instead of, “What would you do if money weren’t an issue?” try,
    “What financial decisions feel most important to you this year?”
    or,
    “What’s top of mind right now?”
    These questions stay anchored in present reality.
3. Use stories and examples
   People relate to narratives better than hypotheticals. “Here’s how another client handled a similar trade-off—does that resonate with you?” is more grounded than “What’s your life purpose?”
4. Iterate over time
    Big answers incubate over months, not minutes. Advisors who return to a theme gently, after trust has been established, learn far more than those who press for instant revelation.

In the End

Financial advising doesn’t need parlor tricks. It needs evidence, humility, and common sense. Research suggests that imagination is unreliable, and experience indicates that clients are more likely to open up when they feel comfortable, rather than on the spot.

A mentor once told me, If you’re smart, you can’t hide it. And if you’re not, you can’t fake it.

So why bother trying tricks?

Good advisors don’t have to perform cleverness. They just have to show up as real people: caring, informed, and willing to listen generously.

Radcliffe was right to mock those questions. They confuse depth with drama. Often, real depth isn’t in what we ask as much as in how we attend to the answer—and in having the care and patience to let meaning emerge, rather than trying to force it.

Disclaimer: The views expressed in this article are those of the author and do not necessarily reflect the views of any firm or organization. This content is provided for general informational and educational purposes only and should not be construed as personalized financial, tax, accounting, or investment advice. Although the author is a CPA and holds the PFS credential, no professional services are being offered through this article. Readers should consult their own qualified advisors before making decisions based on this information. The content may include information from sources believed to be reliable but is not guaranteed and may be subject to change without notice.

Copyright: © 2025 Jean-Luc Bourdon, Original text, structure, organization, and editorial revisions created by the human author. The author used AI as a drafting tool, but exercised creative control by rewriting, restructuring, and contributing original analysis, tone, and expression. Disclosure in accordance with U.S. Copyright Office guidance on AI-assisted works.