Table of Contents
Introduction
Dear Reader, I presume you are not an idiot nor suffering from any cognitive or intellectual impairment. As such I shall spare you the obvious questions that you can collect from any financial advisors’ or associations’ pages. You already know you need to ask your financial advisor where they’re licensed and how they get paid and what products they sell…. Good stuff.
This is a list of questions we have created and curated for maximum tactical impact and insight. These questions are calibrated to elicit useful information for the client that one wouldn’t ordinarily uncover. These questions empower clients.
SKIP THIS SECTION IF YOU DON’T SELL LIFE INSURANCE
And for those of you who are distributors of product I am going to tell you how to make this list into a dynamite prospecting piece.
In all your client relationships you want to be perceived as an expert in your area. One of the ways we gain a reputation as being experts is not by just being able to answer a subjects questions but by guiding subjects to ask great questions they wouldn’t otherwise think about. Take these questions and make a short guide for your clients to help them interview you and other financial advisors. Be the person who gives them tools and information nobody else does.
Not only does it position you as an expert but they will ask the you questions you tell them they should ask - its like studying for an exam on which you already know what all the questions will be!
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Powerful, Effective, Questions to ask When Interviewing a Financial Advisor
Use to detect signal vs. status. Watch for empty phrases.
What belief do most of your clients walk in with that you have to undo?
If someone took your advice and still failed financially, what might be the real reason?
When are you not the right person to work with?
Tell me about a time you lost a client—and why.
Designed to reveal how they think about how they’re paid, and who they serve.
In one sentence, how are you paid and who else benefits when you’re paid that way?
If I asked your most skeptical client what your biggest blind spot is, what would they say?
Walk me through a decision where you talked someone out of buying something.
How do you make sure your incentives don’t warp your recommendations?
To find out whether they play chess or checkers. Beware of vacuous comments and faux-strategic language, 'synthetic smart speak' - basically your opportunity to see if they are smart or just try to sound smart.
What’s your philosophy when the market goes sideways and someone panics?
What’s one financial ‘rule’ you intentionally break for the right client?
If I had $0 and no credit score, and you had to rebuild my financial life, what would you do first, second, third?
When do you tell someone not to get insurance or a specific product?
For flushing out ego, ethics, and worldview in disguise.
What do you disagree with most other advisors about?
If I secretly interviewed your assistant or team, what might they say you do that clients never see?
What do you optimize for? Clients’ sleep/comfort, their returns, or their control?
What’s your test for knowing a client is thinking well about money?
Some questions to 'punch through the mask'. Listen carefully.
What advice do you give that makes people uncomfortable—but you give it anyway?
If everything you believed about money turned out to be wrong, how would you know?
What’s a financial ‘truth’ you believed 5 years ago that you’ve now reversed?
If you could only teach me one mindset about money—and I had to ignore the rest—what would you choose?
DEPLOYMENT NOTES:
Listen to what they say and also take note of what you would expect to hear that they don't mention.
Pause after the question. Don't respond immediately after they say something. Allow them silence and space to compose and speak (and it makes it harder to avoid questions).
Watch for defensiveness, over-rehearsed responses, or overly polished metaphors.
The best interrogation is conversation.