The hardest part of working with a financial advisor is sometimes knowing what to say when you sit down across the table or on a Zoom call. Most people worry they’ll ask the “wrong” question or that the advisor will do all the talking in jargon. But here’s the truth: when you’re the client, you’re the one interviewing them — not the other way around.
I recently joined Jean for a role-play exercise where we flipped the script: she played the advisor, and I played the client, showing exactly what to say in those moments when you need clarity. The goal? To help you feel prepared and confident.
If You’ve Never Worked with an Advisor
Walk in with a clear purpose. A great opening line is: “I’d like to leave today knowing if we’re a good fit. Here’s what I want to accomplish…”
Then ask two simple but revealing questions:
- Who do you usually work with, and how do you help them? What does that look like?
- I know you’re “fee-only,” but how are your clients paying you?
What you’re listening for: Do they work with people just like you? Can they explain their fees clearly (flat fee, retainer, or assets under management)? If they dodge the fee discussion, or brag about their returns, or won’t put their fiduciary duty in writing, that’s your cue to walk away.
If You Already Have an Advisor but Something’s Not Right
Maybe you’ve worked with someone for years, but aren’t sure you’re getting value. Try asking:
- “As an advisor, how are you measuring my success?”
- “Show me the dollar amount I’m paying you, and how you’re earning it?”
Red flag: all they talk about is “watching the market” or vague generalities.
Green flag: they tie success to your goals — like retiring comfortably, making gifts to family, or simplifying your finances.
If Retirement Keeps You Up at Night
Say it out loud: “I’m worried about running out of money when I’m older.” And then ask this question: “Can you stress-test my plan so I can see the risks and the solutions myself?”
Push for specifics: How does the plan hold up if you live to 95? If healthcare costs spike? If the market tanks early in retirement? Don’t settle for “You’ll be fine.” You want to see numbers and guardrails.
If You’ve Been DIY’ing Your Money
You might say: “I’ve managed my investments myself, but I’d like a fresh set of eyes. Where do you see gaps?”
And be clear: “If I wanted a deep dive, what would that cost me?”
Think of it like paying for a second opinion from a doctor. You don’t want a pat on the back, you want an honest critique.
If You’re Comparing Advisors
Interviewing two or three? Ask them all the same questions so you can compare apples to apples. One of my favorites: “Tell me about a client like me. How did you help them?”
You’ll quickly spot the difference between someone who truly listens and someone who hides behind buzzwords. Rule of thumb: if you can repeat their advice in one sentence and it makes sense, that’s useful. If not? It’s jargon.
The One Question You Should Always Ask
At the end of the day, the single most important question is: “As my life changes — my job, my health, the market, my goals — how will you help me make those decisions?”
Because the real test of an advisor isn’t when things are easy. It’s when life throws you a curveball.
The right advisor is a partner, not a salesperson, and this is a collaboration, not a sales pitch. Your role is to feel comfortable asking the right questions and pay attention to how the answers make you feel. The best advisors are not just going to tell you what you want to hear, but what you might need to hear. And when that’s the case, if you walk out of that meeting feeling heard, respected, and clear about next steps — you’re on your way to a real collaboration.
MORE ON HERMONEY:
- The Gen Z Guide For How To Retire Early (And Why the Old Rules Don’t Work Anymore)
- What’s Inside Your 401(k)? More Options, More Complexity—Here’s What You Need to Know
- An Inside Look: How The Right Financial Advisor Brings Clarity and Confidence
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