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Ask a Pro: 56 Questions Every Client Should Ask
Organized by professional type: CFP®, financial advisor, CPA, estate attorney, financial coach & insurance specialist. Walk into any financial meeting ready.
CFP®: Certified Financial Planner
Before committing to a financial planner, make sure they can answer these clearly and honestly.
Are you a fiduciary: always, or only sometimes?
How are you compensated? Fee-only, fee-based, or commission?
What types of clients do you typically work with?
How do you handle clients who look like me: same income level, background, or goals?
What does your onboarding process look like?
How often will we meet, and who will I actually be working with?
Do you coordinate with my CPA or attorney?
What happens to my plan if you leave the firm or retire?
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Financial Advisor
Not all advisors are created equal. These questions help you understand who you're really talking to.
Are you registered as an RIA, a broker-dealer, or both, and what's the difference?
Are you held to a fiduciary standard, or a suitability standard?
What's your investment philosophy: passive, active, or a mix?
How do you handle market downturns with your clients?
How often will you proactively reach out to me, not just when I call?
What's the minimum account size you work with?
How is my money held: through a third-party custodian?
7 more questions to ask
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CPA: Certified Public Accountant
Your CPA should be a proactive partner, not just someone who files your return each April.
Do you specialize in clients with my income type (W-2, self-employed, business owner)?
Do you do proactive tax planning, or primarily tax preparation?
Do you coordinate with my financial planner or other advisors?
What tax-advantaged accounts should I be maximizing given my situation?
How do you handle audits, and have you handled one like mine before?
What's your turnaround time, and do you file extensions by default?
What information do I need to bring to our first meeting?
7 more questions to ask
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Estate Attorney
Estate planning conversations feel hard to start. These questions make it easier.
What documents do I need given my family situation?
Should I have a will, a trust, or both, and why?
How do beneficiary designations interact with my will?
What happens if I die without a will in my state?
How often should I update my estate documents?
What are the estate tax thresholds I should be aware of?
Can you help me structure assets to avoid probate?
Do you work with blended families or multi-generational estates?
8 more questions to ask
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Financial Coach / AFC®
A good coach meets you where you are: no judgment, no products to sell.
What credential do you hold: AFC®, FFC®, or other?
Do you sell any financial products, or are you strictly a coach?
How do you handle clients who've tried budgeting before and failed?
Can you help me work through debt and savings simultaneously?
How do you approach the emotional and behavioral side of money?
What's your experience working with first-generation wealth builders?
How do you measure progress with clients?
7 more questions to ask
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Insurance Specialist
Insurance conversations matter most before you need it. Ask these before you sign anything.
Are you a broker (access to multiple carriers) or a captive agent (one company)?
How are you compensated: commission, flat fee, or both?
Do I need disability insurance, and what does my employer plan actually cover?
What is umbrella insurance and at what net worth does it make sense?
How do I review my beneficiary designations, and how often?
What coverage gaps do you see in my current situation?
How do you stay objective when recommending products?
7 more questions to ask
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Ask A Pro
Experienced financial professionals, sharing real information.
No scripts, no jargon, straight from their own practice.
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Luis Rosa, CFP®, EA
“Tax Traps & Triumphs: How First-Gen High Earners Can Win in Today's Economy”
Watch in full (opens in a new tab)Short clips
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Bill Hampton, AIF®, CFEI, RFC®
Financial Planner & Tax Strategist
“Real Estate Tax Secrets: Building Wealth & Keeping More of It”
Watch in full (opens in a new tab)Short clips
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Gloria S. Garcia Cisneros, CFP®
“Nuances of Finances for First-Gen or Next-Gen Individuals”
Watch in full (opens in a new tab)Short clips
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Nick Walls, JD, CFP®, CLU
Private Wealth Advisor
“Planning for the Unexpected: Business Continuity & Exit Strategies”
Watch in full (opens in a new tab)Short clips
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Keith R. Miles, Esq.
Certified Elder Law Attorney
“Protecting Your Legacy: An Honest Talk About Estate Planning”
Watch in full (opens in a new tab)Short clips
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Shehara Wooten, CFP®
Founder, Your Story Financial
“Protecting Your Legacy: An Honest Talk About Estate Planning”
Watch in full (opens in a new tab)Short clips
Have a question of your own?