Questions a Good Financial Advisor Should Ask (But Most Don’t)

I’ll never forget Bruce’s story about his car—check engine light on, a mechanic insisted it needed a $1,500 catalytic converter. Bruce knew better and fixed it by simply tightening the gas cap. That story isn’t just about auto repair; it perfectly illustrates why questions a good financial advisor should ask matter. Without probing, you might be sold something you don’t need. Competency—not just good intentions—matters.

It’s not about distrust—it’s about asking the right questions so you’re not blindly following advice. And that principle applies fully when choosing a financial advisor, especially when your spouse might need to take over the reins someday.

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Why “Questions a Good Financial Advisor Should Ask” Are Essential

Bruce makes a powerful point: finance isn’t limited to investment products. Just like a mechanic or doctor examines the whole system, a skilled advisor should ask questions that uncover your entire financial ecosystem. Without comprehensive inquiry, blind spots linger—insurance gaps, overlooked risks, or hidden fees can derail your legacy.

Are you unknowingly trusting a financial advisor without knowing enough about your overall financial picture? In today’s complex financial world—from taxes and Social Security to estate planning, insurance, and cash flow—a narrow focus on one product is risky.

Questions a good financial advisor should ask aren’t optional—they’re essential. They give you clarity, align planning with your goals, and ensure your spouse is equipped to manage your shared financial future.

1. The Big Picture: Comprehensive Financial Planning

Bruce sums it up: “You cannot make financial decisions in a vacuum.” Advisors who focus only on investments or insurance miss how those decisions affect cash flow, taxes, estate planning, and more.

• Ask:
  • What are your current net worth and cash flow statements?
  • How do your investments, insurance, and debts interrelate?
• Why it matters:
  Like a doctor who reviews your medical history before prescribing treatment, a competent advisor will want to see your full financial picture before making recommendations.

2. Spouse Financial Preparedness: Including Both of You

Too often, one spouse is left out of discussions and can feel lost if the other dies.
Key questions include:

• Who are your trusted advisors (financial, legal, tax)?
• Does your spouse know how to access online accounts, passwords, and digital assets?
• What’s your “Alternative Income Plan” for the surviving spouse?
• How comfortable is your spouse with the household financial framework?

Bruce and Rachel discuss this as part of the LIFE framework:

• Liquid assets—money accessible within 15 minutes
• Income plan—monthly income goals
• Flexible investments—capital that can be reallocated
• Estate plan—how wealth transfers to future generations

Both spouses should discuss and agree on how these pieces look today and tomorrow.

3. Risk and Protection: Insurance, Deductibles, and Peace of Mind

Bruce shared his own experience with PNC: they asked about deductible choices and emotional tolerance for risk during the house fire recovery process.

Essential questions a good financial advisor should ask include:

• What insurance do you have—life, disability, health, auto, home?
• Are deductibles appropriate to your cash reserves and risk tolerance?
• Are beneficiary designations updated and aligned with estate goals?

These conversations ensure coverage fits your life, not just the product.

4. Tax Strategy and Social Security Planning

It’s easy to ignore tax implications at later stages—retirement income strategies, Medicare surcharges (IRMAA), and estate transfer taxes can significantly impact cash flow. Good advisors will ask:

• How will retirement affect your tax bracket and Medicare premiums?
• Are you maximizing tax-deferred, taxable, and tax-free accounts?
• How do social security strategies fit into your retirement and legacy plan?
• Do you expect inheritances? Are children receiving support or benefits (e.g., special-needs trusts)?

These questions ensure a plan that reduces surprise tax burdens down the line.

5. Legacy Planning: Aligning Values and Wealth Transfer

Planning isn’t just dollars and cents—it’s about values, purpose, and impact. A well-rounded advisor should ask:

• Do you desire to leave an inheritance or values-based legacy?
• What legal structures are in place—wills, trusts, special-needs provisions?
• How are you preparing adult children to steward their inheritance?
• Are you currently supporting adult children or involved in multigenerational cash flow?

Preparing adult children to receive an inheritance well requires intentional communication and boundaries. When ongoing financial support continues without clarity or limits, it can unintentionally foster entitlement. Instead, pausing to realign support with long-term values ensures that wealth is transferred with purpose, not just provision.

6. Financial Alignment Between Spouses

Even couples aligned on values often diverge on financial risk, liquidity, or growth. Bruce suggests advisors encourage couples to complete separate LIFE questionnaires to reveal true attitudes.

Appropriate questions include:

• How much liquidity do you need for emergencies?
• How much guarantee vs. growth do you want in income?
• Would you prefer increased stability or upside, even at a cost?
• How comfortable are you with paying advisor fees, and why?

These conversations often reveal emotional undercurrents—and allow spouses to compromise. For example, a combination of guaranteed income (like an annuity) and growth investments can honor both viewpoints.

Why You Need These Questions

In summary, questions a good financial advisor should ask aren’t an inconvenience—they’re the bedrock of responsible planning. They ensure you and your spouse:

1. See your full financial ecosystem, not just one piece
2. Build a joint future—where both partners are engaged and prepared
3. Protect assets and people through thoughtful risk management
4. Optimize cash flow, reduce taxes, and maximize Social Security
5. Craft a legacy strategy that aligns with your values
6. Bridge differences in risk tolerance through education and compromise

When your advisor asks more than just “how much can I invest”, you’re getting the kind of guidance that gives long-term clarity and confidence.

Ready to Empower Yourself With Questions a Good Financial Advisor Should Ask?

What would your life be like if you actually had:

• A spouse who could take over your finances tomorrow without panic
• A trusted advisor who has asked all the key questions
• A financial plan that truly aligns with your life goals, values, and family legacy

If you’re ready to be ASKED these questions—or to upgrade what you’re already being asked—start here:

Book A Strategy Call

Are you ready to take control of your finances and legacy? We offer two powerful ways to help you create lasting impact:

1. Financial Strategy Call – Discover how Privatized Banking, alternative investments, tax-mitigation, and cash flow strategies can accelerate your time and money freedom while improving your life today. Let us show you how to align your financial resources for maximum growth and efficiency. Book a Strategy Call with our team today.
2. Legacy Strategy Call – If you want to uncover your family values, mission, and vision, and create a legacy that’s about more than just money, we can guide you through the process of financial stewardship and family leadership. Save time coordinating your family’s finances while building a legacy that lasts for generations. Book a Legacy Strategy Call to learn more about how we can help.

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