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Choosing the right financial planner before retirement is about so much more than finding someone who understands investments. You need someone who can guide you through one of life’s biggest financial transitions. The right advisor will help you preserve wealth, minimize taxes, and create a plan that sustains your lifestyle for decades to come.
But how do you know if a financial planner is the right fit? It starts with asking the right questions. The answers will reveal whether they have the expertise, approach, and personalized strategies you need to retire with confidence.
Here are the most important questions to ask a financial planner before retirement, along with what to listen for—and which red flags to avoid.
1. How much money do I need to retire comfortably?
Why It Matters
Everyone’s retirement looks different. Whether you envision traveling the world, downsizing to a quiet home, or continuing to work part-time, knowing your retirement number can help ensure you won’t run out of money later in life.
What to Look For
A strong response should factor in your expected expenses, longevity risk, inflation, and potential healthcare costs. A great planner will offer a tailored projection, rather than relying solely on generic benchmarks.
Red Flags
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A vague or one-size-fits-all answer, like "You need $1 million to retire."
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No discussion of personal spending habits or future goals.
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Failure to account for inflation or healthcare costs.
2. What are the best investment strategies before retirement?
Why It Matters
As you approach retirement, your investment strategy should shift from aggressive growth to a balance of growth, stability, and income generation.
What to Look For
An advisor who considers your time horizon, risk tolerance, and need for liquidity. Look for strategies that prioritize downside protection while still allowing your portfolio to grow.
Red Flags
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Overly risky recommendations without considering your timeline.
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An unwillingness to adjust your portfolio as retirement nears.
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Lack of diversification or reliance on a single asset class.
3. How do I budget for healthcare costs in retirement?
Why It Matters
Healthcare is one of the biggest expenses retirees face, and failing to plan for it can derail even the best financial strategies.
What to Look For
A knowledgeable planner will discuss Medicare, supplemental insurance, long-term care options, and out-of-pocket costs. They should also help estimate future expenses based on your health history and longevity expectations.
Red Flags
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Assuming Medicare covers all costs (it doesn’t).
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No discussion of long-term care planning or potential healthcare inflation.
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Overlooking health savings accounts (HSAs) as a tax-efficient savings tool.
4. How can I minimize taxes on retirement income?
Why It Matters
Taxes don’t stop in retirement—they just change. Poor tax planning can eat away at your savings faster than expected.
What to Look For
An advisor who understands tax-efficient withdrawal strategies, such as drawing from taxable, tax-deferred, and tax-free accounts in the right order. They should also discuss Roth conversions, required minimum distributions (RMDs), and state-specific tax implications.
Red Flags
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No clear strategy for managing withdrawals to reduce taxes.
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Ignoring how Social Security benefits may be taxed.
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Overlooking tax-efficient investment strategies, such as municipal bonds or tax-loss harvesting.
5. When should I start withdrawing from my retirement accounts?
Why It Matters
Your withdrawal strategy affects everything from your tax bill to the longevity of your savings. Withdrawing too early can deplete funds, while waiting too long can trigger higher taxes on RMDs.
What to Look For
A financial planner who customizes a withdrawal strategy based on your income needs, tax situation, and investment performance. They should help you balance cash flow with tax efficiency.
Red Flags
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Recommending a rigid, one-size-fits-all withdrawal rate.
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Failure to address how market conditions impact withdrawals.
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No discussion of how RMDs fit into your overall plan.
6. What role does inflation play in retirement planning?
Why It Matters
Over time, rising costs can erode the purchasing power of your savings. This means it’s absolutely crucial to plan for inflation.
What to Look For
An advisor who builds inflation assumptions into your retirement projections. They should consider strategies like investing in assets that outpace inflation, such as dividend-paying stocks or Treasury Inflation-Protected Securities (TIPS).
Red Flags
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Ignoring inflation entirely in projections.
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Assuming expenses will remain constant throughout retirement.
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No discussion of how different investment types respond to inflation.
7. Should I pay off my mortgage before retirement?
Why It Matters
Being debt-free in retirement sounds appealing, but in some cases, keeping a mortgage may be a better financial decision.
What to Look For
An advisor who weighs the pros and cons based on interest rates, tax deductions, liquidity needs, and investment returns. They should help determine whether paying off your mortgage aligns with your broader retirement goals.
Red Flags
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Automatically recommending paying off the mortgage without considering other financial factors.
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No discussion of opportunity cost—such as whether your money could be better invested elsewhere.
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Dismissing mortgage interest deductions or cash flow flexibility.
8. How do I create a retirement income strategy?
Why It Matters
A well-planned income strategy can provide confidence that your retirement savings will last while providing stability and flexibility. Without one, you risk either overspending too soon or being too conservative and not fully enjoying your retirement.
What to Look For
A financial planner should outline a strategy that includes a mix of income sources, such as Social Security, pensions, investment withdrawals, and annuities. They should also discuss the order of withdrawals (taxable vs. tax-advantaged accounts) and how to balance market fluctuations with stable income streams.
Red Flags
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No discussion of how to structure withdrawals for tax efficiency.
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Relying too heavily on a single income source.
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Failure to address how to adjust withdrawals in down markets.
Preparing for Retirement with Confidence
A great financial planner will be able to answer these questions with depth, confidence, and a clear understanding of your unique situation. Asking the right questions can reassure that you're not just getting generic advice, but a tailored strategy that helps you retire on your terms.
If you want to take the next step in planning for retirement, check out The Pre-Retirement Checklist—a valuable resource to help you prepare with even more confidence!
Related: Navigating Estate Planning: Essential Tips for High Net Worth Families
Disclosures:
Securities and advisory services offered through Commonwealth Financial Network®, Member FINRA/SIPC, a Registered Investment Adviser. Fixed insurance products and services are separate from and not offered through Commonwealth.
Commonwealth Financial Network® does not provide legal or tax advice. You should consult a legal or tax professional regarding your individual situation.