Preparing for retirement is one of the most important financial decisions you’ll ever make. Unlike other financial moves, you get one shot to make your money last throughout your retirement years. The choices you make today will directly impact your lifestyle, security, and peace of mind for decades to come. Working with the right financial advisor can make all the difference—but finding that advisor isn’t just about credentials or experience. It’s about asking the right questions to ensure their approach aligns with your unique goals and vision for retirement.
So, what are the best questions to ask a financial advisor about retirement? These retirement planning questions will help you evaluate advisors, build a comprehensive plan, and secure your financial future. Drawing from our experience helping hundreds of clients navigate their retirement journey, we’ve compiled the essential questions you should ask. Below you’ll find questions to ask a financial advisor about retirement, organized by topics that matter most for your retirement success. Let’s dive in.
These questions to ask your financial advisor about retirement cover everything from choosing the right advisor to planning your legacy.
Questions to Ask Before Choosing Your Retirement Advisor
Think of choosing a financial advisor like hiring an architect to design your dream home. You wouldn’t pick someone without checking their credentials and understanding how they get paid, right?
Q: What credentials do you hold?
Not all financial advisors have the same training. Look for:
Certified Financial Planner (CFP®): The gold standard. CFP® professionals have proven expertise across investments, taxes, estate planning, and retirement. They’re bound by ethical standards requiring them to put your interests first. Learn more about CFP® certification requirements from the CFP Board.
Enrolled Agent (EA): A federally authorized tax credential. An EA has unlimited rights to represent taxpayers before the IRS and can integrate tax strategy seamlessly with your retirement planning—helping you keep more of what you’ve saved. The IRS provides more information about Enrolled Agent credentials.
Other credentials include CFA® (focused on investment analysis and portfolio management), ChFC® (broad financial planning with emphasis on estate and insurance planning), and AIF® (trained to act as a fiduciary, often for employer retirement plans).
Q: Are you a fiduciary?
This is your most important question. A fiduciary is legally required to put your interests ahead of their own—always. It’s like having a trusted guide contractually obligated to point you toward the best path for you, even if there’s a more profitable one for them.
Not all advisors operate this way. Some work under a “suitability” standard, meaning investments need only be appropriate, not necessarily the best available option.
Q: How do you get paid?
Fee-Only Advisors are paid directly by you (flat fee, hourly rate, or percentage of assets). Because they don’t earn commissions on products they sell, their advice is more objective.
Commission-based advisors earn money when you buy specific products. This creates potential conflicts—they might recommend products that pay them more rather than what’s best for you.
Fee-Based Advisors (different from fee-only) charge fees but may also earn commissions, which still presents conflicts of interest.
When you work with a fee-only fiduciary, your advisor succeeds when you succeed—no hidden incentives.
Q: What’s your experience with clients like me?
Ask: How many years have you been helping clients plan for retirement? Do you specialize in my situation (age, assets, goals)? Can you integrate tax planning directly into my strategy?
The combination of proper credentials, fiduciary responsibility, transparent fee-only compensation, and hands-on experience creates a foundation for a trusted relationship—one where you can feel confident the advice you’re receiving is designed to help you achieve the retirement you’ve worked for.
Building Your Retirement Plan
These questions to ask a financial advisor about retirement planning ensure your advisor understands your full picture.
Q: When should I start planning for retirement?
As early as possible. Discovering you’re off track at 45 versus 60 is the difference between adjusting course and running out of runway.
A comprehensive retirement plan pulls everything together: investments, savings, pensions, Social Security, healthcare, and estate planning. Most importantly, it accounts for inflation—that $50,000 lifestyle today might cost $80,000 in 20 years.
For high-net-worth individuals, retirement planning involves additional complexities, such as advanced tax strategies, estate planning, and wealth preservation. Learn more about high-net-worth retirement planning strategies.
The goal for most people is simple: security and confidence that they won’t run out of money.
Q: Am I on track to reach my goals?
This question opens the most important conversation with your advisor. It forces them to understand what you’re truly working toward—and goals change, which is okay.
Make your goals SMART: Specific, Measurable, Achievable, Relevant, and Time-bound. Instead of “I want to retire comfortably,” try “I want to retire at 65 with $10,000 per month in income to cover expenses and travel twice a year.”
Q: What about my non-financial goals?
This is where the “personal” belongs in personal finance. Your money is a tool to support what matters most. Does your advisor ask about your hobbies, family, and desire to give back? Maybe you want to start a charitable giving strategy, move closer to grandchildren, launch an encore career, or pick up new hobbies. These impact how much you’ll need and how you’ll structure retirement.
Q: How often will we review my plan?
An annual review is the minimum. During reviews, your advisor should revisit goals, monitor progress, and ensure you’re on track. Life events such as health changes, major purchases, family shifts, and changes in tax law may require more frequent check-ins.
Ask: Do you offer bi-annual or quarterly reviews? What about on-demand consultation calls? Do you charge extra for them?
Questions About Your Retirement Budget
One of the most important questions about retirement planning involves understanding your spending.
Q: When should I start planning my retirement budget?
Start now—not when you’re six months from retirement. Think of your retirement budget like a road trip: you wouldn’t wait until you’re at the gas station to figure out how much fuel you need.
Your retirement budget is based on your pre-retirement spending. A budget now helps you tackle high-interest debt, spot expenses that will disappear (commuting, work clothes), and plan for new ones (healthcare, travel).
Q: How much will my monthly fixed expenses be in retirement?
Work with your advisor to map out your essentials—housing, utilities, insurance, groceries, and healthcare. Understanding this number tells you the minimum income you need to maintain your lifestyle.
Q: How do you plan for inflation in retirement?
Think of inflation like a slow leak in your tire. Over 20-30 years, that 3% annual leak can cut your purchasing power in half. Not all expenses inflate equally. Most advisors plan for:
- General expenses: 3% annually
- Healthcare costs: 5-6% annually
- Education expenses: 5-7% annually (if helping grandkids)
Your advisor should use inflation-resistant investments and a diversified portfolio to help preserve your purchasing power.
Q: How much can I spend on travel each year?
Be specific. Ask: “If I want to spend $X on travel annually, how many years can I sustain that?” Remember, you’ll likely travel more in your 60s and early 70s than in your 80s.
Q: Can I afford to purchase new cars throughout retirement?
Discuss realistic expectations: How much? How often? One car every 7-10 years, or more frequent upgrades?
Q: What about larger one-time expenses like home improvements?
Before committing to that kitchen remodel or new roof, run it by your advisor. They can show you how it impacts your long-term plan.
Q: How can I protect my retirement savings from unexpected expenses?
Think of an emergency fund as a shock absorber for your retirement plan. Maintain 6-12 months of living expenses in easily accessible accounts (savings or money market), not tied up in investments.
Other strategies include:
- Reducing or eliminating high-interest debt before retirement
- Keeping access to a line of credit as backup
- Building potential expenses into your overall plan
Ask your advisor: “How much should I keep in cash reserves, and where should that money be held?”
Beyond budgeting, questions to ask your financial advisor about retirement should cover income sources like Social Security.
Retirement Income and Social Security
Q: Will you help maximize my Social Security benefits?
The decision of when to claim Social Security, at 62, full retirement age, or 70, is one of the most important choices you’ll make in retirement. There’s no one-size-fits-all answer, and the right timing depends on your unique situation. The Social Security Administration provides detailed information about claiming ages and benefit amounts.”
Why this decision matters: The right timing can potentially provide hundreds of thousands of dollars more in lifetime benefits and extend the life of your savings by several years.
Your advisor should help you evaluate:
Health and life expectancy: If longevity runs in your family, delaying benefits may result in significantly larger lifetime payouts. If you face health challenges, claiming earlier might make more sense.
Other assets: If you have substantial retirement savings, delaying Social Security until age 70 increases your benefit by 8% each year after full retirement age—a guaranteed return that’s hard to beat.
Spousal and survivor benefits: For couples, coordinating when each spouse claims can maximize household benefits and help manage taxes on Social Security income.
An experienced advisor will guide you through various scenarios, showing how different claiming strategies impact your long-term financial security. This decision requires careful planning integrated with your overall retirement strategy, not a generic rule of thumb.
Questions About Managing Taxes in Retirement
Tax planning is one of the most valuable questions to ask a financial advisor about retirement.
Q: What is your strategy for managing taxes in retirement?
This is perhaps one of the best questions to ask. A financial advisor with tax experience can provide immense value because taxes significantly impact how long your money lasts. Here’s the reality: managing taxes in retirement starts long before you retire.
Ask your advisor to walk you through these key strategies:
Tax-efficient withdrawal sequencing: The order you tap your accounts matters enormously. Should you withdraw from taxable accounts first, letting tax-deferred accounts grow? Your advisor should have a clear plan.
Roth vs. pre-tax contributions: While still working, should you contribute to a traditional 401(k) or Roth 401(k)? This decision impacts your taxes decades down the road.
Roth conversions: Converting traditional IRA funds to a Roth IRA means paying taxes now for tax-free withdrawals later. Your advisor should help determine if you’re eligible and if it makes sense for your situation.
Tax-loss harvesting: Selling investments that have lost value can offset gains elsewhere, reducing taxable income. Ask if your advisor has leveraged this strategy with clients.
Medicare IRMAA surcharges: Income above certain thresholds triggers higher Medicare premiums. Ask how your advisor will help you avoid these through strategic income management.
Pre-65 healthcare planning: Strategically reducing taxable income before age 65 can help you qualify for Affordable Care Act subsidies. This is vital to start early—it’s a multi-year process.
Q: What is your approach to managing Required Minimum Distributions (RMDs)?
When you reach age 73, the government forces you to start withdrawing from retirement accounts—whether you need the money or not. Poor planning can result in higher taxes and unnecessary strain on your savings. The IRS provides current RMD rules and distribution tables.
Ask: “How will you help me handle RMDs to avoid unnecessary tax burdens?” This requires carefully timing withdrawals and coordinating them with other income sources. A good advisor should be proactive about RMD planning years before they begin, using strategies like Roth conversions to reduce future RMD amounts.
Investment Strategy and Risk Management
These retirement investment questions help ensure your portfolio matches your goals.
Q: Is my portfolio invested appropriately for retirement?
Your portfolio needs to match where you are in your retirement journey. Early on, focus on growth. As retirement approaches, shift to preserving what you’ve built and generating a reliable income.
Ask your advisor to review:
- Your asset allocation (mix of stocks, bonds, and other investments)
- Diversification across U.S. and international investments
- Investment costs (low-cost funds and ETFs minimize fees)
- Tax efficiency of where investments are held (Roth vs. IRA vs. taxable)
Think of diversification like not putting all your eggs in one basket—it helps you avoid extreme market swings that can gut your nest egg right when you need it most.
Q: How will you adjust my investment strategy as I move through retirement?
Your investment needs change as you age. In your 60s, you might focus on growth to last 30+ years. In your 80s, you’re likely more focused on stability and income.
Your advisor should regularly reassess your portfolio to match your life stage, risk tolerance, and financial needs. Ask: “How do you determine when to adjust my investment mix, and what does that process look like?”
If your portfolio keeps you up at night, it’s not the right portfolio—regardless of performance.
Q: What’s your withdrawal strategy for my retirement accounts?
Having money saved is one thing—getting it out tax-efficiently is another. Your advisor should have a strategic withdrawal plan covering which accounts to tap first, how to minimize taxes, and how to avoid higher tax brackets or Medicare surcharges.
This isn’t a “set it and forget it” plan. It should be reviewed and adjusted regularly in response to tax law changes, spending needs, and market conditions.
Planning for Healthcare and Long-Term Care
Healthcare expenses are often unexpected, but they become more likely as one ages. Planning for long-term care now will provide both you and your loved ones with stability during challenging times.
Q: How Do You Factor Healthcare Costs Into Retirement Planning?
Healthcare expenses can become a significant financial burden as you get older, and these costs cannot be overlooked. Think of Medicare like basic car insurance. It covers the significant expenses, but not everything. Your advisor should help you understand these coverage gaps and plan accordingly.
Medicare and What It Doesn’t Cover: While Medicare handles many healthcare expenses after age 65, it doesn’t cover dental, vision, or hearing care—all expenses that typically increase as you age. Medicare.gov details what’s covered and what gaps you should plan for. Medicare also has limited prescription drug coverage unless you add Part D, and you may need supplemental insurance like Medigap or Medicare Advantage to fill other gaps. Your advisor should help you estimate these costs and determine which additional coverage is most suitable for your situation.
Healthcare Before Age 65: If you plan to retire before you’re eligible for Medicare, you’ll need coverage for those “gap years.” Marketplace plans can cost $1,500 to $ 2,000 per person per month, which can significantly impact your retirement budget. Your advisor should help you budget for this period and explore options such as COBRA or income optimization to qualify for ACA subsidies. If you’re HSA-eligible, they should also discuss strategies for using this powerful tax-advantaged account to pay for future healthcare expenses.
Timing Matters: Missing your Medicare enrollment window can result in permanent penalties that increase your premiums for life. Your advisor should ensure you understand these deadlines and factor healthcare inflation, which typically rises faster than general inflation, into your long-term projections. We assume healthcare inflation is x%.
Q: Do I Need Long-Term Care Insurance?
Most people don’t like thinking about needing help with daily activities, but the reality is that about 70% of retirees will need some form of long-term care. Strokes, falls, chronic illness, or simply the effects of aging can make assistance necessary—and Medicare won’t cover it.
Understanding the Costs: Long-term care is expensive. A nursing home can cost $110,000+ per year, assisted living runs $80,000+ annually, and even part-time in-home care can cost $ 40,000+ per year. These costs can quickly drain retirement savings that took decades to build. Think of it like planning for a potential second mortgage payment that could last for years.
Insurance or Self-Funding? Your advisor should help you decide between three approaches: buying long-term care insurance, self-funding from your own assets, or a hybrid strategy. This decision depends on your health, age, assets, and family situation. For example, if one spouse needs extended care, will it devastate the healthy spouse’s finances? Your advisor should run projections showing different scenarios.
Timing and Options: If you’re considering LTC insurance, timing matters. Premiums increase significantly after age 60, and health issues can make you uninsurable. Your advisor should also explain newer hybrid policies that combine life insurance with long-term care benefits, so you’re not in a “use it or lose it” situation with traditional LTC insurance.
Estate Planning and Legacy
Q: Do I have a comprehensive estate plan?
Your legacy goes hand-in-hand with retirement. In many cases, you’ll want to leave something behind for people or causes you care about—that’s where estate planning comes in.
Planning your estate can be emotionally challenging and mentally demanding. You’re not just dividing assets; you’re focused on caring for your loved ones after you’re gone. Your financial advisor should work alongside your estate planning attorney to help you:
- Create or update your will and trusts
- Transfer assets to heirs efficiently
- Minimize estate taxes
- Avoid probate complications
- Establish powers of attorney and healthcare directives
Think of estate planning as writing the final chapters of your financial story. Without a plan, the state decides how your assets are distributed—and that’s rarely what you’d want.
Q: What’s your strategy for charitable giving and gifting to family?
If giving is important to you, your advisor should help you structure it tax-efficiently. Ask them about:
Charitable giving: What’s the best way to continue supporting my church or favorite causes? Should I consider donor-advised funds, charitable trusts, or direct gifts? How can I maximize the tax benefits?
Family gifting: What’s the most tax-efficient way to give to my children or grandchildren? Should I use annual gift exclusions, 529 education plans, or trusts? How can I help without creating a dependency or a tax burden for them?
Your advisor should coordinate with your estate planning attorney to ensure your gifting strategy aligns with your overall estate plan and doesn’t inadvertently create problems down the road.
Your Next Step
Choosing the right financial advisor will shape your entire retirement. The questions in this retirement planning guide help you find someone who truly understands your goals, operates with transparency, and has the expertise to guide you through every stage of retirement, from budgeting and taxes to investments and legacy planning.
The difference between a comfortable retirement and one filled with financial stress often comes down to having the right advisor in your corner.
Now that you know the essential questions to ask about retirement, it’s time to find an advisor who can answer them. Ready to start the conversation? Our team brings years of experience helping clients navigate retirement planning with confidence. Let’s create the retirement you’ve worked so hard to build.
