Best Questions To Ask A Financial Advisor Before Retirement
- Adam Smith, CFP®
- a few seconds ago
- 16 min read
Updated: 5 hours ago
You are in your early 60s. You have built a portfolio in the seven figures, and you are about to hand it to an advisor to manage for the next 30 years. You have one chance to make your money last twenty-five years or more — and two quiet worries sit under that decision.
You do not want to be sold a product. And you do not want to overpay — potentially by meaningful amounts in fees and taxes over a long retirement. The good news is that a few sharp questions will tell you, fast, whether an advisor works for you or for their own commission.
Quick Answer
A revealing question to ask a financial advisor before retirement is whether they are a fiduciary 100% of the time, in writing — and exactly how they are paid.
Then ask the retirement-specific questions many checklists skip: tax-efficient withdrawal sequencing, Roth conversions and IRMAA, Social Security timing, and the pre-65 healthcare bridge. Ask these, then listen for hedging.
Key takeaways
An important question that exposes everything: “Are you a fiduciary 100% of the time, in writing — and exactly how are you paid?” Any hedging, like “when applicable,” is a red flag.
Fee-only is not the same as fee-based. Fee-only advisors are paid only by you. Fee-based advisors can also earn commissions. Verify it in Form ADV Part 2A and Form CRS — do not blindly trust the label.
The questions that great retirement advisors emphasize are about taxes and income: Roth conversions, RMDs (which begin at 73, rising to 75), IRMAA, Social Security timing, and the pre-65 healthcare bridge.
A good advisor should also confirm you are on track to your goals, hold your money with an independent third-party custodian, and let you verify every credential directly with the issuing board.
Many “questions to ask a financial advisor” lists are generic accumulation-era checklists. They tell you to ask “Are you a fiduciary?” without explaining what that word legally means or how to check. But you are not accumulating anymore. You are about to spend the money.
The questions that matter before retirement expose two things: how the advisor is paid, and how they will handle decumulation — taxes, income, and healthcare.
While there is no definitive list of the perfect questions, we have compiled the most powerful ones based on our experience helping hundreds of clients plan for retirement. We serve this exact audience, so we can do more than list the questions.
We can show you what a good answer sounds like.
“Are you a fiduciary 100% of the time?” — the question we think matters most
A fiduciary is legally bound to act in your best interest at all times. A broker working under a lesser standard does not carry that same ongoing duty. A very revealing question you can ask is whether the advisor is a fiduciary 100% of the time, and will they put it in writing.
Listen for hedging. If the answer includes qualifiers like “when applicable” or “in an advisory capacity,” that is your signal to dig deeper.
Fiduciary vs. Regulation Best Interest vs. Suitability
Three different standards govern financial advice.
The fiduciary duty stems from the Investment Advisers Act of 1940. The Supreme Court recognized the fiduciary nature of the advisory relationship in SEC vs. Capital Gains Research Bureau (1963), and the SEC’s 2019 interpretation spells out what it means today: a registered investment adviser must act in your best interest, disclose conflicts, and serve your interests across the entire relationship.
Regulation Best Interest (Reg BI) is the standard for brokers. Under SEC rules, a broker must not place its own interest ahead of yours at the moment of a recommendation. That is a transaction-level duty, not an ongoing one. (FINRA, Regulation Best Interest).
Suitability is the older bar. It asked only whether a product was “suitable” for you — not whether it was the best or cheapest choice available. Note: since June 30, 2020, Reg BI has superseded the suitability rule for broker recommendations to retail customers, though suitability-style state standards still govern some insurance products, like fixed annuities. (Suitability).
Here is the catch many checklists miss: the “two hats” problem. The same person can wear an advisory hat (fiduciary) one minute and a brokerage or insurance hat the next, in the very same conversation. That is why “Are you a fiduciary?” is not enough. You want “100% of the time,” in writing.
How to verify a fiduciary in 15 minutes
You do not have to take anyone’s word. You can check it yourself.
SEC IAPD — search the firm or individual at adviserinfo.sec.gov.
FINRA BrokerCheck — review brokerage history and any disclosures at brokercheck.finra.org.
Form ADV Part 2A, Item 5 — read exactly how the firm is compensated.
Form CRS — the plain-language relationship summary, which spells out the standard of conduct.
CFP Board and NAPFA — confirm CFP® status and fee-only membership directly with the issuing bodies.
As a fee-only fiduciary RIA, this is the part we welcome. The goal here is not to assume anyone is acting in bad faith. The goal is to know, on paper, which duty you are getting.
“How are you paid?”
AUM, flat, retainer, hourly, or commission
Advisors get paid in a few main ways:
Assets under management (AUM): a percentage of what they manage for you, billed yearly.
Flat fee or retainer: a set dollar amount for ongoing planning.
Hourly: you pay for time, like an attorney.
Commission: the advisor earns a cut of the products they sell you.
The AUM model dominates. Kitces’s Research on Advisor Productivity found that more than 90% of advisors use AUM as at least a part of their fees, typically on a graduated schedule that steps down as your balance grows. (Kitces Research, page 101).
“Are you fee-only or fee-based?” — why one word can change a lot
This is where many smart savers get tripped up, because many marketing materials blur the two terms. The distinction is simple and it matters. A fee-only advisor is compensated only by you — through an AUM percentage, a flat fee, a retainer, or an hourly rate.
A fee-based advisor can do all of that and also earn commissions on products they sell you. One different word, very different incentives.
You verify which one you are dealing with in Form ADV Part 2A (Item 5) and Form CRS — not by trusting the label. Regulators can act against misleading fee descriptions, but the term isn’t uniformly defined — so verify in the ADV, not the marketing brochure.
Industry bodies like NAPFA and the CFP Board hold strict definitions of fee-only, but the marketing brochure on the desk is not bound by them. The paperwork is.
Now a point some advisors may not volunteer, and that we think you should hear: even a fee-only advisor who charges on AUM has a structural conflict. The fee is a percentage of the assets they manage.
This is a conflict every AUM advisor, fee-only ones included, should name out loud. An advisor who discloses it without being asked is showing you exactly the kind of candor you want.
“Am I on track to reach my goals?”
Before you can judge how an advisor will manage the details, you need the big-picture answer: are you on track to reach your goals? Regardless of your stage in life, you need to know this. If your advisor can’t answer it, you can’t expect that they will actually help you reach your destination.
This question is crucial because it prompts your advisor to ask you clarifying questions so they can assess your likelihood of achieving your goals. Your advisor should be well versed in your top financial goals, and you should feel confident expressing them, even if they change.
Goals can be challenging to define, so it helps to have a checklist. If you don’t have one, you can download a master list of goals for retirement and other financial goals here. There is so much to know, and another good place to start is by downloading our free retirement cheat sheets — they’re packed with little-known insights about retirement.
Whatever your goals are, put them in writing and prioritize them.
“How will you set my withdrawal rate and Social Security timing?”
A strong advisor sets your withdrawal rate and your Social Security claiming age together. They can also explain the research behind the number, instead of reciting a “4% rule” that may not apply to you. These are the first of the retirement-specific questions that generic checklists skip.
The withdrawal rate (and why “4%” might be dated)
Ask how the advisor arrives at your spending rate, and whether they revisit it. The current research has moved. Morningstar’s 2026 State of Retirement Income report (published December 2025) puts the base-case safe starting withdrawal rate at 3.9% for a 30-year retirement. (Morningstar).
That assumes a 30 to 50% stock allocation and a 90% success rate, and it is up from 3.7% the prior year. Morningstar also notes that flexible strategies — where you adjust spending in down years — can support a starting rate as high as 5.7%. That flexibility is the trade-off.
More recently, in A Richer Retirement (2025, with CNBC coverage in December 2025), Bengen updated his worst-case figure to 4.7%, and suggested many retirees could take more, depending on their situation. The point of the question is not the exact number — it is whether your advisor can explain it and adjust it based on your needs. (CNBC 4% Rule Updates).
Social Security timing: 62, full retirement age, or 70?
For many retirees, delaying Social Security to age 70 is often the single highest-value way to enlarge guaranteed lifetime income. The right age still depends on your health, your spouse, and your other income. A few 2026 facts ground the conversation, current as of publication and per the Social Security Administration:
Full retirement age is 67 for anyone born in 1960 or later.
The 2026 cost-of-living adjustment is 2.8%.
If you claim early while still working, the earnings limit is $24,480 under full retirement age, and $65,160 in the year you reach it.
Married couples and survivors have extra moves. A widow or widower may be able to collect survivor benefits first and switch to their own benefit at 70 — exactly the kind of coordination a good advisor should raise without prompting.
Read more about Social Security strategy here.
“How will you coordinate my taxes — Roth, RMDs, and IRMAA?”
This is the question that can separate a great retirement advisor from a good investment manager. It is also the one many “questions to ask” lists leave out entirely.
Ask whether the advisor coordinates Roth conversions, required minimum distributions (RMDs), and Medicare IRMAA together. The timing matters. RMDs now begin at 73, rising to 75 in 2033. And a single dollar over an IRMAA threshold — based on your income from two years prior — raises both spouses’ Medicare premiums.
Read more about Roth Conversion Strategies here.
Why your tax bill may not drop in retirement
Many people assume taxes fall in retirement. This may not always be the case. If you have a large pre-tax 401(k) or IRA, the government eventually makes you withdraw it.
Under SECURE 2.0, the RMD age is 73 for those born 1951–1959 and 75 for those born 1960 or later (per the IRS RMD rules, current as of 2026). Those forced withdrawals can push you into a higher bracket than you expected.
One bit of relief: the penalty for missing an RMD was cut from 50% to 25% of the shortfall — and to 10% if you correct it within the SECURE 2.0 window.
The IRMAA trap and the “dual-ceiling” idea
IRMAA — the Income-Related Monthly Adjustment Amount — is a surcharge on Medicare Part B and Part D premiums for higher earners. Three things make it dangerous if it is not planned for. First, it is a cliff, not a phase-in: one dollar of extra income can bump you to the next tier.
Second, it looks back two years, so your 2024 income sets your 2026 premium. Third, it hits both spouses on Medicare at once. One more detail people miss: the income IRMAA measures is MAGI — your adjusted gross income plus tax-exempt interest.
IRMAA reaches only roughly 8% of people with Medicare Part B (CMS, 2026) — but for an affluent household doing Roth conversions, it is a real risk every year. The dual-ceiling approach solves this.
A skilled advisor fills your Roth conversions up to the lower of two ceilings: the top of your current tax bracket, and the next IRMAA threshold. Convert too little and you waste a low-tax window. Convert one dollar too much and you trip the surcharge for both spouses, two years out.
Don’t forget your actual tax return
Tax planning isn’t just about lowering your bill for its own sake — though that’s a benefit. Reducing your tax bill directly mitigates the strain on your savings, which is a meaningful part of making your money last.
A successful retirement should incorporate your total tax picture, so ask your advisor to look at your actual tax return with you and answer:
How can I reduce my federal taxes?
How can I reduce my state taxes?
How can I increase my itemized deductions?
A tax-experienced advisor should also be able to identify tax reduction strategies for both state and federal taxes. If your financial advisor won’t review your tax return, find someone who will.
This article is for educational purposes only and is not individualized investment, tax, or legal advice. Figures are current as of 2026 and subject to change. Consult your own financial advisor and tax professional before acting.
“How will I cover healthcare before Medicare?”
If you plan to retire before 65, ask how the advisor will manage your taxable income to bridge the gap to Medicare. Affordable Care Act (ACA) marketplace subsidies are based on your income, not your assets. You can have a seven-figure portfolio and still qualify for a premium subsidy, depending on how much taxable income you actually report each year.
That changes how a thoughtful advisor handles those early-retirement years. Pulling first from Roth accounts or from the cost basis in a taxable account can keep your reported income — and therefore your premiums — low. But the same lever cuts both ways.
A large Roth conversion can spike your income and push you over the subsidy cliff, wiping out the help entirely. For 2026, the enhanced pandemic-era subsidies have expired, and the 400%-of-federal-poverty-level subsidy cliff has been reinstated.
So the cliff is real again: above that income line, the premium help disappears all at once rather than phasing out. The exact dollar threshold depends on your household size and changes each year, so confirm the current figure for your situation before you act on a conversion.
Notice the connection to the tax section above. The very income that triggers an IRMAA surcharge after 65 can cost you an ACA subsidy before 65. An advisor who sees both at once—who manages your income to the ACA cliff now the way they will manage it to the IRMAA threshold later—is showing the kind of coordinated thinking decumulation demands. (ACA Subsidy Amounts).
“What adjustments should I make to my investment portfolio?”
A good advisor should also discuss all the essential elements of investment advice — how, when, where, why, and what to invest in — and have a solid strategy with a clear history of healthy investment management. Before working with them, make sure their ideas and practices align with your investment philosophy.
A qualified advisor can identify whether you hold the proper asset allocation (the mix between investments like equities and fixed income) for your goals and risk tolerance, and whether your investments are appropriately diversified.
They should also review your investment expenses and, unless you already have low-cost choices, offer solutions for reducing them, like low-cost mutual funds and ETFs.
And their answer should include a specific plan for investing for retirement income — a concerted, strategic withdrawal plan that seeks to maximize your retirement income.
“Should I take my pension as a lump sum?”
While being offered a pension through work is increasingly rare, workplace pensions can contribute a sizable amount to your retirement income. If you have the option of choosing a lump sum payment or a lifetime stream of income, you’ll want to make the right decision.
Several factors must be analyzed to help you maximize your benefit and make your retirement savings last:
How long are you expected to live?
What’s the likelihood your employer will be able to continue payments if they go bankrupt?
What is your current risk tolerance and immediate need for guaranteed cash flow?
How does a pension vs. lump sum impact my heirs?
“What non-financial goals do I want to accomplish?”
It’s time to put the “personal” in personal finance. Your personal goals are just as essential as your financial ones, and you want to work with an advisor who genuinely cares about both. Your money should support the people, places, and things that mean the most to you.
Perhaps you are passionate about giving back. A good advisor should help you create a strategic charitable giving plan using qualified charitable distributions, contributing to donor-advised funds, or donating appreciated stock to offset capital gains tax.
Perhaps you’ll pick up new hobbies, embark on an encore career, or move closer to family to spend more time with grandchildren. Whatever your non-financial goals, be sure you can discuss them with your advisor. They give better insight into your personality and how you plan, and may uncover something you hadn’t thought to mention.
“Who actually holds my money — and what are your credentials?”
Confirm that an independent third-party custodian — such as Schwab or Fidelity — holds your assets. Then verify every credential with the body that issues it. The title on the business card is not your protection. The structure behind it is.
Custody — the Madoff lesson. The single best protection against fraud is that your advisor does not hold your money. An independent qualified custodian does, under the SEC’s Custody Rule, and that custodian reports to you directly. (Custody Rule).
Credentials — what the letters mean. Not all designations are equal in rigor. Here are the ones we think are worth knowing, and you can verify each directly with its issuing body:
CFP® — Certified Financial Planner, issued by the CFP Board; broad financial-planning standard.
CFA — Chartered Financial Analyst; deep investment-analysis focus.
CPA-PFS — a CPA with a personal financial specialist credential; strong tax grounding.
ChFC — Chartered Financial Consultant; planning-focused.
EA — Enrolled Agent; a federally licensed tax specialist.
A credential helps protect you by signaling training and accountability. It does not, by itself, guarantee good advice. Two more things are worth checking beyond the letters.
Experience: designations are great, but you want an advisor with real experience too—at our firm, for example, the average advisor has over 10 years of experience. And specialization: does the advisor specialize in integrating tax planning with retirement planning?
“Do I even need an advisor, and who will I actually work with?”
Here is an honest answer you may not hear from an advisor who is paid only to manage assets: if you are a disciplined investor with a simple portfolio, you may not want ongoing AUM management at all when looking only at cost comparisons.
But the picture changes at the retirement transition, and at higher balances. In these cases, Roth conversions, withdrawal sequencing, and Social Security timing need to be done carefully as part of a broader financial plan, because they can set your income and tax trajectory for decades.
There is also a quieter reason: protecting a less-engaged spouse who would inherit the portfolio and the decisions. Self-management works beautifully right up until the person managing it is gone.
If you do hire someone, ask the continuity questions that generic checklists often forget:
Who will I actually work with day to day? The advisor I am meeting, or someone I have not met?
How often will we meet, and how do you communicate between meetings?
What happens to my plan if you retire, sell the firm, or die?
These matter most in a relationship meant to last the rest of your life.
Bringing it together: the questions to ask, and the answers a fiduciary should give
The questions are only half the job. What matters is listening for the answers a true fiduciary gives. A fiduciary 100% of the time, in writing, who tells you plainly how they are paid. Fee-only, with a clear all-in dollar cost you can see next to the services it buys.
A withdrawal rate and a Social Security claiming age should be set together, grounded in current research. Taxes should be coordinated across Roth conversions, RMDs, and IRMAA—and, if you retire early, across the pre-65 healthcare bridge too.
That is the difference between an advisor who simply names the questions and one who can model the right answers for your situation. While serving households like yours—age 50+, with $1M to $10M invested—coordinated, tax-first planning is work we do every day.
The most useful next step is rarely another checklist. It is seeing how these answers come together in a plan built around your numbers, your taxes, and the retirement you actually want — and the simplest way to start is a no-obligation conversation where we walk through how these decisions interact for households like yours.
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Frequently asked questions
What is a very important question to ask a financial advisor before retirement?
Whether they are a fiduciary 100% of the time, in writing, and exactly how they are compensated. Any hedging — like “when applicable” — is a red flag worth pressing on.
What’s the difference between a fee-only and a fee-based advisor?
Fee-only advisors are paid only by you. Fee-based advisors can also earn commissions on products they sell. Verify which one you have in Form ADV Part 2A and Form CRS, not by the label.
How do I verify a financial advisor is a fiduciary?
Check the SEC’s IAPD at adviserinfo.sec.gov, FINRA BrokerCheck, and Form ADV Part 2A Item 5, then confirm CFP® and NAPFA status directly with the issuing bodies.
At what age must I start taking RMDs?
Age 73 if you were born between 1951 and 1959, and age 75 if you were born in 1960 or later, under SECURE 2.0
Ready to get the help you need to retire with peace of mind?
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About the author:
Senior Financial Advisor
Adam is a Senior Financial Advisor with Covenant Wealth Advisors and a CERTIFIED FINANCIAL PLANNER™ practitioner. He has over 17 years of experience in the financial services industry in the areas of financial planning for retirement, tax planning, and investment management.
Disclosures: Covenant Wealth Advisors is a registered investment advisor with offices in Richmond, Reston, and Williamsburg, VA. Registration of an investment advisor does not imply a certain level of skill or training. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. The views and opinions expressed in this content are as of the date of the posting, are subject to change based on market and other conditions. This content contains certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Please note that nothing in this content should be construed as an offer to sell or the solicitation of an offer to purchase an interest in any security or separate account. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax, or legal advice. If you would like accounting, tax, or legal advice, you should consult with your own accountants or attorneys regarding your individual circumstances and needs. This article was written and edited by a CERTIFIED FINANCIAL PLANNER™ professional with the assistance of AI. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place. Hypothetical examples are fictitious and are only used to illustrate a specific point of view. Diversification does not guarantee against risk of loss. While this guide attempts to be as comprehensive as possible no article can cover all aspects of retirement planning. Be sure to consult an advisor for comprehensive advice.
