5 Questions Pre-Retirees Don't Think to Ask Their Financial Advisor
Sam's List Editorial | 2026-06-06
Most lists of questions to ask a financial advisor before retirement circle the same territory: projected savings balances, target retirement dates, Social Security estimates. That's not useless — but it's also not the stuff that determines whether a retirement plan holds together under real conditions.
The questions below are the ones most people don't know to ask. They're also the ones where a vague or deflecting answer tells you a lot about whether your advisor has actually thought through your specific situation.
One more filter before the questions: if you haven't already, pull your advisor's Form ADV (free at adviserinfo.sec.gov) and check their record on FINRA BrokerCheck. How they answer the questions below matters more if you already know how they're paid and whether they're held to a fiduciary standard.
1. What's My Sequence-of-Returns Risk, and How Does Your Retirement Income Planning Address It?
The order of returns matters more than the average return. That's not intuitive, but it's one of the most important mechanical realities of retirement income planning.
A portfolio that earns -20%, +25%, +15%, +12% over four years produces a very different outcome than one that earns +12%, +15%, +25%, -20% — especially if withdrawals are happening throughout. The portfolio that starts badly while you're pulling income may never fully recover, even if the long-run average looks fine on paper.
The first five years of retirement carry disproportionate weight. This is why some advisors build a cash or short-duration bucket specifically to fund early-year withdrawals, reducing the need to sell equities during down markets. Others use dynamic withdrawal strategies — pulling back spending in bad years based on portfolio triggers.
Ask for the actual mechanism. "We're diversified" is not an answer to this question. You want to understand what specific strategy limits your exposure when markets drop in year two of your retirement.
2. How Will My Income Strategy Change if One of Us Needs Long-Term Care Before the Other Retires?
Married couples almost always plan as a unit. Retirement projections assume two people living together, sharing expenses, drawing Social Security at roughly coordinated times.
That assumption breaks when one spouse needs extended care — often years before the other expected to retire. Memory care commonly runs $6,000–$12,000 per month depending on location and level of care, per industry cost-of-care surveys like Genworth's. That cost hits a couple's combined cash flow hard, often forcing the working spouse to delay retirement further or draw down shared savings well ahead of schedule.
The question isn't only about long-term care insurance. It's about what the income and withdrawal plan looks like under that scenario. Does your plan account for a period where one person is paying for care AND two people still need living expenses? If the answer is "we haven't stress-tested that," the plan has a gap.
Long-term care coverage — whether through a traditional policy, a hybrid life/LTC product, or self-insurance through a dedicated reserve — should be part of the conversation before retirement, not after a diagnosis.
3. What's the Roth Conversion Window Before Retirement Income Pushes My Tax Bracket Back Up?
There's a window most people don't notice until it's already closing: the years between your last W-2 income and age 65 when Medicare begins. During that gap, your taxable income often drops significantly before required minimum distributions and Social Security start pushing it back up.
That gap is frequently the lowest-marginal-rate window you'll ever have for converting pre-tax retirement account balances to Roth. A couple retiring at 63 with modest investment income and no wages may be able to convert $40,000–$80,000 per year at 12%–22% marginal rates — rates they won't see again once RMDs kick in at 73.
The math depends on your specific balances, filing status, and state tax situation. But the strategic framing matters: every dollar converted to Roth at a low marginal rate today is a dollar that grows tax-free and is never subject to RMDs. That changes the tax profile of your estate and your in-retirement income flexibility.
Ask your advisor to run the Roth conversion analysis specifically for the gap years. If they've never raised this with you, raise it yourself.
4. How Does Social Security Timing Interact With My Portfolio Withdrawal Sequence?
Claiming Social Security at 62 versus 70 is an 8-year, 6–8% per year difference in benefit size. For someone with a full retirement age of 67, the Social Security Administration's own formulas put the age-70 benefit roughly 77% higher than the age-62 benefit. But the strategy question isn't just about break-even age — it's about how the timing decision interacts with what you're pulling from your portfolio.
Delaying Social Security to 70 and funding those early retirement years from your portfolio can produce meaningfully more lifetime income, particularly for people with longer life expectancies. You're drawing down the taxable account earlier (which may actually be tax-efficient), preserving a larger guaranteed income stream for later years when portfolio withdrawals would otherwise be higher.
But this requires actual numbers. The right answer depends on your portfolio size, other income sources, health history, and whether you're married — survivor benefits matter enormously here. A spouse with a lower earnings history has every reason to think carefully about when the higher earner claims.
Rules of thumb — "always wait until 70" or "take it while you can" — miss the interaction effects entirely. Ask for a model that shows both scenarios with real numbers attached to your situation.
5. Are My Beneficiary Designations Aligned With My Current Estate Wishes and the Current Tax Code?
Beneficiary designations on IRAs, 401(k)s, and life insurance policies are legal transfer mechanisms. They override your will entirely. An IRA listing a former spouse as primary beneficiary will pass to that former spouse regardless of what your current will says, regardless of how long ago the divorce happened.
This is more common than it sounds. People update their wills and forget their account beneficiaries. Major life events — divorce, remarriage, death of a named beneficiary, a child reaching adulthood — all warrant a review.
There's also a substantive tax planning layer under the SECURE Act of 2019. Most non-spouse beneficiaries who inherit an IRA can no longer stretch distributions over their lifetime; they generally must empty the account within 10 years. That changes the calculus on how much you leave in a traditional IRA versus a Roth, and it can change whether leaving a Roth IRA to a child in a high earning bracket is more efficient than leaving other assets.
The beneficiary review isn't a one-time task. It belongs in the pre-retirement checklist every few years, and it requires coordination between your advisor and your estate attorney.
Work Through These Questions With a Reviewed Advisor
These questions require real analysis, not general guidance. If you're within a decade of retirement and haven't gone through sequence risk, Roth conversion windows, and beneficiary alignment with your advisor, a focused review conversation is overdue.
A vague answer to any one of these five questions is your signal to get a second opinion before retirement — not after the plan is already in motion.
Bull Oak works with pre-retirees and retirees on exactly this kind of structured retirement income planning. Read their profile and client feedback before you get on a call: Bull Oak on Sam's List.
Sam's List is a platform where financial advisors and accountants are reviewed by real clients — so you can find someone who has been through this process with people in situations like yours.