5 Questions Pre-Retirees Don't Think to Ask Their Financial Advisor

Sam's List Editorial | 2026-06-06

5 Questions Pre-Retirees Don't Think to Ask Their Financial Advisor 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–