This article lays out three focused questions to ask your financial advisor before retiring in 2027: how they get paid and whether they are required to put your interests first, the best way to draw from your nest egg without running out or paying unnecessary taxes, and how you’ll cover healthcare costs in retirement. It highlights what compensation models mean for advice, the mechanics of sustainable withdrawals, and the timing and cost of health coverage before Medicare. It also points out a commonly missed Social Security opportunity and why it matters to your overall plan.
So you’re on the brink of retirement — that mix of relief, excitement, and a little dread. After years of saving and decisions, the questions stop being hypothetical and start being immediate. Now is exactly when you need clear, practical answers instead of vague reassurance.
First, ask a blunt question about how your advisor is compensated and whether they’re legally required to put you first. Compensation shapes behavior: salary, client fees, and commissions each create different incentives. If a recommendation comes with a commission, it’s reasonable to dig deeper into whether it truly serves your goals.
Prefer advisors who are fee-only and who operate as fiduciaries whenever possible. Fee-only arrangements make the cost transparent and reduce the temptation to push products that benefit the advisor. Also look for credentials such as CFP or AIF, which often indicate a stronger commitment to professional standards and best practices.
Second, nail down how you should draw from your nest egg and at what pace. The move from accumulation to distribution is jarring for many retirees, and mistakes can be expensive. Rules of thumb like the 4% rule exist, but they are only a starting point; your advisor should model withdrawal rates against your lifespan, market risk, and income needs.
Taxes are a huge part of this conversation and they should not be an afterthought. Different account types — traditional IRAs, Roth accounts, taxable brokerage accounts — behave very differently when you withdraw, and timing matters. A good advisor will show scenarios that minimize lifetime taxes and protect against sequence-of-return risk.
Third, get clear about healthcare coverage and the timing of Medicare enrollment. Most people sign up for Medicare Part A and Part B at 65, but if you retire earlier you’ll need interim coverage and that can be costly. The enhanced tax credits intended to subsidize Affordable Care Act (ACA) premiums expired at the end of 2025, affecting approximately 22 million enrollees, which changes the cost picture for many retirees who leave employer plans.
Your advisor should be able to sketch out how your withdrawals affect subsidized coverage, Medicare premiums, and the tax cliff that can raise costs unexpectedly. Small changes in taxable income can push you into higher premium brackets or phase out assistance, so distribution strategy and healthcare planning need to be coordinated. If they can’t explain this clearly, that’s a red flag.
Don’t forget to ask about Social Security timing and strategies, because many retirees miss easy wins. The phrase “Social Security secrets” exists because a handful of timing tricks and design choices can boost benefits materially for some households. The $23,760 Social Security bonus most retirees completely overlook may not apply to everyone, but asking about spousal strategies, delayed claiming, and survivor implications should be part of your conversation.
Finally, demand specifics and documentation: a written plan that shows how fees, withdrawal rates, taxes, healthcare costs, and Social Security moves interact. Ask for stress-test scenarios and the assumptions behind them so you can make an informed choice rather than hope. If your advisor hesitates or gets vague, get second opinions until you find someone who gives straight answers and a clear path forward.
