Secure Your Retirement with Confidence: 6 Smart Questions to Ask Your Financial Advisor in Your 60s

Retirement isn’t just about kicking back on a beach or finally taking that long-awaited RV trip across the country—it’s also about feeling confident that your finances can support the life you’ve worked so hard to build. If you’re in your 60s, now is the time to make sure your plan is airtight. Whether you’re already retired or just about to be, talking to a financial advisor is one of the best ways to stress-test your strategy. But not all conversations are created equal.

Asking the right financial advisor questions can make a huge difference. From understanding how they’re paid to deciding when to claim Social Security, the right guidance can help protect your nest egg, optimize your income, and prepare for whatever lies ahead. In this guide, we’ll walk you through six essential questions that every baby boomer should ask their financial advisor. These aren’t just theoretical—they’re practical, real-world prompts designed to help you retire smarter, not harder.

1. Are You a Fiduciary and How Do You Get Paid?

First things first: you need to know whether your advisor is truly working in your best interest. A fiduciary is legally obligated to act in your favor, rather than recommending financial products that might pay them a higher commission. Ask them directly, “Are you a fiduciary 100% of the time?” If the answer isn’t a clear yes, it’s time to dig deeper. You should also understand their fee structure. Are they fee-only, charging a flat rate or percentage of your assets? Or do they earn commissions from the products they recommend? Transparency here is non-negotiable. Knowing how your advisor gets paid helps you spot any potential conflicts of interest and ensures your retirement planning stays focused on your goals—not theirs.

2. Is My Retirement Savings on Track to Last?

Let’s face it—one of the biggest concerns for baby boomers is outliving their savings. Ask your advisor to walk you through detailed projections: are your assets aligned with your desired lifestyle? Have they been tested against inflation, healthcare costs, and possible market downturns? Many advisors use tools to simulate worst-case scenarios, such as a prolonged bear market early in retirement. You’ll want to know if you’re withdrawing too much too soon or if you need to adjust your spending. As a rule of thumb, many financial experts suggest saving at least 10 to 12 times your final salary before retiring and sticking to a 4% withdrawal rate. But your specific situation—like health, pension availability, and living expenses—makes a personalized analysis essential.

3. Should I Change How My Money Is Invested?

Your 60s are a financial turning point. You’re no longer investing for long-term growth—you’re investing for stability and income. Ask your advisor if your current portfolio matches your retirement timeline and risk tolerance. As you get closer to living off your savings, your investment mix may need to shift from aggressive growth stocks to more conservative assets like bonds, dividend-paying stocks, or even annuities. You’ll also want to discuss something called “sequence of returns” risk. If you start withdrawing money during a market downturn, your savings may deplete faster than expected. A good advisor will help create a withdrawal strategy that shields you from this risk by balancing cash reserves with long-term investments.

4. When Should I Start Taking Social Security?

This is a hot-button topic for many retirees—and it’s not as simple as it seems. While you can start claiming Social Security at 62, doing so means a permanently reduced benefit. On the other hand, waiting until full retirement age (66 to 67 for most boomers) or even age 70 increases your monthly check. Ask your advisor to help calculate your breakeven point—how long you’d need to live to make delayed benefits worth the wait. They should also take into account your other income sources, taxes, and whether you’re still working. For couples, strategic claiming—such as having one spouse delay benefits while the other starts earlier—can help maximize total household income. This one decision can have lasting effects, so it’s worth a deep dive.

5. How Do I Prepare for Health Care and Long-Term Care Expenses?

Health care is one of the largest expenses in retirement—and it’s not always fully covered by Medicare. You’ll want to know what to expect when it comes to premiums, co-pays, deductibles, and prescription costs. Ask your advisor to walk you through your options for Medicare Advantage, Medigap plans, and drug coverage. But don’t stop there. Long-term care (LTC) is a major concern for many baby boomers. Statistics show that about 70% of people turning 65 will need some form of long-term care in their lifetime. It’s critical to ask how you’ll pay for it. Options include long-term care insurance, hybrid life insurance with LTC riders, or earmarking specific savings to cover those costs. A good advisor will help you plan ahead—so a sudden health issue doesn’t derail your financial future.

6. How Will Taxes and Inflation Affect My Retirement Income?

Taxes don’t disappear in retirement—in fact, without careful planning, they can eat into your nest egg more than you expect. Ask your advisor to review how taxes will impact your Social Security benefits, pensions, IRA withdrawals, and investment income. Required minimum distributions (RMDs), which now begin at age 73, can push you into higher tax brackets if you’re not careful. One strategy many advisors recommend is converting some traditional IRA funds into a Roth IRA in your early retirement years to reduce future tax liabilities. Also, don’t forget about inflation. Even modest inflation can erode purchasing power over a 20- to 30-year retirement. Talk to your advisor about investments that can help hedge against inflation—such as Treasury Inflation-Protected Securities (TIPS) or dividend-growth stocks—and make sure your income plan has built-in flexibility.

Final Thoughts

Retirement doesn’t have to be stressful—but it does need to be strategic. The key to a confident retirement isn’t just having money saved—it’s knowing your plan can stand up to the realities of aging, taxes, and the unexpected. These six questions are more than conversation starters—they’re tools to make sure your financial advisor is on the same page, helping you protect what you’ve earned and enjoy the life you’ve imagined.

So don’t be shy. Set up that meeting. Bring your list. And ask the big questions. Because when it comes to retirement planning for baby boomers, knowledge isn’t just power—it’s peace of mind.