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Oct 23, 2025

Questions to Ask Your Financial Advisor About Retirement

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Lori Gann Morris, CIMA®, AIF®, CeFT®, Co-Founder / Managing Partner

A financial advisor is a great resource when you’re planning for retirement, but in order to get the best help possible, it’s important to ask the right questions. Confidence in your financial future makes for peace of mind in the present. If you’re not sure where to start, here’s what you should be asking regarding retirement planning to protect your future.

How Much Do I Need to Retire Comfortably?

The answer depends on your lifestyle, expected healthcare expenses, and the impact of inflation over time. Based on these nuances alone, expert help can help iron out the uncertainties. A financial advisor can help you settle on a realistic number based on your specific goals.

Related to this is your withdrawal rate, which is how much you can safely take from your savings each year without running out of money. Ideally, your investments may even be able to sustain withdrawals based off of interest earned and therefore not reduce your savings at all. 

Finally, you’ll need to plan on rising costs as well. Everyday expenses, especially healthcare, tend to increase, and this is not just due to inflation. 

What Retirement Accounts and Investment Strategies Should I Use? 

Not all retirement accounts are the same, and the right mix of investments can make a significant difference in your financial future. A financial advisor can walk you through options like 401(k)s, traditional and Roth IRAs, and taxable investment accounts. 

But it’s not as black and white as selecting a retirement account and walking away. By integrating an investment strategy that is fluid with your age and financial goals, you can home in on the best way to manage your assets. As such, here are some further questions you can ask your financial advisor:

  • Should I consider a Roth conversion? Converting a traditional IRA to a Roth can provide tax-free withdrawals in retirement, but it’s not the right move for everyone.

  • How should I adjust my investment risk as I near retirement? The closer you get to retirement, the more you’ll need to shift toward lower-risk investments to protect your savings.

  • What’s the best way to balance stocks, bonds, and other assets? A diversified portfolio helps manage risk while still providing growth potential.

How Will Taxes Affect My Retirement Income?

Without a solid tax strategy, you could end up paying more than necessary and watching your hard-earned savings shrink faster than expected. A financial advisor can help you structure withdrawals to keep more money in your pocket and less going to the IRS. To follow up with more information, you might want to ask about minimizing taxes on retirement income, withdrawing from tax-deferred or taxable accounts first, and how required minimum distributions (RMDs) will affect your taxes. 

What's the Best Strategy for Claiming Social Security?

Social Security benefits aren’t as simple as just signing up when you hit retirement age. The age at which you claim will directly impact your monthly payments. This change to the baseline payment you rely on may affect your overall financial security entering into retirement. Taking benefits as early as 62 reduces your monthly amount, while waiting until full retirement age—or even delaying until 70—can increase your payments substantially.

In many ways this comes down to weighing the pros and cons. The right strategy depends on factors like your health, expected lifespan, and other retirement income sources. But at this stage of life, most people wonder whether the extra money is worth the extra years spent working. This is also an integral part of the strategy, and a financial advisor can help weigh your options and create a gameplan that aligns with what you need.

How Should I Plan for Healthcare and Long-Term Care Costs?

Healthcare is one of the biggest expenses retirees face, and it only gets more expensive with age. Medicare helps, but it doesn’t cover everything (which is why many retirees consider supplemental insurance or health savings accounts), and out-of-pocket costs can add up quickly. Planning ahead for medical expenses—including routine care, unexpected health issues, and potential long-term care—can make a huge difference in your financial security. By asking this question up front, you can rest assured that one of the biggest variables is soundly accounted for.

How Do I Ensure My Estate and Legacy Plans Are in Order? 

Retirement is a great time to finalize your estate plan to make sure your loved ones are taken care of and your assets are protected. A well-structured estate plan helps avoid unnecessary taxes, legal disputes, and confusion for your family. Without one, state laws could determine what happens to your estate, and that rarely works out in anyone’s favor.

Here are key questions to discuss with your advisor:

  • Do I need a will, trust, or both? Understanding the differences can help you decide which option best protects your assets.
  • How can I minimize estate taxes for my heirs? Proper planning can reduce tax burdens and ensure more of your wealth is passed on.
  • What’s the best way to pass on assets while maintaining control? Strategies like trusts allow you to set terms for asset distribution while keeping oversight.

How Do I Ensure My Estate and Legacy Plans Are in Order? 

Retirement planning is an ongoing process that requires careful thought and expert guidance. Reach out to AMG Wealth Advisors today to get the personalized advice you need to navigate these crucial decisions with confidence.

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Disclosures

All Investment Advisory Services are provided by Waterloo Capital d/b/a AMG Wealth Advisors, an SEC Registered Investment Adviser. Registration with the SEC does not imply a certain level of skill or expertise. AMG Wealth Advisors is not affiliated with Waterloo Capital. Additional information about Waterloo Capital d/b/a AMG Wealth Advisors, is available in its current disclosure documents, Form ADV Part 1A, Form ADV Part 2A Brochure, and Client Relationship Summary, which are accessible online via the SEC’s investment Adviser Public Disclosure (IAPD) database at www.adviserinfo.sec.gov. Waterloo Capital does not offer or provide legal or tax advice. Please consult your attorney and/or tax advisor for such services.

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