The Six People You Need to Talk with Before Retiring — and the Best Questions to Ask

A retired couple sit on a couch talking with a financial adviser.

(Image credit: Getty Images)

Too many Americans aren’t financially ready for retirement — a precarious position for career professionals to be in as they draw closer to day one of their golden years.

Most U.S. adults 10 years away from retirement are “woefully unprepared” for their post-working years, according to a 2024 Prudential survey, with 2/3 of 55-year olds afraid they will outlive their retirement savings.

The study showed that the median retirement savings for 55-year olds is $50,000, versus the recommended goal of eight times a worker's annual salary by that age. Citing the rise of so-called "Silver Squatters," the study showed that nearly 1 in 4 55-year olds expect to need financial support from their family in retirement, more than twice the amount for retirees a decade older.

From just $107.88 $24.99 for Kiplinger Personal Finance

Become a smarter, better informed investor. Subscribe from just ~~$107.88~~ $24.99, plus get up to 4 Special Issues

CLICK FOR FREE ISSUE

https://cdn.mos.cms.futurecdn.net/flexiimages/y99mlvgqmn1763972420.png

Sign up for Kiplinger’s Free Newsletters

Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of expert advice - straight to your e-mail.

It’s increasingly clear millions of Americans nearing retirement aren’t on sound financial footing. The good news is that engaging with trusted retirement experts can change that equation and get older career professionals on a clear path to a better retirement.

“Deciding when and how to retire is arguably one of the biggest decisions you must make and should not be made without ample preparation and consultation,” says Tony Gerard, trust relationship officer for Greenleaf Trust in Kalamazoo, Mich.

“To make sure you’re fully prepared, the first step that anyone seriously contemplating retirement should take is to assemble a team of qualified professional experts to build a plan that is structured to your goals and reviewed at least annually,” he said.

Here are the experts you should consider talking to before you commit to retirement. The sooner you get going, the better.

1. A financial planner

In building your retirement team, you’ll need experts and specialists with skill sets that complement one another. But your team will need a quarterback first, and that’s where a financial planner fits the bill.

“A fiduciary financial advisor can lead your retirement conversations as they will know your full financial picture and your specific long-term wishes and goals,” says Kevin Melchiorre, co-founder and managing partner at Tenet Wealth Partners in Champaign, Il.

A good financial planner understands your primary concerns and what lifestyle you’ll want to live and can also help determine what other experts to bring to the team.

“Your planner can make sure your investment portfolio is aligned with your retirement needs, review your cash flow to ensure you have an income plan designed to sustainably meet your expense needs for the long-term, and also review the potential impacts of retirement on other areas of your financial situation,” Melchiorre says.

Key questions to ask

Based on my current savings and projected expenses, when can I realistically afford to retire?
What investment strategies do you recommend to generate income and maintain growth in retirement while minimizing risk?
How should I withdraw money from my retirement accounts to minimize taxes and make my savings last?

2. A tax specialist

Retirees should also partner with a Certified Public Accountant (CPA) or other credentialed tax expert.

“A CPA can provide valuable guidance on tax planning, pre-and post-retirement,” Gerard says. “Your CPA can help you understand the tax implications of different retirement income sources and will be able to explain how your pension, Social Security benefits, and withdrawals from retirement accounts will be taxed.”

A qualified CPA can also provide strategies to minimize your tax burden, “such as Roth IRA conversions, tax-loss harvesting, and charitable giving,” Gerard says.

Key questions to ask

How will my pension, Social Security benefits, and withdrawals from retirement accounts be taxed?
What strategies can I use to minimize my tax burden in retirement, such as Roth conversions or tax-loss harvesting?
Are there any tax implications regarding my specific investments or assets?

3. An estate planning specialist

Retirees also need to think long-term with their team, and that’s where a solid estate planning advisor can pitch in.

“An estate planning specialist can make sure your estate is set up properly, and your legal affairs are in order,” says Bobbi Rebell, a certified financial planner and personal finance expert at CardRates.com.

Even if a retiree doesn’t think they have much money to leave behind, their beneficiaries will appreciate having a roadmap for what they want to happen with various assets.

“An estate planner will make sure their retired clients have a will and, if appropriate, some trusts,” Rebell says. “Retirees should also properly set up beneficiaries for things like IRAs and 401(k)’s and other financial accounts.”

It’s also a good idea to set up a power of attorney (POA) and health care directives, and a good estate planner can help on both fronts, Rebell adds.

An estate planner is extremely important should you become incapacitated. “In that scenario, you’ll want to ensure you have the right individual named to manage your finances and healthcare decisions for you,” Gerard says.

Key questions to ask

Do I need a will or trust, and what are the benefits of each?
How can I ensure my assets are distributed according to my wishes?
How can I minimize estate taxes for my heirs?

4. An insurance adviser

An insurance adviser or broker can help you evaluate your insurance needs before and in retirement, Gerard says. “They’ll assess the necessary level of coverage you require and help to understand any unique situations or conditions that could impact your coverage options.”

Insurance specialists also know about the various types of health insurance coverage options needed in retirement. “Your insurance expert can assist with comparing policies from multiple insurance providers to help you find the best and most affordable options,” Gerard notes.

Insurance advisers also take the time to help clients understand the details of their policies, including benefits, premiums, and any policy conditions. “They’re also invaluable with assisting clients in navigating Medicare and supplemental health insurance options,” Gerard adds.

Key questions to ask

What does Medicare cover, and why do I need supplemental insurance?
Do I need long-term care insurance, and what are the different policies available?
What other types of insurance should I consider, such as life insurance or disability insurance?

5. A senior living advisor

Your insurance specialist can also steer you to another potential retirement expert — a senior living advisor.

“With people living longer, planning for aging is becoming necessary,” says Michael E. Fiffik, managing member of Fiffik Law Group in Pittsburgh, Pa.

“For example, if you have a prepaid funeral arrangement but no aging plan, you’ve skipped a very important step to your happiness and quality of life," Fiffik said. "Understanding the senior care spectrum is something too many people leave until it’s too late.”

A senior living specialist can also educate you on longevity care options and develop a plan for paying for it. “They can identify tech tools that make living at home longer more feasible,” Fiffik notes. “Your senior planning can relieve a huge burden for your family if they are called upon to help you as you age or lose your capacity to care for yourself for any reason.”

Key questions to ask

How can I best save for senior living care?
What conversations should I have with my children and family?
What are my best senior care options?

Another critical step in preparation for retirement is understanding your Social Security benefits, and that’s where a knowledgeable Social Security adviser can help.

“While someone at the U.S. Social Security Administration is not a professional expert, like a credentialed financial planner, they are well versed in providing critical information to assist you in making informed retirement income decisions,” Gerard says.

It's crucial to contact the Social Security Administration prior to retirement to understand your benefits and when it’s most advantageous for you to claim them.

“Many different complex factors beyond your age, such as the death of a spouse, disability, or divorce can play a role in determining when it is most advantageous to take your benefits,” Gerard said. Making the right decision comes down to asking the right questions.

Key questions to ask

How are my benefits calculated?
What is my full retirement age (FRA)?
How are my benefits impacted by my marital status?

Bottom line

Historically, Americans don’t like talking to anyone about money, let alone perfect strangers. Yet that’s precisely what they should do instead of making money a taboo subject. Better yet, the more candid you are about money and the more questions you ask, the better you’ll plan for a comfortable retirement.

The good news is that qualified and trusted financial specialists aren’t that hard to find, and they want to help you.

“It's essential to find qualified and experienced professionals who specialize in retirement planning,” Gerard said. “You can ask for referrals from friends, family, or colleagues, or search for professionals with relevant certifications like Certified Financial Planner (CFP) or Chartered Retirement Planning Counselor (CRPC).”

“By consulting with these experts, you can understand your financial situation clearly, make informed decisions, and confidently transition into a fulfilling retirement,” he adds.

Want more guidance on retirement savings? Sign up for Kiplinger's six-week series, Invest for Retirement.

A former Wall Street bond trader, Brian O’Connell is the author of two books: “The 401k Millionaire” and “CNBC’s Creating Wealth.” He's written for national finance publications such as TheStreet.com, CBS News, The Wall Street Journal, U.S. News & World Report, Forbes, Fox News and others. With 20 years of experience covering business news and trends, he believes education is the best gift a financial consumer can receive – and brings that philosophy to his work. Brian is a graduate of the University of Massachusetts, and currently resides in Palmas del Mar, Puerto Rico during the winter, and in Bucks County, Pa., when Mother Nature cooperates.