Getting Answers

Tough questions about care, health, and the future to ask your aging parents

Fact checked by Shannon Sparks

Money. Physical health. Cognitive decline. Death. Between adult children and their aging parents, few topics are as emotionally charged — or as essential to discuss. The challenge, however, is that these talks can easily go off track if they’re not approached with the right timing, tone, and questions.

“The secret sauce to cooperation in our caregiving conversations is knowing how to approach our parents or elders in a way that they can begin to feel safe,” says Joy Loverde, best-selling author of The Complete Eldercare Planner. “That’s what makes it so difficult.” 

Too often, adult children start the conversation from a place of worry, which can prompt aging parents to protect their privacy, Loverde says. That risks leaving crucial questions unanswered — until crisis strikes. 

Instead, Loverde recommends a gentler, more strategic approach. Look for natural opportunities, she says. Use real-life situations as springboards. For example, ask for advice on your own retirement planning to open the door to a conversation about how they’ve approached theirs.  

And timing matters. Don’t bring up serious topics at breakfast if your parents aren’t morning people. Avoid noisy restaurants if hearing is an issue. Choose a setting that allows for calm, focused conversation.

Here are some of the tough — but important — questions that Loverde and Jennifer Prell, founder of the elder care organization Elderwerks, recommend asking your aging parents. 

Financial and legal issues

No matter your parents’ income level, it’s essential for adult children to have some insight into their financial affairs. “The worst thing that happens is our elder is in the hospital, they can’t talk. They’re incapacitated, but the bills come in,” Loverde says.

She recommends starting with these questions:

1. Who provides your legal and financial advice? Can you share their contact information, or would you like me to connect with them in case of a future emergency?
2. Where do you keep your emergency contact information: family, neighbors, and doctors? How can I access that information if something happens to you?
3. How do you manage your digital life: Where are passwords stored to access devices such as phones, computers, and tablets?

 

Scam prevention is another key topic, Prell says. With phone and email scams becoming increasingly sophisticated, consider asking: 

1. What steps are you taking to protect yourself from scams?
2. Do you answer unknown phone calls or emails?
3. Do you follow news stories and local police updates about the latest scams?
4. Have you added yourself to the Do Not Call Registry?

Living situation

Most older adults want to remain in their homes as long as possible. But aging in place requires forethought and planning, Loverde says. These questions can help parents consider whether staying at home is realistic — or whether a different setting might better meet their changing needs.

1. Can you afford services like house cleaning, yard work, and in-home nursing care to stay at home safely?
2. Is your home age-friendly and accessible? If not, can you afford necessary improvements, such as a first-floor bathroom or stair lifts?
3. Are there reliable in-home support services in your area, such as on-demand transportation and caregiving help?
4. Is isolation a concern for you? If friends stop visiting, do you think you might feel depressed or lonely?
5. Do you have a plan for weather-related emergencies? Who would help you evacuate?

Health

As parents age, chronic health conditions, limited mobility, and cognitive changes often become more pressing concerns. The goal of health-related conversations is to understand their medical situation — and to ensure you have the information needed in case an emergency occurs. 

Consider asking:

1. What kind of insurance coverage do you have? Do you have long-term care insurance?
2. Who are your current doctors — including specialists — and when did you last see them?
3. What medications are you taking, and how do you keep track of them?
4. How are you feeling lately? Are there any new aches, pains, or health issues you’ve noticed?
5. Would you be open to me accompanying you to medical appointments?

End-of-life

End-of-life questions may be the most difficult, but they’re critical to honoring your parents’ wishes. Prell suggests starting with: 

1. What are your preferences for medical decisions if you become unable to speak for yourself? Do you have a healthcare proxy or living will? Where can I find those documents?
2. If you couldn’t make decisions on your own, what would you want us to do regarding care? Would you prefer an urban or suburban setting? Large or small building? What city would you prefer to live in or near?
3. What would you like for your funeral or memorial service? How would you like to be remembered? Would you like a celebration of life, a traditional funeral, or cremation?

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Originally published in the Summer/Fall 2025 print issue.