These conversations aren’t easy.

Bringing up long-term care or estate planning with aging parents can feel like driving down a New England road filled with potholes—uncomfortable, emotional, maybe even a little intrusive.

But if you wait until something happens—a fall, a diagnosis, a hospital stay—you're not just having the conversation late. You're having it under pressure.

So how do you start the talk without it turning tense?

Here’s a guide to help you open the door with empathy, avoid common missteps, and get a little more clarity about what your parents want and need.
 

Start With Empathy, Not Instructions

It’s tempting to jump straight into action plans.

But parents aren’t spreadsheets to be sorted. They’re people with feelings, fears, and maybe even a little resistance.

Instead of jumping into the “what ifs,” start with how they feel. Ask them about their preferences. About their hopes. About what makes them feel safe.

For example:

Try asking: “If you couldn’t live on your own anymore, what would you want?”

Not: “Have you thought about assisted living or a nursing home?”

The first shows care and curiosity. The second can feel like you’re making a decision for them.
 

Keep the Focus on Care, Not Crisis

You’re not planning a funeral. You’re helping make sure the people you love are supported, protected, and respected—no matter what the future holds.

That’s why it’s helpful to frame questions around caregiving, not worst-case scenarios.

For example:

Try asking: “If one of you needed help and the other didn’t, what would that look like?”

Not: “What happens when one of you dies?”

You’ll get further when the conversation feels like collaboration instead of a countdown.
 

Don’t Assume Nothing’s Been Done

Only 24% of Americans have a will in place¹—so the odds are decent your parents don’t have everything buttoned up. But here’s the thing: they might have done more than you think.

Instead of calling out gaps, start with what’s already in place.

For example:

Try asking: “What do you already have in place?”

Not: “You don’t have long-term care insurance, do you?”

Leading with trust helps the conversation feel like support, not judgment.
 

Ask About Worries, Not Diagnoses

Many people feel uncomfortable opening up about cognitive changes. Even those diagnosed with dementia often keep it private out of fear they’ll be treated differently².

That’s why asking about fears can be more productive than asking about specific conditions.

For example:

Try asking: “What worries you most about getting older?”

Not: “Are you scared of getting dementia?”

This opens the door to a more human, more meaningful conversation.
 

Suggest Support, Not Solutions

Estate planning and long-term care decisions can be complicated. And when emotions run high, having a third party—like a financial advisor—can bring clarity without the drama.

For example:

Try asking: “Would it help if we talked to a financial advisor together?”

Not: “Don’t you think you should talk to someone about this?”

When you extend an invitation instead of delivering a verdict, people are more likely to say yes.
 

Bringing It Together

You don’t need a perfect script. Just the right starting point.

Pick one question. Use it over coffee. During a family gathering. On a short check-in call.

This isn’t about wrapping up everything in one conversation. It’s about creating a safe space to keep the conversation going.

And if you’d like a partner to facilitate that conversation—with financial context, resources, and support—we’re here to help.

Because the best plans aren’t made in crisis. They’re made deliberately, with care and time to consider what matters most.

Sources:

1. Caring.com, 2025 [URL: https://www.caring.com/resources/wills-survey]
2. Gerontological Society of America, 2025 [URL: https://doi.org/10.1093/geront/gnae186]

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