How to Talk to Your Aging Parents About Estate Planning (Without Making It Tense)

James Abbott

Nov 7, 2025

Estate Planning·Family·Health·Disability·Insurance·Risk Management
How to Talk to Your Aging Parents About Estate Planning (Without Making It Tense)

These conversations aren't easy.

Bringing up long-term care or estate planning with aging parents can feel like stepping on a landmine—awkward, 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.

Here's a guide to help you open the door with empathy, avoid common missteps, and get 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, hopes, and what makes them feel safe.

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 ensure the people you love are supported, protected, and respected—no matter what the future holds.

Frame questions around caregiving, not worst-case scenarios.

Example:

Ask: "If one of you needed help and the other didn't, what would that look like?"

Not: "What happens when one of you dies?"

This approach helps the conversation feel collaborative rather than stressful.

Don't Assume Nothing's Been Done

Only 24% of Americans have a will in place—so the odds are decent your parents don't have everything organized.

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

Example:

Ask: "What do you already have in place?"

Not: "You don't have long-term care insurance, do you?"

Leading with trust makes the conversation feel supportive.

Ask About Worries, Not Diagnoses

Many people feel uncomfortable discussing cognitive changes. Even those diagnosed with dementia often keep it private out of fear.

Asking about worries is more productive than asking about conditions.

Example:

Ask: "What worries you most about getting older?"

Not: "Are you scared of getting dementia?"

Suggest Support, Not Solutions

Estate planning and long-term care decisions are complicated. Emotions can run high.

Having a third party—like a financial advisor—can bring clarity without drama.

Example:

Ask: "Would it help if we talked to a financial advisor together?"

Not: "Don't you think you should talk to someone about this?"

Inviting support encourages participation rather than defensiveness.

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, or a short check-in call.

This isn't about wrapping up everything in one conversation. It's about creating a safe space to continue talking.

If you'd like a partner to facilitate the 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:

Disclaimer:

This content is for informational purposes only and is not tax or legal advice. Individuals should seek guidance from their own tax or legal counsel. Estate planning should be conducted with a qualified team. Copyright 2025 Advisor Websites.

Five Star Professional Disclosure: James W. Abbott is awarded The FIVE STAR Wealth Manager Award in the Wealth Management Category, based on 10 objective criteria associated with providing quality services to clients such as credentials, experience, and assets under management among other factors. Wealth managers do not pay a fee to be considered or placed on the final list of 2023 Five Star Wealth Managers. The inclusion of a wealth manager on The FIVE STAR Wealth Manager Award list should not be construed as an endorsement of the wealth nor should it be inferred that the responses used from the survey represent the experience of any clients. This award does not evaluate the quality of service provided and the wealth manager may have had unfavorable ratings. The rating is not indicative of the wealth manager's future performance. Five Star Professional conducts market-specific research to identify service professionals who provide quality services to their clients. Five Star Professional joins forces with city and regional magazines to make the research results available to consumers in more than 45 markets across the United States and Canada. Five Star Professional was founded in 2003 and is based in Minneapolis, MN. For more information, go to: www.FiveStarProfessional.com.

Claro Advisors LLC ("Claro") is a Registered Investment Advisor with the U.S. Securities and Exchange Commission ("SEC") based in the Commonwealth of Massachusetts. Registration of an Investment Advisor does not imply any specific level of skill or training. Information contained herein is for educational purposes only and is not to be considered investment advice. Claro provides individualized advice only after obtaining all necessary background information from a client. Disclosures and Terms of Use.

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