Nearly 55% of U.S. adults don’t have a will or estate plan in place, and when no clear plan exists, probate can consume 3–7% of an estate’s value and drag on for months or even years. Even more striking, 58% of families without an estate plan report disputes or conflicts after a loved one’s passing. These numbers matter—but the holidays offer a gentle, human way to approach the topic.

The holiday season brings something rare: multiple generations gathered in one place. Warm meals, familiar stories, and long-standing traditions make these moments feel especially meaningful. Amid all the laughter and reconnecting, these quieter, heartfelt settings can also inspire conversations about the future—conversations that bring clarity, not tension.

Estate planning may not be the first topic that comes to mind during the holidays, and that’s okay. It’s normal for the idea to feel tender or even uncomfortable. But talking about it now, even briefly, can bring tremendous peace of mind for everyone involved.

Questions Adult Children Can Ask Their Parents

Because adult children often step into support roles during emergencies, clarity is essential. These questions help open the door with care and curiosity:

Do you have an up-to-date will or trust in place?
Who have you chosen to make financial and medical decisions if you’re unable to?
Have you shared your wishes for medical care and end-of-life planning?
If something happened tomorrow, would we know where to find your important documents and accounts?
Are there heirlooms or traditions you’d like us to know the stories behind?
Do you feel confident that the people you’ve chosen to handle your affairs are still the right ones?

Questions Parents Can Ask Their Adult Children

Parents often want reassurance that their children will be prepared—both practically and emotionally—if something unexpected happens. These questions can help spark thoughtful, two-way dialogue:

Do you know where to find my important documents in case of an emergency?
Have you considered creating your own will or an estate plan?
If you received an inheritance tomorrow, would you know what to do with it — or who to turn to for help?
Are there family keepsakes or traditions you’d be heartbroken not to have carried forward?
If you had to step in to help us — financially or medically — what support would you need?

Why These Conversations Matter

Estate planning isn’t just about documents. At its core, it’s about:

Control – Ensuring your wishes—not assumptions—guide key decisions.
Clarity – Reducing confusion when emotions run high.
Care – Protecting loved ones, including children, dependents, and pets.
Efficiency – Minimizing costs, taxes, and delays.
Legacy – Passing down values, stories, and traditions alongside assets.

For adult children, asking questions now can prevent painful surprises later. For parents, encouraging younger generations to plan ahead fosters responsibility and continuity. These conversations help protect what truly matters—family understanding and unity.

How to Bring Up the Topic Gently

You don’t need a formal family meeting or a detailed agenda. Sometimes the best conversations happen during a quiet walk, over morning coffee, or while cleaning up after a meal. A simple opening like, “I’ve been thinking about planning for the future—can I ask you something?” can be enough to get started.

Framing the conversation as a gift makes it feel less intimidating. Estate planning is ultimately an act of care—an effort to remove future burdens and bring peace to the people you love most.

If you’re unsure where to begin or want guidance on navigating these conversations, consider reaching out to a trusted advisor. A little clarity now can prevent confusion later—and that’s a gift every family can appreciate.