Estate Planning Conversations Around the Holiday Table

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 stretch on for months or even years. More than half of families without a plan experience conflict after a loved one’s passing. These numbers highlight just how important it is to have thoughtful conversations—especially when families are finally together.

The holidays bring a rare kind of togetherness. Generations gather under one roof, sharing meals, stories, and traditions that bind a family’s history. These warm, emotional moments also create a natural opportunity to talk about the future—specifically, estate planning.

It may feel uncomfortable at first, but these conversations bring clarity, reduce uncertainty, and offer peace of mind for everyone involved. Approached gently, they can strengthen family connections rather than strain them.

Questions Adult Children Can Ask Their Parents

Adult children often want to understand their parents’ wishes so they can support them confidently when the time comes. These questions help open the door with empathy and respect:

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 may want reassurance that their children are prepared, both to support them and to manage their own futures. These questions encourage thoughtful preparation:

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?

Tips for Bringing Up the Conversation

These discussions don’t need to happen over the main meal or turn into a formal meeting. A quiet moment after dessert, a relaxed morning coffee, or even a short walk can create the perfect space. Keep the tone calm, curious, and supportive, emphasizing that the goal is clarity and care—not pressure.

Why Planning Ahead Matters

Estate planning isn’t just about documents. It’s about:

Control – choosing who will handle your finances, healthcare, and estate.

Clarity – ensuring loved ones aren’t left guessing your wishes.

Care – protecting children, dependents, or even pets.

Efficiency – avoiding unnecessary probate costs, taxes, or delays.

Legacy – passing down not just assets, but stories and values.

Framing estate planning as a gift can make these conversations easier. It’s an act of love—one that prevents confusion, legal disputes, and emotional strain later. Even a brief holiday discussion can set your family on a more secure and thoughtful path.

If you’re unsure where to begin, or want help navigating these conversations, consider reaching out to a trusted advisor. A little guidance now can make all the difference in the future.