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 and stretch on for months or years. Even more striking, 58% of families without an estate plan report disputes or conflicts after a loved one’s passing. These numbers highlight just how important it is to plan ahead — not just for finances, but for family harmony.

The holidays offer something rare: multiple generations gathered under one roof, sharing meals, memories, and traditions that have shaped your family for years. Between the laughter, familiar dishes, and stories retold each season, there’s a natural sense of connection. These warm moments can also create the right environment to gently discuss the future — including estate planning.

While the topic can feel uncomfortable, framing it around care, clarity, and legacy makes the conversation easier. Estate planning isn’t only about distributing assets. It’s about ensuring loved ones know your wishes, avoiding unnecessary stress, and preserving the traditions and values that hold your family together.

Questions Adult Children Can Ask Their Parents

Adult children often want to help but aren’t sure where to begin. These questions open the door with empathy and curiosity:

Do you have an up-to-date will or trust in place?
Helps ensure that everyone understands your parents’ current wishes and that the proper legal documents are in place.

Who have you chosen to make financial and medical decisions if you’re unable to?
Knowing this ahead of time prevents confusion during emergencies.

Have you shared your wishes for medical care and end-of-life planning?
Encourages clarity around deeply personal decisions.

If something happened tomorrow, would we know where to find your important documents and accounts?
This prepares family members to act quickly and responsibly when needed.

Are there heirlooms or traditions you’d like us to know the stories behind?
Helps preserve family history that might otherwise be lost.

Do you feel confident that the people you’ve chosen to handle your affairs are still the right ones?
Ensures that your parents’ choices still reflect their current relationships and needs.

Questions Parents Can Ask Their Adult Children

Parents can also encourage thoughtful planning for the next generation. These questions foster responsibility and open communication:

Do you know where to find my important documents in case of an emergency?
Provides peace of mind that loved ones can help if needed.

Have you considered creating your own will or an estate plan?
Encourages younger adults to protect their families and assets.

If you received an inheritance tomorrow, would you know what to do with it — or who to turn to for help?
Prompts financial preparedness and responsible planning.

Are there family keepsakes or traditions you’d be heartbroken not to have carried forward?
Helps identify what matters most emotionally — not just financially.

If you had to step in to help us — financially or medically — what support would you need?
Builds understanding about capabilities and expectations.

How to Bring Up These Conversations

There’s no need to turn the holiday gathering into a formal meeting. These conversations often happen best in quiet, unhurried moments — a walk around the neighborhood, time together in the kitchen, or a relaxed chat after the meal. The goal isn’t to cover everything at once, but simply to open the door with compassion and understanding.

The Gift of Planning Ahead

Estate planning offers control, clarity, care, efficiency, and legacy. It keeps families aligned, reduces the chance of conflict, and ensures decisions reflect your true wishes. When framed as a gift of love and clarity, it becomes much easier to talk about — even during the holidays.

If you’re unsure where to begin or want guidance in navigating these conversations, reaching out to a trusted advisor can help make the process more comfortable and supportive. A little planning now can bring peace of mind for years to come.