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. More than half of families without a plan report disputes or conflict after a loved one’s passing. These numbers show why clarity is such a meaningful gift.

The holidays offer something we rarely get the rest of the year — multiple generations gathered around the same table. Between shared meals, family stories, and warm traditions, these moments remind us how deeply connected we are. They also create a natural, gentle opportunity to talk about the future, including estate planning.

It’s normal for these conversations to feel uncomfortable at first, but approaching them with empathy, curiosity, and calmness can bring tremendous peace of mind. Estate planning isn’t about money — it’s about control, clarity, care, efficiency, and legacy.

Questions Adult Children Can Ask Their Parents

These questions help avoid confusion later and ensure loved ones know how to support each other when it matters most.

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

These prompts encourage the next generation to think ahead and consider how they’d handle future responsibilities.

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?

Making the Conversation Comfortable

These discussions don’t need to happen over the main holiday meal or in a formal setting. A quiet moment after dinner, a relaxed walk around the neighborhood, or time spent wrapping up the evening can make the conversation feel more natural and less intimidating.

Why These Conversations Matter

For adult children, these talks help prevent painful surprises and ensure they know what to do if urgent decisions arise. For parents, they encourage younger generations to prepare for their own futures and understand the values and traditions they want to carry forward.

Framing estate planning as an act of love helps ease the tension — it’s a way of protecting the people you care about most and relieving them of potential burdens later on.

If you’re unsure how to begin or want support navigating these conversations, consider reaching out to a trusted advisor. A little clarity now can spare a great deal of confusion, stress, and emotional hardship down the road.