Holiday Conversations That Matter: Estate Planning Questions to Ask Around the Table

The holidays bring families together and provide a rare chance for meaningful conversations about the future. The holidays are also a special time—filled with laughter, traditions, and togetherness. But beyond the festive meals and family stories, they also offer something else rare: uninterrupted time with the people who matter most. That makes it the perfect moment to talk about the future—specifically, your family’s estate plans, wishes, and legacy.

Estate planning conversations can feel uncomfortable at first, but they don’t have to be heavy or somber. These discussions are about clarity, connection, and care—ensuring that every family member knows how to honor one another’s wishes and keep the family’s values alive.

At Elder Legal Solutions LLP in Fort Lauderdale, Florida, we encourage families to use the holidays as a gentle opportunity to begin these important conversations. Whether you’re a parent wanting to share your plans or an adult child hoping to understand your parents’ wishes, here are some thoughtful questions that can open the door.

Kids Can Ask Parents:

• Do you have an up-to-date will or trust?
  Laws change, and so do family circumstances. Confirming that estate planning documents are current helps ensure your parents’ wishes will be carried out smoothly.

• Who will make decisions for you if you’re unable to?
  It’s essential to know who holds power of attorney or healthcare proxy status so that decisions can be made confidently if needed.

• Have you shared your medical and end-of-life wishes?
  Discussing medical directives, preferences for care, or end-of-life wishes ensures loved ones aren’t left guessing during emotional times.

• Would we know where to find your important documents?
  Even the best estate plan can’t help if no one knows where it is. This question encourages organization and transparency.

• Are there family heirlooms or stories you want us to carry forward?
  Estate planning isn’t just about finances—it’s about legacy. This question invites meaningful stories and the preservation of family traditions.

• Do you still feel confident in the people you’ve chosen to handle your affairs?
  Executors, trustees, and agents should be reviewed from time to time to make sure they still reflect your parents’ current wishes and relationships.

Parents Can Ask Kids:

• Do you know where to find my documents in an emergency?
  If something unexpected happens, your children should know how to locate wills, trusts, and key contacts.

• Have you started your own estate plan?
  Estate planning isn’t only for older generations. Encouraging your children to protect their families and assets is a wonderful gift.

• If you received an inheritance, would you know what to do?
  This opens a conversation about financial literacy, responsible stewardship, and the family’s values around money.

• What family traditions mean the most to you?
  Passing down values and stories is just as important as passing down wealth. This question invites reflection and connection.

• If you needed to help us financially or medically, what support would you need?
  Honest dialogue about roles and limitations ensures that future caregiving decisions are made thoughtfully.

Bringing It All Together

These questions aren’t just about logistics—they’re about love. When families communicate openly, misunderstandings are avoided, and everyone feels more secure about the future. Whether you discuss them over dessert or during a quiet moment together, even small conversations can make a big difference.

At Elder Legal Solutions LLP, we help Fort Lauderdale families create estate plans that reflect their values, protect their assets, and preserve harmony for generations to come. Thoughtful planning and honest communication go hand in hand—and the holidays are the perfect time to start.

If you’d like guidance on updating your will, establishing a trust, or reviewing your family’s estate plan, our team is here to help. You can reach Elder Legal Solutions LLP at (561) 814-8387 to schedule a consultation.