Essential Questions to Ask Your Parents This Holiday Season

The holidays are a time for connection, reflection, and family traditions. They’re also a rare opportunity to have meaningful conversations with loved ones about their wishes for the future. While these topics can feel uncomfortable, asking the right questions now can prevent confusion, conflict, and heartache later.

Here are three essential questions to ask your parents this holiday season:

1. What do you want your end of life to look like if you become seriously ill?

Why It’s Important: This question goes far beyond life support or medical interventions. It’s about understanding what matters most to your parents in their final days—whether that means being surrounded by family, remaining in their home, or making specific decisions about when to end life-sustaining treatment.

How to Approach It: Lead with empathy and curiosity.“I want to make sure I honor your wishes. What would be most important to you if you became seriously ill?”

2. What do you hope any money you leave us will do for us?

Why It’s Important: Inheritance can be a sensitive subject, but understanding your parents’ intentions allows you to make choices that reflect their values. Ask what they want the money to accomplish—and what they worry could go wrong.

How to Approach It: Keep the tone open and caring.“What impact would you love for your money to have on our lives? Is there anything you’d hate to see happen with it?”

3. If you became incapacitated, would you want to stay at home or go to a nursing home?

Why It’s Important: Deciding between in-home care and a facility can be emotionally and financially overwhelming. Knowing your parents’ preferences now helps you plan realistically and respectfully.

How to Approach It: Be clear and compassionate.“If you couldn’t care for yourself, would you prefer to stay at home or consider a nursing home? What kind of care would help you feel safe and comfortable?”

Planning for the Future Is About More Than Paperwork

These conversations aren’t always easy, but they’re necessary. Estate planning isn’t just about signing documents—it’s about truly understanding your loved ones’ wishes and ensuring they feel protected. This holiday season, start the conversations that bring peace of mind to your entire family.

We Can Help

We help families create thoughtful, comprehensive estate plans every single day. Start by booking a Peace of Mind Planning Session. We’ll answer your questions, review your options, and outline your next steps if we decide we’re a good fit.

The session is normally $450—but mention this article and we’ll waive the fee.

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