The Most Important Question You’re Probably Not Asking: Do You Have a Will?

Why hard conversations now can spare you stress, confusion, and regret later

When it comes to death, we often think about what we’ll leave behind, but not enough about the people we’ll leave behind to figure it all out. While wills are meant to provide clarity, they only work if someone knows they exist and where to find them.

That’s why asking about a will before someone dies isn’t uncomfortable or inappropriate. It’s responsible, respectful, and one of the most loving things you can do.

Why We Avoid These Conversations and Why We Shouldn’t

Talking about death is hard. Whether it’s superstition, discomfort, or not wanting to seem greedy, many families avoid these topics until it’s too late.

But here’s the reality: not asking can be more harmful than asking. If a will exists but no one knows where to find it, the court may treat the estate as if there is no will at all. That can mean assets get distributed according to state law, not the person’s wishes.

Having the conversation now avoids:

• Rummaging through drawers or computer hard drives in a panic

• Accidentally overlooking important documents or insurance policies

• Family disagreements or suspicion about someone “hiding” information

Still not sure how to bring it up? This guide can help you talk to aging parents about legacy and end-of-life planning without it feeling awkward or forced.

What to Ask When Someone Has a Will

If your loved one already has a will, your next step is to gather basic but essential information. Here’s what to ask:

• Where is the original copy stored? (Safe deposit box? Filing cabinet? With a lawyer?)

• Is there a digital copy and how do I access it?

• Who else knows where to find it?

• Was it prepared by an attorney or created online?

• Are there other documents, like a trust or power of attorney, I should know about?

Knowing these answers can dramatically reduce stress during a time of grief. It ensures your loved one’s wishes are honored and gives them peace of mind that someone will carry out what matters most to them.

What If They Haven’t Created a Will Yet?

If the answer is “no,” that’s okay. Don’t push or panic. The goal isn’t to pressure, but to support. You can offer gentle encouragement by saying:

“I know it’s not fun to think about, but I’d feel so much better knowing your wishes are written down. If you ever want help getting started, I’m happy to look into it with you.”

Instead of diving into legal jargon or overwhelming details, point them to something simple and approachable. Our Estate Planning Essentials Checklist is a great place to begin—it walks through what to consider, what documents to gather, and how to take the first step without feeling lost.

Planning doesn’t have to be daunting. It just has to begin.

These Conversations Create Clarity, Not Crisis

At End of an Era, we believe that legacy isn’t just what you leave behind. It’s the clarity and peace you create for those you love. Asking about a will is one of the simplest, kindest ways to do just that.

Don’t wait for the “right time.” The right time is while you still can.

Next Steps You Can Take Today

• Start the conversation: “Do you have a will?

• Use our Estate Planning Essentials Checklist to guide what to ask and what to prepare

• Organize your own documents as a model for others

• Bookmark or share this blog with someone you love

It’s not about preparing for the worst. It’s about making life easier for the people you care about most.