How to Talk to a Loved One About Planning Their Estate

Talking about estate planning can feel tough. It’s about what happens to someone’s money, house, or stuff after they pass away. No one likes thinking about that, especially not your loved ones. But it’s a conversation worth having. It can save a lot of stress later. Here’s how to bring it up in a kind, simple way that doesn’t put anyone off.

Start with Love, Not Law

Don’t jump in with big words like “will” or “trust.” That can sound cold or pushy. Instead, start by showing you care. Say something like, “I want to make sure everything goes the way you’d want it to someday.” Or maybe, “I’d feel better knowing you’re taken care of, no matter what.” This keeps it about them, not some legal chore.

Pick the Right Moment

Timing matters. Don’t bring this up at a noisy family dinner or when they’re already stressed. Find a quiet time—like over coffee or during a relaxed walk. You want them to feel calm, not cornered. If they’re having a bad day, wait. A good mood makes a big difference.

Keep It Simple

Estate planning sounds fancy, but it’s just figuring out who gets what and how. You could say, “Have you ever thought about who you’d want to take care of your house or your favorite things?” Or, “What if something happens—how can I help make sure it’s all handled your way?” Break it down so it’s not overwhelming. You’re not asking them to write a whole plan right then—just to think about it.

Share a Story

Sometimes a real-life example helps. Maybe you know someone who didn’t plan, and their family argued over stuff after they were gone. Or someone who did plan, and it made everything easier. Keep it light, like, “I heard about this guy who didn’t say anything, and his kids fought over his old car. Funny how a little planning could’ve stopped that.”

Offer to Help, Not Control

No one likes being told what to do. So don’t act like you’re the boss. Say, “I’d be happy to help you figure this out if you want—maybe we could talk to someone together?” That “someone” could be a lawyer or financial advisor, but you don’t have to name-drop them yet. The point is to be a teammate, not a know-it-all.

Expect Pushback

Some people might say, “I’m not old!” or “Why talk about that now?” That’s okay. Don’t argue. Just smile and say, “Fair enough—I just want you to have peace of mind.” Then drop it for a while. You can try again later. Pushing too hard makes it worse.

Suggest Small Steps

If they’re open to it, suggest something easy to start with. Like writing down a list of what they own—house, bank accounts, jewelry—and who they’d want to have it. Or picking one person they trust to handle things. Little steps feel less scary than a big “estate plan.”

Why It Matters

Here’s the heart of it: planning isn’t about dying. It’s about making sure their wishes come true and their family isn’t left confused or fighting. Tell them that. Say, “This is about you being in charge, even if you’re not here. And it’d help me feel less worried too.”

Wrap It Up with Care

End the chat on a good note. Thank them for listening, and maybe switch to a happier topic. Leave them feeling loved, not pressured.

Talking about estate planning doesn’t have to be a big deal. With patience and kindness, you can help your loved one take a step toward something smart—and keep your relationship strong too.