How to Talk to a Loved One About Creating a Will or Trust

Why People Avoid These Conversations

Before we get into the how, it helps to understand the why. Avoiding conversations about wills and trusts is common. People might resist because:

• It feels like tempting fate.

  Talking about death can feel superstitious or like inviting something bad to happen.

• They think it’s only for “rich people.”

  Some assume estate planning is only necessary if you have significant assets.

• They don’t know where to start.

  The process can feel overwhelming or too “legal.”

• They’re afraid of upsetting others.

  Some worry that making a will means picking favorites or creating family drama.

• They just don’t want to think about it.

  For many, avoidance is easier than facing mortality or making hard decisions.

Acknowledging these blocks can help you bring more empathy into your approach.

When You’ve Tried and It Didn’t Go Well

Maybe you’ve already brought it up—and hit a wall. Maybe your loved one changed the subject, got defensive, or said, “I don’t need that yet.” Don’t be discouraged.

Resistance doesn’t mean you did something wrong. It just means they weren’t ready. The key is to shift from pushing a task to offering support—and trying again with fresh language.

How to Start the Conversation (Gently)

Here are a few ways to open the door:

• Lead with your own story. “I’ve been working on my own will lately, and it made me realize how helpful it would be to know your wishes too.”

• Frame it as an act of care. “I know it’s uncomfortable to talk about, but I want to make sure we honor your choices if something ever happened.”

• Acknowledge the discomfort. “This isn’t easy to talk about, but I’d rather we have a hard conversation now than deal with uncertainty later.”

• Use a life event as an opener. “After what happened with [friend/family member], I’ve been thinking about how important it is to have things in writing.”

Remember, the goal isn’t to have the entire conversation in one go. It’s to open a window and invite reflection.

What to Say If They Still Resist

If they respond with something like...

• “I’m not old enough for that.” “That’s fair—and I hope you’re around for a long time. But having a plan is helpful at any age, especially if something unexpected happens.”

• “I don’t have anything to leave behind.” “Even if it’s not about money, it’s about making sure the right people can help if something happens—and knowing your wishes are followed.”

• “I’ll get to it later.” “I totally understand. If it helps, I can even support you with the research or paperwork.”

Ways You Can Offer Support

Your loved one may be more open if they feel like they won’t have to do it all alone. You can offer to:

• Research simple will and trust options online.

• Find an estate planning attorney or notary.

• Help them gather documents or make a list of assets.

• Sit with them while they fill out a basic will template.

• Talk through who they trust for decision-making roles (like executor or healthcare proxy).

You don’t have to take over—but showing you’re willing to help can ease the weight.

What Matters Most

This isn’t just about legal documents. It’s about helping someone you love feel seen, supported, and in control of their future. It’s also about reducing future stress and confusion for everyone else involved—especially during times that are already emotional or difficult.

Whether they act on it now or later, you’re planting a seed. That’s meaningful.

If You Need Help, We're Here

At Helpful, we support families through these kinds of conversations every day. We can help you:

• Understand the difference between a will and a trust

• Find templates or referrals based on your state

• Talk through tough family dynamics or emotional blocks

You don’t have to navigate this alone.