Like most people, talking about estate planning with your family probably isn’t something you’re looking forward to. It brings up tough topics—aging, money, death—which aren’t light dinner conversations. However, knowing how to talk to your family about estate planning is one of the most important things you can do to avoid confusion and conflict in the future.
Most people I speak with say the same thing: they don’t want to leave a mess behind. They want to ensure their affairs are in order so their family can manage without stress or second-guessing. If this is your goal, ideally, you want to complete your estate plan before something happens. It’s best to take time now to make sure your family won’t be left wondering what you would’ve wanted.
So, how do you start that conversation in a way that doesn’t feel like a lecture—or worse, a confrontation? Let’s walk through it.
Why It Matters
You first want to understand why estate planning is important and communicate the importance to your loved ones. Sadly, my office has spoken to families where a loved one passed away without a will or trust. Often, families weren’t sure about who was supposed to take charge and what to do next. Sometimes, disagreements about what to do with the loved ones’ bank account, house, and other items would arise.
What should have been a time to grieve often turns into months of stress and tension among family members.
These are precisely the kinds of situations we want to help families avoid. When everything is spelled out in a will or trust— such as who’s in charge and what goes where—your loved ones don’t have to second-guess your wishes or scramble to figure things out during an already emotional time.
When Should You Bring It Up?
Spring is when family members pop in more often—someone’s birthday, an early barbecue, or just a quick visit because the weather’s finally nice. And while no one wants to sit down and talk about legal issues, sometimes these informal gatherings offer a great opportunity to discuss your wishes.
You don’t have to make it a big deal. You could say something like, “Hey, I’ve been meaning to talk about some of the planning I’ve been doing—nothing urgent, just stuff I want you to know in case something ever happens.”
It may feel awkward. That’s okay. The point is to start the conversation—not solve everything at once.
Lead With the Why
If you jump straight into legal or financial details, you might lose people quickly. Instead, explain what motivated you to start planning in the first place.
Maybe you’ve seen what happens when someone passes away without a plan. Maybe you want to make sure your kids aren’t burdened later. Whatever your reason, share it. You don’t want your family to get stuck later trying to figure out what you would’ve wanted—or worse, arguing over it.
Give People Space to React
Not everyone will be ready to have this conversation. Some might feel uncomfortable, and others may brush it off. That’s okay. You don’t have to push if they’re not ready to talk about it. Just let them know this is something you want to come back to—and that you’ll be available when they’re ready. These things usually take more than one discussion anyway.
Keep It Simple
Don’t worry about explaining every detail upfront. Focus on the basics:
- Who should make decisions if you can’t?
- What happens to your home and savings?
- Where can your essential documents be found?
Taking the Next Step
Once you’ve laid the foundation and after speaking with the key people involved in your plan, it’s a great time to move forward with setting up your will, trust, and other estate planning tools. If you already have an estate plan, it may need updating if your circumstances have changed. Meeting with an estate planning attorney can guide you through this process.
If you’re in New York, we’re here to help. When you’re ready to take the next step, book a Discovery Call or a Life, Family, and Legacy Strategy Session with us. We’d love to help you create a customized plan that reflects your family, values, and goals.
