3 Estate Planning Conversations Every Family Should Have

You’ve been meaning to bring it up, but it never feels like the right time.

Over dinner. In the car. Just before a vacation. You’ve been trying to find the right moment to say something like, “We should probably discuss what would happen if….” but it always feels too dark.

Estate planning is one of those topics that feels too “heavy” for a regular conversation. It can feel awkward to bring it up, and you don’t want to sound morbid or make anyone uncomfortable. But you do want to make sure your family is protected, ideally without stirring up a family debate.

Here’s the good news: After many years as an estate planning attorney, I can confidently say that it’s very possible to have these conversations in a way that feels grounded, practical, and even like a huge relief.

In this article, we’ll talk about the 3 estate planning conversations every family should have, why they matter, and how to bring them up.

Why we avoid estate planning conversations

Most people avoid the subject of estate planning—not because they don’t care, but because they care too much. It’s an emotional, uncertain process, and it forces us to think about the one thing most of us are careful not to dwell on: what happens after we’re gone.

Add in the family dynamics (old wounds, conflicting opinions, or an unspoken “we don’t talk about that stuff” policy), and it’s no wonder estate planning usually ends up in the someday pile.

Here’s the problem I hope you never have to learn the hard way: Having the conversation is far less painful than avoiding it.

And the earlier you start, the calmer and cleaner those conversations tend to be.

Conversation #1: With your spouse

If you’re married or partnered, this is the foundation for every other conversation about your estate plan. When you create a plan together, it becomes about more than who gets what. It’s about protecting what you both value most.

Here are a few questions to guide your conversation:

Who do we want to protect first and foremost? (Kids, parents, pets?)
What do we want life to look like for each other and our kids, if one or both of us is gone?
Are there family heirlooms, traditions, or causes that matter deeply to us?
Who do we trust to make our medical or financial decisions if we can’t?

You don’t have to decide everything in advance or solve it all in one sitting. Start small—take a walk, talk over coffee, or discuss before you meet with your attorney. The goal is simply to open the door and agree that you both want to make things easier for each other and your loved ones.

Conversation #2: With your parents

Talking to your parents about their mortality can feel like crossing into sensitive territory. But here’s what I’ve seen over and over again: most parents want to have this conversation. They just aren’t sure how to bring it up with you, either.

Here are a few ways to ease in:

Use shared experiences. Mention a friend or relative who went through a difficult probate situation and say, “I’d love to make sure we have a clear plan so we don’t go through that.”

Ask about their values, not just logistics. Questions might look like, “What’s most important to you?” or “Who would you most want to handle things if you couldn’t?”

Clarify what already exists. Asking whether they already have a will or a trust, where the documents are located, and when they were last updated helps ensure that someone knows where to find things after your parents pass away.
Offer help. Oftentimes, one spouse or partner is in charge of paying the bills and managing household accounts, while the other has little to no idea where to find those details. You might say, “Let’s all get a handle on what you own and what bills you pay so I can help if the need arises.”

Remember: you aren’t prying, you’re preventing confusion (and potentially conflict) later on.

If your parents don’t have an estate plan yet, this can be a great segue to encourage them to start the process, especially if they own property or have remarried.

Conversation #3: With your kids

If your children are young, this conversation is really for you and your spouse. You’ll want to decide together who would care for them and how their inheritance would be managed.

If your kids are older, the conversation shifts. You don’t need to disclose exact numbers or account details, but it helps to reveal enough so they know what exists and where to find it when the time comes.

What to cover with adult children:

Who will serve as executor or trustee (and why)
Where to find key documents, and how to access them
Your wishes for major assets like the family home or a business
Medical directives or living wills

If you have minor children who are old enough to understand, it’s helpful to tell them who will take care of them if anything happens to you.

The goal isn’t to overwhelm your kids, but to reassure them that you’ve already handled the hard stuff. When your kids know what to expect, they’re less likely to argue, stress, or make irreversible mistakes later on.

How clear communication makes estate planning easier

When I meet with couples to plan their estate, the ones who have already discussed their values and wishes are light-years ahead. They make decisions faster, feel more confident in their choices, and leave our planning meeting visibly relieved.

This doesn’t mean they make every decision ahead of time. Part of my job is to answer the questions that help couples decide, and these are big decisions that may take several conversations to finalize. But it helps to get started before you meet with an attorney, so at least you have some momentum before you put a plan on paper.

Estate planning is, at its core, about communication and clarity. A good plan puts everyone on the same page, in a way that’s easy to understand and act on.

Worried you’ll say the wrong thing?

I know it’s easier said than done, but try not to worry. I’ve seen hundreds of these conversations, and the hardest part is bringing it up in the first place. Once you do, everything else gets easier.

Ready to turn your talk into a plan? I can help. Click here to book a discovery call and get your questions answered.