How to Start an Estate Planning Conversation (Without It Getting Awkward)
Have you ever tried to talk about estate planning with a spouse, parent, or adult child who wants absolutely nothing to do with it? I certainly have people like that in my family, and I’ve heard from many others who do, too.
On the flip side, perhaps you’re the one who doesn’t want to talk about it.
I get it. It’s not easy to bring up something that reminds us of losing someone we love – or facing our own mortality. Even though estate planning is meant to protect and support the people we care about most, it can still feel uncomfortable.
Whether you’re trying to share the plans you’ve made or encourage someone else to get theirs in place, it can definitely be a tough topic to raise. And even more so, it’s hard to know when and how to bring it up without it feeling weird.
That’s why the way you frame the conversation makes all the difference. Try to keep the focus off dying and on caring – putting things in place so your loved ones aren’t left with chaos, confusion, or family conflict during an already difficult time.
With a little preparation and the right mindset, these conversations can actually be thoughtful, caring, and even empowering. And yes, maybe even a lot less awkward.
I’m not an expert on having these conversations, but I follow others who are. Here are a few of my favorite ideas from them on how to start:
1️⃣ When you’re trying to get clarity on a specific question or concern
“I was reading this article/listening to an interview/saw this Facebook post…and it made me realize I’m not entirely clear on what your wishes would be if you get really sick.”
“Dad, Alex and I were just talking about what matters most to us if we ever face a serious illness. Have you thought about that?”
“I remember you once said that when it comes to receiving medical treatment, you want the ‘whole enchilada.’ What exactly did you mean by that?”
“Dad, I know you and I talked about what quality of life means to you - has anything changed given everything happening right now?”
2️⃣When you want to share your own planning first
“Bob and I just had this conversation, and I wanted to let you know he’s my decision maker if I can’t speak for myself. Do you have a decision maker?”
“Remember that movie we watched the other day? That scene made me think about how important it is to share what matters most to me.”
“I was reviewing the advance directive we talked about last year and realized I have a few updates – I wanted to make sure you knew.”
3️⃣ When you’re focusing on them, not you
“Mom, I know you don’t love talking about this, but I want to be sure I can honor what’s important to you.”
“I think I’ve heard you say XYZ - is that right? Anything else you’d want me to know?”
“I’ve been thinking about how much I want to make things simple for everyone in case something ever happens. Can we talk about how we’d handle things as a family?”
“I just updated my health care directive and realized we’ve never talked about what each of us would want in a medical emergency. Would you be open to sharing your thoughts too?”
4️⃣ When timing and setting matter
A casual coffee or even a walk together can be a great time for an open, relaxed chat.
If you’re gathering for the holidays, using a few of these ice-breakers for a family conversation can take the focus off just one person. It might be the perfect time to talk about family traditions, caregiving preferences, or even charitable giving.
Once everyone’s comfortable talking about those values, it’s a natural step to discuss how legal tools - like wills, trusts, or powers of attorney - can help protect them.
Helpful Resources
If you’d like to learn more on this topic, I highly recommend checking out The Conversation Project. They offer many free downloadable guides to help you think through your health care wishes and end-of life decisions – and how to talk about them.
They also have some great videos (some surprisingly funny!) that show how these conversations can be more natural than you might think. 👉 Check them out here.
You might also like their related blog post: 11 ideas for when someone is having a hard time talking about their wishes for health care.
Starting the conversation is just the beginning. If you or your loved ones want a little clarity before meeting with an attorney, I offer complimentary 15-minute consultations – just enough time to get direction, feel more confident, and save time (and money) when you take the next step. Scheduling it is easy - connect with me here.
You can also check out my book, A Very Simple Estate Planning Guide, which walks you through each step in plain language — the same way I teach it in my workshops and community presentations.
Bottom line:
Estate planning isn’t really about death — it’s about making life easier (and often happier) for the people you love most. With a little care and the right tools, these conversations can bring families closer, not drive them apart.
