Can we talk about your will? A guide to conversations with parents.
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Does the thought of talking with your parents about wills, advanced directives, living arrangements, and finances excite you? No? Me neither. Elder estate planning is not at the top of my list of fun topics. These conversations can feel awkward, intrusive, and skirt the edge of disrespectful if not approached with care (as in, “Hey Mom, you’re not looking too hot. By the way, have you made a will yet?”). But now, as my dad battles stage 4 cancer and my mom struggles with mobility and early cognitive decline, I keep thinking: I wish we’d talked sooner.
My younger brother and I are now mapping out the next few months to fly across the country, helping our parents sell their house and prepare to move out West, closer to where both of our families have settled. I’ve been writing scripts to help make these essential conversations easier to navigate. Because even though we can’t go back and change the timing of this wildly stressful transition, we can learn from it and make the road ahead a little smoother.
I still remember my mom casually telling me where her will was, “just in case something happened with the plane”, as they headed to the airport. That was the first time we’d ever talked about it. It doesn’t have to be that way for you.
You can start the conversation now. And here are some scripts to help you do it.
The Scripts
1. Wills: “Do You Have One—and Is It Up to Date?”
It might feel awkward to bring up, but understanding if a will exists (and where it’s kept) is a basic form of preparedness.
To start, try saying:
“Hey, can we talk about something that’s been on my mind? I know it’s not the most fun topic, but I just want to make sure we’re all prepared, just in case. Do you and Dad have a will?
I’m not asking to know what’s in it or who gets what. I just want to know where it is and that it reflects what you both want. The last thing I’d want is confusion or stress for any of us if something unexpected happens.”
If the answer is yes, try saying:
“Okay, that’s great. Is it the most recent version, or has anything changed since you last updated it?
Can you tell me where you keep the signed copy, or share your lawyer’s contact information, just so I know where to find it if ever needed? I will not access the will unless it’s time (and trust me, I hope that is very far in the future)!”
If the answer is no, try saying:
“Thanks for being honest. I’d like to help you find a local attorney or an online resource so you can get started. Even just drafting something simple can really help avoid confusion later.
I can do some research and share a few options with you. How does that sound?”
If the answer is vague, try saying:
“That’s ok. This is not an easy topic and even I don’t really want to talk about it. But we need to be a team and support each other by having this ironed out. Do you want me to check in with you next week instead?”
2. Advanced Directives: “Let’s Make Sure Your Wishes Are Known”
An advance directive (or healthcare power of attorney) ensures your parent’s voice is heard, even if they can’t speak for themselves.
Try saying:
“Have you ever set up something like an advanced directive or healthcare power of attorney?
I know it can feel a little uncomfortable to think about, but honestly, it would give me peace of mind to know what your wishes are in case there’s ever a medical situation where you can’t speak for yourself.
You deserve to have your voice heard, no matter what. If you want help filling one out or updating it, I’m happy to look into it with you.”
If the answer is yes, try saying:
“That’s good to hear!
Do you remember where you keep a copy, and who has it on file? Sometimes hospitals want to see it right away.
If you’d like, we can make sure your doctor and the hospital have it too, so there’s no delay if something ever comes up.”
If the answer is no, try saying:
“I understand, it’s not the easiest thing to think about.
Would you be open to talking through what you’d want, or even writing down a few preferences so we have them in case of an emergency?
I can help find a simple form or set up time with a professional to walk you through it.”
If the answer is vague, try saying:
“That’s okay. Maybe we can take a few minutes to look through your files together or call your doctor’s office to see if they have anything on record.”
3. Living Arrangements: “Where Would You Feel Most Comfortable Long-Term?”
The goal here isn’t to push them to move but it’s to understand their wishes while they’re still fully able to make decisions.
Try saying:
“I’ve been thinking ahead a bit and I wanted to ask how you see the future in terms of where you’d want to live.
Do you imagine staying in this house long-term? Or would you ever consider something smaller or more manageable? I’m not trying to push for any change. I just want to understand what you want so I can support that when the time comes.”
If they want to stay, try saying:
“Is there anything you’d want to modify here to make it easier over time, like grab bars, a stair lift, or other adjustments?
I’d be glad to help look into those options whenever you’re ready.”
If they want to consider downsizing, try saying:
Would you want to start exploring some options together, like looking at communities or smaller places?
We don’t have to decide anything now, but maybe gathering some information could help you feel clearer about what’s out there.”
If the answer is vague, try saying:
“I get that this might feel far off, but having the conversation now means we can make choices that feel right to you, instead of scrambling if something unexpected happens.”
4. Finances: “Are You Feeling Okay About Money?”
Money is personal and can be emotional but it’s also just math homework that needs to get done.
Try saying:
“I’ve been thinking about how everything is getting more expensive and I want to check in. Do you feel comfortable with where things stand in terms of retirement savings, income, and bills? Is there anything you’re worried about?
If the answer is yes, try saying:
“That’s wonderful. If anything changes or you start to feel uneasy, please tell me. I’m always here to help you figure things out or look into resources if you need them.”
If the answer is no, try saying:
“Thank you for trusting me enough to say that. Can we sit down together and look at everything to see if we can find some solutions?
We could also consider talking with a financial advisor to see what options are available.”
If the answer is vague, try saying:
“I get that, it’s easy to lose track when things change over time. Can I help you gather statements and bills so we have a clearer picture? No pressure. We can just start with the basics.”
Start Small, But Start Soon
There you have it! You can, of course, customize these scripts to fit your own communication style. My family has always handled tough conversations with a mix of laughter and a touch of dark humor. Do what feels right for you.
But sometimes, when you’re nervous it really helps to stick to the script. This way you’re not fumbling for the right words when the moment comes. (Although, knowing my family, they’d probably joke, “And that’s how Mom went – choked on her words. We could have seen that coming!”)
I challenge you to have at least one of these conversations with one (or more) of your parents, parents-in-law, or step-parents in the next month. Let me know how it goes in the comments!
