If you have aging parents, you may have started to get that gnawing feeling in the back of your mind. Are they set up financially? Should Mom still be driving? Am I the backup plan? Am I the ONLY plan?
Life is busy, so it isn’t always easy to keep tabs on how your parents are doing, whether they’re across the island or over on the mainland. That’s why holiday visits can be such a critical time, not just for noting if Dad’s moving a little slower than usual, but for bringing up the topic of your parents’ estate plan. You don’t want to wait until something happens to figure out what comes next.
However, knowing what to do is completely separate from knowing how to do it. So let’s talk about how to discuss estate planning with your parents.
Step 1: Repeat After Me: This is Necessary and Good
Listen, this is awkward! It’s uncomfortable to be the one who follows up “Pass the potatoes, please” with “Hey Mom, who gets the house when you die?” I get it, but the alternative is often even harder to deal with. Many families end up in painful, drawn-out disputes because nobody wants to be the one to bring it up first. Breaking the ice on family estate planning is a healthy step toward open communication and prioritized relationships.
The holiday season also provides the perfect opportunity to do so. For many women, this is one of the only times they and their parents are actually in the same room, at the same table, without a screen between them. That makes it a rare opportunity to open a door that’s easy to keep closed the rest of the year.
Step 2: Make a Plan
Don’t wait for the topic to come up organically between dinner and dessert. Squeezing in a heavy discussion while someone is packing for a flight or after the table has shifted to politics is a recipe for tension. Instead, look for low-pressure side-by-side moments that feel more like a conversation than a board meeting:
- Clearing dishes in the kitchen
- Taking a morning walk
- Catching a quiet cup of coffee before the rest of the house wakes up
If you have siblings, loop them in first and make sure they understand that the goal is open communication, not pressure. It also helps to decide ahead of time what you actually want to know. You don’t need account balances or dollar figures; that’s not the point, and leading with money is one of the fastest ways to put everyone on the defensive. What you’re really after is just a broad idea of what to expect:
- Is there an up-to-date will or trust?
- Has someone been named to make healthcare decisions if your parents can’t speak for themselves?
- Is there a financial agent in place?
- When was any of it last reviewed? A plan created twenty years ago might inadvertently leave out new partners or grandkids.
Step 3: Take the Plunge
When it’s time to actually say something, keep the tone collaborative and curious instead of clinical. “What do you hope your life looks like as you get older?” is a much more inviting conversation than “Who do you expect will take care of you?” Position yourself as someone who wants to help carry the load, not someone auditing their decisions.
Now comes the hard part: let them answer at their own pace. Some parents will be relieved someone finally brought it up and will open up right away. Others will need a few passes at the topic before they’re ready to talk specifics. The most important thing is to start the conversation while keeping it grounded in compassion. You can always follow up with “I’d love to make sure I can support you in the ways you want. Can we make some time to continue our talk about your estate plan?” Make it a breakfast date, or ask if they’re comfortable with you joining the next meeting with their financial advisor or estate attorney.
You Don’t Have to Wing It
This is definitely more work than just bringing a side. But if finding the right words, knowing what to ask, and figuring out how to bring your siblings into it without starting a family feud all sounds overwhelming, I’ve got a guide for that. The Sibling Survival Guide to Aging Parents: How to Protect Your Family’s Peace (and Assets) is full of plain-English scripts for opening the conversation with your parents and siblings, along with a simple way to start organizing the essentials once the conversation gets going.
You don’t have to solve everything over dessert. You just have to open the door so that the next time that gnawing feeling shows up, you already know the answer.
