Thanksgiving is just around the corner, and many of us are mentally preparing for the holidays and spending time with family.
Something you’re probably not preparing, though, is a list of questions to ask your parents before they die. (Uh, morbid! Why?)
We’re totally aware—death, money, and inheritance are some table topics that many families won’t touch with a ten-foot pole. With that said, please hear us out on why Thanksgiving is a great time to check in with your family about their affairs, and how to broach the subject in a way that isn’t totally cringey.
Thanksgiving: A Portal of Gratitude, Sentiment, and Tradition
Thanksgiving is the season of gratitude, and for many, family makes it to the top of that list. By bringing up estate planning in ways that honor gratitude and sentimentalism can show them that you care.
We’re asking you to consider this for a few key reasons:
Talking to your loved ones about estate planning is crucial.
Thanksgiving is one of the key family gatherings of the year.
Awkwardness and procrastination can prevent these conversations from happening, leaving everyone in the dark.
With the right framing, estate planning conversations can be meaningful…fun, even.
With the right approach, these conversations can be heartfelt and meaningful. The angle here is to find out if your loved ones have their affairs in order, and what memories, traditions, and legacies they wish to pass down. Here are some conversation starters that don’t totally suck. Choose a topic that feels like the best fit for your family dynamic, and customize the script as you see fit.
1. Start with Gratitude
The holiday spirit is all about giving thanks, so why not use that as a way to open the door? Try saying something like:
"You know, this year has made me really grateful for all of you, and it got me thinking about how important it is to make sure everyone is taken care of, no matter what happens."
This approach sets a positive tone and reminds your family that estate planning is an act of love and foresight, ensuring that they’re protected and looked after in the future.
2. Tell a Family Story
A shared memory or family anecdote can provide a natural transition into more thoughtful conversation. For example:
"Do you remember when Grandma used to talk about the things she wanted to pass down to each of us? It’s a good reminder that we should all think about how we want to keep our family traditions and values alive."
By reflecting on past family traditions, you can guide the conversation toward the legacy you want to leave behind and the importance of planning ahead.
3. Bring Humor to the Table
Lightening the mood with a bit of humor can make estate planning feel less intimidating. For example:
"Well, I’ve decided who’s going to inherit my secret pie recipe—just kidding, but seriously, it got me thinking we should probably talk about making sure everything’s in order down the road."
This kind of playful opener can turn what might normally be a serious topic into something more approachable, helping your family feel at ease.
4. Frame It as a Gift
Sometimes, people view estate planning as uncomfortable because they associate it with unpleasant topics like illness or death. Reframe it by focusing on the benefits:
"One thing I want to give all of you is peace of mind, knowing that everything will be easy to manage when the time comes. Have you ever thought about how you want things handled for your own family?"
This shifts the perspective, showing that estate planning is a gift of clarity and security for your loved ones, rather than a burden.
5. Ask Open-Ended Questions
If you’re unsure how to begin, asking open-ended questions can spark a meaningful conversation naturally. Try something like:
"Has anyone thought about how they want to be remembered, or what traditions we should make sure to keep alive for future generations?"
This type of question encourages your family members to share their thoughts without feeling pressured, and it allows everyone to reflect on the values that matter most.
6. Bring Up Recent Events
Sometimes current events can offer a gentle entry into more serious discussions. For instance:
"Did you hear about [celebrity or news story] and how they didn’t have a plan in place? It made me realize how important it is to make sure everything’s organized ahead of time."
Using a story in the news or social trends can help normalize the conversation and make it less daunting.
Gain Insights to Family Values, Memories, and Traditions
Questions to ask your parents before they die don’t have to be uncomfortable or morbid.
After reviewing these conversation starters, we hope you gained some clarity on how to facilitate some heartfelt conversations with your loved ones. They can help show them that you care, and encourage the sharing of important family values and traditions.
Just keep these tips in mind! If you don’t find the right opportunity to bring it up…there’s always the next holiday.
Ready to get an estate plan of your own? Walk the talk! Explore the benefits of a Will Plan and Trust Plan, so that you can share your experiences with your loved ones this holiday season. Here’s the conversation starter: “I just made my estate plan through Trust & Will. I did it all online and was surprised at how easy and affordable it was! I’m happy to talk more if anyone wants to do the same!”
At Trust & Will, we’re here to help keep things simple. You can create a fully customizable, state-specific estate plan from the comfort of your own home in just 20 minutes. Take our free quiz to see where you should get started, or compare our different estate planning and settlement options today!
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Trust & Will is an online service providing legal forms and information. We are not a law firm and we do not provide legal advice.
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