When it comes to Real Estate, aging parents, and family changes like death and divorce, people know what they need to talk about. Most of the time though, the hardest part is knowing how to start the conversation. How do you bring up a topic that many people naturally want to avoid or ignore?
A well-chosen conversation starter can make the difference. It can be the entry point that lowers defenses, shows authenticity, and invites input, turning avoidance into action.
Below are practical, gentle ways to begin that conversation during the holidays so it comes from a place of care and concern, instead of conflict and confrontation.
Seven Conversation Starters (Start using branded image)
1. Start With Gratitude (Use branded image here. Put number)
“I’m so grateful for the memories this house has given us… birthdays, holidays, and even the little moments. It got me thinking: how do we make sure this home, and everything we’ve built, stays in the family the right way?”
2. Use the Spirit of Giving (Chanukah & Christmas) (Video: Chanukah / Menorah)
“We’ve all been focused on giving gifts this season. The biggest gift we can give each other isn’t under the tree or in a box. It’s making sure we don’t leave behind a mess. Have we thought about how the family property should be passed down?”
3. Tie It to New Year’s Resolutions
“Everyone’s making resolutions right now, from getting healthier to saving more money. One resolution I’ve been thinking about is getting our parent’s property and estate plans in order. Are you open to talking about that and making it a family goal this year?”
4. Lead With a Story
“I heard about a family recently where the parents passed away without planning. It was a financial hardship and their kids spent years in probate fighting over the house. I don’t want that for us. What can we do now to avoid that?”
5. Frame It Around Protection
“Something keeps coming to mind. If something happens tomorrow, I want to make sure no one has to worry about the house, our investments, and other assets. How can we put things in place so it’s all smooth and simple for the next generation?”
6. Invite Input, Don’t Dictate
“So, I’ve been thinking about our family’s assets, especially the Real Estate. I’d really like to hear what everyone’s thinking and what feels right for how we handle it.”
7. Use Humor to Break the Ice
“We’re all stuffed from dinner. Now let’s talk about something lighter… probate court! (Okay, maybe not lighter, but definitely important.) Seriously though, how do we want to handle the family properties when the time comes?”
Conclusion
A key piece is asking if they are willing to have the conversation. If not, you need to re-strategize. If they are willing, then the focus is when to schedule it.
To create the best results, don’t make this a one-time, one-direction talk.
Frame it as the first step in a healthy, smart, and ongoing family conversation about legacy. Even breaking ground on the conversation and planning to talk more soon is a huge win.
Emphasize the focus of preserving family harmony, ensuring peace of mind for your parents, protecting assets, and making life easier for children and grandchildren.
If this article made you think about how to start your own family’s Real Estate or Legacy conversations, please like, comment, and share it with someone who might need it too.
One meaningful comment and a shared post may be the spark that empowers another family to talk, plan, and find peace of mind.
Your Concierge of Good Deeds
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