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5 Great Legacy Conversation Starters

In working with families, I find that while they are good at the business of getting together as a family, they leave unspoken some of the questions and the stories that are pivotal to the history of the family.

In many cases, the family simply needs help to move beyond the surface level conversations. Similarly, there are too many assumptions—people within families assume that other family members know what is going on in their lives. Or worse, they assume that what is going on in their lives is not important enough to talk about. You’ll find below 5 legacy conversation starters:

  1. Go around the circle and ask family members to provide an update over the happenings of the past year—key events, things they are learning, highlights, lowlights, etc.
  2. What’s a key childhood memory of yours where you learned a lesson?
  3. When you think about your business career what was a hard lesson you had to learn?
  4. What family heirloom do you want to pass on to future generations and why?
  5. What’s a family story that you would want future generations to tell one another?

If you’ve got your own legacy conversation starters, please send them my way. Or if you’ve used any of these with success, please send me an email at

About Bill High

Bill is CEO of the Signatry: A Global Christian Foundation. He works with families, individual givers, and financial advisers to share the foundation’s message regarding biblical generosity and charitable giving. » Learn More. He is the co-author with David Green of Giving It All Away and Getting It All Back Again: The Way of Living Generously.

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