The Investment Letter - November 2025
How to Talk about Generational Wealth Transfer
When you gather around the family table this holiday season, taking in turkey, tinsel, or whatever your family tradition may be, savor these moments with your loved ones, and appreciate the pause from the daily grind that the holidays offer. The holidays can also be a time to start, or come back to, conversations about what matters most to us as individuals, and families. How we celebrate our holidays, and even the holidays we celebrate, reflect our beliefs, values, and priorities.
Wealth is a complex subject for many families, and death doesn’t simplify it. While discussing money may feel awkward, especially across generations, approaching it with a plan can transform potential tension into clarity, connection, and even relief.
This holiday season, consider using this time together to open dialogues about generational wealth transfer. These conversations can be a way to pass down wisdom and help you understand your family’s priorities so you can prevent confusion or conflict later.
Why Start the Conversation Now?
The holidays bring a rare opportunity to shed our commitments and gather multiple generations under one roof. We share meals, watch the afternoon fade into early evening, and invest the time we need to bring up topics that might otherwise intimidate us when our careers and families are spinning from Monday to Friday and beyond.
Starting a conversation about wealth transfer now can help:
• Learn about the value and legacy intentions of your family’s older generations.
• Reduce the chance of surprises and confusion about plans, or lack thereof, for charitable giving, trusts, or other structures.
• Encourage emotional and practical understanding before decisions need to be made.
Not Every Conversation Needs a Dramatic Opening
These conversations can be light at first. Sharing stories, traditions, or even the “whys” behind past decisions often opens doors. Candor can make space for crafting a plan that aligns your intentions and needs. Future discussions about wealth transfer can feel less intimidating when everyone feels heard and involved.
You may feel more prepared to launch into a purposeful conversation with some strategic planning. Before the holidays arrive, consider the questions for which you want answers.
• What do you hope to learn about family values, and the history that has contributed to them?
• How do you see yourself carrying those values into the future and what information now would help you do that?
• What are the personal priorities, both financial and non-financial, for all living generations?
How to Structure a Conversation about Wealth Transfer
Whether you’re most comfortable approaching your conversation in a formal setting, such as a holiday dinner, or an informal setting while watching the logs smolder in the fireplace, it’s important to consider how you will structure the conversation.
Set the stage. The goal of any conversation about legacy and values across generations is clarity, not conflict. Frame the discussion around your shared values, the stories that are important to your family, and how best to protect the legacy of the older generations and those who have passed away.
Start with emotions. Share what’s most important to you, e.g., tradition, philanthropic priorities, and lessons you’ve learned along the way.
Introduce the practical side, gradually. Once you’ve agreed on how to define your family’s values, move into discussions about structures, trusts, or inheritance strategies.
Encourage questions. Give everyone space to express curiosity or concerns, or to shift the discussion in a direction you may have overlooked.
Don’t assume. Everyone brings their own beliefs, feelings, and understandings to this discussion. It’s important to recognize that they may misread your intentions. That’s okay. Clarity comes from conversation.
Common Pitfalls when Discussing Generational Wealth Transfer
Allow yourself to feel apprehensive, approaching these conversations, and realize that this is a normal reaction. Most people “don’t have it all figured out” and many are afraid to broach what can be an awkward conversation. The motivation to press on, even if you’re having second thoughts, may come from considering what happens if you don’t proceed.
Misunderstandings can strain relationships and result from what is said as much as what is not. Confusion about charitable gifts or wealth distribution can have lasting effects that will last years or generations. Missed opportunities to learn the values of the older generations may lead to an impossibility to learn later.
What if You Need Help?
If you’re feeling uncertain about how to approach a conversation about generational wealth transfer or the technical questions you may need to ask, this is where professional guidance can help.
For decades, LaFleur & Godfrey has been helping clients and their families navigate these conversations, blending financial planning with a personal touch that recognizes that all discussions about finances begin by acknowledging what makes us human.
We can help you:
• Prepare for family meetings, balancing emotional and practical priorities.
• Help family members from all adult generations communicate and understand philanthropic goals.
• Educate you and your family about structures, trusts, and planning.
• Translate intentions into actionable strategies that align with your legacy.
We can help you create clarity, understanding, and alignment before the time comes to make formal (and often final) decisions.
Happy Holidays!
As you gather with your family this holiday season, consider these moments to begin meaningful conversations among the generations of your family. While they can be awkward initially, many families feel relief after these details are communicated, and plans can be made.
Share your stories, around the table, and remember to consider the values that are important to you and your loved ones. You may just come away strengthening both understandings and relationships, while addressing what may be unspoken anxieties.
LaFleur & Godfrey stands ready to walk with you every step of the way. We can help you structure your conversations, consider the path they may take, and clarify your plans. This holiday season, ensure that the story of your family and its hard-earned resources stand ready for the generations to come. Happy Holidays to you and yours!