When families gather around the table during the holiday season, some of the most meaningful things shared across generations are not financial assets, but family traditions.
Someone tells a story one generation has heard before, but is new and fascinating to the next. Grandparents talk about where they came from, as parents reflect on traditions they hope will continue, and younger family members bring their own ideas about what matters to them.
These seemingly ordinary exchanges can reveal your family’s idea of legacy. Legacy is more than the assets a family has accumulated; it’s also made up of the values, experiences, and sense of purpose that give that wealth meaning. Conversations like these can help families explore what they hope to carry forward. Thoughtful estate and wealth transfer planning may offer an opportunity to consider how both financial and non-financial aspects of a legacy can be preserved.
Connecting family legacy to the story behind the wealth
For many families, conversations about wealth can be difficult. Parents may worry that sharing information about a future inheritance could affect a child’s motivation or expectations. Different generations may also have different ideas about money, work, generosity, and success.
Preparing the next generation for wealth transfer doesn’t necessarily mean beginning with conversations around account balances, estate documents, or specific bequests. Families may instead share stories that explain the values behind their plans. How was the family’s wealth created? What challenges shaped previous generations? What did parents or grandparents learn about work, education, generosity, or stewardship?
These stories provide the context that financial information alone cannot. Take, for example, a letter of intent from a grantor whose youth was shaped by hardship. In the letter, he describes the life experiences that impacted his values and the charitable causes he hopes his family would continue to support. Rather than simply outlining expectations, he explains the deeply personal reasons behind them. Preserving stories like these – whether in writing or through family conversations – may help connect an estate plan to the history and values that inspired it.
Making family conversations part of legacy planning
Start Family Legacy Conversations Early
The holiday dinner table is probably not the ideal setting to unveil an estate plan or explain the intricacies of a trust. However, it can provide a natural opportunity to discuss what it means to be part of a family and what the family values. These conversations may also become easier the earlier they occur. Talking about family history, generosity, and shared values while children are young can help create a kind of “muscle memory” for increasingly sophisticated discussions as family members get older.
Find Natural Ways to Talk Across Generations
These discussions don’t have to feel like a formal family estate planning meeting. Simple traditions may provide some of the best openings. For instance, using Thanksgiving as an opportunity for each person to share what they are grateful for may naturally lead to stories about loved ones who are no longer at the table, what family members value, and what their goals or hopes are for the future.
Families might ask:
- What family tradition do you hope we always continue?
- What did your parents or grandparents teach you that has stayed with you?
- What causes or issues matter most to you? Are there any organizations you’re interested in supporting?
- What do you hope our family is known for?
The goal isn’t to steer every holiday gathering toward estate planning. Rather, it’s to create opportunities for generations to better understand one another and the legacy they will share.
Exploring philanthropy as a family
For families that prioritize charitable causes as part of their family traditions, philanthropy can be another natural entry point into conversations about legacy. Unlike a discussion centered on inheritance, philanthropy turns the family’s attention outward. Talking about why a family supports a particular organization, community, or cause can open broader discussions about shared values without immediately introducing questions about individual financial interests.
Invite the Next Generation into the Conversation
Families interested in including philanthropy in their estate plans may consider asking children or grandchildren which causes matter to them and why. Volunteering together or inviting multiple generations to participate in giving decisions may help younger family members develop their own relationship with generosity. Importantly, the next generation’s priorities may not look like those of the generation before it. Making room for those new perspectives can turn the conversation into a dialogue rather than a lecture.
How informal family conversations help prepare for an estate planning meeting
Conversations about mortality and transition can be difficult. According to recent data, most family members report some difficulty discussing financial and legacy matters with one another. Three ways you can make these conversations easier include:
Building Understanding Before Discussing Financial Details
For high-net-worth families in particular, these conversations can be tricky. Parents may hesitate to discuss the extent of their family wealth for fear that knowledge of a future inheritance could affect their children’s motivation, independence, or expectations. At the same time, avoiding the subject entirely can leave the next generation without the context needed to understand the responsibilities and values associated with that wealth – and the legacy the family hopes to leave behind. Fortunately, open communication doesn’t necessarily require complete financial disclosure all at once.
One way to help bridge the gap when communicating across generations about wealth and legacy may be to start with values before numbers. Families can discuss work ethic, education, philanthropy, responsibility, and family history in relaxed conversations around the holiday table before sharing specific financial details.
These discussions may help younger generations understand the assets they could one day inherit and the purpose and intentions behind them. This context can make a difference because assumptions can develop in the absence of communication. For example, some heirs may expect an inheritance that is different from what is planned. Others may eventually learn that parents intend to direct a substantial portion of their estate toward charitable causes rather than leaving everything to the children.
Using communication to help preserve family harmony
Family members may also interpret a parent’s intentions differently based on their individual relationships and experiences. Discussing the values behind an estate plan earlier may help family members approach a future family estate planning meeting with greater understanding.
While communication can’t eliminate misinterpretation, it can provide an opportunity to clarify intentions, ask questions, and potentially support the preservation of family harmony before families are forced to navigate grief or other major transitions.
Eventually, these informal conversations may lead to more structured discussions about a family’s estate and long-term plans. A trustee can play a role in that process beyond administering financial assets.
Understanding the Trustee’s Role in Family Legacy
Cumberland Trust can participate in and help facilitate family meetings alongside other professional advisors, drawing on experience working with families across a range of circumstances.
As an independent trustee, Cumberland Trust provides an objective perspective, without the emotional history that family members naturally bring to the table. Thoughtfully including the family legacy in wealth transfer planning can mean considering not only how assets may transfer but also the intentions that shaped those decisions. Understanding a family’s history, values, and long-term vision can provide important context as a trustee works to administer a trust according to its terms.
Building Family Relationships Supports Successful Wealth Transfer
There’s no need for holiday gatherings to turn into an estate-planning seminar. These occasions, however, can offer a chance for multiple generations to listen, ask questions, and tell the stories that show a family’s history and heart.
Long before the details of an estate are discussed, families are already building a legacy in the traditions they keep, the causes they support, the lessons they share, and the conversations they make time to have.
Cumberland Trust brings specialized experience in trust and estate administration and a relationship-focused approach to serving families and their advisors. As an independent corporate trustee headquartered in Nashville, Tennessee, we understand the importance of thoughtful administration, discretion, and carrying out the intent behind each trust.
See how Cumberland Trust provided tailored trust administration to help a high-net-worth family navigate its unique needs. Read the case study.
