Estate Planning

The Holiday Guide to Legacy Conversations

December 15, 2025
Kent Phelps

In many families, the holidays are a time for warmth, connection, and creating cherished memories. They are not, typically, the time for sensitive discussions about who gets the family home or the specifics of an estate plan. Yet, these gatherings often present a rare opportunity when multiple generations are together in one place. For estate planning attorneys, the goal is always clear: facilitate a smooth, surprise-free transfer of assets. A family meeting is the most effective tool for achieving this transparency.

The idea of bringing up an estate plan over Christmas dinner likely makes most people anxious. The fear of “ruining the holidays” is valid. The key is not the “what” but the “how” and the “when.”

 

The Case for Transparency in Wealth Transfer

Many families operate on the principle that finances and estate details are private matters. This inclination to keep things under wraps, often with good intentions to “protect” children or avoid conflict, can backfire spectacularly after the parents have passed away. Surprises in an estate plan (for example, a Revocable Living Trust plan) often lead to feelings of betrayal, anger, and family feuds. The unexpected nature of a bequest or a specific appointment (like who will be executor) can trigger intense emotional responses precisely because the conversation was never had.

Psychologists and financial experts agree that transparency fosters healthier family dynamics in the long run. By initiating an open dialogue, parents can manage expectations, explain their reasoning, and answer questions while they are still able to.

 

Expert Insights on Disclosure and Family Legacy

The benefits of financial and estate transparency are well-documented in professional literature.

The Importance of Shared Values Over Money

Dr. James Hughes, a prominent expert in family wealth and the author of Family Wealth: Keeping It in the Family, emphasizes the importance of shared family values over mere financial distributions. He advocates for families to communicate openly about their “human, intellectual, and financial capital.” Hughes argues that a legacy is about much more than money; it’s about preparing heirs to be responsible stewards of the family’s values and wealth. Open discussions help align the family’s mission with the parents’ intentions, making the transfer a legacy of shared responsibility rather than a mere transaction.

Inheritance Communication and Family Harmony

A study published in the Journal of Financial Planning highlighted the significant correlation between parental communication about inheritance and family harmony. The research found that when parents proactively disclose their intentions, adult children report feeling more prepared and less anxious about the eventual distribution of assets. The act of communication itself serves as a preventative measure against future conflict, providing clarity that the children value highly.

Shifting from “Telling All” to “Telling Enough”

Dr. Susan Turnbull, a prominent authority in estate planning communication and the founder of the Trusts & Estates Symposia, often speaks on the “human dynamics” of estate planning. She stresses that secrecy is the “enemy of harmony.” Turnbull encourages families to shift their mindset from “telling all” to “telling enough.” The goal is not a line-item veto session but a general overview of the plan, the identification of key fiduciaries (agents, executors, trustees), and the reasoning behind major decisions (e.g., leaving an unequal inheritance due to differing financial needs or previous gifts). This approach respects privacy while preventing surprises.

The Holiday Dilemma: Timing and Tone for Success

Bringing this up requires finesse. The key is to separate the holiday celebration from the “business” conversation. The holidays serve merely as the logistical backdrop for gathering everyone.

1. Announce it in Advance:

Don’t spring a meeting on your family the moment they arrive. Send an email a few weeks beforehand. Frame it as a necessary family “business” meeting or a “legacy conversation” that you would like to schedule during the time everyone is in town. This sets expectations and allows people to mentally prepare.

2. Choose a Neutral Time and Place:

Do not hold the meeting at the dinner table. Schedule a specific time, perhaps the day after Christmas, in a comfortable, quiet space away from the main festivities. A living room with closed doors, a quiet study, or even a pre-arranged conference room if the family is staying at a hotel, can work well.

3. Keep it General (Initially):

The first meeting is about opening the door, not revealing the safe combination. Start with the “why”: your desire to ensure everyone is taken care of, to minimize conflict, and to share the family’s values. Discuss the process of estate planning and introduce the concept that a formal review will occur.

4. Involve Your Professionals:

For more complex situations, consider having your estate planning attorney or financial advisor join the meeting (via phone or video conference if necessary). This provides a neutral, authoritative voice and removes the pressure from the parents to be the sole source of information and potential conflict.

The Power of Review and Dialogue

A family meeting is an ongoing conversation, not a one-time event. The estate plan itself is a living document that should be reviewed periodically as laws change and family circumstances evolve. Using the holiday gathering as an annual check-in point helps normalize the process.

By embracing transparency and managing expectations through well-timed and thoughtfully executed family meetings, you are providing a final gift to your loved ones: the gift of harmony and clarity. While it might seem daunting to initiate the conversation, the long-term emotional and financial benefits far outweigh the temporary discomfort, ensuring that the legacy you leave behind is one of connection, not conflict.

 

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Kent Phelps

TRAJAN ESTATE COFOUNDER AND ATTORNEY​ - As a second-generation estate planning attorney with over 25 years of experience, Kent Phelps appreciates the positive impact a customized estate plan can have on his clients and the generations that follow. Kent has been admitted to the State Bar of Arizona. He received his Bachelor’s degree from Arizona State University and his J.D. from the University of the Pacific. Additionally, he is a member of the Wealth Counsel and the Arizona State Bar Probate & Trust Section.