With family holiday gatherings approaching for many, now may be a good time to introduce or revisit estate planning conversations with your family. We spoke with Alasdair “Al” Halliday AB ’82, a Harvard Gift Planning director with more than 20 years of experience in the field, for some expert advice on how to approach these sensitive—but necessary—conversations.
Why is it important to discuss estate planning with your loved ones?
These conversations can be challenging. They ask us to confront mortality—our own or that of those we love—and they often concern money or other family resources that can carry deep emotional weight. A gift may symbolize approval or affection, while its absence can feel like disapproval or distance.
Yet despite their delicate nature, these conversations can be profoundly meaningful. They offer a chance not only to avoid confusion and conflict, both now and in the emotional aftermath of loss, but also to bring families closer together. When approached with honesty, transparency, and respect, they create space for loved ones to share their hopes, concerns, and values, and they can become a lasting source of connection—threads that strengthen the fabric of a family across generations.
When should these conversations start and how often should you revisit them?
The short answer to the first part of the question is: before they become necessary. Too often, competing priorities or a natural reluctance can cause families to delay until a sense of urgency sets in. By then, emotions may be heightened, and thoughtful dialogue can become more difficult.
Once started, you might frame these discussions as part of an ongoing conversation, not a one-time event. This can make them less fraught, and revisiting them every few years allows the plan to evolve alongside changing circumstances—externally and within family principles and priorities.
What are some of the most common mistakes people make when broaching the topic of estate planning with their loved ones?
We’ve touched on two common missteps: starting the conversation late and treating it as a one-time event. I’d add a third: focusing too narrowly on money and other financial assets.
In our work at Harvard, we’ve found that a family’s shared understanding of the meaning and purpose of their financial assets, and of the meaning and purpose of family more broadly, matter just as much as the assets themselves.
In our view, these deeper considerations aren’t peripheral to estate planning; they are essential to it. Over time, planning conversations should expand to explore what supports a family’s ability to build not just financial capital but also intellectual, human, social, and spiritual capital. They should ask: What is the best use of these forms of capital across generations? And what role could—or should—philanthropy and generosity play?
What advice do you have to improve estate planning conversations?
We often recommend approaching these discussions as a three-part conversation, beginning with the parents speaking privately with the goal of reaching alignment or at least gaining a clear understanding of one another’s views. In the second phase, those perspectives are shared with other family members—individually or as a group—and their reflections are invited. Finally, after taking time to consider the input they've received (with no obligation to adopt it), the parents share their decisions with the family.
We also encourage families to foster, over time, a spirit of generosity. A member of the Harvard alumni community once told me that when she was a child, her parents regularly emphasized the importance of giving beyond the family. The parents were philanthropists, but this teaching focused less on large gifts and more on everyday acts of kindness. When asked whether that ethic also shaped how family members treated each other, her response was immediate: “Of course—how could it not? It would have made no sense to be generous to others and not to one another.”
When the time comes to decide how family resources will be shared, a culture of generosity can be a gift in itself.
To learn more about including philanthropy in your plans, visit the Harvard Gift Planning website. You may also order a copy of Wealth in Families by Charles W. Collier MTS ’73, former senior philanthropic advisor at Harvard.