Why teaching the next generation to choose well matters more than what they inherit
By Kimberly Frasca-Delaney, Senior Vice President, Client Advisor, Whittier Trust
Most families think of wealth transfer as a single moment—a signature, a distribution, or a reading of the will. In practice, the transfer that determines whether wealth lasts one generation or many more happens long before that moment, in the countless decisions that shape how it will be received, managed, and passed on again. Sound decision-making, not distribution, is the real inheritance. And it starts with strategic wealth transfer planning long before the financial hand-over happens.
Every Plan Begins With Choices—and Needs Flexibility
Before a single dollar moves, the wealth creator has to decide what they want. What assets should go to the heirs? What needs to go to the government via taxes? Does philanthropy have a place in the plan? Those choices become the roadmap the next generation inherits, whether it’s written down or not.
The instinct to plan for every contingency is understandable, but a roadmap only works if it leaves space for adjustments along the journey. Some wealth creators want to control outcomes indefinitely—control from the grave, as clients sometimes put it—but that’s simply not realistic. The better approach sets boundaries rather than constraints, with room built in for the plan to evolve as the family does.
Reading the Next Generation Honestly
Parents know their children in ways no advisor can approximate: their maturity, their health, their financial fluency, and their capacity for responsibility. Those differences matter enormously when families decide who might eventually serve as trustee or co-trustee. Not every capable adult child wants that role, and few are trained for it, because trust administration carries real legal and fiduciary obligations most people have never encountered. Just as important is impartiality. Asking one sibling to make decisions for another is asking for conflict, and most siblings know it before anyone else does.
This is where an outside advisor earns its place at the family wealth succession planning table. Whittier Trust can step in as the neutral party, tasked with educating heirs on fiduciary duty, walking them through the financial and charitable dimensions of the plan, and explaining not just what their parents decided but why. That documentation removes ambiguity, and removing ambiguity removes a great deal of family friction.
The Plan Is Never Finished
Decision-making doesn’t stop with the first generation, and it doesn’t stop once a plan is signed. Consider a widow in her eighties who, after her husband passed, realized the charities named in their plan no longer reflected her own interests. Nothing was stopping her from redirecting those gifts toward causes, such as the opera, the church, the arts, and an animal rescue, that mattered to her personally. As long as she remained of sound mind, she could change her wishes at any time. She found that liberating rather than burdensome, because it meant she was still the one making decisions about her own legacy. Her advisors here helped make sure the amended plan was executed smoothly.
Communication Turns a Plan Into a Family Effort
The most effective family legacy planning tool is often the simplest: a conversation. A letter of wishes—distinct from the binding terms of a trust—lets a family put its values and hopes for the next generation into words without locking anyone into rigid requirements. Delivered in person, ideally well before it’s needed, it tends to open a dialogue rather than close one. Families that go through this process together, asking questions and revising as they go, consistently report more harmony than those who let a will do the talking on its own.
For situations that call for more than financial guidance, Whittier Trust also maintains a vetted bench of outside professionals—covering everything from family counseling to business-transition support—so families never have to work through a difficult chapter alone. When those entities are needed, the advisors who know the family already are involved in helping choose the professional who will be the best match for them.
Preparing the Next Decision-Maker
The families who transfer wealth most successfully are the ones who let the next generation practice decision-making long before it’s required of them. That means visibility into how earlier choices were made, access to the same caliber of advice their parents relied on, and the confidence to say, “Let me talk to my advisor,” when an outside opportunity looks too good to be true.
A philanthropic component in particular can double as a teaching tool: assets placed in a trust, foundation, or donor-advised fund come with guidelines, and learning to work within those guidelines is often a family’s first real lesson in stewardship. This can provide a way for parents or grandparents to work alongside their heirs to model good stewardship and build closer bonds, all while allowing the next generation to flex their critical thinking skills under the watchful eye of an advisor.
Assets can be transferred in an afternoon. The judgment to steward them well takes considerably longer to build—and that is where a family office proves its worth.
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Kimberly Frasca-Delaney is a Senior Vice President, Client Advisor in Whittier Trust’s Pasadena office. A former practicing attorney in estate planning and family law, she assists in the wealth planning and client advisory for high-net-worth individuals and their families, focusing on estate plans with complex legal structures.
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