The best approach to succession planning for family wealth is sharing knowledge across generation
By Whittier Trust
For many first-generation wealth creators, it’s easy to think that everything’s under control. One person built the business, opened the accounts, and knows every advisor by name. Often, the rest of the family trusts them completely—and knows almost nothing.
That gap rarely matters until it does. When it does, families are grieving, but they’re also flying blind, with no idea the scope of what they don’t know.
“There’s always the couple where one person has basically handled all the finances,” says Whittier Trust Senior Vice President, Client Advisor Rebecca Duguid, who works closely with ultra-high-net-worth, multi-generational families. “For example, perhaps the wife has stayed out of financial matters, and now they’re getting to the point where they’re afraid that the husband’s going to pass away. They’re getting older and thinking, ‘How is she even going to know how to pay a bill?'”
That question—how will she even know how to pay a bill?—highlights a problem some families don’t think of until they’re in the thick of a crisis or loss. One real risk to family wealth management isn’t just market volatility. It’s what happens when a single person becomes the bottleneck for everything: the accounts, the entities, the relationships, and the institutional knowledge about the family’s financial landscape. It’s something that Duguid, along with her colleagues at Whittier Trust, caution client families against so that they can enjoy the best possible outcomes.
When It’s Too Late
Duguid has seen what happens when families wait until a crisis forces the issue. In one case, a father passed away first, leaving a mother with three kids. The mom, who was also ill, tried to bring in an advisor before she passed away, but ran out of time. “She ended up passing away sooner than she anticipated,” Duguid recalls. “That created a challenge. Bills slipped through the cracks because we didn’t know about them. We had to scramble to get in there and help the family.”
The same pattern shows up in more complex estates, where one person controls a web of LLCs, real estate, and business entities with no named successor. “Wealth brings with it complexity. Having one person who controls all the entities, without keeping a trusted partner aware, makes a transition much more difficult,” Duguid says. Without succession planning, the strain isn’t limited to the family—it extends to business partners and anyone tied to those entities.
Why Families Wait
Part of the delay is practical, while part of it is psychological. Duguid points to control and secrecy as deeply ingrained habits in many families. “We have seen a lot of families have one primary person who is used to controlling every detail,” she says.
Another recurring pattern is what Duguid calls the “golden child” dynamic—one heir is groomed for significant decision-making authority while siblings are excluded. Families like this often function well on the surface, but the internal imbalance of power and affection breeds underlying resentment and leaves the wealth structure fragile especially if that one favored child is unavailable or unprepared.
More often than not, it takes a scare to change course. Duguid says, “Something almost happens, and then they realize, ‘Oh, I’ve got to do something differently.'”
Bringing Advisors—and the Next Generation—In Early
The alternative to a crisis-driven wake-up call is early, intentional involvement. Duguid describes this as one of the clearest value propositions a family office or advisor can offer. “The transition when you pass away is a lot easier if a firm like Whittier Trust is already involved,” she says. “We know you, your spouse, and your heirs.”
For some families, that means the advisor becomes a trusted consultant who simply knows where everything is. “We meet every week simply to talk about what’s going on financially in her life,” Duguid says of one client. “If something happens, the kids know to call us. We know where everything is, how to access all of the necessary accounts,and we’re apprised of what we have to look out for.”
For others, the work is about actively building financial literacy and shared decision rights across generations. That may mean inviting adult children into investment reviews, walking through balance sheets, or opening the books at a family meeting. “It really depends on the family and the person leading it,” Duguid notes, “but a family meeting is one way to say, ‘Let’s talk about what’s going on and what is important to the family. Let’s open the books.'”
Philanthropy as a Governance Lab
One of the more effective on-ramps Duguid has seen is philanthropy. As part of its family office services, Whittier Trust works with families that have multiple generations and organizes family meetings around their donor-advised fund, where each generation can choose charities individually and then work together on a shared gift.
“The parents want their children to be engaged in giving money away and continuing the family’s legacy and impact,” Duguid says. Crucially, the advisor—not the parent—runs the process. “It’s not like, ‘Oh, this is Mom and Dad’s thing that we have to deal with.’ We’re trying to get the kids excited about it versus seeing it as a chore.” Whittier Trust’s philanthropy department helps make sure everyone is invested in the outcome, a process that can promote family unity.
It’s also a low-stakes way to practice the same skills that matter for the larger estate: communication, shared judgment, and comfort with financial decision-making before real dollars and real consequences are on the line.
From Bottleneck to Shared Stewardship
The families that navigate wealth transfer most smoothly aren’t necessarily the ones with the most sophisticated structures. They’re the ones who spread understanding and decision rights before they’re forced to. That means bringing in advisors early, holding candid conversations about money, and giving the next generation practice making decisions while the stakes are still manageable.
The question isn’t just what happens to your assets when you’re gone. It’s whether the people you love will have the clarity, confidence, and support to be responsible stewards.