For many families, wealth planning isn’t just about today. It’s about creating a legacy that supports children, grandchildren, and future generations. But when is the right time to start planning for multigenerational wealth?
That’s a question Megan Trask, Partner and Managing Advisor at Connecticut Wealth Management (CTWM), helps families explore through thoughtful planning conversations —conversations that consider financial complexity, personal values, and what families want their wealth to support over time.
A Helpful Framework: Thinking in “Decision Trees”
When approaching multigenerational wealth planning, one of the first considerations is whether a family is likely to face estate taxes. That distinction often shapes both the timing and complexity of planning.
“I tend to think about this almost like a decision tree,” said Trask. “One really important branch point is whether a family is likely to be subject to estate taxes, because that ends up driving so much of the planning work that needs to happen.”
For families with significant wealth, this distinction often influences not just tax strategy, but how early planning begins, how assets are structured, and how much flexibility exists over time.
“If we expect there will be an estate tax exposure, starting to plan for the transfer of wealth as early as possible is really important,” said Trask. “This allows us to proactively strategize, be more flexible, and can give us the ability to meaningfully reduce future tax exposure.”
For families who are not expected to face estate taxes, timing is often guided more by preference than urgency. Conversations tend to focus on values, transparency, and how wealth should be shared over time.
One exception applies to all families: unexpected events. Incapacity or major life changes can quickly accelerate the need for multigenerational conversations, making advance preparation especially important.
Financial Education: The Foundation for Every Family
Regardless of wealth level or tax exposure, one element of multigenerational planning applies to everyone.
“Something that really applies to everyone is financial education for the next generation,” said Trask. “You can do that without disclosing anything about family assets, and in my opinion, you can’t start that too early.”
Financial education often begins when the next generation starts making decisions on their own: during college, early careers, or major life transitions. Topics may include saving, investing, taxes, employer benefits, and building sustainable financial habits.
At CTWM, this education is a core part of how we partner with families. Advisors frequently meet one-on-one with next-generation family members, tailoring conversations to their personal goals, life stage, and evolving financial responsibilities. For many advisors, these relationships are among the most meaningful aspects of their work.
Transparency, Roles & Behaviors
As planning deepens, families often begin to explore questions around transparency and structure. How much should the next generation know and when?
Many families choose to start by discussing the structure of their financial and estate plans rather than specific dollar amounts. These conversations might cover who the key advisors are, what roles exist within the estate plan, and how decisions would be made without disclosing numbers.
“For most families, it’s not really about conflict. It’s more about how knowing an inheritance is coming might influence behavior, how hard someone works, or the decisions they make,” said Trask.
By keeping early discussions high-level, families can communicate expectations and values while avoiding unintended influence on motivation, career decisions, or risk-taking.
Aligning Wealth with Family Values
For families with strong philosophies around responsibility, productivity, or purpose, planning tools can help reinforce those values.
“We work with families who want their wealth to support certain values, like responsibility or productivity. Sometimes that shows up in trust language, and other times it’s about how and when money is shared,” said Trask.
Some families choose to structure distributions around earned income to reinforce independence and accountability. Others prefer matching savings or supporting meaningful investments—such as a first home, a business venture, or long-term investment accounts—rather than providing unrestricted lump sums.
Clarity matters. When expectations exist but aren’t clearly communicated or structured, that’s when misunderstandings can arise. When families are intentional, the transfer of wealth often becomes more fulfilling for everyone involved.
Preparing for the Unexpected
Another important aspect of multigenerational planning is preparing the next generation for future responsibilities, particularly in the event of incapacity or loss.
“When people understand the structure of the plan and what their roles might be ahead of time, they’re much better prepared,” said Trask. Those roles usually come into effect during emotionally charged moments, when it’s difficult to absorb new information or make confident decisions.
Sharing this information in advance allows family members to ask questions, gain clarity, and emotionally prepare, often leading to better outcomes during difficult transitions.
An Ongoing Partnership
Multigenerational wealth planning is not a “set it and forget it” exercise. The frequency and depth of family conversations vary, but ongoing communication is key.
“There’s no single right way to approach multigenerational planning. What matters is taking the time to understand a family’s situation, values, and preferences, and building from there, which is exactly what we do,” said Trask.
At CTWM, multigenerational planning is a foundational part of our approach. By combining education, experience, and thoughtful facilitation, we help families align their wealth with what matters most, supporting not just financial outcomes, but clarity, confidence, and lasting legacies for generations to come.