Leaning on Trust and Communication for Successful Family Transitions with Amy Castoro

Today, I have the pleasure of speaking with Amy Castoro, President and CEO of The Williams Group, where she leads a team dedicated to ensuring the smooth transfer of wealth across generations. Amy is a recognized expert in preparing high-net-worth families to successfully transition wealth while maintaining family unity and control over assets. She is also an accomplished author, keynote speaker, and senior family coach known for her direct yet compassionate approach, which fosters long-term relationships and delivers measurable results.

Amy is the author of Bridging Generations—Transitioning Family Wealth and Values for a Sustainable Legacy. She is a long-time friend of FOX and has been a speaker at FOX events and council meetings.

Amy has helped many UHNW families navigate intergenerational transitions, and she shares her experience on what are the hallmarks of a successful wealth transition and what role trust and communication play in achieving such successful transitions. Throughout her career, Amy has created a framework for how to build, repair, and manage trust in a family. She tells us about this framework and highlights how families can successfully leverage it.

One practical tip Amy offers to many families is how to have challenging conversations and how to structure this often-uncomfortable process. She provides her recipe for success with necessary but difficult discussions within the family.

Another practical tool Amy has developed is her “10 Questions Quiz” that she uses to help families strengthen relationships with each other and prepare for a smooth and successful intergenerational wealth transition. She describes the 10 questions and how she applies the quiz to help families succeed.

Enjoy this insightful conversation with a leading advisor of UHNW families and practitioner in the field of family transitions and wealth transfer.