By: Amy Castoro, B.Sc., M.A. / President & CEO, The Williams Group
When trust falters in a family or family business, even families with strong bonds and significant wealth can experience conflict, estrangement, and emotional pain. We see breakdowns in trust in every angle, from parents distrusting their children, children distrusting each other, and children’s distrust of their parents.
In family enterprises, trust is particularly critical because it shapes not only personal relationships but also how resources, legacies, and responsibilities are shared across generations. Learning how to repair broken trust is a vital skill—yet it is rarely taught or practiced in family communication. Based on our research of more than 2,500 families and our 60 years of supporting families to transition wealth, 60% of the reason for failed wealth transfers comes down to trust and communication. We have found the following strategies can help repair relationships.
Install high-trust behaviors
Learning to observe, manage, and repair trust is essential for any high performing family or team. Charles Feltman, author of The Thin Book of Trust breaks down trust into four domains – sincerity, reliability, competence and care.
Sincerity is the alignment with what one says and what they do. Reliability is the ability to manage the commitments made to others. Competence means you have the skills, resources and capacity to deliver on what you say you can do. Care demonstrates you have the other person’s best interest in mind.
You might trust someone in three domains, but not the fourth. For example, the senior generation may see someone as reliable, sincere, and caring, but not competent to hold a particular role in the company. Rather than a blanket statement of “I don’t trust them to perform that role well” the conversation can become more actionable and less judgmental by stating the standards expected. We see this in families when the eldest son is named a trustee. The other siblings may distrust their sibling to hold the role because in their mind, all that person did was cheat in monopoly when they were growing up. Sincerity is in question, along with a clear understanding of what is required in the role.
A father of a highly successful family enterprise contacted us because his relationship with his eldest daughter had hit a rough patch, leaving them barely speaking. He was distraught, fearful that he would not see his grandchildren, and his wife insisted that he was at fault. The daughter felt estranged from her parents and disconnected from the rest of the family. The breakdown stemmed from a misunderstanding, which is often the case when feelings are hurt.
As the family enterprise grew, the father allocated plots of land to his five children. One child, operating a growing agricultural business adjacent to his sister’s land, hoped to expand. The father approached his daughter to discuss giving a portion of her land to her brother. Although she was initially unhappy with the idea, he promised to obtain a valuation and keep her informed. When the land transfer occurred with some additional money included, the daughter hit the roof. On the surface, it appeared that the father had made the decision without her approval, but as they discovered through facilitated communication, the deeper issue was that the daughter felt her voice had not truly been heard—a recurring concern throughout her upbringing that was magnified when the land was involved. She felt ignored and hurt, and just underneath her anger was a deeper longing for being cared for. Together they committed to spend more time with each other. That included doing philanthropic events, making a point of having dinner together more frequently, and committing to family vacations.
From Distrust to Shared Vision
We see this in the first generation attempting to rule from the grave out of distrust that the next generation will squander the wealth. This can often result in a fight over power and control, with the “winner” being the one with more authority. The cost of the win is a relationship based on fear, insincerity, and ultimately estrangement. For example, three affluent siblings lost their father suddenly. Ranging in age from 21 to 32, they were bewildered by the responsibility of continuing their father’s legacy while stewarding family wealth. Existing dynamics of a blended family added stress, resulting in two siblings ultimately becoming estranged due to distrust over how family resources were being distributed. Through facilitated conversations, the siblings were able to uncover what was most important to each of them and engage with trustees as a united voice—co-designing a path forward that met individual goals while honoring their father’s wishes.
Rebuilding Trust Across Generations
In another example where a 20 year relationship was repaired, the 32-year-old son of a first-generation wealth creator admitted he had never felt his father wanted him to join the family business. Despite a graduate degree with honors from Duke University and increasing responsibility within a highly competitive organization, he was haunted by past mistakes from his high school and college years leaving him to question if his dad could ever forgive him. Over time, their relationship became increasing cordial, distant, and not fully connected. When business succession was discussed in a family meeting, honest dialogue allowed them to address lingering concerns. The son stepped bravely into a conversation and asked if his dad would be willing to consider starting a new division within the business to diversify. Dad’s response was immediate: “I thought you would never ask!” What had once been fear was replaced by relief and new opportunities, demonstrating how courageous conversation can repair strained relationships.
Techniques to Repair Broken Relationships:
- Plan how to have the conversation. Establish shared expectations for dialogue. For example: “I’d like to have a conversation about our relationship. To do this well, I want us to slow down and ensure we understand what is really important to each other before responding.”
- Give up being right for the sake of connection. Co-design new possibilities that honor both perspectives, moving beyond transactional discussions to care for the person.
- Be brave. Difficult conversations often require temporary discomfort but yield long-term relational gain. Honest and open sharing is the best way to honor and strengthen relationships.
Restoring trust takes patience, empathy, and courage, but the rewards are profound. Families that take time to learn how to prioritize trust create legacies not just of wealth, but of belonging, mutual respect, and connection. By choosing vulnerability and communication over fear and silence, broken relationships can become opportunities for deeper understanding, cooperation, and shared purpose across generations.
FOOTNOTE:
Amy Castoro is president and CEO of The Williams Group, a family coaching and consulting firm celebrating 60 years. She is also the co-author of Bridging Generations: Transitioning Family Wealth and Values for a Sustainable Legacy. Amy and her team advise ultra-high net worth families how to build trust, navigate the challenges of intergenerational wealth transition, manage conflict, design governance strategies, and build sustainable succession plans. Amy holds a B.Sc. in Organizational Psychology from Adelphi University, and a Masters in coaching from the Strozzi Institute. Amy has trained extensively with Dr. Fernando Flores. Amy is a trusted partner of Tompkins Insurance.
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