By: Amy Castoro, B.Sc., M.A. | President & CEO, The Williams Group
David is 43 years old. He has an MBA from NYU, has spent fifteen years working for the family business, expanded into an entirely new vertical, bringing in an additional 60M in revenue, and has a clearer view of where the market is heading than anyone else in the organization. He is also, functionally, invisible. His father, the founder, still sharp, still commanding, still the gravitational center of every important conversation, and hasn’t discussed succession once. Not directly. David doesn’t push. The family office advisor watches this dynamic play out at every annual meeting and wonders: “Is it my place to say something? And if so, what exactly do I say?”
If you serve families in a trusted advisory capacity, you already know David. You may serve several of them. Worse, when the next generation isn’t meaningfully engaged, you are at risk of becoming irrelevant to them.
What the founder Is actually afraid of
Before an advisor can help the next generation find its voice, it helps to understand why the founder is holding on so tightly because it is almost never simply about control.
In our experience, founders who remain dominant well into the next generation’s adult careers are typically navigating one or more of three quiet fears: the fear that stepping back means becoming irrelevant; the fear that the legacy they sacrificed to build will be squandered by people who didn’t have to earn it; and the fear, rarely spoken aloud, that their entire identity is wrapped up in the business.
None of these fears are unreasonable. And none of them get resolved by an estate plan or succession strategy.
This is the critical insight that advisors must carry into every conversation with both generations: the founder’s reluctance to cede authority is not primarily a governance problem. At least half of the families we support through the succession process come to us with excellent governance structures. What is missing is the skill to have the difficult conversations and work well as a team to implement the strategy as intended.
Four Fault Lines That Lead to Family Business Breakdowns
Power and control impact family businesses, just like any other enterprise. What makes the inevitable power and control struggles even more complex in a family business are the family dynamics that play a significant role in decision-making and succession planning. We work with families to diagnose the “fault lines” in their enterprises by assessing their current levels of trust, sense of a shared purpose, and clarity around decision-making. Here are the four most common:
- Lack of trust Only 30% of family businesses survive into the second generation. In the remaining 70%, often the family loses control of the assets and relationships are potentially destroyed. A lack of trust and communication are responsible for 60% of that failure rate. Trust, once eroded between a founder and a capable heir, does not repair itself, it requires deliberate, sustained effort from both sides.
- Lack of a shared purpose Although family members in different generations may have different values, a shared purpose can help align interests in support of a common mission. Without it, the next generation’s ambitions and the founder’s vision operate on parallel tracks that never converge, and the founder is unwilling to give up control.
- Control vs. care Family businesses can go under for many reasons, including conflicts over money, poor management, and fighting about the succession of power from one generation to the next. What makes this fault line particularly insidious is that both sides usually believe they are acting out of care for the family while experiencing the other side as acting out of control.
- Cordial hypocrisy Family members too often avoid tough issues by avoiding meaningful conversation. The next-generation member nods along at the family meeting. The founder interprets silence as agreement. Left unaddressed, these tensions increase distrust and obstruct performance until something finally forces the conversation, usually a crisis.
What advisors can actually do — Without a coach in the room
When no formal family coaching engagement is in place, the trusted advisor or family office professional often becomes the only neutral figure with credibility on both sides of the generational divide. That is not a small thing. Here is how to use it:
Help next-gen members find their voice
Next-generation members often undermine themselves by staying silent because they don’t want to rock the boat or “push on a nerve” and upset the founder. Coach them privately by having one-on-one confidential conversations to reveal their perspective on transition, timing, and roles and consider inviting the patriarch to a conversation to explore those possibilities. Ask specific questions such as: “What is at stake if a transition is not successful?” or “What does a successful transition look like to you, and what are the next steps to put in place?” or “What does the founder need to see to have more trust that the next generation is ready?” Quiet, consistent follow-through is far more persuasive to a founding-generation member than any declaration of readiness. You end the meeting with an action step: “What’s one commitment you both could make in the next 90 days that furthers your goals of a successful transition?”
Reframe their contributions around shared purpose, not personal ambition
When next-generation members frame their input around the family’s collective mission rather than their own desire for authority the conversation almost always lands better with the founder. A useful question to put to a next-gen member before a major family meeting: “How does what you want to propose connect to what your parent has spent their life building? Can you say that part out loud, first, before you get to your idea?” It sounds simple. It changes everything.
Introduce small, structured communication rituals
In the absence of formal family governance, advisors can suggest low-friction protocols: a standing agenda item at the annual family meeting for next-generation input; a brief written summary that next-gen members prepare before major decisions are finalized; a quarterly touchpoint where they share observations from their area of the business. These structures do not require a coaching engagement; they require only that someone with credibility in the room has the standing to propose them. That someone is often you.
Advocate for bottom-up ideas in the right context
Founders who would never accept a direct challenge to their authority are frequently open to a well-prepared proposal that makes a contribution. Next generation family members often have ideas for a new division, a restructuring of roles, a governance improvement, or a market observation. The advisor’s role here is to help the next-generation member prepare that proposal well, in a balanced way, and to create the meeting conditions where it can be heard. For example, in a recent full family meeting, the topic of business succession was raised, and we invited the two next-gen heirs to submit their proposals on the roles, compensation, and timing of the business transition. This got the ball rolling and gave them action items to keep it rolling. You might say to the founder: “Michael has been working on something I think you’d find interesting. Would you give him twenty minutes at the next meeting?” That sentence costs nothing. It can change the trajectory of a family.
Be a consigliere – Name the dynamic privately, and with care
Sometimes the most powerful thing an advisor can do is simply acknowledge, in a one-on-one conversation, what is not being said. You might be able to say what everyone in the room already knows but no one will say: “I notice you have a perspective on this that hasn’t been fully heard. Would it be useful to think through how to bring it forward?” That single communication signals that the next-generation member is seen. It can unlock months of frozen silence. For the founder, a parallel conversation might sound like: “I’ve noticed that when you feel strongly about something, the conversation is not a discussion but a one-way directive. David raises ideas in the group, but you move the conversation forward before he finishes. I don’t think that’s your intention but I wonder if he experiences it that way.”
Watch for the warning signs
As you deepen these relationships, stay alert to signals that the dynamic is worsening rather than improving: unwillingness to attend family meetings; declining participation at family gatherings; next-generation members who hold titles but are bypassed on real decisions; siblings or cousins jockeying for position; the cordial hypocrisy of agreeing to plans in the room while complaining about them outside it; drive by complaints about how much work they are putting in for an unsatisfactory level of compensation; timeline keeps shifting; no clear announcements of roles; no agreed on timeline when control transfers. Your client is counting on you to say what others are reluctant to say, and advise them in ways that takes care of their family, not only their assets.
What Becomes Possible
We once worked with a family stalled in their transition plans. During a series of facilitated dialogues, we supported them through some challenging conversations that paved the path forward for rebuilding trust. We then led the family to design a shared purpose for their business so they all had confidence they were working toward the same vision. Clarifying roles around their common mission enabled family members to express their individual talents in support of collective goals, and to use a common framework for coordinating action.
In another family, a daughter who had been relegated to designing showrooms for a family car dealership was finally asked how she could contribute more meaningfully. Trained as an interior designer, she spearheaded the design of an entirely new automobile line targeting buyers her age, launching a new division for the business. No one had thought to ask. When the founder saw the results, he could not understand why it had taken so long.
The capability had always been there. What was missing was the trusted advisor willing to step forward and begin the conversations.
The Urgency Is Now
According to Cerulli Associates, $68 trillion will transfer from baby boomers to the next generation over the next quarter century. Yet research consistently shows that a majority of next-generation family members feel underprepared and underheard in decisions about the wealth they are expected to steward. The gap between what founders intend and what heirs actually experience is where family legacies are quietly lost.
The payoff of aligning a family business’s shared purpose, mutual trust, and collective decision-making is well-documented. Credit Suisse studied 280 family companies globally and found that family businesses outpaced public companies in revenue growth even during the global recession of 2011–12. Effectively aligning power and family dynamics bolsters business performance, strengthens relationships, and creates the conditions for wealth to be a genuine force for good across generations.
If you are serving a family where the founder is still in charge and the next generation is struggling to be heard, the conversation cannot wait for a formal engagement to begin. You are already in the room. You already have the relationship. The question worth sitting with: Is there a David in one of your client families right now — and does he know you’re in his corner?
FOOTNOTE:
This publication is protected by copyright. Tompkins Insurance is not engaged in rendering tax or legal advice. TOMPKINSights contains a general discussion of certain tax and legal developments and should not be construed as tax or legal advice.
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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