Confronting the Unspoken: Why Difficult Conversations Are the Cornerstone of Family Governance

Christina Wing
December 9, 2024

Family enterprises operate at the intersection of emotion and business—often with explosive consequences. Avoiding critical conversations about succession, governance, and expectations may feel like self-preservation in the moment, but it ultimately undermines the family’s ability to sustain its enterprise across generations.

Governance Is a Family-Wide Responsibility

When we think of family governance, our minds often go to the business—its board structures, management policies, or succession plans. Yet governance spans far beyond the operating company. It encompasses wealth, philanthropy, and, most importantly, the family itself. Without clear expectations and open communication, every one of these areas can become a source of conflict.

The avoidance of difficult conversations is often the root cause of these conflicts, preventing families from establishing governance that supports long-term success.

Avoiding these conversations leaves families vulnerable to common conflicts, such as:

Engaging in these conversations allows families to establish governance policies—such as distribution policies, buy-sell agreements, family employment and in-law policies, prenuptial agreements, and family constitutions. These frameworks create clarity and help avoid conflict by putting policies in place before things become personal.

Advisors: The Facilitators of Change

Families aren’t alone in their avoidance; advisors often hesitate to confront hard truths, fearing conflict or even losing the relationship. However, as trusted guides, advisors have a responsibility to create safe spaces for these conversations. It’s not enough to develop strategies or draft policies—facilitating dialogue is just as critical.

To be effective, advisors must adapt their approach to the audience. Different generations and family members hear things differently, and successful communication requires tailoring the message to each person. At the same time, consistency is key. Transparency and a shared understanding among all parties form the bedrock of effective governance.

Addressing the Hard Topics

Families often avoid conversations about succession planning, wealth governance, and expectations due to cultural norms, fear of conflict, or a reluctance to appear ungrateful. Yet delaying these discussions only leads to ambiguity and future discord.

For example, many leaders delay succession planning, associating it with their own mortality. This hesitation leaves the Rising Gen uncertain about the Now Gen’s intentions, creating frustration and making it difficult to plan their own roles within the family enterprise (or outside of it). Reframing succession as an ongoing process rather than a one-time event fosters collaboration and shared purpose.

Similarly, money is often a taboo topic. Families may avoid discussions about wealth, inheritance, or financial responsibilities, which can lead to misunderstandings or false expectations. Advisors can play a crucial role by encouraging Now Gens to embrace transparency, helping to prepare the Rising Gen for their future roles and responsibilities. They can also help families think through structures that provide support and guidance while avoiding the risk of “spoiling” the Rising Gen, fostering a sense of accountability and stewardship.

Best Practices for Difficult Conversations

Whether you’re a family member or an advisor, the goal of a difficult conversation should be alignment, not confrontation. Some best practices include:

Governance is not a one-time task but a continuous process. Avoiding these conversations does more than delay decisions—it threatens the cohesion of future generations.

Building a Lasting Legacy

Governance empowers families to align their goals, avoid unnecessary conflicts, and ensure sustainability. Families and advisors who embrace these conversations lay the groundwork for stronger relationships, clearer governance, and enduring legacies.

Policies before it’s personal—this principle underscores the importance of addressing challenging issues proactively. Engaging in these conversations is difficult, but it is essential for safeguarding the future of family enterprises.

Let’s keep talking. Thriving multigenerational enterprises are built on clarity, communication, and the courage to address the unspoken.

Want more content? Check out Wingspan Insights.

Author Thumbnail

About Christina Wing

Christina founded Wingspan Legacy Partners to help Founders and Families navigate the intersections between Family dynamics, business operations, wealth, legacy and philanthropic impact.