Every family enterprise has subjects that everyone knows matter, but no one wants to discuss.
Who will lead next? What happens when the founder can no longer work? Who should inherit? Should family members receive jobs automatically? How much money is available, and who gets to decide how it is used? What happens when family loyalty conflicts with business performance?
These questions do not disappear because they remain unspoken. They move underground, where they become assumptions, resentment, and avoidable conflict.
That is the central lesson of my new book, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them. The book is not simply about communication. It is about how families, leaders, and organizations protect relationships and institutions by finding the courage to say what needs to be said.
I wrote Unspeakable because, in my work with family enterprises and in my classroom, I kept seeing the same pattern: people were often willing to discuss strategy, markets, and financial performance, but they struggled to talk about the human issues underneath those subjects. They avoided questions about identity, power, money, fear, disappointment, and belonging until those questions became impossible to ignore.
When succession becomes personal
One of the examples I chose to begin the book with describes a long-serving business leader whose sons believe he has stayed too long, while he sees himself as essential to the company’s continued success. The sons face an impossible choice: challenge their father and risk humiliating him or remain silent and risk damaging the business.
What would you say if you were in their position?
This scenario captures one of the most difficult dynamics in family enterprise. Succession is often treated as a single event triggered by retirement, illness, or death. I argue instead that it should be an ongoing conversation about readiness, development, leadership needs, and purpose.
Discussing succession is not an accusation that someone is old or no longer valuable. It is an act of stewardship. It gives the rising generation room to prepare and gives the current generation the opportunity to shape a meaningful next chapter.
When an inheritance plan becomes a family secret
In the third chapter, I recount the story of an extremely wealthy couple whose estate plan differs dramatically from what their children expect. The children believe they will inherit most of the family’s wealth. Instead, the parents plan to place family homes in trust and direct much of the remaining estate toward philanthropy, with the grandchildren involved in governing the foundation.
The parents know the plan may disappoint at least one child, so they are tempted to say nothing.
But what feels like protection to one generation can feel like betrayal to the next. A legal document can distribute assets. It cannot explain values, intentions, or trade-offs. Those require a conversation that happens while everyone is still able to ask questions and be heard.
When the “right” career is not the right career
One example that many families may relate to involves an MBA student whose family expects him to join the family business after graduation. He is not interested, but he avoids telling them because he fears disappointing his parents.
When the conversation finally happens, he discovers that his parents’ desire is not primarily about business continuity. They want to remain close to their son. Once that hidden concern is surfaced, the family finds a creative alternative: he can pursue his own career while serving on the company’s board and visiting regularly.
This is an important lesson for families navigating the rising generation. Positions, ownership, and succession plans often carry emotional meanings that are never acknowledged. A conversation focused on curiosity rather than persuasion can reveal the real interests underneath the stated demands.
Sometimes the question is not, “Will you come work in the business?” It is, “How can we remain connected if you choose a different path?”
How do we begin these conversations?
I wrote Unspeakable not only to explain why people avoid difficult subjects, but also to offer practical ways to approach them. I encourage readers to begin with curiosity rather than persuasion. Ask what the other person is worried about losing. Try to understand what a decision means to them before arguing for your own position.
Prepare for the conversation. Set an appointment instead of ambushing someone at the breakfast table. Choose a neutral setting when family history or hierarchy may make honesty harder. Establish a shared goal, even if that goal is simply clarity rather than agreement.
And remember that one conversation rarely resolves a complex family or business issue. The first conversation may simply open a door. The work is in returning to the subject, writing down what was heard, and continuing the dialogue.
The most dangerous sentence in a family enterprise may be: “We’ll deal with it when the time comes.”
By then, the founder may be ill, the estate may be contested, the next-generation leader may have left, or years of resentment may have hardened into distrust.
Unspeakable is an invitation to start earlier, speak more honestly, and discover what becomes possible when families stop treating difficult conversations as threats and begin treating them as acts of care.
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Learn more about Unspeakable and order a copy here: https://www.christinawing.com/book/
