Imagined Conversation

In family businesses, some of the most important conversations never happen — not because the issues aren’t known, but because family members rehearse worst-case outcomes in their heads until they convince themselves the conversation isn’t worth having. CFAR founder Nancy Drozdow calls these “imagined conversations,” and in this article she unpacks why they are so paralyzing and how to break the cycle. Drawing on the three interconnected layers of family business dynamics — the interpersonal, the role, and the enterprise — and offers five concrete steps to help family members move past avoidance and engage in the candid, productive discussions that both the business and the relationships depend on.