R. Adam Smith welcomes Emily Bouchard and Jim Benedict from PNC Private Bank Hawthorn for an insightful discussion on guiding ultra-high-net-worth families through business transitions. As leaders in family enterprise advisory, they share complementary perspectives on the multifaceted challenges families face before, during, and after selling a business. The conversation explores crucial pre-sale considerations including family dynamics, wealth structure, and emotional preparation along with effective governance models for family wealth office transitions. Bouchard, who leads the Institute for Family Business Success, emphasizes the importance of preserving family identity beyond the business, while Benedict provides strategic insights on recapitalization alternatives, tax considerations, and mechanisms for sustaining family harmony through structural planning. Their holistic approach demonstrates how financial planning must integrate with family financial planning to maintain legacy and purpose across generations.