This article by Richard Stup of Cornell Agricultural Workforce Development explores how leadership needs evolve as dairy farms grow, drawing on Ram Charan's "Leadership Pipeline" framework. As farms expand from owner-led operations to organizations with dozens of employees, leadership must shift from an obsession with production performance to an obsession with developing leaders at every level. Using the case of Sergio, a top herdsman promoted to supervisor, the article illustrates the first "leadership passage": moving from leading oneself to leading others, which requires new work values, time use, and skills such as delegating and coaching. A second case, Mary, a parlor manager turned site manager, illustrates the passage from supervisor to senior leader, requiring a shift toward leading other leaders rather than individual performers. The article closes with three actions for senior dairy managers: clarifying leadership expectations, holding supervisors accountable for leadership behaviors and actively coaching supervisors through these difficult transitions to build a sustainable workforce.