Leader development is a continuous, lifelong learning experience which involves learning through both automatic and controlled processes of leader development. The cognitive demands of leadership performance, inconsistent practice conditions, and increasing complexity of the leadership context across individual and organizational changes present significant challenges to leaders’ skill acquisition and developmental growth. Leadership coaching is a developmental relationship that helps a leader work through these challenges through one-on-one interaction with a coach. This chapter presents an interactional framework of coach, coachee, and organization through which outcomes for the coachee and the collectives to which the coachee belongs are achieved. For the organization, consideration is given to who should coach, who should be coached, and how the organization can support coaching. For the coach, consideration is given to coaching behaviors (encouraging, collaborating, and facilitating) and coaching relationships. For the coachee, consideration is given to coachee readiness and developmental planning.