This chapter explores Artificial Intelligence Coaching (AIC) as a tool for training and supervising leaders within organizations. Drawing on empirical research comparing human-based and AI-based coaching conversations, and studies investigating leaders’ schema changes in AIC conversations, the chapter synthesizes findings related to reflectivity, schema regulation, and competencies augmentation. It proposes a framework illustrating how AIC facilitates reflective practice, leading to cognitive and affective schema changes, thereby augmenting essential leadership competencies and enabling leaders to self-supervise in the flow of work. The chapter discusses theoretical and practical implications, highlighting opportunities for scaling development initiatives while considering current limitations and outlining a future research agenda.