This study investigates the nature of the mentor/protege relationship of community college presidents, and likens it to that of teacher/pupil. The qualitative study focuses on how a mentoring relationship evolves and matures over time to create a learning experience that fosters the development of cognitive leadership complexity. Six strategies of the leadership learning process are analyzed: affirm (including listen, support, reflect, and mirror), motivate, evaluate, create networks, be and model, and make people aware of leadership development. Ultimately, the mentors created cognitively complex learning cultures that fostered the development of leadership.