Reflection is often used as a professional development tool in coaching and mentoring leaders. Outside of education, research is underway to learn how managers can develop as learning facilitators in the workplace. However, the current focus on learning communities and learning organizations within education makes reflective thinking particularly relevant for school principals and their supervisors. Reflection is essential to administrator capacity to think about and improve upon practice as well as challenge internal faulty perceptions and beliefs. In a professional development setting, a supervisor of school principals has the opportunity to play a pivotal role in leading them toward a deeper understanding of self, work roles, and performance. In particular, reflective thinking helps principals see gaps in their knowledge base and problem-solving skills, as well as leads to creative solutions. The consistent practice of reflective thinking is key to the development of expertise and effective administration. In effect, supervisors can move principals from being novice problem solvers to expert problem solvers through the development of reflective thinking. Supervisors of practicing principals are in a unique position to help principals increase their capacity to reflect upon their own practices, thinking, beliefs, and their manner of making sense of the daily struggles of the principalship, while gaining and refining their own knowledge and skill through reflection during this process. The authors contend that facilitating reflective thinking through mentoring or coaching is a necessary and useful process that supervisors of practicing principals can continually utilize to help reduce isolation and improve administrative skills along with improving student learning.