In this distrustful, unstable, and ethically polarized era, there is a need to prepare school administrators to resolve a myriad of moral dilemmas. As professors of school administration, how can we make sure that our future leaders have the capacity to make thoughtful, ethical decisions? How do we prepare these leaders to develop, foster and lead tolerant and democratic schools? What follows is a small action research project aimed at elevating moral and ethical wherewithal among graduate students studying school administration. Ninety-six percent of the students indicated that learning through dialogue or Socratic questioning, deepened their understanding of the topic. Most importantly, one-third of the students indicated that the dialogue caused them to uncover errors and incorrect assumptions in their own thinking and change them as a result.