Ethical challenges confront each and every one of us in our daily lives. How honest should we be with our co-workers? To whom do we owe our greatest loyalty? How do we balance between our responsibility to family, community, profession, and self? Many view these kinds of challenges as obstacles to be overcome; others, however, see them as opportunities for schools to grow and find their most deeply held values. Much like a real-life Kohlbergian values-clarification exercise, the process of dealing with the challenges sometimes matters as much, if not even more than, the actual results. The process can help examine questions such as: Whose interests does the school place at the core? Who is involved in addressing the problem? What criteria are established for determining the most appropriate course of action? These questions touch the heart of the school’s identity, and it is questions like these to which we devote this issue of Jewish Educational Leadership.