There is a silent crisis undermining school improvement efforts. As in any major organizational change effort, leadership is a key ingredient to success. However, in educational leadership, the abilities to communicate, coordinate, and make decisions are not enough to address the “painful” trade-offs regularly faced by leaders in education. Their challenge is not just about making good decisions, which is daunting enough. They must also manage highly-public and often emotionally-charged issues among a diverse student and adult population. The state of our leadership pipeline, though, and our efforts to support their work, call for a dramatic shift in approach.