In this letter, I respond to comments from David Gabbard regarding my article on the Broad Superintendents Academy. Energized by Gabbard's critique, my letter points toward a position for educational leaders that works both within and against dominant systems. I ask: How can we model in our own communities the kind of caring, inclusion, and dialogic relations that we espouse in our graduate seminars? This type of leadership carries the challenge of working in ways that are both effective and subversive, both oppositional and affirmative.