As individuals contemplate a new worldview of leadership education, they must step back to reflect on what now shapes and constrains leaders in schools. Their understandings of traditional leadership are rooted in organizational theory that is focused on rationality, effectiveness, and efficiency of bureaucratic institutions, defining the education of leaders, for the most part, in terms of specific skills and performances that can be quantified. Without interrogating the fundamental ideas and beliefs underpinning existing school structures, they cannot respond to widespread calls for a different kind of school leader--one whose actions embody justice, respect, ethical values, care, spirituality, and equity. The leverage point for change is not to insert these qualities into existing school structures and leadership education programs but to transform the organizational structure of schools to one driven by a new set of assumptions epitomizing these ideals. The author argues that one's challenge in higher education is to initiate tough conversations, nurture relationships, respect others' knowledge, listen carefully through collective inquiry, be open to what is emerging, and examine the implications of recreating schools as living systems.