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International research data unambiguously correlates effective educational leadership with improved student learning. Such leadership not only improves the professional performance of teachers but also models learning excellence. Undoubtedly, students learn so much from what they observe others doing. But how can educational leaders model what they have not experienced, themselves? How can today's educational leaders model learning excellence when there is an ever-increasing disparity between contemporary improvements in pedagogical approaches and the lived reality of leadership? To prepare world class educational leaders of learning, it is essential that the process for learning about leadership is closely aligned to what is now considered to be best practice in promoting student learning. If enactivism is the new bench mark in pedagogical practice, how could it be applied to the preparation and practice of leaders? This chapter applies the assumptions and intentions of enactivism to the context of leadership. Although this process enables educational leaders to resume their pivotal place as models of learning excellence, it has profound implications for leadership expectations and accountabilities.