The magnitude and pace of change in the health care environment demand that medical schools change. Leading in a time of great change is difficult, and it is ironic that just when stability in leadership is most needed, the average tenure of deans is dropping. Indeed, the path to leadership in academic medicine is strewn with inherent ironies, paradoxes, and idiosyncrasies. For example, few people who become leaders in academic medicine aspire to, plan for, or seek training for leadership, yet leadership skills are essential to meet today's complex institutional demands. Also, most medical school deans were once medical students, and were selected and trained to be assertive, independent physicians, not to collaborate. For faculty, the medical school environment traditionally values individual autonomy and rewards individual achievement, not behavior that supports a larger community interest. Yet today's deans must be skilled at collaborative behavior, since they must have a vision for their schools and find ways to offer direction to the faculty and others to realize that vision. The author offers ideas about leadership and its development, and stresses that good leaders must above all curtail their egos in order to do what is best for their institutions. What a dean does as an individual is not nearly as important as what a dean enables others to do. The author also provides a checklist of dean's characteristics and responsibilities to help deans-to-be understand the job and current deans to think about how to succeed and thrive. He concluded by reiterating that the culture of individual faculty success based on individual entrepreneurism is passé. To operate in the new collaborative culture, today's successful dean must meld persuasion with educational statesmanship, always informed by a vision of how the school can prosper and serve.