As educational leaders, the authors are and will be continually challenged to overcome new obstacles, address issues, take risks, and improve their organizations beyond the point at which they entered them. Educational leadership preparation programs are implored to enable graduate students to become the leaders who will face these difficult challenges. As faculty in those programs, the authors ask doctoral entrants to play simultaneously and effectively their role as students while preparing them for their professional roles in public schools, colleges, and universities after degree completion. In other words, they ask doctoral students both to learn to take future professional risks and to face current personal risks, but they have not always been effective as faculty at modeling and preparing them to do so. Furthermore, little has been written about the leader as risk-taker, both in terms of academic generations, that is, how doctoral students learn to deal with risk in leadership situations or how faculty prepare them to be risk-takers. The purpose of this paper is to explore how cultural milieu and gender differences affect risk-taking behavior in leadership preparation programs by investigating the intersection of these academic generations, that is, doctoral students and faculty.