As the most-studied form of leadership across disciplines in both Western and Chinese contexts, transformational school leadership has the potential to suit diverse national and cultural contexts. Given the growing evidence showing the positive effects of transformational leadership on various school outcomes as it relates to school environment, teacher and student achievement, we wanted to explore the factors that gave rise to transformational leadership. The purpose of this study was to identify and compare the antecedents fostering transformational leadership in the contexts of both the United States and China. This paper reviews and discusses the empirical studies of the last two decades, concentrating on the variables that are antecedent to transformational leadership mainly in the educational context, but also in public management, business and psychology. Results show that transformational leadership is related to three sets of antecedents, which include: (1) the leader’s qualities (e.g., self-efficacy, values, traits, emotional intelligence); (2) organizational features (e.g., organization fairness); and (3) the leader’s colleagues’ characteristics (e.g., follower’s initial developmental level). Some antecedents were common to both contexts, while other antecedents appeared to be national context specific. The implications of the findings for future research and leader preparation in different national contexts are discussed.