This qualitative study explores the preparation and practice of school leaders in Taiwan based on indepth interviews and observations with six Taiwan school directors serving geographically diverse student populations. The journey leading to school leadership and the challenges that this representative group of educational leaders face are discussed and also compared to the preparation of American school leaders and the challenges that U.S. counterparts experience. As educational systems around the globe work toward educating more students to higher standards of achievement in order to increase national productivity, the insights gained through this study can be used to inform conversation regarding the restructuring of school leader preparation programs to answer the persistent question of "How are great school leaders developed?" within specific cultural contexts.