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Effective school leadership is crucial to a school’s success. Yet attracting and retaining qualified school leaders is often a formidable challenge. To discern ways in which we may recruit and retain competent school leaders, this study compares the extent to which principals in three industrialized countries, Germany, China, and the United States of America, value the characteristics of their positions as principals. Survey responses of principals in these three countries reveal many factors that gratify and some factors that disappoint principals about their work environments. Comparing the similarities and differences of the principals’ responses in these countries provides insights into ways in which we may learn from each other about factors that influence the recruitment and retention of qualified principals.