In Germany and the U.S.A, the importance of effective school leadership toward creating successful schools is undisputed. Yet in both countries, attracting, developing, and retaining highly qualified school principals is a continuing challenge. The current study examined the impact of nine work-related factors that influenced the motivation of 145 German principals and 134 U.S.A. principals to become school leaders. Through survey data and follow-up interviews, researchers identified similarities and differences in the factors that shaped the motivation of principals in the two countries. These findings offer opportunities for Germany and the U.S.A. to learn from each other regarding ways to entice people to become school leaders.