This study explores the perceptions of successful school administrators in their roles within the changing context of schooling in Ontario, Canada, and the US states of Arizona and New York. This research considers district and campus administrators' work experience and contemporary challenges related to province- or state-specific expectations, school improvement issues, resource distribution and accountability. Focus groups of practicing principals reflected the ways in which school leadership was defined and enacted across borders, providing significant commonalities within the international perspectives of the participants, as well as context-specific differences in the interpretation of their perspectives.