In this article, we report on our initial work with the International School Leadership Development Network. In doing so, we present two cases of principals leading high-need schools, and conclude with some key observations in relation to what is distinctive about leading these schools. The first case features a principal leading a suburban school in the large metropolitan city of Melbourne prepared by Drysdale and Gurr. This school is the result of the closure and amalgamation of several failing secondary schools, in what was termed a "regeneration project." The second, prepared by Wildy and Clarke, is a personal account of a principal coping with leading a small school serving an Aboriginal community in a remote location (the nearest shop is 303 km away via an unsealed dirt road).