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The purpose of this research was to identify exemplary, award winning secondary school leaders to discover ways in which they have transformed their schools for 21st century education and student achievement. This paper discusses three diverse case studies and identified ways that school’s leader and leadership team has transformed its context into an exemplary, award-winning school. The data revealed multiple factors that these cases shared in school transformation but also articulated the ways each of these leaders approached his/her school’s individual culture, circumstances, and issues. This study offers insight into the challenges and skills current school leaders must face to leverage technology to improve student learning and school improvement.