Various research studies have asserted the significance of school leadership on student learning. Although the research-based knowledge about principalship continues to grow, there is a paucity of practical information about how to perform the essential tasks. How do principals develop and then act upon a deep understanding of supporting teachers? What steps do principals take to promote student learning? How do principals transform schools and foster powerful teaching and learning for all students? Providing answers to "how-to" questions is useful for all principals but will be especially helpful to principals in schools serving students who are most at risk of low achievement or failure. In this article, the authors present the strategies employed by principals of Breakthrough High Schools (BTHS). These principals have successfully led schools that serve large numbers of students who are potentially at risk of failure. BTHS schools have achieved an astounding result: postsecondary education attainment for at least 90% of the students. The experiences and practices of these schools can offer some lessons that may help answer the vexing how-to questions.