Research is clear: school leadership is second only to classroom instruction as the most powerful school-based factor influencing student learning. Effective principals can generate the equivalent of two or more additional months of learning per year, and leadership accounts for up to 27% of variance in student outcomes. Yet many leadership development programs underperform, with limited connection between leadership learning and what actually changes for students. This session addresses that gap directly. Schools and districts across urban and rural contexts invest heavily in leadership development, but the return on that investment often fails to reach classrooms. In urban systems, this disconnect often appears as misalignment between district initiatives and school-level implementation. In rural contexts, it shows up as isolation, limited access to coaching, and development models that do not reflect local realities. Drawing on experience designing and implementing leadership development systems in a large urban district, this session introduces a structured diagnostic framework for aligning leadership learning with instructional practice and student outcomes. Participants will examine why common approaches fall short, including lack of structured application between learning and practice, weak connections to classroom instruction, and limited accountability for results at the student level. Through guided analysis, participants will map their own leadership development efforts using a practical diagnostic tool that identifies gaps across leadership learning, application, and student-level impact. They will explore strategies to strengthen alignment across leadership practice, teaching quality, and student outcomes, including connections to career readiness pathways, equitable access to advanced coursework and opportunity, and teacher retention across diverse school contexts. Participants will leave with a clear framework, a practical tool, and concrete next steps that can be immediately applied to redesign leadership development systems in ways that produce visible, measurable results.