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In the evolving and interconnected 21st century world, learners need to develop capacities for critical reasoning, knowledge application, and problem-solving along with analytical and communication skills. Providing learning experiences that nurture these skills—deeper learning—requires a transformation of school structures and classroom practices. Likewise, conceptions of school leadership, and leadership preparation, need to evolve so school leaders can acquire the knowledge, skills, and dispositions needed to enable, encourage, and sustain deeper learning. This study uses a multi-case study approach to understand what deeper learning leadership looks like and how leadership preparation and professional development programs can best prepare principals for this new type of leadership. It also includes policy recommendations to support leadership preparation for deeper learning at scale.