The purpose of this exploratory qualitative study was to better understand how the leadership of 11 principals impacted their schools' level of engagement in a district-wide deep learning initiative. Findings clustered in three primary areas of principal leadership: vision for learning, leadership approach, and mindset toward others. Principals leading highly engaged schools placed equal emphasis on students' acquisition of knowledge, skills, and dispositions; distributed school leadership widely; and spoke about their work with other-centric language. Principals at less engaged schools placed more importance on content knowledge acquisition, were either disengaged or top down in their leadership approaches and spoke with more egocentric language. This article provides implications for schools and districts interested in pursuing deep learning and leadership, along with recommendations for future research.