Purpose: This article details findings on how leaders of deeper learning schools establish, maintain, and propel unique teaching and learning environments. In this case study, the authors present findings from data collected through interviews with 30 leaders of self-proclaimed deeper learning initiatives and site visits to those elementary and secondary schools. Design/methodology/approach: Using a case study approach, the authors collected data from interviews and observations of 30 school leaders. Findings: The study's findings indicate how leaders of schools that engage in deeper learning tend to adhere to three core practices. First, the leaders of deeper learning schools in this study intently listened to the community to ascertain needs and desires; this drove the vision. Second, leaders of deeper learning schools created learning spaces that empowered students and gave them voice, agency, and choice. Third, leaders of deeper learning schools sought to humanize the schooling experience. Practical implications: This study provides actionable examples of what leaders currently do to engage kids and teachers in deeper learning. These leaders offer insights into specific actions and practices that they espoused to make the schooling experience markedly different. Originality/value: Previous studies focused on the deeper learning of schools and students. This is one of the first studies to focus on the interplay between deeper learning and school leaders.