District-level central office administrators (COA) and school principals influence the efficacy of reforms aimed at improving outcomes for marginalized students. This qualitative case study examines the experiences of COA and principals from one reform-oriented school district during their participation in a master's degree program in leadership offered by a business school. Thematic content analyses of course syllabi and semi-structured interviews of program participants revealed that the program content reflected the market-based contexts school leaders and mid-level COA faced by focusing on business leadership principles with little emphasis on instructional leadership. Integrating principals and mid-level COA into one cohort fostered a boundary-spanning community of practice that could facilitate district-wide reform efforts. This exploratory study questions the boundaries often present between the professional development of principals and COA and invites further research on the potential of cross-boundary professional development. [Note: The publication year (2023) shown in the citation on the PDF is incorrect. The correct publication year is 2024.]