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This qualitative multi-case study examines the organizational structures that impact principals’ work in large organizations using mayoral control for reform. This study focuses specifically on principals to understand their unique role as mediators occupying a pivotal space between policy and practice. This study centers on two groups of principals: those that are career educators with strong institutional ties in their district and those that came to the principalship through non-traditional routes under mayoral control. Preliminary findings suggest that the nature of structural change in the institutional environment surrounding schools may be intentionally incremental and at times “creatively ambiguous”. As senior leadership clarify the direction for schools’ policies, they work to orient or reorient the districts’ structures to support policy goals.