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School districts are spending millions of dollars to reorient the roles of principal supervisors to develop principals as instructional leaders. However, the theory and practice on which the role of the principal supervisor is based has yet to be articulated. This qualitative multiple case study profiles three principals and their supervisors in one district that was an early adopter of this model of principal supervision. Data was gathered from interviews of principals and principal supervisors, observations of collaborative work, and documents over an eight month period. Findings revealed that principals refined their leadership practice with the coaching support they received, but practices used by the principal supervisor, and steps taken to lead instructional improvement by the principal, differed across schools.