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This case study examined how an executive coaching program was implemented at five low performing schools. The program’s purpose is to improve the instructional leadership capacity of principals via embedded, ongoing professional development. Semi-structured interviews were conducted in person and by telephone. This study found that the majority of sites reported changes in principals’ leadership practices after engaging in “joint work” with an executive coach for at least two years. Furthermore, differences in implementation of the program at various sites were linked to individual coaches’ philosophies about the purpose of coaching.