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This paper presents findings from a study of central office instructional leadership practices, structures, and routines that are likely to facilitate organizational change. Using concepts from organizational sensemaking theory to highlight the collective sensemaking and “sensegiving leadership” necessary to build the shared organizational understandings required for fundamental change, this qualitative case study examines the uptake of a change initiative around principal professional development planning in a large urban school district. Findings suggest that routines and structures that create time and space for continual, collective revision of instructional leadership work, as well as deliberate, hands-off guidance from a high-level district leader are vital ingredients for fundamental shifts in school district instructional leadership practice.