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Numerous large urban districts have moved to a model of principal supervision focused on providing job-embedded learning to principals. We sought to understand how principals describe how supervisors differentiate their practice to support their instructional leadership growth. Through this qualitative multiple case study, we found that principal supervisors were perceived as supportive experts in the areas of: (1) instructional leadership and (2) school demographics. Principals experienced their supervisors as flexible coaches who used the approaches of: (1) inquiry, (2) feedback, and (3) reflection. In sum, when principal supervisors differentiated their support as informed by school context and principal needs, principals formed positive partnerships with their supervisors, leading to the opportunity for them to engage in instructional leadership learning.