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This study extends the growing base of research on principal coaching by examining how coaches adjust their strategies for principals in different contexts, further considering how these adjustments influence the coaching relationship. Data include interviews, observations, and coaching logs from a sample of principals and coaches in a University-based principal coaching program. Findings explore the balance of trusting relationships with necessary accountability structures. Coaches employed directive and facilitative strategies variably based on each principal’s individual needs. The study concludes with a number of recommendations for improving the supervision and support provided to principals, in particular, considerations for how coaching might complement the work of central office leaders in the supervision of principals.