Purpose: To identify key issues that university-based leadership coaches act upon in work to fortify the developmental opportunity of the clinical experience for aspiring principals, and how leadership coaches act upon these issues. Research: Data include roughly 75 hours of interviews with two cohorts of aspiring principals and 25 hours of interviews with the five leadership coaches assigned to these aspirants (N = 25). Drawing theoretically upon brokering and social networks brokerage, analysis of transcripts used both deductive and inductive coding. Findings: We identified five key issues acted upon by leadership coaches, including--(a) relational issues between the aspirant and the mentor; (b) insufficient time between the aspirant and the mentor; (c) aspirant identification of and engagement with clinical work of developmental importance; (d) aspirant access to and/or authority for clinical work; and (e) the developmental supports provided to aspirants by mentors. Drawing upon theories of brokering, social networks brokerage, and third-party influence as we examined how coaches acted upon aspirant issues, we found that coaches regularly worked as brokers and third-party influencers in these pursuits. The structuring and design of coaching as well as coaching tools proved vital to this work. Conclusion: Leadership coaches tethered to principal preparation programs can play an important role in fortifying the developmental opportunity of the clinical experience. Our findings suggest an assortment of implications for leadership preparation, the deployment and design of university-based leadership coaches, and the development of such coaches tied to principal preparation.