This article presents the findings of a qualitative study conducted in 2014 with 16 experienced heads of school in the New York metropolitan area. The study was designed to better understand the skills and practices that they view as critical to leading and managing independent schools. The data collected speak to each head's ability to manage the school's leadership team and board of trustees, communicate effectively and empathically with all constituencies, and build meaningful relationships based on trust. Due to the study's limited geographical scope, further qualitative research is needed to build a more complete understanding of independent school headship. The findings, however, provide a framework for leadership skills and models of tried management practices that may enhance the capacity of school heads, present and future.