Since Fall 2014, the number of students attending private school in Massachusetts has decreased from 150,000 students per year to just 120,000 students in 2019. This number is projected to continue to decrease due to many challenges independent schools are facing in the 21st century. This decrease in enrollment has led to a crisis for private independent schools; therefore, schools have had a need to reevaluate what skills are needed to manage this change. Participants of this study were 14 leaders who served as head of school from independent schools across New England. A case study methodology was used as part of this study, with semistructured in-depth interviews as the main source of data collection. Thematic analysis was the method of data analysis with an open coding technique, followed by axial coding to generate final themes and results of this study. This technique aligns with Yin's (2018) postpositivist phenomenological approach due to the step-by-step nature to thematic analysis. Researchers can choose from a number of techniques to analyze data, and the step-like nature of thematic analysis helped me make meaning of the data and keep them organized. Top challenges identified as essential for leading in an independent school according to participants were: (a) maintaining a positive relationship with their governing board of trustees, (b) accessibility and privilege, (c) financial stability, and (d) the enrollment crisis. Participants identified communication, listening, strategic planning, and understanding as the critical skills needed for independent school leadership. Understanding the institution, an innovative mindset, flexibility, and building relationships were identified as essential leadership qualities crucial for leadership success. The results and findings informed a framework for use in future hiring practices for independent heads of school. Skills and qualities could also potentially serve as indicators to the Principles of Good Practice Standards developed by the National Association of Independent Schools. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]