Independent schools face a head of school problem, as sitting heads of schools approach retirement at a high rate. The head of school role is complex, all-encompassing, and the newly appointed head of school is likely ill equipped to manage the role without mentorship. There is a gap in the literature regarding what challenges a newly appointed independent school leader faces; the perceptions of veteran heads of school regarding effective leadership; and the experiences of mentoring from the perspective of both the veteran head and the newly appointed head of school. This qualitative study explored the unique challenges a newly appointed head of school faces and the strategies veteran heads of schools identified to help address such challenges, all within the context of a mentoring relationship. Through purposeful sampling, six veteran heads and six newly appointed heads from various geographic locations in the United States were recruited and interviewed individually over Zoom. Data were analyzed using reflexive thematic analysis. Themes for newly appointed heads included quickly learning and embracing the school culture; faculty relations; initial lack of trust within the school community; financial aid and fundraising; rely on a mentor who truly understands; visibility; and professional growth. Themes for veteran heads included school affordability; building trust while leading; board relations; being mission-centric; personally connecting, assemble an excellent administrative team, self-care and work boundary strategies; reciprocal benefit of mentoring; and informal mentoring structure. Active listening and clear communication are implications of practice for a newly appointed head. [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.]