Despite the complexities and challenges faced by principals on a daily basis, the literature posits that mentoring can be impactful to the individual mentee, as well as the potential benefits to the system in which they serve (Gross, 2009). While the benefits of mentoring are reviewed from the perspective of psychosocial development (Mertz, 2004), professional development (Gray et al., 2007), career development (Williams et al., 2009), the topic of readiness for principal mentoring is lacking in the literature. This study is a qualitative interview study conducted with five middle school principals and five middle school assistant principals in South Carolina. The study explores the attributes of principals who demonstrate readiness for mentoring, their self perceptions, and the perceptions of assistant principals. My research goal is to contribute to developing and enhancing the principalship pipeline for local and state education agencies through on-the-job support and mentoring. As many schools and communities struggle to staff schools with highly qualified school leaders, this study seeks to serve as an impetus for intervention through mentoring relationships between assistant principals and principals. In response to Title II, Part A of The Every Student Succeeds Act (ESSA), states have the option of setting aside a discretionary 3% of Title II, Part A funds as outlined in ESSA to support the professional growth and development of principals, in order to retain them in schools while supporting their leadership skills in order to provide high quality instructional programming for students (U.S. Department of Education, 2016). This study will provide research, practice, and policy recommendations for a mentoring framework to support in-service and aspiring principals at district and state level. [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.]