The purpose of this qualitative descriptive study is to explore how senior district administrators and principals describe the influence of the mentoring they received as a novice principal led to their transformative learning resulting in new capabilities and influencing career choices in the Southwest. The overarching research question was: How do senior district administrators and principals describe the influence of the mentoring they received as a novice principal led to their transformative learning and built new capabilities? The theoretical foundation was transformative learning and mentoring. The sample comprised ten principals and five senior district administrators in a single school district in the Southwest. Data collection for this qualitative descriptive design included the Learning Activities Survey, semi-structured interviews, and focus groups. Data analysis included descriptive statistics, reflexive thematic analysis, and a description of the phenomenon. The findings from this study identified twelve key themes resulting in the illustration of the phenomenon. This study generated sufficient data to warrant further study of the model as described in the phenomenon. Therefore, recommendations for future studies include exploring why principals leave the profession, district support of principals and the impact on retention, and the most important competencies to develop in principals. [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.]