This dissertation in practice aimed to address the critical missing link in the relatively new research area of self-compassion by focusing specifically on the connection between self-compassion and transformational leadership behaviors. This quantitative correlational research study addressed that gap by determining if, and to what extent, a relationship exists between self-compassion, transformational leadership behaviors, and gender of heads of school and principals of independent schools in the United States. The hypothesis that was posed for this investigation was that there is a statistically significant relationship between self-compassion and transformational leadership behaviors after controlling for gender. The results showed self-compassion was significantly positively correlated with transformational leadership (r = 0.78, p < 0.001), indicating that participants with higher levels of self-compassion tended to have higher levels of transformational leadership behaviors. The aim of this study was to create a series of recommendations for school leaders and educational leadership programs, including requiring self-compassion training for new and veteran leaders and offering self-compassion training programs in a variety of settings. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]