The origins of the American educational system have always included a character education component. Teaching students moral values and the ability to know right from wrong is a component of the educational mission of our society. Character education evolved over the centuries, yet the core values of implementing right from wrong and the necessity of building moral values into our nations fabric has not changed. As we continue to move into the 21st century, technology and social issues have evolved, and character education programs and curriculum must adapt and evolve to our modern times in order to meet the needs of all students, as well as our society as a whole. The purpose of this qualitative study was to explore how principals have implemented The Leader in Me (TLIM) program in elementary schools in a large urban school district. Through interviews with 12 principals, the researcher gathered information about their experiences with the TLIM program, including why and how the principals implemented the program, how they measured its success, what they have learned, how they have adapted the TLIM program for their own school environments and cultures, what they would change, and what advice they would give to other school leaders. The findings from this study suggest that all 12 participants agreed that TLIM program had a positive impact on the culture and communities of their schools and that although the program is costly, many participants were eligible for TLIM grant funding. Additionally, the results revealed that the participants acknowledged the all-inclusive nature of TLIM program and were able to measure the success of TLIM through multiple evaluation systems. Participants saw a decrease in disciplinary referrals as well as student suspension rates. Additionally, the findings revealed that participants found implementing TLIM in their schools had little to no push back from the school community. Participants acknowledged that they had autonomy in celebrating success of TLIM in their schools as well as autonomy in the orientation and implementation process of incorporating TLIM in their schools. The insights gained from this study will inform and assist other schools leaders in implementing TLIM and other character education programs. [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.]