The rapid shift in schools' demographics across the United States calls for a strategic and thoughtful change in the recruitment, retention, and development efforts of school districts as they cultivate the leadership pipeline to prepare future school leaders. District leadership pipeline programs must strategically and actively recruit and prepare ethnically diverse and culturally competent leaders who better reflect the demographics of the students they serve. The purpose of this descriptive qualitative case study was to investigate how Latino principals overcome the barriers and challenges faced while advancing in their careers. In addition, this study identified the recruitment and development practices employed by district leadership pipelines to increase Latino representation in the principalship. This study aimed to uncover useful information through the lived experiences of three Latino principal participants to strengthen Latino participation in district leadership pipelines. A series of three semi-structured interviews in a two-week time sequence was used to capture their lived experiences. The findings of this study suggest that having systems of support through mentoring and sponsorship increases Latino participation in leadership positions. Intentional pairing of mentors must go beyond looking at only professional affiliation. Understanding and leveraging the cultural assets that aspiring school leaders bring to the role of the principalship will be critical in supporting Latinos on their leadership journey. [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.]