This qualitative case study examined leadership development and mentoring in a chapter of Jack and Jill of America (JJOA), a national organization for African-American women and their children focused on leadership, cultural awareness, and civic duty. While JJOA is a national organization, individual chapters are self-governed, and there is no nationwide mentoring program to help mother members provide the necessary guidance, training, education, and skills to teen chapter leaders. Insufficient mentoring creates missed opportunities for teens as they transition into leadership roles in the future. The purpose of the study was to answer three research questions that focused on teen members', alumni members', and past and present JJOA officers' perspectives of the value of a mentoring program to teens' and alumni's future personal and professional lives. This study examined the role and importance of mentoring from the perspective of different members of a single JJOA chapter in the Eastern region of the United States. A total of 10 individuals from the Southern Maryland Chapter of JJOA participated in the study. The study's sample consisted of teens, alumni, and past and present chapter officers. Data collection included semi-structured interviews, in-person observations, and photo elicitation. The data were then analyzed to answer the study's three research questions. The findings indicated that without a formal mentoring program, teens lack (a) the confidence to pursue leadership roles, (b) the skills needed for success in college and beyond, and (c) communication and leadership acumen prior to running for office. Based on the study's findings, JJOA chapters should explore formal mentoring as a way to promote leadership development among teen members. [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.]