The purpose of the qualitative phenomenological study was to explore educational leaders’ perceptions of the factors that influence unwed pregnant and parenting students enrolled in a school-based parenting program to complete high school by conducting in-depth interviews of 20 educational leaders in Dougherty County, Georgia. The chosen leaders were personnel from the Network of Trust School Health Program, a division of Phoebe Putney Memorial Hospital. Findings of the study reflect ways that school leaders can employ teen pregnancy prevention programs more effectively to reduce dropout rates and improve graduation rates. The results could help to employ new pregnancy prevention instructional strategies replicating the lived experiences of 20 educational leaders. Data collected from the interviews were transcribed and coded in a qualitative software analysis program and organized into the following themes: (a) perceptions and experiences, (b) services and support, (c) assessing students’ performance, (d) barriers in school-based parenting program, (e) perceived needs of unwed pregnant and parenting students, (f) childbirth/parenting curriculum, (g) professional development, (h) reducing dropout rates and improving high school graduation rates, (i) services and programs provided by community partners, and (j) role of education in policy evaluation. The results of the study led to the construction of the school-based parenting leadership model to assist school district personnel in developing educational programs and community outreach programs focused on reducing dropout rates and improving high school graduation rates through education and collaborating together with federal, state, and local governments. The partnership of synergism can be a powerful tool to renew individual lives, both academically and socially.