This study explored the extent that the Houston Independent School District's (HISD) assistant principal leadership training program (AP1/AP2) facilitated reflective learning of the 2014-2015 cohorts. In addition, the evaluation examined the academic achievement of students in schools of AP1/AP2 cohort participants. Leadership training applied the ISLLC framework that focused on creating a shared vision within the community, a culture of student learning, efficient management, and ethics to prepare participants for roles as principals. A total of 79 HISD leaders were identified as AP1 cohort participants and 66 leaders were AP2 cohort participants. Eleven training sessions were provided to strengthen their practice as leaders, increase their instructional knowledge, skills, and strategies; and inform their future feedback with teachers in 24 skill areas. In general, all ISLLC standards were reflected by AP1/AP2 survey respondents in at least one of the training sessions, with data for monitoring and improvement, district curriculum implementation, and mentoring staff/modeling as the three most prevalent skill areas considered as benefits in their reflective learning. Gaps were noted in participants' reflections of benefits in skill areas related to clean and safe schools, effective presentation skills, team leading and building, and technology. This may be related to these areas being emphasized in principal leadership training rather than AP1/AP2 training. Considering HISD's focus on literacy, the majority of AP1 and AP2 cohort schools made positive changes on the STAAR reading and English I EOC tests from 2014 to 2015. Recommendations are to continue to develop the program by strongly addressing all state and national educational standards to support assistant principal's roles as leaders and their potential roles as principals in HISD.