Focus on social and emotional intelligence competencies to improve effective leadership has become commonplace in the corporate arena and is now considered by many a prerequisite to successful job performance and outcomes (Antonakis, Ashkanasy, & Dasborough, 2009; Grant, Curtayne, & Burton, 2009; Spence & Grant, 2007; Kampa-Kokesch & Anderson, 2001; McGovern, Lindemann, Vergara, Murphy, Barker, & Warrenfeltz, 2001). Only recently has a similar trend become recognized and more accepted in the field of education (Patti, Senge, Madrazo, & Stern, 2015; Patti, Holzer, Brackett, & Stern, 2014). Few studies exist that study the role that educational leaders’ social and emotional competencies in play in their job performance and effectiveness; none exist that explore such development with aspiring school leaders. This quasi-experimental pilot study evaluated the effectiveness of a post-graduate development program for aspiring school leaders that incorporates social and emotional intelligence based on the Goleman-Boyatzis model (Goleman, Boyatsis, & McKee, 2001) and inspired by the original concept of emotional intelligence (Salovey & Mayer, 1990). The interrelated social and emotional competencies explored in this study form four core clusters that include: 1) self-awareness, 2) self-management, 3) relationship management, and 4) social awareness (Brackett, Rivers, & Salovey, 2011; Goleman, 1996; Salovey & Mayer, 1990; Zins & Elias, 2007). This study’s sample consisted of 32 aspiring leaders who participated in a post-graduate educational leadership program at a university in New York. The study evaluated whether or not there were any effects of focused social and emotional intelligence content and skills on aspiring leaders’ emotional intelligence (EI) and other related characteristics such as assertiveness, empathy, mental health, personality, and openness to experience. Post-tests on the various characteristics after one semester found no statistical significance in the tested variables. However, after two years, when the social and emotional intelligence competencies were post-tested (ESCI-U), there were significant findings in the student candidates’ self-reported competencies directly related to leadership. Paired t-test comparisons of the means of Observer raters’ scores did not find statistically significant differences in the competencies assessed. This article discusses these findings as well as the strengths and challenges of implementing social and emotional intelligence development within an aspiring school leaders program; finally, it provides recommendations for further program development and studies.