Two questions are posed in this study: What is the role of social and political acumen in dynamic educational leadership, and what are the implications for leadership development programs? The philosophical, psychological, and the sociological characteristics of leadership were investigated to understand the role of social and political acumen in dynamic educational leadership, and the implications for planning and implementing leadership programs. Information from sociology, philosophy, and psychology provided the theoretical framework. Literature on leadership supported this framework. The research component included school principals from two large Albertan school districts. Artifacts from these school districts regarding leadership were reviewed. Research methods included a survey, focus group, school visits, and face-to-face interviews. Qualitative methodology was used in the research design, and it was supported by quantitative analysis. Conclusions to the study provided suggestions for the planning and implementation of leadership development programs that could support individuals achieving dynamic leadership.