The conducted research evaluates the leadership characteristics of 178 executive directors in non-profit organizations throughout seven cities in North America; six in the United States and one Canadian. This research provides schools of social work quantitative data regarding the educational and employment backgrounds of non-profit executive directors and the leadership behaviors and activities they employ in their work in organizations. This research, critical to planning for the future leadership needs and training of non-profit leaders, resulted in significant differences in relocation practices, boundary spanning activities, as well as identifying a period of time in which non-profit organizations began employing executive directors with non-social work educational backgrounds and having for-profit experience. Implication for social work academia include the leadership curriculum and succession planning investments in social work, as it relates to non-profit leaders newly entering the field from other disciplines.