With two-thirds of new leaders being women, it has become increasingly more clear that the face of our educational organizations is changing both symbolically and substantively. The demands placed on public education have also grown exponentially. If society demands that schools become better, then it is necessary to investigate the approaches that school leaders utilize in making decisions. The purpose of this research was to explore the different approaches that educational leaders implement during their decision-making processes. The present study asked 20 school leaders within Miami Dade County Public Schools to report and explain their personal approaches to leadership to determine if these individuals utilize the reporting categories of masculine, feminine, or multidimensional decision making. Following a four-round modified electronic Delphi technique, involving an open-ended questionnaire, a situation specific decision making survey, and two subsequent rounds of reflection, it was determined that the majority of school leaders use a multidimensional approach in making decisions; however, these individuals did not adhere strictly to any one of the specific reporting categories discussed. The study showed that the incorporation of several approaches contributed to the decision-making processes of educational leaders. Although contrary to relevant literature in the field, participants’ leadership approaches were not stringently tied to whether they happened to be male or female. The results of the current study suggest that research in sex-role orientations and gender studies, especially in the fields of organizational and educational leadership, may be evolving. The complex nature surrounding leadership in schools may imply that the infusion of a diverse or multidimensional approach to decision making is a necessary part of steering an organization towards a path that meets contemporary education demands. The environment particular to each school determines the leadership approach that is appropriate. Environmental variables may include the school’s history, the demographics of students and personnel, and details involving the type of organizational culture that has been fostered. Practical implications of the current study include exploring appropriate leadership and the role that multidimensional leadership approaches have in fulfilling the needs of specific schools. These leadership styles not only incorporate masculine and feminine leadership approaches, but also integrate approaches that can be considered androgynous and multidimensional.