This article is intended to explore the theoretical background behind complexity science in management and leadership and provide ways to approach educational leadership research through the use of strange attractor metaphors. Historical and contemporary leadership strategies have incorporated modernistic models that sometimes perpetuate problematic aspects of educational management rather than provide progressive solutions. Several leadership researchers have shown, however, there is tremendous potential for the emergent properties of complexity theory in organizational dynamics. The recognition and utilization of strange attractors as metaphorical constructs of chaos theory also provide us with an elaboration of teaching and educational leadership theory. Strange attractors seem to exist metaphorically in many aspects of the organizational dynamics of our educational institutions. The use of metaphors in lived experience is described, the scientific background behind strange attractors is introduced, and connections are made between strange attractors and human interaction. Strange attractors are then metaphorically described in organizational settings as shared vision, team processes, and information flows used as positive feedback mechanisms.