Education and business, as professional disciplines, seem, at first glance, to be linked. Both are social enterprises involving relationships and processes derived to accomplish a particular set of tasks. However the track record of injecting business methodology into school communities has been poor. Historically the introduction of management practices borrowed from parallel industries and inserted into school systems has been a matter of routine. Any lack of success in implementing new management techniques in educational operations is always explained as a good idea poorly executed. The suitability of the tool is never questioned. This paper examines the operational and strategic issues that separate business ideology and school management in an attempt to describe why the marriage has been unsuccessful. In particular, the reductionist methodology of business management is compared to the systemic nature of educational enterprises. The contrast in the fundamental characteristics of the two disciplines may serve as a cautionary tale for school leaders who are encouraged to use modern business management tools to improve the efficiency of their operations. Given the lack of convergence as described in the paper, it is interesting to contemplate how we train educational leaders and consider what tools are provided for school-level administrators to help them lead their communities.