The last couple of decades have seen a proliferation of approaches in education which attempt to either extract the essence of individual achievements, and apply these universally, or devise policies almost as an ideological thought experiment, and then construct a series of aims, objectives, and targets, to be engineered into particular institutions. Both of these approaches ignore a critical mediating factor – the individual context. This is a fatal mistake, as it ignores the personal understandings of local situations, and therefore the humanity and appropriateness of the educational exercise. This article then argues that context is critical to a proper appreciation of the challenges of education leaders at the beginning of the twenty-first century. It will, however, suggest that context is not a simple term, as there are both different meanings and different levels to the term. It therefore discusses the meanings of context before arguing that there are at least four levels of context. In so doing, it suggests that an appreciation of current contexts suggests the need for four leadership dispositions – what are called ironic, autonomous, ecological, and public dispositions.