This essay argues for the utility of a sociohistorical theoretical perspective on culture and agency in the analysis of context-specific educational leadership. First, we review literature that addressed the importance of context, frameworks that richly described context, and we discuss research that purposefully documented principals' interactions with their context. Through this review, we show that the literature lacks a clear theorization of how one engages their agency through the context. Next, we describe how the anthropologists Holland and colleagues used the concepts of figured worlds and authoring selves to outline the way a person's agency is developed. We therefore argue for the utility of a sociohistorical theoretical perspective on culture and agency in the analysis of context-specific educational leadership. We test the utility of these concepts by applying them in a secondary analysis of published case studies of context-specific educational leadership. We argue that the concepts of the "figured world" and "authoring selves" highlight the processes of context-specific leadership and that the framework is, therefore, useful if one wants a description of not only 'what' school leaders do but also 'how' they do it.