There is increasing interest in the field of leadership preparation about the opportunities that robust performance assessments may provide to capture and evaluate the complexity of school administrators' work. Heretofore, the conversation about administrator performance assessment in leadership preparation has mainly centered on the development and impact of large statewide assessments that grow out of a Cartesian epistemology of individual knowledge possession, in which individuals must demonstrate mastery of a set of static knowledge and skills. We analyzed the characteristics of a performance assessment system that deliberately accounts for the organizational complexity of practice and knowledge generation in its design. Candidates are assessed by faculty and coaches on state-wide and program standards, but instead of producing evidence of their practice as individuals, they are assessed within simulated practice-based scenarios that require them to both draw on their extant individual and collective knowledge and build and act on new knowledge as they move through the simulation. Our analysis enables us to dimensionalize issues related to state mandated performance assessments and their implementation by preparation programs.