This paper proposes a strategy for ethnographically investigating politically disparate education organizations. I develop the notion of researching as a critical secretary: a method of participant-observation conducted alongside those observed to hold the least formal power. Drawing on data from an initial empirical effort to implement this approach, I reflexively examine how this strategy supported my efforts to problematize gendered and racialized relations of power encoded in organizational structures, roles, and routines. I conclude by discussing how researching as a critical secretary animated the aims of critical ethnography and consider how it might function as a broader anti-oppressive scholarly praxis beyond the temporal and situated contexts of fieldwork.