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This paper develops the idea of researching as a critical secretary: a reflexive strategy of participant-observation that explores how power is encoded in organizational texts, roles, structures, and routines. I weave critical and institutional ethnographic methodologies to build toward a practical four-stage model for enacting this strategy. I then draw on data from an initial effort to conduct research as a critical secretary to illustrate how this strategy allowed me to analyze the ways in which structures of gender and race shaped the values and norms evident in two contrasting digital education reform organizations. I conclude by discussing how researching as a critical secretary animated an anti-oppressive scholarly praxis beyond the temporal and situated contexts of ethnographic fieldwork.