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In this paper we introduce a novel method—generative critical conversation (GCC)—which we propose can develop educator and researcher reflexivity and enhance criticality in enterprise and entrepreneurship education (EEE). We ground this method in literature from the field of educational research and reflexivity scholarship. We hybridize three methodological elements—the self-study strategy of reflecting on recorded material; exploring lived experiences through cogenerative dialogue, and a focus on critical questioning—to facilitate the development of educator-researcher reflexivity. We use illustrations from our own conversations to show how GCC opens up space over time to access and move between levels of reflexive interpretation. We suggest enabling conditions that support GCC and its potential as a method for developing educator-researcher reflexivity across EEE, initial teacher education, and other fields of research.