This chapter narrates elements of collaboration amongst three ‘critical management studies’ researchers who have a shared interest in enhancing their teaching and facilitation practice. The chapter is framed by personal narratives where the authors reflect on concerns in relation to their experiences teaching/facilitating in particular higher education and industry contexts pertaining to various institutional expectations and constraints. In narrating their subjective vignettes, they open up a dialogue regarding the complex, relational, and emergent nature of our intersubjective social experiences, and engage techniques of ‘critical reflexivity’ drawing on ‘in the moment’ interactions with participants/students to enhance learning processes. A key contribution of the chapter is the attempt to take autoethnography beyond its prevailing individualist uptake by revealing the potential of autoethnography as a collaborative learning process.