Decades of interest in responsible leadership has drawn critical attention to how future leaders are formed by academic leadership education. It has forced teachers to increasingly contemplate what leadership ideas and pedagogical practices they bring to the classroom, and who they are in the light of the ideas and practices they adhere to. In this ‘Leading Questions’ we take an interest in how leadership educators’ identities are formed and exploited in everyday teaching. The questions and comments we present are part of an ongoing conversation on identity work triggered by the controversies we experienced when co-teaching a course titled Rethinking Leadership at a renowned international business school. Where most discussions of identity work in a business school context only highlight the distressing and unfavourable aspects of identity work, we take a different approach. We confess how we struggle with our own identities as leadership educators. We then argue this identity work comes with pedagogical potential, yet to be accounted for, especially relevant to future education of critical and responsible leaders. Finally, we confess that even if our years of conversation on our different teacher identities did not result in a distinct pedagogical model, it dramatically changed and charged our ability to intentionally make space for controversial identity work in the leadership classroom.