This article is an account of our experience as educators, of using Boal's theatre in the management classroom to enhance career reflexivity in future managers. We developed the "Career Stakeholders exercise" to facilitate students to draw upon their individual and collective experiences in making conscious career choices. Adapted from Boal's "Cop in the Head" techniques, this exercise is aimed at identifying and working with internalized messages and expectations that influence career decisions. Our use of Boal's theatre in this format provides a playful, non-threatening and experiential approach for reflection, reflexivity and dialogue. Here, we discuss the premise and context of our course, rationale and process of developing this exercise, our experiences and insights as facilitators, and student feedback, to present the benefits and challenges of introducing Boal in the management classroom.