This paper focuses on a challenge within the School of Design at Glasgow School of Art, namely how to support critical and contextual discussion in a workshop setting. It is my experience that some students do not feel able or want to contribute to the critical dimension of these sessions; others object to the tone or contribution from other students; and there is a difficulty for everyone in knowing how to address sensitive or challenging subjects. Within design education, it is accepted that while the acquisition of procedural knowledge is important, more important still is that students become active critical thinkers and communicators. But what makes a critical space in an Art School and how is it cultivated? What is my role as the educator leading critical and contextual discussions, and how can I work with and support students to develop their critical skills? Furthermore, what pedagogical strategies would be useful to support critical engagement? This paper draws on pedagogical research conducted as part of a Practitioner Enquiry Research Project for the PG Cert in Higher Education Learning, Teaching in the Creative Disciplines. The project examined how to cultivate critical discussion and the ingredients necessary to support it in the context of my Year 3 course ‘The Politics of Space’. In this project I tested out different ways to ‘choreograph’ a critical discussion about public space that allowed for honesty, nuance and robust debate between participants, while maintaining a safe, respectful environment. This paper will discuss that research into different methods, such as the extent to which collaborative learning and scaffolding of critical thinking skills is helpful when crafting teaching sessions. I will also reflect on the dynamics within a critical discussion, with the ultimate aim of improving as an educator.