Dissertation supervisors (undergraduate as well as graduate level) currently face two key challenges – (1) how to develop students’ analytic thinking in a context where proper use of artificial intelligence (AI) is rapidly evolving; and (2) how to effectively supervise increasingly large student groups. This PDW will explore these challenges from the human side, asking: how to motivate students to use their own brains; how to harness peer group dynamics; and how to work with the underlying dynamics of these relationships. To open novel perspectives in this PDW, we will draw on two systems-psychodynamic concepts that have informed us in our experience with hundreds of students. Attachment theory (Bowlby, 1944; Ainsworth, 1985) provides insights related to the supervisor-supervisee relationship, and group dynamic theory (Bion, 1952) touches on the effectiveness of peer study groups. Although grounded in theory, our presentation is practical. In this PDW we outline a framework and toolkit for supervisors for guiding and supporting their students through this cognitively and emotionally challenging process. We will also invite participants to share difficult supervision experiences, providing material for a “supervisor supervision” approach in this session.