This chapter describes how leaders learn from difference, learn from each other and learn from practice through a ‘leadership exchange’ - a reciprocal research programme in which participants receive orientation to reflexive methods, training in observation skills, and then partner up to shadow each other for three days, before being debriefed and coached to deepen the learning from this experience. We developed the method on an executive masters program in the late 1990’s. Since then it has been successfully deployed on a large scale in global post-merger integrations, customised organisation development interventions, in Masters of Arts (MA) and open executive programmes, and as part of personalised coaching. It therefore contributes to a broad array of applications including research training, leadership formation and organisational development. To explore how it works, and why some distinctive features are important, we utilise psychoanalytic insights into unconscious processes such as ‘pairing’, containment and voyeurism; and systems psychodynamic concepts of role, task and boundaries.