ABSTRACT Starting in Vienna in the 1920s, Anna Freud’s first tentative attempts at observing children became a crucial component of the ‘double approach’ which integrated direct child observation with psychoanalytic reconstruction. This approach enabled the detailed study of unfolding developmental processes and the construction of a theory of normative as well as pathological child development. Direct child observation was an integral component in the curriculum of the Psychoanalytic Master’s degree at Anna Freud’s Hampstead Clinic (later, the Anna Freud Centre) in London. The process, experience and value of observation for students of psychoanalysis is described, focussing on observers in a therapeutic parent-toddler group. The experience of observing or being observed is discussed from the perspective of staff facilitating the group, students, parents and children.