This paper was written initially for educators, school psychologists and counselors. It follows a long and mostly fruitful relationship between psychoanalysis and education. We touched on this history and focused on some of Freud's central comments regarding education where he discussed the subjective needs of the student and the educator. Here, the insights of psychoanalysis served to support the revolutionary idea of his time of making the schools consider the pupils' educational and psychological needs. Insights from the training of psychoanalysts also served to define the professional and personal developments that can serve the educators. In our view, educators like psychoanalysts, are involved in growth promoting interactions that require self examination and openness to understand the other. In the paper, we outlined our own work with educators and principals. We demonstrated how principals learned to apply key psychoanalytic terms to their own work, and their own personal reactions to situations. Educators who were supported bv "a potential space that evolved in the training groups, proved to be more open to listen to the overt and covert needs of pupils and staff.