This paper explores the role that first impressions play in two different relational contexts: psychodynamic treatment and negotiation. Although the goals of therapy and negotiation are very different, both endeavors rest on the capacity of the participants to engage in a process of constructive dialogue, and “to get things done” via a relationship. We argue for the utility of an interdisciplinary conversation between psychoanalysis and negotiation, and specifically suggest that exploring these similarities and differences about first steps in building a working relationship may be instructive for practitioners in both professions.