The study includes an analysis and results of a Deliberately Developmental Organization (DDO) effort in an academic department. In this study Kegan and Lahey's conception of a DDO is coupled with the Circular Questioning technique to deepen the intensity of the employees' participation. The ultimate goal of a DDO is to enhance the employees' personal development and thus improve the organization. The authors point to the communication perspective as a way to understand the centrality of dialogue in the Unauthenticated DDO process. It was found that Circular Questioning as a means of intervention allowed the members to generate new thoughts and actions thus building an understanding of their interdependence. It was clear their communication acted as a constitutive force, shaping the lives of the interactants and their future understanding and work in the organization.