The purpose of the chapter is to explore design conversation as it is lived out in the communication processes amongst stakeholders involved in school change and design of new learning environments. School reform efforts in various countries look for increased participation in design and decision-making at the local level. Design conversation, embedded in the theoretical framework of systems thinking and systems design has not, to date, been researched as a theoretical construct. Experiences and perceptions gathered in a phenomenological research study are presented. Data were gathered at three internationally dispersed sites in the Czech Republic, Germany, and the United States of America. The results indicate that teachers do value the process, describe changing mindsets, designing visions, concrete strategies, equitable participation, trust, and risk taking. The study hopes to lead those interested in school change to increased use and evaluation of design conversation in educational systems design.