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This article proposes a design theory for collaborative technologies based on pragmatism and multiple discourses (Habermas 1984; Schultze and Leidner, 2002). The practical value of the theory is explored via empirical data gathered in the context of an intervention enabled by group support systems (GSS) in regional governance and comprehensive urban planning. During the study representatives of the regional council and territorial authorities meet to evaluate three scenarios prepared over a seven-year period. Qualitative measures were obtained of the degree of confusion (lack of understanding) and conflict (lack of trust) before and after the meeting, and participant performance and satisfaction with electronic discourse. The focus question is "do electronic discourses enhance participant's understanding and trust in scenario planning?"