This article envisions GSS-enabled interventions as electronically supported discourses, designed and evaluated against a gold standard of ideal speech in a perfect communication environment. A model incorporating Habermasian validity claims is employed to evaluate an urban planning meeting (including the use of the Groupsystems software tool) and meeting follow-up. Support is found for four propositions, all of which focus on the degree to which the application of the model unlocks practical value. The paper concludes with a discussion of the nature of the knowledge discovered in GSS-enabled interventions and the potential for a Habermasian analysis of the knowledge discovered in other collaboration systems and technologies.