Designing interaction for the global society entails addressing multiple issues and challenges, ranging from the technical and economic to the legal and ethical. Usability guidelines recommend or prescribe courses of action and thus play a significant role in designing universally usable systems. Approaches to organizing and applying usability guidelines need to support processes of deliberation and tradeoff, especially when designing for bridging diversity in shared interaction contexts. This paper describes a deliberative approach to addressing some of these design challenges in a rational way. It argues for organizing guidelines by using concepts from Habermas’s discourse theory and Toulmin’s model of argumentation. Application of the approach is illustrated through a set of research-based Web design and usability guidelines. This paper contributes to the HCI literature by providing a theory-based approach to managing and deliberating on many usability guidelines and related usability issues.