The multi-perspective decision-making paradigm [2, 15, 9] is extended to include a dialectical process to assist in developing decision support systems in inwickedlg situations with much conflict among stakeholder groups. A dialectical methodology is proposed and applied to a wicked decision problem namely, urban infrastructure management, to illustrate the model. The dialectical analysis highlights conflict among stakeholders and helps to focus DSS design attention on areas that may be problematical during implementation.