The Singerian model of inquiring organizations is reviewed (Proceedings of the Americas Conference on Information Systems, Phoenix, Arizona Aug. 16–18,1996:443–445; Australian Journal of Information Systems, 1998;6(1):3–15, reprinted in Foundations of Information Systems: Towards a Philosophy of Informative Technology, http://www.cba.uh.edu/~parks/fis/fisart.htm.) and two cases of organizations representing the Singerian approach are analyzed. The Singerian organization, based on Churchman's (The Design of Inquiring Systems: Basic Concepts of Systems and Organizations, New York, NY: Basic Books Inc., 1971.) Singerian inquiring system, has ethical purposes, treats employees, customers and other stakeholders with trust and respect, and pursues socially responsible goals, including a respect for the environment. Decision making in Singerian organizations is holistic and systemic, and includes diverse stakeholders, thus requiring an open, cooperative culture, wherein debate is encouraged. Authority is diffuse. Measurement is fundamental. A system of measures is continuously monitored, refined, compared and revised to assess progress. Cooperation and communication are supported with various types of groupware, including e-mail, electronic meeting systems, group support systems, negotiation support systems, discussion forums, knowledge bases, knowledge management systems and the like. The Internet and World Wide Web may serve as resource and dissemination agents for “exoteric” knowledge created by the organization. Two organizations, an Energy Service Company and an academic Center for the Management of Information Systems, are analyzed for their conformance to and success with the Singerian approach. The organizations tended to prosper when the model was followed, but ran into difficulties when it was not.