Some problems confronted by managers include ill-formulated wicked planning problems, a type of problem that is difficult to solve because, in part, it is difficult to know what the problem is. The Churchmanian Knowledge Management Systems (CKMS) (Richardson & Courtney, 2004) is comprised of design principles for aiding system designers, managers, and clients who make decisions pertaining to these ill-formulated wicked planning problems. Problemography theory is proposed as a method for developing a CKMS. The method aims to measure CKMS development by using development tools that enables stakeholders and theoreticians to clarify CKMS development. A study was conducted to test a proof-of-concept development tool. The tool tested is a proposed list of processes that occur during CKMS development, processes derived from Churchman's (1971) Singerian inquiring systems theory. A gap analysis was performed whereby the proposed processes were compared with the processes found during a case study of people confronting issues related to the 'wicked' problem of Florida's invasive plant problem. A second study was conducted to explore possible design principles for developing a CKMS. Two proposed design principles, Every Person Principle and Connectedness Caretaker Principle, were used to develop a Describe a Wicked Problem Inquiring System (DAWP), a Web site which aims to enable inquirers to confront wicked problems. Participants in the study formulated problems related to Florida's native plants and suggested potential solutions. Using Wengraf's (2001) theory-driven qualitative research, interviews with participants were analyzed and the results suggest that the Web site being developed enabled the consideration of the ethical ramifications of knowledge.