Complexity and uncertainty have long been problems for organizations of all types. Organizational members do not do a very good job of dealing with the complexity and uncertainty as research shows that when faced with complex situations humans often turn to the same sources of information repeatedly (a practice that will eventually betray them), and/or reduce the amount of scanning that they do (Weick 1995; Boyd and Fulk 1996). Organizations often turn to information systems to help them deal with the complexity, but they often take a techno-centric view of knowledge that does not incorporate the human qualities needed for unstructured decisions (Malhotra 1997; Courtney 2001; Malhotra 2001). Additionally, there are times when the information systems that we are using may hinder the processes of dealing with the complexity (Weick and Meader 1993). Weick's (1995) concept of sensemaking is believed to help us to deal with this complexity. In his work with Meader (1993) he wonders what the effects of a sensemaking support system would have, but he does not have the answer because they state that it has not been asked. This dissertation answers the call of Weick and Meader as well as other scholars that have called for sensemaking and human intuition to be included in our information systems. This is accomplished by viewing sensemaking from an inquiring systems perspective (Churchman 1971) to develop a kernel theory that will be used in the context of design science to develop design requirements and principles for a sensemaking system. These design principles are then used to build an instantiation of the system in the form of SenseMan, a system designed to help a local government agency deal with complexity in the context of software updates. Finally the design is evaluated for its effectiveness in dealing with the complexity of in this context using both quantitative and qualitative methods.

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.