In this dissertation, I examine how IT can support individuals, and in turn their organizations, in learning about and knowing their external environment on the Web. Specifically, I examine novel-knowledge discovery in the context of the multi-level organizational learning process, focusing on cognitive developments and changes to mental models. Novel knowledge is defined as knowledge that is potentially strategically important to the organization, not currently known to the organization, indirectly relevant and therefore difficult to find. Novel knowledge is proposed to be one of three different types of knowledge that organizations seek to discover in their environment. A theoretical framework is developed to identify the sets of tool characteristics, collectively referred to as levels, which are proposed to support the discovery of different types of knowledge, as well as different modes of learning and learning processes. In addition, extensions to the 4I organizational learning process model are proposed, specific to searching and learning on the Web: 1) adding a fifth process – information foraging and search-term development, and 2) adding a fourth level to the learning process – the machine-level. A competing theories approach is used to develop a rich understanding of knowledge discovery and learning on the Web. Understanding which types of tools are useful in different learning contexts has implications for learning effectiveness and may help firms understand how to “manage” their learning. Tools for the discovery of highly novel knowledge are less prevalent than tools to support the other levels of knowledge discovery. Accordingly, a design theory for novel-knowledge discovery tools is proposed based on organizational learning theories. An instantiation of the design theory, a novel-knowledge discovery tool, is developed and tested within the organizational learning process and compared to tools at the other two levels of knowledge discovery. In addition, different processes involved in using a novel-knowledge discovery tool at the group level are examined. Three separate studies were conducted, including a lab and field experiment, and case study. The results are proposed to demonstrate how novel-knowledge discovery tools can support organizational learning. / Thesis (Ph.D, Management) -- Queen's University, 2008-08-26 09:25:31.367