The last decade of the 20th century saw explosive growth in discussions about knowledge—knowledge work, knowledge management, knowledge-based organizations, and the knowledge economy (Cortada & Woods, 2000). Against this backdrop, enterprises including educational institutes are challenged to do things faster, better, and more cost-effectively in order to remain competitive in an increasingly global environment (Stalk, Evans & Shulman, 1992). There is a strong need to share knowledge in a way that makes it easier for individuals, teams, and enterprises to work together to effectively contribute to an organization’s success. This idea of knowledge sharing has well been exemplified in the notion of a learning organization (LO) (Senge, 1990; Garvin, 1993; King, 1996; Levine, 2001). Essentially, a learning organization could be considered as an organization that focuses on developing and using its information and knowledge capabilities in order to create higher-value information and knowledge, to modify behaviors to reflect new knowledge and insights, and to improve bottom-line results. Consequently, there are many possible instances of information system (IS) design and realization that could be incorporated into a learning organization. The acronym “LOIS” (Learning Organization Information System) (Williamson & Lliopoulos, 2001) as applied to an organization is often used as a collective term representing the conglomeration of various information systems, each of which, being a functionally defined subsystem of the enterprise LOIS, is distinguished through the services it renders. For example, if a LOIS could support structured and unstructured dialogue and negotiation among the organizational members, then the LOIS subsystems might need to support reflection and creative synthesis of information and knowledge, and thus integrate working and learning. Also, if each member of an organization is believed to possess his or her own knowledge space, which is subject to some level of description, and thus may be integrated into an organization’s communal knowledge space (Wiig, 1993; Davenport & Prusak, 1998; Levine, 2001), the LOIS subsystems should help document information and knowledge as it builds up, say, by electronic journals. Or, they have to make recorded information and knowledge retrievable, and individuals with information and knowledge accessible. Collectively, a LOIS can be considered as a scheme to improve the organization’s chances for success and survival by continuously adapting to the external environment. That way, we stand a better chance of increasing social participation and shared understanding within the enterprise, and thus foster better learning. More importantly, the philosophy underlying the LOIS design should recognize that our knowledge is the amassed thought and experience of innumerable minds, and LOIS helps capture and reuse those experiences and insights in the enterprise. Indeed, the cultivation of an organization’s communal knowledge space—one that develops new forms of knowledge from that which exists among its members, based on seeing knowledge as a social phenomenon, and not merely as a ‘thing’—is fundamental to enterprises that intend to establish, grow, and nurture a learning organization, be it physical or digital (Hackbarth & Groven, 1999), where individuals grow intellectually and expand their knowledge by unlearning inaccurate information and relearning new information. The theme of this article is to examine the knowledge processes required of the learning organization viewed from the community of practice viewpoint, to develop and sustain the communal knowledge space through the elaboration of suitable LOIS support so as to expand an organization’s capacity to adapt to future challenges.