New technologies, increasingly demanding customers, new aggressive competitors, and innovations in products and value now characterize our current competitive environment. Organizations of the 21st century have no choice but to invest in new technologies, especially knowledge management tools to enhance their services and products in order to meet the demands of today’s information-driven, globally competitive marketplace. Knowledge embedded in systems, brains and technology has always been the key to economic development. However, knowledge management is increasingly being viewed as a strategy to leverage a firm’s knowledge and best practices to serve customers and to be competitive. Several organizations have already started experimenting with knowledge management initiatives to capture and capitalize on knowledge assets and thereby claim the enormous benefits afforded by such endeavors, including improved profitability and transformation of their businesses into new generation businesses. This chapter develops a technology assessment model for knowledge management indicating what kinds of computing and communication systems any organization needs in order for it to have a sound knowledge management approach.