Organizations are increasingly turning to enterprise portals to support knowledge work. Portal deployment can be intradepartmental across several business units in one organization or even inter-organizational. Currently in the industry, most of these portals are purchased solutions (e.g., collaboration and smart enterprise suites) and many of these purchasing and selection decisions are primarily driven by the interest of a small group of stakeholders with strong influence from IT vendors. The true requirements for the portal as well as the strategy for its medium- to long-term phased deployment are, in general, poorly addressed. This, together with other reasons, has lead to many failures or to a low adoption rate of the enterprise portal by staff at various levels of an organization. Common problems that hinder portal adoption include lack of an overall governance model, mis-alignment with business processes, poor or non-existent content management (process, tools, and governance), and technical problems associated with the development and configuration of portlets. This article focuses on one critical issue that directly influences the success of an enterprise portal deployment, namely the correct elicitation of user requirements (which in turn lead to the chosen portal’s features and to the style of the portal interface). Taking into consideration the advancement and landscape of commercial portal vendors in the market, this article discusses a bottom-up approach to the identification of high-level drivers for portal usages for its users.