This paper examines the idea of creating information systems (IS) support for knowledge work through the elaboration of typical organizational scenarios. Specifically, our research is driven by a belief that the design issues of IS support must be situated in the context of social processes in which, in a specific organizational scenario, a particular group of people can conceptualize their knowledge work and hence the purposeful action they wish to undertake. This provides the basis for ascertaining what information support is needed by those who undertake that action, and how modern information technology can help to provide that support. Thereby, designing IS support for knowledge work requires attention to the purposeful action which the IS serves, and hence to the meanings which make those particular actions meaningful and relevant to particular groups of people in a particular situation. This is often facilitated by the provision of an important enquiry process constantly attended to, and integrated into organizational activities by which IS professionals could learn of the organization’s continual adjustments to its changing world. Our discussion here brings forth the notion of the learning organization information systems (LOIS), through which each member of the organization is enabled to create his or her own knowledge space, which is subject to some level of description, and thus may be architected and integrated into an organization. Importantly, in order to develop the various LOIS support for knowledge work, we need the correspondent organization scenarios to contextualize the IS design. And we attribute this development philosophy to the essence of systems thinking in conceiving IS support. The paper concludes by reiterating the work of the organization architect, which entails understanding, analyzing, designing, and communicating the most relevant parts of the organization and how they fit together.