Recent developments in systems thinking (Fuenmayor & López Garay, 1991; Fuenmayor, 1991a,b,c; Fuenmayor, 1997; López-Garay & Suárez, 1999) linked to the phenomenological perspective, are changing our understanding of systems, and organizations. In this chapter, we will introduce a new image of organizations as holistic practices —an image based on these developments— and examine how this image may enrich Checkland’s phenomenological design of information systems The application of a phenomenological approach to information systems design (ISD) is not a new idea. Boland (1985) and Checkland & Scholes (1990), among others, brought the attention of information systems designers to this fruitful approach years ago. To phenomenology, reality is socially constructed, the product of continuous social interaction. Sense-making becomes then the focus of the systems designer, rather than the positivistic search for the “true” organization and the “true” requirements of the system to be designed (usually the main concern of the classical systems expert in every study). In the phenomenological perspective, organizations are socially constructed. Such systems can be described in relation to different particular world views of the members of the organization (Checkland & Scholes, 1990) and their interpretations. Therefore, information is the meaning that results from an engagement with the different perspectives a human organization handles. In this connection, information systems have to be designed as systems to support the organization’s central meaning-creation processes, and hence, their social construction of organizational reality (Boland 1987).