Organisational semiotics as pioneered by Stamper (1973) and the subsequent body of research works conducted by his associates have been used with rewarding results in the domains of information systems analysis and design, electronic data interchange and behaviours of intelligent search agents in Internet-based e-commerce. The other chapters in this book and the various titles cited in their references provide ample testimony to this statement. This chapter is an exploratory study of the use of organisational semiotics in understanding some activities in the information planning phase of information systems, namely an examination of the utility of Strategic Information Systems Planning (SISP) beyond its espoused aims. In the language of organisational semiotics or the interpretative tradition of organisational studies, such unintended uses are at the levels of pragmatics and social world. Our approach would conceptualise SISP as a communicative, sense making and socio-cultural process, highlighting interpretative, communicative, ritualistic and sense-making activities.