Information systems evaluation is embedded in many social and organisational processes, and thus is a particularly complex decision process. Evaluation happens in many ways (e.g. formally, informally), uses diverse criteria (e.g. financial, technical, social), follows rigorous methodologies or gut feelings and often becomes a political instrument which influences the balance of organisational power. The existing literature (Ballantine et al., 1995; Farbey et al. 1992; Willcocks and Lester 1994; Ward et al. 1996) identifies noticeable gaps between academic theories, commercially available methodologies, and actual evaluation practice within organisations. Such gaps between theory and practice are not unusual and they have been reported in other research areas. Hsia (1993 p.14) for example argues: “The truth is that most companies have two sets of practices; one real, the other recommended.” In other words there are the formal evaluation practices promoted by organisational rules and structures, the informal practices implemented by stakeholders involved, and finally the academic recommendations which in many cases recognise the delicate nature of evaluation and suggest more interpretive considerations. The better theories tend to emphasise the complexity and richness of the evaluation problem situation or context while the available methodologies tend to oversimplify the process through cookbooks that focus on the more measurable aspects of the outcome of IT/IS investment. Meanwhile, the actual use of such methodologies in practice is often largely determined by the subjective views of individual stakeholders facing a combination of business, organisational and technological pressures.