In this chapter, the author describes an alternative approach to evaluating Information Technology (IT) projects, which involves developing a holistic view of IT interventions. The main methodological problem in evaluating any intervention is to choose the right indicators for the measurement of success or lack of it. These indicators will obviously be linked to the aims but will also be relevant to the objectives chosen to achieve these aims. Acknowledging the difficulty of choosing appropriate measures of performance, the author proposes the use of Soft Evaluation. The approach used brings together formal work in evaluation with a qualitative process of investigation based on Soft Systems Methodology in order to allow us to make judgements about the outcomes of an implementation in a systemic manner and from a number of different viewpoints or perspectives.