This thesis explores the problem of information systems evaluation by conceptualising it as a process in which the manager comes to an understanding about a system. In other words, information systems evaluation is a hermeneutic process. The thesis explicates this notion through an argument that is itself hermeneutic in its development, beginning with the mainstream functionalist view of information systems evaluation, and then considering an interpretive view of IS evaluation, each of which points to one of two stereotypes of IS evaluation and the manager engaged in this process: the objective/rational manager utilising objective/rational methods versus the subjective/political manager engaged in political manoeuvring, utilising objective/rational methods only as ritual or symbolism. Neither of these opposing stereotypes is satisfactory. Instead, this thesis proposes a dialectic view of information systems evaluation, in terms of which, rather than being a decision maker, the manager is in-the-world, evaluating systems in order to get the job done, on the basis of her thrownness in-the-world. This conceptualisation provides an intuitively appropriate account of evaluation on the part of an individual manager, but we must still consider how managers as members of the organisation, reach a common understanding about a system. This they do through a process of organisational learning as encultured knowing, in terms of which a narrative, situated, pragmatic knowledge is most useful in evaluation. Evaluation, in other words, happens in the course of skilful conversation. Such conversation is, however, not always skilful because the organisation is not just a collection of individuals but also a network of power relations. Conversations as generators of meaning are never held outside of power: systems evaluations as conversations cannot take place outside of a regime of truth. A post-dualist view of action as both constituted by and constituting structure, however, suggests that there is always the potential for genuinely hermeneutic and ethical conversation, provided it is both improvisatory and deconstructive. Having understood the requirement for improvisation and deconstruction, it is possible to suggest some heuristics for information systems evaluation based on these ideas. / Dissertation (Phd (Information Technology))--University of Pretoria, 2003. / Informatics / unrestricted