Asset managing organisations utilize a variety of information systems to support the lifecycle of their assets. Traditionally, engineering enterprises take a deterministic approach to technology adoption. Evaluation of these systems, therefore, is an important aspect of managing IT investments in these organisations. Information systems evaluation is not an inert or stagnant activity, in fact it is highly influenced by the organisational environment. There are certain conceptual and operational issues and challenges that impede the employment of an effective evaluation mechanism. This paper provides a discussion on the conceptual and operational dimensions of the evaluation of the information systems utilized in asset lifecycle management. It highlights that an effective approach to information systems evaluation calls for pluralism, which demands qualitative as well as quantitative measures, involving context based cultural, social, economic, political, technical, and organisational aspects.