Managers, in today's companies, rely increasingly on the use of intelligent information systems to obtain insights and analysis which aid in their decision making process. Based upon a review of the current literature and a series of interviews held with major transportation customers, this paper discusses the development of an application that is aimed to aid decision makers in the assessment and evaluation of the wide variety of complex interacting variables involved in the evaluation of e-business investments within the railway industry. The model defines that to complete a holistic assessment of any e-business implementation it is necessary to carry out a holistic assessment that includes both internal and external aspects of the organisation, as well as the technical architectural aspects. A preliminary fuzzy evaluation combined with analytical hierarchy process and linguistic scaling is used to give an assessment of the current state of eMaturity within the organisation, the state of the external environment and the proposed core functions of the system being implemented. This determines the selection of the critical attributes which will impact the potential value and risk of the investment to the organisation. These attributes are then assessed using a technique of fuzzy evaluation to determine the "real worth" current value to the organisation.
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