Clinical trials are big business, incorporating information from many participants and situations and creating challenges in the acquisition, storage, and sharing of information amongst healthcare researchers. As institutions consider which clinical trial informatics system to choose for their capital investment, it will be important to identify an approach for choosing a satisfactory system. This paper outlines a proactive approach in helping institutions in selecting a shift to an ideal clinical trial informatics system. This approach is organised under the new acronym P3IT, consisting of product, price, people, industry context, and technology trends. This includes internal analysis to explore product attributes and price, and human resource capacity (people), as well as external analysis to explore a Porter's five forces assessment of competitor rivalry; and technology and trends (external analysis to consider future technology and trends in clinical trial informatics systems and the case study product). Using this approach, this paper then explores a case study analysis of the Cancer Biomedical Informatics Grid (caBIG), developed by the National Cancer Institute, and its Clinical Trial Management System (CTMS) workspace which uses Clinical Trials Suite software.