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Although there has been much discussion of the strategic role of information systems, there have been few attempts to capture or quantify the extent to which information systems complement company strategy and impact performance. This dissertation research develops, validates, and applies measurement instruments and accompanying procedures to assess information systems (IS) strategy and IS strategic fit (the synergy between business strategy and IS strategy).; The research is based on Venkatraman's work. He developed and tested an approach for measuring realized business unit strategy. This dissertation extends his work, applying it to the assessment of IS strategy and IS strategic fit.; The research was carried out in two main phases:(I) Instrument development and pilot testing, and (II) Survey-based instrument refinement and validation. Initially, twelve hundred North American financial services and manufacturing firms were selected for study using Dun & Bradstreet directories. Of these, nine hundred were sent questionnaire packages. Using the data gathered and multivariate analytical techniques (primarily Partial Least Squares analysis), the instruments developed were shown to be reliable and valid. The relationships between realized business strategy, realized IS strategy, IS strategic fit, IS effectiveness, and business performance, although not strong, were found to be statistically significant.; Potential implications of the research for practising managers include the creation of simple tools to improve IS planning, evaluation, and effectiveness. Implications for researchers include the operationalization of the IS strategy construct …