In 2003, GartnerG2 and Forbes.com hosted a senior executive survey to find out their beliefs and attitudes towards information technology(IT)(MacDonald, 2003). Seventy percent of the respondents agreed that companies that invest heavily in IT have a strong competitive advantage. However, Carr(2003) argues that IT is not always associated with competitive advantage, hence investment in IT should be reduced. These two different points of view leads to this research to examine how companies make IT investment decisions. This study adopt a contextualist framework to explore how a continuing education institution(CEI) evaluate the IT investment