This research-in-progress builds upon the mindshift learning theory by pursing a further understanding of why individuals have difficulties transitioning to new technologies. The theory is expanded by incorporating the circumstance when multiple shifts in mindset are needed as a result of the introduction of a new technology – a necessary contribution since information technology innovations are often accompanied by complementary organizational innovations. This is achieved by bridging the mindshift learning theory with the innovation literature and proposing a technology mindshift matrix consisting of two variables; degree of newness and degree of change. By incorporating the degree of change, the extent that a new technology impacts services and/or development processes, we expand the learning component of the theory. Research hypotheses are identified and a methodology is proposed to evaluate them. There are several implications that this research has for both practitioners and researchers. A pilot study will commence in the spring of 2008.