The current study is about task-technology evolution and it suggests that feedback inquiry, individuals’ proactive search for evaluative information relating to their strategy, influences the sustained performance of individuals. The study will undertake on both qualitative and quantitative methods to longitudinally examine the linkage between task-technology fit and individual performance. I theorize that computer self-efficacy interacts with technology characteristics to enhance individuals’ chances to choose attractive execution sequences. Execution sequences are defined as different approaches used for addressing an underlying task (Goodhue, 2006). Once a sequence has been applied and performance effects have been experienced, there will be different kinds of feedback opportunities. Individuals that proactively search for feedback are likely to choose more attractive sequences in the future. The feedback inquiry process is iterative as the loop is theoretically indefinite. Finally, I propose that task complexity is expected to interfere with individuals’ choices of execution sequences, hindering performance.