The present study examined the relationship between novice learners' counterfactual thinking (i.e. generating what if and if only thoughts) about their initial training experience with a computer application and subsequent improvement in task performance. The role of anticipated emotions towards goal attainment in task performance was also assessed. Undergraduate students (N = 42) with minimal experience in using computer spreadsheets underwent basic training in using Microsoft Excel. All participants were assessed on their anticipated positive and negative emotions regarding goal attainment at the outset. After completing their first task, participants allocated to a counterfactual condition received instructions to generate counterfactual thoughts regarding their initial task performance, whereas participants in a control condition did not. The counterfactual group showed only marginally greater improvement in task performance (measured by task completion time and accuracy) than the control group. However, we also found that positive anticipated emotions were associated with improvement in task performance but for the counterfactual group only. Our data have implications for incorporating counterfactual thinking into information technology skills training to enhance learning outcomes for novice learners.