In Uganda’s insurance sector, salespersons’ ability to tailor their strategies to customer needs is a key driver of success. This study examines how Technology Self-Efficacy (TSE) influences the relationship between Lead-Qualification Skills (LQS) and Adaptive Selling Behaviour (ASB). Using a cross-sectional quantitative approach, data were collected from 364 licensed sales agents through structured questionnaires across various insurance companies. Correlation and regression analyses were performed, with the Hayes Process Macro applied to test the moderating effect of TSE. The results indicate that both LQS and TSE are positively associated with ASB, and regression analysis confirms their significant predictive roles. Moreover, TSE strengthens the link between LQS and ASB, enhancing salespersons’ capacity to adjust their selling approaches effectively. These findings contribute to the literature on adaptive selling in Uganda by emphasizing the combined importance of technological confidence and lead-management proficiency. The study recommends that insurance firms prioritize training programs that develop these competencies to boost adaptive selling performance in an increasingly dynamic market.