Presently, sustainable leadership has emerged as an effective leadership style to cope with sustainable challenges. Extent literature has recommended exploring the mechanism and conditional boundaries for the significant effect of sustainable leadership on sustainable performance. Therefore, this study would investigate the mediating mechanism of organizational learning and the psychological empowerment as conditional factor on the sustainable leadership–sustainable performance relationship. The cluster-sampling approach was employed to collect data from 369 small medium enterprises in selected ASEAN countries: Malaysia, Indonesia, and Brunei Darussalam. The response rate is 41%. Structural equation modeling (variance-based) analysis was performed to empirically confirm the proposed hypotheses. By running PROCESS Macro in SPSS, the moderated-mediation analysis was conducted in this study. The research outcomes revealed that higher level of psychological empowerment will result in a higher indirect effect of sustainable leadership on sustainable performance through organizational learning. Based on the present empirical evidences, implications and future research directions have also been added at the end of study. To date, this study has preliminary investigated the interplay of sustainable leadership, organizational learning, empowerment, and sustainable performance.