We investigate how self-monitoring combines with the degree of perceived job autonomy to affect contextual performance. We explore both a mediation model, built on theories on individual differences in the perception of job characteristics, and a moderation model, built on theories of the interaction between personality and perceived job situation. Empirical evidence suggests that self-monitoring and perceived job autonomy significantly predict contextual performance. In addition, an interesting paradox emerges: high self-monitors are likely to perceive higher job autonomy than low selfmonitors but appear to benefit less from perceiving high job autonomy than low selfmonitors. This paper provides a richer understanding of the controversial nature of the self-monitoring construct and offers a new specification of the combination between perceived situational and personality variables in the prediction of behavioural outcomes.