Purpose - The purpose of this paper is to determine whether political skill is equally effective in its prediction of job performance for different job demands. Design/methodology/approach - This paper uses self-report sources of employee performance and self-report of political skill after several weeks along with three ratings of target individuals' job demands. Findings - Results support the hypothesis that Holland's enterprising category (i.e. because of its job demands and requisite job competencies to be effective) will moderate the relationship between political skill and job performance, demonstrating stronger predictability under high enterprising job demands. Research limitations/implications - The present results suggest that political skill is a better predictor of job performance under situations of high enterprising job demands than under conditions of low enterprising job demands. Furthermore, social and conventional job demands do not significantly moderate the political skill-job performance relationships, implying that these job demands act as an important boundary condition. Practical implications - Politically skilled individuals are more likely to succeed in environments (e.g. enterprising jobs) where they have the opportunity to exercise interpersonal influence, and where that interpersonal influence is directly related to their performace. Originality/value - This paper makes several contributions to theory and practice in vocational achievement and political skill. Perhaps, most significant is the identification of job demands as a boundary condition in the political skill-job performance relationship.