The globalization of business has resulted in both large numbers of workers living and working abroad, as well as an increasingly multicultural domestic work environment. Organizational research has shown that cross-cultural training mitigates or proactively guards against the frustrations, misunderstandings, and culture shock often resulting from cross-cultural interactions that lead to poor adjustment and job performance (Harris & Kumra, 2000). Despite the recent surge of studies in this area, previous cross-cultural effectiveness studies have failed to take into account a number of moderating variables. Particularly, the role of the expatriate's supervisor and the personality and motivational differences of the expatriate have not yet been explored. Thus, the present study draws upon cross-cultural training theory, in addition to the leader-member exchange framework, in proposing that cross-cultural training for the supervisor of an expatriate subordinate will moderate the impact of cross-cultural training on the expatriate subordinate's adjustment and job performance. Furthermore, self-efficacy, openness to experience, and extraversion were tested as moderators of the relationship between cross-cultural training and job performance. Participants were individuals from a variety of countries who were coming to the United States for practical training. They took part in a web-based cross-cultural training study before leaving for the U.S. or shortly after they arrived. Results indicate that supervisor cross-cultural training does impact the effectiveness of cross-cultural training on job performance and work-related adjustment. Additionally, results support the predictions that self-efficacy and extraversion moderate the relationship between cross-cultural training and job performance.