Despite considerable advances in methods to examine leaders’ personal characteristics using at–a–distance assessment, few studies have applied such techniques outside of the national level. This study reveals that such approaches can provide analytical leverage for examining executive heads of intergovernmental organizations (IGOs). The personal characteristics of six United Nations Secretaries–General and four European Union Commission Presidents were measured via content analysis of their responses to questions. Separately, their behavior in office was measured via historical accounts and analyses. In general, executive heads with higher expansionist leadership style scores displayed a greater willingness to try to enhance the status of their organizations.