The impact of geopolitics on business activities is an undeniable reality, as reflected in the fact that a growing number of companies consider geopolitical risks as a substantial risk to their cross-border operations. Against this background, this article advocates developing the critical geopolitical awareness of management learners to allow them to better understand the risks and challenges posed by the rapidly changing and highly uncertain external environment. After explaining the specificities of the critical geopolitical approach, we discuss three selected case studies that show how it can be applied to complex crisis situations in which companies can become involved. We then highlight how developing critical geopolitical awareness could be beneficial to management learners as part of an incremental critical learning process. The latter is presented as a three-step process, aiming to: (a) increase knowledge of the international and local context by using the triangular framework of analysis (space-power-representations), which provides a deeper understanding of the external environment and how the strategies of both state- and non-state actors may affect business activities; (b) enrich traditional political risk models with a relational and multiscale approach to geopolitical risk; and (c) reconsider the role of corporate leaders and companies as (geo)political actors.