The European Global Strategy (EUGS) is a significant document that came out at a critical time. Decision makers and scholars need to identify and assess the challenges the EU is facing in its effort to pursue its new Strategy. This paper addresses the lack of a tool for identifying those challenges and assessing the EU's ability to respond to them by introducing a new analytical framework based on the conceptualization of the EU as a small power in the international system, and the literature about the international relations of small states. The framework combines the factors that impact upon a small state's behaviour and performance in the international system and consists of the following elements: a) the EU's relations with the great powers in the system, b) developments in the EU's neighbourhood, c) the EU's politics, and d) the EU's reputation. After discussing each one of them, the paper contributes a comprehensive assessment of the EU's ability to implement its Strategy. It concludes that in order to implement its Strategy, the EU should respond to specific challenges. Therefore, the framework this paper introduces can improve our understanding of both the EUGS and the Union's strengths and weaknesses, shed some light on what measures should be taken for the Union to respond to challenges that lie ahead and be used as a yardstick to assess the Union's progress. Moreover, the framework can be applied to other areas of the EU's external action and contribute to both drafting better informed strategic documents and supporting their implementation.