Making decisions about the structure of a future military fleet is a challenging task. Several issues need to be considered such as the existence of multiple competing objectives and the complexity of the operating environment. A particular challenge is posed by the various types of uncertainty that the future might hold. It is uncertain what future events might be encountered; how fleet design decisions will influence and shape the future; and how present and future decision makers will act based on available information, their personal biases regarding the importance of different objectives, and their economic preferences. In order to assist strategic decision-making, an analysis of future fleet options needs to account for conditions in which these different classes of uncertainty are exposed. It is important to understand what assumptions a particular fleet is robust to, what the fleet can readily adapt to, and what conditions present clear risks to the fleet. We call this the analysis of a fleet's strategic positioning. This paper introduces how strategic positioning can be evaluated using computer simulations. Our main aim is to introduce a framework for capturing information that can be useful to a decision maker and for defining the concepts of robustness and adaptiveness in the context of future fleet design. We demonstrate our conceptual framework using simulation studies of an air transportation fleet. We capture uncertainty by employing an explorative scenario-based approach. Each scenario represents a sampling of different future conditions, different model assumptions, and different economic preferences. Proposed changes to a fleet are then analysed based on their influence on the fleet's robustness, adaptiveness, and risk to different scenarios.