The purpose of this study is to introduce the Strategic Assessment Model (STRATAM), a model designed to assist in the prevention of strategic failure. STRATAM aids firstly in the assessment of a strategy, as well as its crafting and evolution; secondly, it aims to enable and possibly streamline civil-military strategic debates on military operations. It is argued that strategic blunders in many cases result from latent organizational failures on one’s own side. Therefore, STRATAM combines Clausewitz’ theory of war and strategy with organizational failure theory. To demonstrate the use of this model, this paper uses Operation Cast Lead (or the Gaza War) of 2008-2009 as a case study. The paper’s findings include that the ultimate reasons for strategic failure were on one hand Clausewitzian; on the other hand, the Israeli Defense Force’s failure in organizational learning from a previous war two years earlier. The timely, strategic assessment and an effective civil-military debate about the effects of ongoing military operations might have prevented this failure. STRATAM would have provided the necessary language, structure, and relevance to identify actual and potential strategic failures with the goal to evolve the strategy.