Can strategic sense be taught, and how? This article engages with this crucial question. First it explores the generic strategist’s desirable qualities, how strategic sense fits in, and what that sense actually is. It then turns to edu-cation for strategy and the standard understanding as needing to mix deep his-tory and good theory, but this interpretation stems from professional military education which tends to rely on the students already possessing certain insights which civilian students may not have. Thus the article ends with an exploration of gaming as a teaching tool, identifying a function of gaming which is not often discussed: helping students develop an actually strategic way of thinking which, with sufficient experiential repetition, might become habitual.