Senior executive strategic decision making is a prized skill. The analysis of available literature yields three key conclusions: i) strategic decision-making skills, especially in high complexity and ambiguity leverage ‘adaptive expertise’ which is very different from the dominant discourse on narrow domain ‘expert performance;’ ii) unlike focused skills which can be developed by concentrated, high repetition practice, adaptive expertise requires higher order meta-cognitive skills in addition to wide domain knowledge and managerial skills. Third, emerging literature suggests serious games can help to improve capabilities in decision making and cognitive skill, but there is a limited range of games or research explicitly focused on strategic decisions, while there is extensive body of knowledge on such simulations and measures for in-the-moment type decisions. The authors propose several frameworks and design requirements incorporating three levels of skills including higher cognition.