Many discussions on design theory applications within military contexts often revolve around a small population of design practitioners using complex terms and exclusive language, contrasted by a larger population of design skeptics that routinely demand a universal, scripted, and complete examples for “doing design right.” Design, a form of conceptual planning and sense making, continues to gain traction in strategic political and military institutions, yet faces misunderstanding, disinterest, and outright rejection from military strategists and operational planners for a variety of reasons. This article aims at moving this discourse toward how several design theory concepts are valuable for strategists and decision makers, and how select design concepts might be introduced and applied in a simple language where military practitioners can traverse from strategic intent into operational applications with tangible results. As a lead planner for the Afghan Security Force reduction concept and the 2014 (NTM-A) Transition Plan, I applied design to strategic and operational level planning using these design concepts as well as others