For many years, we have noticed that different courses of action (COA) developed by Joint Operational Planning Groups (JOPG) for solving the same mission seldom rarely differ more than marginally. This can lead to plans that are predictable for an opponent. If we want to be able to expose an opponent to surprise and complex problems, predictable plans are not good.Planning doctrine only based on the past experience is most often not the best when preparing for missions in future operations, therefore more creative and divergent thinking is needed.In this paper we discuss conditions for COA development that stimulate creative and divergent thinking. We also discuss how planners continually alternate between divergent and convergent thinking before and during execution of operations.