This article contributes to problem solving, design, and planning in defence organisations by arguing that a ‘problem’ or a ‘challenge’ is never objective, natural or ready-made. Challenges are contingent to the conditions under which individuals perceive and formulate them. As a result, this article understands ‘challenges’ and ‘approaches’ to address them as co-dependent on one another. This article recommends that officers should attempt to generate the most interesting and, we hope, innovative problem-solution pair or challenge-approach pair in order to integrate this insight into practice when problem solving, designing, or planning. Leaders and their teams can learn to inhabit this mind-set by finding inspiration in three modes observed through practice: initial challenge framing, challenge curation and co-evolution. For each of these modes, the article proposes reflexive methods and tools for enhancing introspection in challenge framing and formulation namely the Five Whys, question-storming, and loyal opposition. The article supports these recommendations and methods through insights gleaned from philosophy of knowledge, design theory, and on design experiences with the North American Aerospace Defence Command (NORAD) in 2019.
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