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Organizations are confronted with problems and political risks to which they have to respond, presenting a need to develop tools and frames of understanding requisite to do so. In this article, we argue for the necessity of cultivating “political judgment” with a “sense of reality,” especially in the upper echelons of organizations. This article has two objectives: First to highlight how a number of recent interlinked developments within organizational analysis and practice have contributed to weakening judgment and its accompanying “sense of reality.” Second, to (re)introduce some canonical works that, although less in vogue recently, provide both a source of wisdom and frames of understanding that are key to tackling today’s problems. We begin by mapping the context in which the need for the cultivation of political judgment within organizations has arisen: (i) increasing proliferation of political risks and “wicked problems” to which it is expected that organizations adapt and respond; (ii) a wider historical and contemporary context in which the exercise of judgment has been undermined – a result of a combination of economics-inspired styles of theorizing and an associated obsession with metrics. We also explore the nature of “political judgment” and its accompanying “sense of reality” through the work of authors such as Philip Selznick, Max Weber, Chester Barnard, and Isaiah Berlin. We suggest that these authors have a weighty “sense of reality”; are antithetical to “high,” “abstract,” or “axiomatic” theorizing; and have a profound sense of the burden from exercising political judgment in difficult organizational circumstances.