Questioning of ‘good’ theory invites revision of both criteria for assessing and bases for developing theory in management and organization studies (MOS). To this end, we make three contributions: First, we introduce a new criterion for assessing theory development – ‘that’s challenging!’ – when theory is informed by unconventional combinations of research assumptions. Second, we introduce a process for developing challenging theory – ‘disciplined disruption’ – applying heuristic reversal to cultivate provocative theory construction. Drawing comparisons with Weick’s (1989) celebrated ‘disciplined imagination’ approach to theorizing, we propose disciplined disruption as the purposive and sequential introduction of rift or non-alignment among paradigmatic assumptions and levels (i.e. ontology-epistemology; epistemology-human nature; and human nature-methodology), drawing on theory development in critical realism as an illustrative example. Third, in extending this discussion, we assess the case for advancing disciplined disruption in light of three prominent positions on theory development – viz. problematization, pragmatic empirical theorizing, and analogical and counterfactual reasoning.