This article proposes that duality theory plays a role in obtaining more nuanced and textured insights into the complex, paradoxical stability–change nexus by illustrating how tensions are managed not through definitive resolution toward one pole or the other, but through improvised boundary heuristics that establish a broad conforming imperative while opening up enabling mechanisms. Duality thinking also reinforces the need to discard assumptions about opposing values, instead replacing them with an appreciation of complementary concepts. The article explores the characteristics of dualities to allow managers to chart what they are seeking from their management interventions and subsequent choices in structural support systems. A key benefit of identifying and explaining duality characteristics comes in attempting to understand how to mediate between two contradictory dimensions of organizing, such as continuity and change. Our argument is that both need to be encouraged, but this requires a particular mindset where the problem of mediation viewed as the need to work towards simultaneity and synergistic mutuality rather than resolution of action between the two opposing dimensions.