The diverse challenges associated with anti-doping work in sport can result in multiple, competing viewpoints amongst stakeholder groups working to solve the problem. Coupled with the complexity of the problem itself, this has the potential to generate chaotic or disordered work contexts that impede rather than promote progress towards a solution. A visible lack of progress can be magnified to a public perception of anti-doping work as ineffective. We offer the Cynefin Framework, informed by Complexity Theory, as a novel theoretical and methodological lens for sense-making in the changing global context of anti-doping work. The framework’s applicability at both individual and collective levels makes organisational sense for managers, professionals working in the field and interested onlookers. This sense-making contributes to an environment where the use of context-tailored strategies, and suitable management and decision-making approaches can emerge. Rather than seeking impossible simple solutions, these can be aimed at the ongoing generation of complementary multiple partial solutions as contexts evolve. In this paper, we describe the Cynefin framework, its application to the global context of anti-doping work in sport and recommend its use in other complex contexts.