Compelling global challenges and the COVID-19 pandemic have multiplied calls for embedding complexity theory in management research and education to develop more effective analytical skills and organizational practices. Yet, educational curricula adopting complexity theory are still very sparse. This conceptual article explores the relationship between complex adaptive system (CAS) theory, individual and organizational learning, and sensemaking to inform a novel integrated framework for teaching and learning complex reasoning. We outline several cognitive challenges hindering the adoption of complex thinking in managerial settings, such as the tendency-to-simplify of reductionist thinking, the counterintuitive nature and continuous evolution of complex systems’ behavior, the difficulty of updating cognitive frames, and the tendency toward immediate decision-making. We thus propose the need for dynamic preparedness as a core competence for embedding complex reasoning in management learning and practice. Based on CAS core concepts, namely nonlinearity, feedback loops, system delays, path dependency, multiple interacting agents, and autopoiesis, we argue how dynamic preparedness can be nurtured through an abductive, situated educational approach, which develops intuition to sensemaking and the ability to recognize the boundary conditions of simplified models. The proposed framework provides a timely contribution to complexity-oriented education, crucial to increasing societal resilience toward future systemic crises.