In a high-risk sector, such as power system, transparency and interpretability are key principles for effectively deploying artificial intelligence (AI) in control rooms. Therefore, this paper proposes a novel methodology, the evolving symbolic model (ESM), which is dedicated to generating highly interpretable data-driven models for dynamic security assessment (DSA), namely in system security classification (SC) and the definition of preventive control actions. The ESM uses simulated annealing for a data-driven evolution of a symbolic model template, enabling different cooperative learning schemes between humans and AI. The Madeira Island power system is used to validate the application of the ESM for DSA. The results show that the ESM has a classification accuracy comparable to pruned decision trees (DTs) while boasting higher global interpretability. Moreover, the ESM outperforms an operator-defined expert system and an artificial neural network in defining preventive control actions.