Premeditation of evils: Risk planning in the age of generative AI

In cyber security, anticipating the worst is not paranoia — it is strategy. This paper introduces creative thinking frameworks designed to help leaders and security teams collaborate with generative AI (GenAI) to stress-test assumptions, identify opportunities, explore edge-case risks and uncover blind spots, often caused by cognitive biases, before they become breaches. Drawing inspiration from Stoic philosophy’s premeditation of evils — the practice of imagining future harms to build resilience — this paper repositions GenAI from its role as an operational efficiency tool to one where it serves as a creative partner in strategic planning. The paper explores how GenAI can enhance strategic imagination through various techniques that will expand security teams’ field of vision and be equipped with actionable tools for improving red teaming, scenario planning and creative problem-solving. This article is also included in The Business & Management Collection which can be accessed at https://hstalks.com/business/.