Premeditation of evils: Risk planning in the age of generative AI
Abstract
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/.
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Author's Biography
Leslie Grandy is a global, first-to-market product executive, author and board advisor with a more than 25 year career delivering game-changing products for top brands — Best Buy, T-Mobile, Apple and Amazon. Leslie co-created and serves as Lead Executive in Residence for the Product Management Leadership Accelerator at the University of Washington Foster School of Business. Leslie founded The Product Guild, a company through which she has advised early stage ventures and numerous publicly traded companies on innovation and new product development. Leslie’s book, ‘Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI’, was published by Wiley in May 2025.
