This case uses four vignettes to examine the strategic tension faced by leaders in adopting Generative AI (Gen AI). While these vignettes focus on marketing examples, the lessons can be generalized to other managerial disciplines. The vignettes span diverse industries (Retail, CPG, Luxury, B2B Industrial Technology) and applications (personalization, synthetic research, creative design, content generation). Together, they highlight the complex challenges companies face in deploying Gen AI in various applications. The core dilemma is determining whether the value created by Gen AI applications (efficiency, speed, savings) outweighs the value it may destroy (reputational harm, brand erosion, legal liability). The case is structured to guide students in inductively developing a robust decision framework for Gen AI adoption.