Cutting-edge technologies provide opportunities to enhance human performance by assessing cognitive processing markers, honing these metrics with predictive AI, and providing insightful feedback to improve executive performance. In this chapter, we illustrate the practical application of rationality, cognition, and ‘factfulness’ in crafting and refining decision-making paths. By accurately predicting and acknowledging individuals’ capacities, inherent and adaptable decision-making styles, and individualized problem-solving methods, we establish a beneficial dynamic that strengthens an organization’s feedback mechanisms and appropriately situates individuals within a company’s sociocultural landscape. However, this application of AI, where a silicon-based entity sometimes holds a deeper understanding of human performance than the carbon-based human, raises ethical concerns. Similarly, the practical use of physiological data, collected through body-attached sensors, presents implications for privacy and data protection. Our discussion primarily centres on case studies involving eye-tracking technology, along with interventions in regulated environments like aviation or high-pressure corporate cultures such as top-level management and investment banking.