This chapter explores the evolution of leadership in the context of data-driven decision-making and artificial intelligence (AI). Beginning with the historical example of Ramses II’s failure at Kadesh, it underscores the timeless importance of accurate and timely information in leadership. The discussion then transitions to the modern organizational landscape, where traditional leadership models based on intuition and experience are contrasted with data-driven leadership, which emphasizes evidence-based decision-making, transparency, and measurable outcomes. The chapter outlines the fundamental principles of data-driven leadership, including objectivity, avoidance of bias, the establishment of measurable goals through Key Performance Indicators (KPIs), and the cultivation of a strong data culture that promotes data literacy and accountability. Further, the integration of AI and big data analytics is examined as a transformative force that enhances strategic planning, risk management, and operational efficiency while presenting challenges related to ethics, privacy, and algorithmic bias. The chapter concludes that effective data-driven leadership bridges the gap between strategic vision and operational execution by converting complex datasets into actionable insights. Ultimately, leaders who successfully embed data and AI into their organizational culture can anticipate risks, adapt to changing environments, and foster sustainable innovation and competitive advantage in the digital age.