This project delves into the burgeoning practice of managerial decision delegation to Artificial Intelligence (AI), examining the detailed workings of such delegation. It juxtaposes two distinct organizational settings — a well-established corporation and an emergent startup — to examine AI’s influence on decision-making. Delegation in this sense is a significant shift from traditional decision-making practices, wherein managers cede decision-making powers to AI systems, affording them a degree of autonomy and authority that was once the exclusive domain of human decision-makers. This shift involves a nuanced process of delineating the boundaries of AI’s decision-making scope and the level of independence granted. It also requires a foundational trust in the AI system's capabilities and an openness to the ramifications of decisions made by AI, which may operate beyond the immediate oversight of human counterparts. Through a qualitative research design, the project aims to illuminate the critical interplay between AI implementation and managerial decision-making, shedding light on how AI's integration in decision-making can reshape organizational dynamics, affect managerial trust and control, and potentially redefine leadership in the digital age. The outcomes of this research are poised to offer insights into the adoption and normative integration of AI in organizational practices, informing a broader discourse on AI's evolving role in shaping today's organizations.