Abstract: This article examines the evolving landscape of organizational leadership as Gen Z and millennials increasingly comprise the workforce, revealing their diminished interest in traditional corporate hierarchies. Unlike previous generations, these younger workers prioritize flexible arrangements, meaningful impact, and work-life balance over conventional career advancement. The research highlights their preferences for collaborative environments, continuous learning opportunities, and transparent leadership structures, driving them toward alternative career paths such as entrepreneurship, horizontal moves, and portfolio careers. Organizations seeking to attract and retain this talent must adapt by flattening hierarchies, offering developmental rotations, formalizing flexible work arrangements, and measuring social impact. The case study of Redfin demonstrates successful implementation of these strategies, suggesting that companies embracing these leadership transformations will better position themselves for future success in an evolving workforce landscape.