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Despite substantial investment in digital technologies, many digital transformation initiatives fail to deliver the strategic, operational, and organizational outcomes expected of them. The persistence of such failures suggests that the problem cannot be explained only by technology selection, implementation delays, or budget overruns. Instead, digital transformation failure reflects a deeper managerial misunderstanding of what transformation actually requires. This perspective article argues that digital transformation fails when it is treated as a conventional management project rather than led as a long-term process of organizational change. Project thinking encourages managers to focus on systems, milestones, budgets, and delivery schedules, while underestimating leadership commitment, cultural adaptation, and strategic coherence. As a result, organizations may install digital tools without transforming how decisions are made, how people work, or how value is created. The objective of this article is to diagnose three interconnected managerial failure mechanisms: leadership gaps, cultural resistance, and strategic misalignment. Leadership gaps weaken vision, commitment, role modelling, and digital literacy. Cultural resistance blocks behavioral change, reinforces legacy routines, and reduces employee willingness to engage with new digital ways of working. Strategic misalignment disconnects digital initiatives from the core business agenda, producing fragmented efforts that rarely scale. The article develops an evidence-based perspective by synthesizing peer-reviewed and practitioner-oriented articles published. It does not present new empirical data. Instead, it uses critical synthesis, conceptual reasoning, and practical interpretation to explain why digital transformation failure is fundamentally a management problem rather than a technological inevitability. The article concludes that digital transformation requires a shift from project management to organizational leadership. Managers must move beyond treating digital transformation as an implementation programme and instead lead it as a continuous process of strategic renewal, cultural adaptation, and capability development. Only then can digital initiatives become embedded in the organization’s operating logic and contribute meaningfully to transformation outcomes.