In the modern fast-paced and ever-changing business world, successful organizational change management (OCM) plays an important role in maintaining competitiveness and responsiveness. This research explores the interrelated functions of strategic planning, leadership, and employee engagement as key pillars that facilitate successful and sustainable change. Through qualitative multiple case study analysis of two internationally acclaimed organizations Kodak and Apple based only on secondary data, the study investigates how differing focus and implementation of these factors impacted their own change outcomes. The results illustrate that Apple’s success was supported by a responsive and vision-oriented strategic planning strategy that aggressively looked forward to technological revolution and market transformation. Balancing this approach was transformational leadership that energized and enabled employees, coupled with substantive employee involvement creating a sense of ownership, innovation, and resilience. Confronting, Kodak’s fall was in significant part due to its inability to shift its strategic vision during digital disruption, risk-averse and centralized leadership stifling change momentum, and constricted employee involvement that amplified resistance and cultural inertia. These findings underscore that lasting change is not predicated on isolated factors but, instead, on the synergistic blending of lucid, adaptive strategy; inclusive, dedicated leadership; and engaged, authentic employee participation. Omitting any one of these factors can critically disenable change efforts and organizational sustainability. This research therefore contributes to OCM theory by providing a comprehensive, human-oriented paradigm that prioritizes the dynamic interactions between strategic intent, leadership efficacy, and workforce empowerment. Practically, organizations are urged to create adaptive capacities, build transformational leadership skills, and implement continuous employee engagement to heighten readiness and success in complex change contexts for final organizational survival and growth