Digital transformation (DT) is a global priority. Current Digital Leadership frameworks are predominantly based in Western developed economies, where infrastructure is strong and regulatory systems are well established. This study tries to bridge the theoretical gap by exploring the distinct leadership challenges encountered in Developing and Least Developed Nations (DLDNs). Based on a qualitative integration of Industry 4.0 and institutional theory, this study tries to Contextualised Digital Leadership Framework (CDLF). This paper provides the fundamental concept of Digital Leadership and highlight the Digital Leadership in Developing and Least Developed Nations. The paper tries to explore the technological concerns, institutional utilization of technology, skill development of the stakeholders and socio-economic challenges. The framework highlights some essential dimensions of Digital Leadership, like- Digital Competencies, Contextual Intelligence, Strategic Alignment and Sustainable Impact. Its impact helps leaders to navigate inclusive and sustainable digital transformation effectively.