Study determination is to deliver a framework for overpowering the obstacles headed digital readiness of the organizations, which are not prepared for upcoming industrial difficulties. Interrelated theoretical lens of contextual leadership theory and strategic alignment model along with data analysis of 279 top manager from IT sector in Pakistan. Result examination shows that organizational optimizations including top management commitment, strategic planning and inter-organizational collaboration mediates the relationship between digital leadership and firm’s digital readiness. Study consumes significant professional and theoretic suggestion that no matter how strong is the leadership, means through which the desire outcome could be achieve should not be ignore.