Leadership skills play a vital role in the management of any successful organization in present digital era. The strengths of digital literacy, on the other hand, lie in the ability to employ what is being encouraged by the leaders of any organization. A focus on the role of transformational leadership skills to guide and direct staffs’ effective use of digital literacy in achieving student engagement has led to alarming success rates in higher education. The purpose of this paper is to reveal the beneficial role of transformational leadership in encouraging the use of digital literacy amongst their staff. Some of these benefits include the capability to inspire and lead positive change within an educational setting, ensure a technology-oriented basis for organizational change, and provide a platform for empowering staff’s use of digital literacy and inspiring effective student engagement and collaboration. The critical assessment of several literature reviews of various scholars points out the role of leadership skills as a starting point upon which the management (leaders) in higher education institutions can effectively implement the use of digital literacy amongst staffs in the educational setting. The methodology considered for this paper include the selection and search strategy as well as the use of database. The analysis finds transformational leadership skills a great determinant of digital proficiency and competency in higher education institutions. Findings reveal the effectiveness of leadership skills in encouraging the effectiveness of digital competence amongst staffs and learners. Also, the ability to integrate the know-how in their day-to-day learning and teaching activities. Secondly, educational supervisors demonstrate a better understanding of the technologies that are appropriate for educational improvement which also positively impacts on their engagement with students. Thirdly, staff have a better understanding of the pedagogy and appropriate technology to best integrate in promoting teaching and learning. Finally, these transformative leadership skills helps foster self-efficacy and autonomy of staffs increasing their capacity to innovate and digitally accomplish daily tasks. Such leadership skills nurture educational technology by effectively guiding their institutions in this digital era, thereby improving on staff and student engagement and collaboration.