Leadership, in all its guises, is complex, messy, elusive and often times enigmatic. Talented leaders fail and average leaders thrive in all sectors of society, including universities. Dynamic leadership situations with the right timing and a little luck create great leaders; complex situations also result in failure for some of the most talented leaders. And, occasionally a leader’s talent transcends even the most complex situational context resulting in sustainable transformational change. This paper is a descriptive analysis of one leader who has captured the hearts, minds and imaginations of people across the world – President Volodymyr Zelensky of Ukraine. The article askes: Does Zelensky’s leadership contribute to the field of leadership? Do the Zelensky’s files [lessons] provide leadership options for university leaders? The author concludes yes to both research questions. Indeed, this article is not a political statement nor advocacy for any particular position. It is a discussion and analysis of leadership – and not simply for presidents and senior CEO leaders but all leaders within universities and schools, particularly those in educational technology and online digital learning. Education is at a crossroads and it is increasingly clear that institutions of the future must be resilient, adaptive and agile organisations capable of responding rapidly and effectively to societal trends and change. Future-proofing education against uncertainty, change, and complexity is simply not a viable option. Organisations will need a dynamic, humanistic and inspirational approach to leadership centred around empathy, empowerment, engagement and execution. Leaders of digital online learning units and managers of educational technology will need The Zelensky Files as much as chief executives.