This chapter reflects on the challenges and opportunities of leading educational change in today’s digitally connected world. It offers personal insights and critical reflections on learning leadership framed by a wide-angle, multifocal lens that helps zoom in and out to visualize preferred futures. Before outlining a collection of leadership touchstones and critical questions for guiding institutional transformation and then reporting their application in the practice of digital education, the chapter begins by illustrating how the new learning ecology is complex and entangled in competing images of the future. Efforts by educational leaders to build agile and sustainable transformative organizational cultures need to be guided by a clear sense of direction and anchored in a living institutional mission. The role of the National Institute for Digital Learning (NIDL) hosted at Dublin City University (DCU) in Ireland is central to this story, as harnessing the transformative potential of new digital technology is at the heart of its change agenda. After briefly introducing DCU, the chapter reports how the NIDL’s commitment to leadership development and active engagement in global networks are helping to reshape the higher education landscape with a critical digital edge. However, forging a future-focused mission based on multifocal criticality and transformative leadership is not something for the faint-hearted; it requires agency, relational capital, and strategic foresight to move from digital in part to digital at the heart of your organizational culture.