There is an increasing responsibility on education leaders to critique and reconcile fundamental tensions within global policy and governance structures that privilege neoliberal hegemony and undermine future democracy. Therefore, political acuity and Critical Leadership Praxis are essential characteristics of contemporary principalship, and correspondingly, a critical aspect of current and future leadership preparation and development. Drawing on empirical data from interviews with participants in an Enhanced Political Awareness (EPA) programme in Scotland, this study problematises the concept and practice of leaders’ political acuity as a conduit to their critical foresight. Education leaders report on their learning, the development of their societal and political ‘nous’, their critical consciousness, and their hope and vision for a socially just future—What could be? despite rapid changes in technological, political, social and cultural spheres, where stability is rare, and volatility has become the norm. The study also reports on factors that supported or limited participants’ enactment of the learning and ideas from EPA, in their respective contexts, suggesting the learning → practice transfer of such professional learning as one of two proposed areas for future research. The conclusion proffers a future vision for education leadership preparation and development through a praxis of hope, alongside implications and provocations for the ‘system’ to realise this vision in action.