In this article we challenge the widespread advocacy for leadership learning to be tied to decontexualised lists of "best practice," especially at an international level. After reviewing some of the reasons for why such lists may do little to promote the improvement of leadership practice we suggest that energy could be more usefully concentrated on leadership learning and what has been labeled "informed" (Dimmock, 2000) or "wise" practice (Davis, 1997). Building wise practice stems from an awareness of how leaders learn best and the conditions which allow these methods to take root. Such conditions include resilience, intuition, ego, voice, curiosity and experimentation. As such, we suggest learning leadership and the results of this learning are often one in the same. Learning to be a better leader, however, does not simply happen; it needs to be purposefully framed with the individual and organizational context within which it resides. To this end, we conclude the article by outlining four flexible learning gateways which school leaders may use to inform their practice. The four gateways are: what I believe is important; what others think about me; what I am dealing with now and; what ideas are out there.