This paper begins from the premise that the challenges characterising the contemporary education environment call for more flexible approaches to leadership than the traditional reliance on codified knowledge. These more flexible approaches are likely to involve new ways of learning, dispositions and behaviours, which enable educational leadership to progress from "best practice" to "next practice". The paper, therefore, has two main aims. First, it seeks to illuminate a potential "modus operandi" for contending with the complex challenges that have become integral to the landscape of educational leadership. Second, it seeks to encourage consideration of the implications of this "modus operandi" for processes of leadership thinking, learning and development. For this purpose, the nature of the challenges purported to define the landscape of educational leadership now and into the future is first discussed. This is followed by an examination of three interrelated leadership concepts in enabling appropriate judgements to be made in dealing effectively with highly complex circumstances, namely, "phronesis", "contextual intelligence" and "negative capability". The paper concludes by discussing the circumstances within the professional milieu that either constrain or promote the kind of educational leadership that is deemed to be required for embracing the three concepts in question.