© 2015 International Professional Development Association (IPDA). Given the turbulence of the contemporary education environment this paper argues it is necessary to adopt more flexible approaches to leadership than has traditionally been the case and involving new ways of learning and behaviours. In this regard, the paper investigates the paradoxical concept of ‘negative capability’ and its potential value for enhancing school leadership in circumstances of uncertainty, change and complexity. First, the nature of the challenges purported to permeate the school leaders’ world and which are likely to escalate into the future is described. Attention is then given to the concept of negative capability and its usefulness for one approach to leadership that might be appropriate in dealing effectively with highly complex contexts. Finally, some practical ways in which individuals’ sense of negative capability may be enriched, especially through promoting the ‘inner leader’ rather than observable competencies in school leadership development, are examined.