“Negative Capability” is an expression that was coined by the English romantic poet John Keats, and suggests a peculiar disposition to stay in mysteries, doubts, and uncertainty without the irritable reaching after fact and reason. The phenomenological research was conducted with 14 leaders in order to explore their lived experience under conditions of uncertainty and ambiguity, using the interpretative phenomenological analysis (IPA) methodology. The study draws on ancient and contemporary literature in Dialogism, Dialectics, Buddhism, and Psychodynamics to understand the true essence of negative capability. It not only raises the Keatsian construct to a canonical status, but also suggests how it may be deployed in post-modern times to alleviate the pitfalls of polarized thinking. It is an attempt to open the "negative space" for scholar-practitioners who are interested in pushing the envelope.