This article studies leadership from a systems intelligence perspective. Referring to Lincoln, Martin Luther King and a number of other exemplary leadership cases, we argue that the holistic, contextual and choice-intensive features of systems intelligence make it an illuminating frame of reference for understanding the actual practice of leaders. The key words in the article include “the need to act”, “the living presence”, “the in-between”, “systems intelligent interventions“, “flourishment”, “choice”, ”connectivity”, “sharing”, ”change”, “microbehaviors”, ”sensibilities”, “superproductivity”, ”thinking on the fly”, “emergence”, “systems of holding back”, ”positivity”, “hope”, “human potential”, and “the symbolic order. ”We indicate three critical systems intelligent leadership questions, and conclude with a discussion of the focus points of a systems intelligent leader.