This chapter examines some current limitations of leadership theory which focuses on leadership in rather than of the organisation and which underplays the skills of leading across diverse and sometimes competing interests both inside and outside the organisation. We propose an alternative view of leadership which we call leading with political awareness but political astuteness, or political savvy are also expressions of this capability. The chapter is based on a large UK research project with middle and senior private, public and voluntary sector managers, which involved a literature review, focus groups with 41 managers; a survey of 1,475 managers and 12 interviews (details in Hartley et al., 2007). The chapter does not report on the empirical findings, but rather sets out some themes concerned with why leadership increasingly needs to take into account political awareness skills; the contexts where such skills are needed; how politics and therefore political awareness is conceptualised; and crucially, a framework of political skills. The chapter argues that political awareness skills raise new questions for leadership theory because the research takes into account the leadership of difference leadership outside as well as, inside the organisation, and the strategic context of leadership.