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Outcomes for school students in London, especially for those from disadvantaged backgrounds, have improved dramatically over the last two decades. Leadership at the level of individual schools appears to have been a particularly crucial driver of these improvement processes. We conducted qualitative interviews with eleven headteachers and senior leaders from eight highly effective London schools with a very large proportion of disadvantaged students. The objective of this paper is to explore one element of their leadership, which emerged from the data, namely “raising aspirations and expectations”. The data show that schools make considerable efforts to encourage and equip their students to aspire to higher education instilling in them a belief that they could take any career path they chose.