This paper reports on evidence from five school principals regarding leadership practices that work in multiple deprived contexts. The South African educational landscape is complex, often described as a cocktail of first and third world institutions. Looking at the schooling system on a continuum, on the one end there are first class schools which can compare favourably with the best in developed countries. On the other extreme there are dysfunctional schools. However, along the scale there are few schools in multiple deprived areas which display high degrees of resilience and perform at levels comparable to first class schools in terms of Matriculation examination results. This paper draws from a study based on the proposition that leadership was the greatest factor to explain such performance. The study was then informed by a quest for knowledge regarding the nature of such leadership. Such knowledge is needed as the country fights to turn around the many dysfunctional schools there are. While there is a corpus of scholarship that "speaks" to this matter internationally, there remains need for home-grown insights in that regard. Two theoretical lenses (servant leadership and the asset-based approach) were applied. The study employed a qualitative approach involving individual face-to-face semi-structured interviews with five purposively selected school principals each representing their school. Findings suggest that the schools in question adopted inside-out development approaches involving the philosophy that they were masters of their own destiny. Time, commitment, and accountability were some of their greatest assets, things that did not have to come from outside the schools. Internal success paved the way for stronger and more fruitful synergies with the "outside world." We conclude that schools in areas of multiple-deprivation need leadership that moves them away from notions of victimhood and deficit thinking towards asset-based approaches.