The contemporary attempts to tackle poverty and child poverty in the United Kingdom have been seriously hindered by the effects of the economic crisis (Hirsch, 2008a; Mooney, 2011). The prevailing discourses of the recession and intergenerational poverty can lead to a view that the effects of child poverty and the consequent detrimental impact on school education and future prospects for some young people are intractable (Sinclair & McKendrick, 2009). There can be insufficient emphasis on the successful attempts, however fragile, to intervene in the cycle of deprivation. This article reports on research conducted in two contrasting groups of secondary schools in the city of Glasgow, located in areas of deprivation, as they work to secure initial positive school leaver destinations for young people. This small-scale case study highlights the importance of a strong leadership vision committed to initial positive school leaver destinations, but complemented by distributed leadership and support from external partners to enable sustained successes. It also highlights the importance of individual attention to all young people to support and motivate them and the effectiveness of intervention at an early stage. (Contains 3 tables and 10 notes.)