This research compares the accounts of two experienced urban primary headteachers based in Kinshasa (Democratic Republic of the Congo-DRC) with two others based in Sheffield/Doncaster (England), in order to make sense of their leadership pathways, challenges and approaches. Engaging these school leaders through leadership conversations within a narrative research tradition, the extracted data were analysed thematically and using phenomenological interpretive analysis. Despite differences in their stories of actions regarding the researched themes, a comparative theory of context(s) emergences which adds to how school leaders can think and act locally and globally and, in the case of African school leaders, decolonise their practice of any dominant normativity as they define what is best for their schools. This involved headteachers being attuned to their personal, professional and comparative dimensions of ‘the gospel according to the headteacher’ metaphor and ultimately deploying their connect comparative core values to rise above the subjective or objective scope of one’s context in order to bring about change that primarily benefits children.