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An in-depth analysis of how senior managers in a large multinational corporation interpret their social and environmental responsibilities revealed that, notwithstanding formal corporate interpretations, discrepancies persisted in their interpretation of what was expected of them and how to implement it. Two fault lines emerged: (1) an instrumental versus a normative interpretation of corporate societal responsibilities, and (2) a focus on ‘doing less/no harm’ versus ‘doing more good’. This chapter introduces a theoretical framework that combines these fault lines to form four quadrants that each represent a different set of challenges managers face as they commit to improving their organisation’s impact on society. Rather than adjudicate between them, a holistic interpretation of corporate social responsibility (CSR) takes all four types into account. But the four types of challenges differ considerably in nature and thus in the strategic approach that is necessary to deal with them. In this chapter, each quadrant is discussed in detail. What characterises the issues in this quadrant, what mindset, and what strategy are necessary to address them? The chapter concludes with the observation that the framework, and the taxonomy of types of CSR challenges that it brings to the fore, creates greater awareness of how industries are confronted with different sets of challenges and thus need different strategic approaches. A better understanding of these differences may lead to more support, in particular for those managers who work in industries that face a disproportionate share of one particular type of challenges, the ‘nasty trade-offs’.