Trade-offs between the conflicting aspects of corporate sustainability (CS) have hindered the realization of win-win opportunities that advance both sustainable development and the bottom line. The question today is no longer whether these trade-offs are encountered in the pursuit of CS, but under which circumstances they occur, with which responses, and how best to navigate them. This study conducted a systematic review and content analysis of the trade-off literature published to-date at both conceptual and applied levels. Through this process, a hierarchical framework is proposed for the analysis of trade-offs based on their different categories, their root tensions, their interconnections, and where they are encountered in the practice of CS, from policy to implementation. Based on this, a number of recommendations are provided on how managers may better navigate the hierarchy of trade-off decision-making, to ultimately transform trade-offs into synergies. Several suggestions for future trade-off research are also provided.