This chapter discusses how emotions and values influence senior executives’ decision-making in the context of competing organizational demands. We draw on a paradox-hermeneutic phenomenological study of 10 top executives operating in highly institutionalized and complex contexts to show if and how executives are influenced by their emotions and values when making important organizational decisions. Executives who adopt a slow, circular, values-based decision-making process are guided by their values and by what “feels right.” To compensate for the emotional strain caused by tensions from competing demands, executives strive for emotional equanimity by balancing a values-based personal purpose with continuous self-care. In contrast, executives who adopt a linear analytical decision-making process are less influenced by emotions and values. The executives’ level of paradox mindset, encompassing both cognition and emotions, contributes to explaining these different decision-making processes.