In this chapter we focus on the type of uncertainty that is characterized by a sense of urgency and by the severe consequences in the case of failing to act or of making a mistake. We discuss how attention to detail goes alongside acknowledging and responding to contextual complexities to address their uncertainties effectively. We outline the different factors which are critical for organizations and their responses to organizational complexities, uncertainties, and dynamics. We discuss how the separation of causes and effects in both time and space, and the contradictory effects of solutions in the short and long term, help to construct a more complex world view that challenges deterministic certainty of actions and their outcomes. Other critical aspects that we address in this chapter are routines and automated behaviors together with organizational and individual mindfulness and alertness. We highlight the importance of understanding luck in successes and failures and the lightness decision makers need when facing today’s increasingly complex and uncertain world.