The aim of this study, which is grounded in decision-making theory, is to explore whether the occurrence of meaningful coincidences can positively influence executive confidence, allowing hospitality industry organizations to cope, if only for short periods, in chaotic and uncertain contexts and settings, such as the COVID-19 pandemic. Through a qualitative study with 24 interviews, conducted both in person and via Microsoft Teams, this study focuses on Italian hospitality facilities in the Campania Region of southern Italy to explore how executive confidence led by meaningful coincidences can influence managerial decisions. The results highlight the process through which meaningful coincidences lead to the three different characteristics of executive confidence during a decision-making process – overestimation, overprecision, and overplacement. The insights that emerge suggest a number of positive and beneficial aspects for decision-making in a crisis such as the COVID-19 pandemic. To the best of the authors’ knowledge, this is the first study in the literature aimed at investigating, by means of qualitative methodologies, the positive outcomes of executive confidence in decision-making led by meaningful coincidences during crisis periods in the specific context of the Italian hospitality industry.