Since the outbreak of the COVID-19 pandemic, teleworking has experienced a significant resurgence and has become the focus of extensive research. While various aspects of telework have been explored, the influence of cultural elements—particularly control and trust—as well as prior experience, has received less attention. To address this gap, this study aims to comparatively examine how these factors influence managers’ decisions to implement telework. To this end, data were collected from executives in three countries—France, Switzerland, and Canada—using an online survey. The comparative analysis focused
on 359 questionnaires collected from the three countries. The results show that all three countries demonstrate favorable conditions for teleworking, based on cultural elements and prior experiences. However, Canada exhibits a stronger adaptation to teleworking compared to the other two countries. Furthermore, the role of control was more pronounced in France compared to the other two countries, whereas in Canada, a lower level of control is exercised. Additionally, trust plays a key role in explaining the stronger adaptation to teleworking.