With the outbreak of COVID-19 in spring 2020, small, medium, and large companies were forced to cope with the unexpected circumstances. Faced by this health emergency, it was necessary to ensure that staff remained motivated and that they could continue to carry out their duties despite the obstacles. The main goal of this exploratory research was to characterize employees who teleworked and who did not, and their motivation during the lockdown. A total of 11,779 workers from different-sized companies in various sectors answered an ad hoc questionnaire. By using non-parametric comparisons and Classification and Regression Trees (CRTs), the results show differences in both the assessment of strategies put into practice by the companies and the level of motivation of teleworkers and non-teleworkers, with the latter being more highly motivated. Nonetheless, teleworkers assessed their companies’ strategies and the role of their managers and colleagues more positively. This research helps to understand how different sectors have dealt with the crisis, according to the degree of teleworking implemented in each sector, and to what extent the motivation of the employees has been affected. The analysis of the large amount of data obtained confirms the importance of the role of managers in sustaining the motivation of their subordinates in times of crisis. In this sense, it is necessary to develop managers’ competencies in order to develop and maintain relations of trust and support with their coworkers. On the other hand, it is necessary to foster employees’ sense of meaningfulness and responsibility at work in order to keep them motivated.