This paper presents a systematic literature review of the challenges faced by managers during COVID-19, with a focus on teleworking. The study consists of an analysis of 53 articles published in the period 2020–2023 in journals indexed in the Elsevier’s Scopus and Clarivate Analytics’ Web of Science databases. The inclusion criteria were: (1) peer-reviewed articles; (2) empirical articles; (3) written in English. Five themes were identified: Leadership Styles, Organizational Support and Communication, Telework Productivity, Challenges Related to Telework, and Leaders’ Attitudes Towards Telework. The positive results show that telework can improve work performance with the right equipment, training, and leadership. Telework can also improve sustainability by limiting commuting and providing decent work with greater autonomy and flexibility. The paper concludes with recommendations for future research on this topic.