With the increase of telework during the COVID-19 pandemic, employees’ interactions with colleagues have shifted almost exclusively to digital channels. Hence, it is critical to understand the underpinnings of successful collaboration and individual wellbeing in digital working structures. Combining qualitative experience reports and quantitative surveys from 145 teleworkers, this study sheds light on teleworking from a psychological perspective, taking social norms as a conceptual frame. The qualitative reports revealed five types of typical conflicts related to communication in the telework context, including both (1) technical problems (e.g., a bad connection) and psychological aspects such as (2) uncertainty or a lack of social feedback, (3) norm violations, (4) a lack of rules or meta-communication about appropriate behavior, and (5) digital communication barriers. Respondents’ quantitative ratings of qualities of telework versus working on-site revealed benefits of telework regarding task fulfillment and efficiency, but lower levels of motivation, conflict management, leadership, team spirit, inspiration and creativity. Participants qualitative reports on perceived challenges in remote work conditions included feelings of loneliness and increased demands related to self-management, creating boundaries between private and working life, motivation and self-regulation. This paper connects these findings with theoretical concepts from psychology and human-computer interaction and discusses implications for leadership and technology design.Practical Relevance: This article discusses practical implications for leadership and technology design, e.g., interventions against conflicts in the context of digital work.