As happens for many processes of historical evolution, the first half of 2020 will be remembered forever as an epochal moment in the history of work activities since, following the Covid-19 public health emergency globally, in order to survive organizations found themselves forced to use the only tools they had at their disposal to avoid fatally interrupting their operations: technology and smart working. Once the emergency ended, not only these new ways of working remained, but they are in this post covid era, the protagonists of nowadays work operations. However, if from one hand digitalization and new hybrid work models have positively impacted organizations and people performance, from the other hand psychological safety seems to be in danger as these important changes led to increased work-related stress for employees (especially for knowledge workers) who are not always able to cope with the actual intrusive digital professional reality that is difficult to keep under control. In fact, 2 recent reports from Indeed and Deloitte shows that 50% of people believe that their company/institution isn’t doing all it can to improve employee wellbeing and happiness at work and more than 40% employees believe that well-being is not good because of the heavy workload, stressful job and not having enough time because of long work hours. The aim of this work is to provide knowledge on the topic of organizational wellbeing. It provides practical examples, it includes the perspective of different stakeholders and it concludes with tips that come from experience and prior shared knowledge among managers and practitioners, highlighting the need of a digital leadership to both manage performance and guarantee people psychological safety. In other words, digital transition is not only facilitating remote work and this seminar may be helpful to knowledge workers who are currently facing these issues in their daily working reality.