Digitalization has been a debated subject in the 21 st century, especially during the SARS-CoV-2 pandemic when telework has become the base pillar for sustainable economy. This is the reason why, in this paper, the authors are analyzing the interplay between leadership, digitalization and how these two concepts are affecting the productivity in the business world. Starting from the recent articles and studies, our focus is to investigate how the organizations are implementing digital transformation, while aiming for better results and outcomes.The analysis was carried out by referring to international literature for which the authors have enumerated different ways and situations where productivity was affected by telework; nevertheless, given that the pandemic is not over yet and that the timeframe these studies for mass remote working are less than a few years, there is a lot of room for further research on the effect of remote working, connected to productivity when longer periods are used as reference.By exploring the results of the literature review and studies performed on different industries and in different countries, as well as by running a quantitative analysis of leaders' perception toward digitalization, telework and productivity in Romania, the authors identified a viable, long-lasting or even permanent trend for many leaders -to continue to work remotely as a beneficial and much better business plan with positive results in productivity. Furthermore, the article develops a better understanding of future leadership trends and at the least, point toward three fundamental objectives specified as follows: identifying the growth rate of teleworking in the last two years, identifying specific decisions of organizations and leaders willing to prevent decreased productivity levels by changing their processes, and identifying possible new leadership trends for post pandemic business sustainability.