The worldwide Covid-19 pandemic caused lockdowns in countries across the globe and forced organizations to conduct remote work solutions, contributing for challenges to arise. Therefore, the purpose of this study is to investigate main challenges related to remote leadership caused by external disruptions. Further, this study has conceptualized remote work conditions and distinguishes between remote leadership derived from proactive changes and reactive changes to create the concept of “proactive remote leadership” and “reactive remote leadership”. A qualitative and exploratory method was applied through semi structured interviews, with nine managers at a global organization named Leaseplan. The empirical findings from the data collection discovered noticeable differences in challenges between the two remote leadership concepts. Main challenges found within reactive remote leadership which had not been highlighted in previous studies focusing on remote leadership were organizational silos, information sharing, transparency, workload, employee wellbeing and motivation. The findings suggest that it is important for both scholars and managers to put context to leadership to find nuanced challenges but also opportunities.