Even though studies of expatriates from Nordic countries have been conducted, qualitative data on expatriates in Sweden has barely been generated. This research is the first explorative study within this context. The authors have chosen a qualitative approach, interviewing both assigned and self-initiated expatriate leaders currently working in Sweden. The data is presented in the form of five case studies including three European and two non-European citizens. The cross-case analysis confirms the GLOBE study’s main finding that leadership effectiveness is contextual. It has become clear that expatriate leaders face several challenges in the Swedish business culture. These are mainly related to the speed of working, the need for consensus in the decision-making process, and the conflict avoiding tendency. These drivers demonstrate that there are certain cultural aspects unique to Sweden. Expatriate leaders need to be flexible in adapting their leadership style and be engaging with their followers in order to work successfully in Sweden.