A growing body of research has emphasized coaching as a key approach to the professional development of school leaders. In many countries, coaching in one form or another is integrated into national school leadership programs. This article reports on a study exploring a specific form of coaching, group coaching, integrated into two national school leadership training programs in Norway and Sweden. The study aims to contribute extended knowledge about how group coaching integrated into such programs can support school leaders’ professional development by examining how a similar yet different group coaching approach, might impact the challenges school leaders bring forth for coaching and how school leaders experience the significance of group coaching in dealing with the challenges in their daily practices. A qualitative collective case study design was adopted, and data was collected through observations, interviews, and questionnaires. Qualitative reflexive thematic analysis was performed. The study shows differences in the type of challenges the school leaders participating in the Norwegian and the Swedish programs brought forth for group coaching and how they experienced the group coaching process to support them in reflecting, understanding, and acting on the challenges in new ways.