This paper explores how Holistic Debrief, a new concept in the field of debriefing and reflective processes, can contribute to restitution, reflection and learning in professional teams following stressful events and routine tasks. Interviews were conducted with Norwegian military aircrew mission commanders following deployment to Afghanistan in 2010. Phenomenological analysis in the frame of social learning theory revealed that reflective processes were easier to facilitate after stressful events than after routine tasks. Challenges identified included lack of trust during the early stages of team establishment and poor conceptual repertoires among aircrew commanders undertaking facilitation. Relational trust and reflective processes tended to improve after stressful events. Repeated interactions in Holistic Debrief tend to increase familiarity, trust and learning potential over time. This study reports data from the war context, an environment not often available for qualitative research. The findings are relevant for military and other operational units who wish to develop their debriefing practice and create an experience-based learning environment.