The ability to reflect is an important generic competence especially for underperforming students as they have to analyse their previous learning experiences to improve on future academic performances. This action research describes the process of a team when developing a reflection guiding tool (RGT). As the underperforming students may have difficulty in comprehending what is expected from them while using a reflective approach, we designed the RGT based on the six steps in Gibbs cycle; 1) Description, 2) Feelings/Reactions, 3) Evaluation, 4) Analysis, 5) Conclusions, and 6) Personal action plan. These underperforming students reflected on how, and why, they failed their assessments based on the proposed RGT. Findings revealed that RGT was able to make students aware of what reflection skill is and thus fulfilled its objective. It helped Year 1 and Year 2 underperforming medical students to reflect on their academic failure.