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This paper describes the process of developing a participatory monitoring and evaluation strategy for a Kenyan youth-based NGO. The iterative nature of the study including the process of narrowing down indicators to measure and methods to monitor/evaluate these is well documented. A discussion on the extent to which the process achieved participation and was empowering for the participants reflects on existing power relationships and cultural context of Kenya and points to the need to create opportunities for youth where they engage with the broader community. Lessons that emerge out of the study focus on the importance of prioritizing monitoring and evaluation, the potential of youth to carry out effective monitoring and evaluation, and the need for researchers to engage respectfully with communities and participants.