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Reentry organizations often face unique challenges related to service delivery and programmatic growth. These entities create additional barriers to successful implementation and long-term sustainability. This paper presents findings from interviews with frontline staff and leadership at a localized, education-based reentry service organization. Participants highlighted challenges associated with working inside correctional institutions, collaborating with external partners, and strengthening internal organizational capacities. In response, we propose a user-centered design for capacity building activities aimed at preparing organizations to become evaluation ready. This framework offers a new approach to designing evaluability assessments and prioritizing organizational growth by centering the factors that most directly affect service delivery and staff operations.