Abstract: Strategic planning is a key determinant of performance and sustainability in community-based organizations. This study investigates the influence of strategic planning practices, specifically goal setting, leadership assignment, communication pathways, and risk identification, on the performance of grassroots initiatives in Kenya, through a project management lens. Utilizing a descriptive quantitative design, data were collected from 169 group members in Kenya’s Lower Eastern region and analyzed using SPSS (v25) through descriptive statistics, Pearson correlation, and multiple regression. The findings reveal a statistically significant but modest positive correlation (r = 0.190, p < 0.05) between planning practices and project success, with educational attainment (β = 0.312, p = 0.001) emerging as the strongest predictor. The results validate the relevance of Goal Setting and Systems Theories in informal grassroots contexts and underscore the need for inclusive, simplified planning tools. The study recommends targeted training, context-appropriate planning models, and supportive policy frameworks to institutionalize strategic planning in community-based development. These insights offer actionable, data-driven guidance for practitioners and policymakers seeking to strengthen the performance of self-help groups and similar grassroots initiatives. Keywords: Strategic planning, Practices, Project management, Self-help groups, Community-based organizations |