This study determines the factors influencing macadamia nut productivity among smallholder farmers in Zimbabwe's Chipinge District. Despite favourable agro-ecological conditions, smallholder productivity (1.89t/ha) significantly lags behind commercial farmers (3.9t/ha) and global benchmarks (7.17t/ha). Using cross-sectional data from 284 registered smallholder farmers collected in 2023-2024, ordinal regression analysis identified critical productivity determinants. Results revealed that farming experience significantly increases productivity, with each additional year of experience raising the log odds of achieving higher productivity by 18.4% (p<0.05). Labour availability positively influences productivity (p<0.05), particularly during labour-intensive operations like pruning and harvesting. Farm resilience score, capturing innovations that reduce field losses and improve market access, exhibited a strong positive effect (p<0.01). Unexpectedly, financial management skills (FMS) and risk management skills (RMS) demonstrated significant negative effects (p<0.05), suggesting a "formalization penalty" where sophisticated management systems incur overhead costs that fail to yield proportional returns in contexts of pervasive market failure, price volatility, and liquidity constraints. The study concludes that while farm experience, labour capacity, and resilience-building investments enhance productivity, the effectiveness of formal management skills is constrained by fundamental market structure failures. Policy recommendations emphasize capacity building in experiential learning, labour skill development, resilience-enhancing technologies, and most critically the market structure reforms to enable formal management systems to function effectively. Addressing transaction costs, information asymmetry, and capital access constraints must precede investments in sophisticated farm management training.