General Background School principals act as primary leaders responsible for educational success, organizational management, and teacher competence enhancements. Specific Background This descriptive qualitative study investigates the strategic management implemented by the principal at SMK Negeri Widang Tuban Regency to support teacher performance, alongside monitoring evaluations and associated obstacles. Knowledge Gap Although administrative strategies are crucial, practical execution often suffers from constraints such as inadequate facilities, limited teacher technology mastery, and suboptimal monitoring schedules. Aims This study aims to identify and analyze principal strategies, monitoring evaluations, and strategic implementation obstacles. Results Findings show that principals utilize motivation and training strategies, combined with observational monitoring, interviews, and discussions, though faced with infrastructure shortages, low technology proficiency, and scheduling issues. Novelty This work details the practical synchronization of personal familial approaches, work motivation, and structured academic supervision within a vocational secondary school setting. Implications These findings establish that reinforcing principal leadership approaches, upgrading school facilities, and improving supervisory scheduling are vital for overcoming performance barriers and optimizing educator effectiveness. Highlights: Principal strategies rely on personal familial approaches, work motivation, and professional training programs to foster educator development and work ethic. Monitoring and evaluations are executed via classroom observations, instructional interviews, and evaluative discussions to measure institutional program success. Primary implementation barriers include inadequate infrastructural facilities, low technological mastery among teachers, and rigid supervisory scheduling. Keywords: Principal Strategy, Monitoring and Evaluation, Teacher Performance, School Management, Vocational Education
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