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Amid declining enrollments and increased accountability pressures, strategic planning has become essential in higher education institutions. However, persistent gaps still exist in execution, adaptability, and integration with performance systems. This study explores these organizational challenges across four areas: leadership, execution, adaptability, and performance. Through interviews, focus groups, and document analysis, the study identifies key obstacles such as governance fragmentation and limited data use in decision-making. Insights gained helped develop and validate a pilot survey instrument with expert input. The findings highlight the importance of inclusive leadership, flexible planning structures, and integrated assessment tools. This research enhances understanding of how organizational leadership can improve strategic capacity and promote institutional transformation in higher education.