The acquisition of skills amongst learners is integral for their survival. This is the reason why most of the pedagogies integrate them as part of the core learning objectives. However, the advent of technology has revolutionized teaching approaches as well as skills training. Many of the skills in 21st century education highlight ingenuity, critical analysis and IT literacy. Though it is understood that these prepare learners to be efficient in the future, there are significant underlying issues and challenges in how schools partake in the training process or how skills acquisition amongst learners are monitored and promoted in the schools' advocacies. This research is aimed at evaluating primary school administration how 21st century skills should be reflected in the school system. Identified factors that help promote 21st century skills were analyzed using content analysis and focus group discussion of ten (10) experts and later on evaluated and confirmed statistically through Confirmatory Factor Analysis (CFA). Four hundred respondents: two hundred (200) school directors and two hundred (200) academic head teachers from 322 schools in southern Thailand were considered as samples. A 5-rating scale questionnaire was used for data collection. Through second-order confirmatory factor analysis, the results confirmed eight (8) factors that promote 21st century skills in primary school administration. Arranged in descending order by goodness of fit, these factors were: (1) teacher quality development (0.97), (2) educational evaluation (0.92), (3) teaching and learning management (0.90), (4) learning environment (0.88), (5) curriculum, learning media, and technology (0.87), (6) budget for education (0.84), (7) community cooperation (0.66), and (8) volunteer supervision (0.64). The measurement of all factors (R[superscript 2]) also indicated positive reliability ranging between 0.41-0.94.