The inception of KESSHA dates back to the colonial era when a small group of headteachers, motivated by national interests, conceived the idea. During a time when European, Asian, Arab, and African schools faced varying needs and challenges, headteachers required a platform to stay informed about changing educational scenarios and how to address them. What began as a dream to form an association for headteachers has since become a reality.

The creation of the KESSHA secretariat, comprising various departments, significantly addressed several challenges the association had encountered. This move marked a pivotal moment in KESSHA’s history, as having a dedicated secretariat is crucial for any organization to streamline operations, enhance coordination, and improve overall efficiency. In August 2004, KESSHA further advanced its professional outreach by launching its first publication, “The Principal” magazine, which captures and documents activities at national, county, and sub-county levels.