This research aims to explore and propose strategies for effective monitoring of decentralized Skill Development Programs (SDPs). SDPs play a vital role in promoting capacity building leading to employment or entrepreneurship, and addressing gaps in the workforce. However, monitoring the progress of these programs poses significant challenges such as accurate and consistent reporting. This research examines the hurdles faced in monitoring SDPs implemented at scale and identifies key technology-supported strategies to overcome them. The major challenge lies in the decentralized nature of SDPs, which involves multiple centers located in diverse geographical and multiple linguistic areas. To address these challenges, a custom mobile-based monitoring tool was developed and implemented. This tool provides real-time updates, targeted reports, and a centralized database, eliminating the reliance on analog-based data collection processes such as paper-based forms and enabling effective monitoring of all centers. This research also explores the involvement of trainers in the monitoring process. The implementation of the monitoring tool consisted of a multi-phased approach, which examined a series of strategies to facilitate the implementing team’s effective use of technology for monitoring and evaluating each training center.