As a student at the University of Cincinnati, while accompanying his dad to scout a Cincinnati Woodward High School game, Cronin was offered a job coaching the freshman team and assisting with the varsity by then-Bulldogs coach Jim Leon. From 1991 to 1996, he served as a varsity assistant coach and junior varsity coach at Woodward High. Cronin compiled a 57–3 record in three seasons as JV coach, and as a varsity aide, Woodward claimed three city championships. While at Woodward, Cronin helped develop six players who went on to play Division I college basketball, including former University of Louisville players Eric Johnson and Dion Edwards, and former Cincinnati guard Damon Flint.