Construction workers are more prone to safety hazards compared with workers of other industries according to reports of the U.S. Bureau of Labor Statistics, and transportation maintenance workers are no exception. The nature of the work for this unique audience exposes them to different hazardous conditions, which increases the probability of injuries. As part of a project to improve safety performance for the Kentucky transportation cabinet (KYTC) maintenance workers, this study outlines the development of a pre-task safety talk program. By analyzing safety recordable incidents claims of KYTC maintenance employees for a 10-year period between 2005 and 2015, the top leading reasons for claims were determined. The results show 12 leading reasons that were repetitive among 10 typical operations for KYTC maintenance workers. Because the majority of the accidents could be avoided if some safety precautions were followed, specific safety practices are suggested according to the nature of the operation and the identified leading reasons. A final product of this project is a pre-task safety tool that workers can use before starting any of their typical work operations. This study identifies the leading reasons behind work-related incidents in highway maintenance and the sizable gap in safety measures targeting this unique sector of the construction industry.