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This field study examines factors influencing hotel employees’ ability to transfer the concepts that they learned in job training when they return to work. The study was conducted during a major hotel company’s training program. The training objective was to ready front-desk associates to operate a new property management system (PMS). Past business research suggests that trainee characteristics, training design, and work environment factors can positively impact an employee’s transfer of training. Role-play exercises and surveys were used to explore the validity of this research in a hospitality setting. This study’s findings suggest that proper management of these impact factors can foster enhanced transfer of training in hotels. Strategies are offered to help hospitality human resource professionals improve training transfer in hotels.