It is common to observe great variation in dairy personnel turnover and performance within and between dairy herds. The objective was to assess the types of training requested by stakeholders for their dairy personnel and the actual problems reported by personnel. A total of 1,100 individual written requests for dairy personnel training were assessed to determine the perceived needs for training by stakeholders (farm owners, managers, veterinarians, or consultants). All training sessions consisted of ~1 h lecture followed by ~1–2 h of demonstration and supervised hands-on practice designed to improve knowledge and skills. At the conclusion of each training session, dairy personnel were asked to list the problems that they believe should be addressed to improve their work performance. Written feedback from 2,900 individual workers representing 450 dairy herds (conventional and certified organic) were assessed to determine the actual needs by personnel responsible to execute the daily tasks. The top 5 requests for personnel training, according to stakeholders, were (1) milking routine and mastitis control, (2) nutrition management (TMR and feed bunk), (3) health screening for cows and calves, (4) replacement heifers (calving, colostrum), and (5) development of protocols. The top 5 areas to improve work performance, according to personnel, were (1) lack of communication with coworkers or managers, (2) lack of written protocols and resources for the tasks, (3) lack of facility maintenance (e.g., broken gate or hose), (4) properly organize and schedule tasks, and (5) schedule regular meetings to communicate and discuss tasks. While dairy personnel agreed (48%) or strongly agreed (52%) that the content of the training sessions were relevant to their work, and they gained significant knowledge and skills (P < 0.05); their self-reported actual problems were not necessarily associated with lack of knowledge and skills in the areas requested by stakeholders. Fully trained workers know what to do and how to do it; however, the self-reported areas likely affected their attitude which in turn reduces their overall work performance. Training for personnel is an essential management tool; however, the trainer must take into account the underlying problems negatively affecting performance.