Training transfer is a ubiquitous but frequently unmet goal of training initiatives amounting to billions of dollars lost annually and masses of under-skilled workers due to the lack of application of training content to their job. Although research supports the impact trainee proactive personality, conscientiousness and motivation have on training transfer processes, their interrelationships remain understudied. To fill this gap, we utilized data from a multinational sample of trainees and examined a conditional, indirect process model, where proactive personality interacts with conscientiousness to influence transfer intentions through their effects on motivation to learn. Our results suggest that trainee proactive personality positively influences transfer intentions partially through its influence on motivation to learn and that higher levels of conscientiousness weakens this relationship. Our findings provide further evidence supporting the importance of proactive personality and conscientiousness as factors that need to be accounted for in the design of talent development solutions.