Personality has been considered an important factor influencing trainee efficiency & organizational productivity. Similarly, work climate factors have been recognized as primary influencers in post training context influencing productivity. But research concerning the impact of personality and work climate on trainees’ learning motivation has been very scant and mostly conducted in the western context. The present study was an attempt therefore, to extend this line of research in the Indian context involving educational sector of the State of Jammu & Kashmir. A sample of 517 teacher trainees was drawn for the present study using convenience sampling method. Results indicate that personality traits (i.e., conscientiousness, openness to experience, and internal locus of control) do not influence training transfer directly or indirectly, while, transfer climate factors do affect training transfer both directly as well as indirectly via learning motivation. The implications of the results are discussed and the limitations of the study are noted, along with suggested avenues for future research.