While there has been extensive research in the past in the field of training transfer, there has been little empirical work done examining the influence of personality. Specifically, the paper examines the role of participants’ age in moderating the relationship between proactive personality and motivation to transfer and training transfer. The study used random sampling from 187 employees working in a large paint manufacturing company based in India. Data was analyzed using OLS regression followed by multi-group mediation analysis using bootstrapping. The discussion provides insights into training initiatives within the organisation and recommendations for practice.