(1) Background: To empower and facilitate mental health promotion for nearly 18 million youth, a pioneering state-wide Life Skills Training and Counselling Services Program (LSTCP) was implemented in Karnataka, India. This study assesses the changes in life skills scores, level of life skills and factors associated with increased life skills among participants of the LSTCP. (2) Method: This pre–post study design was conducted on 2669 participants who underwent a six-day structured LSTCP. Changes in mean life skills scores and level of life skill categories pre- and post-LSTCP were assessed. Multivariate logistic regression was performed to assess the factors associated with increases in life skills. (3) Results: The LSTCP resulted in significant changes in life skill scores and level of life skills, indicating the effectiveness of the training. All life skill domains, except empathy and self-awareness, increased post-training. There was a positive shift in the level of life skills. Age (AOR = 1.34, CI = 1.11–1.62), gender (AOR = 1.39, CI = 1.15–1.68), education (AOR = 1.44, CI = 1.05–1.97) and physical (AOR = 1.02, CI = 1.01–1.03) and psychological (AOR = 1.02, CI = 1.01–1.03) quality of life was associated with an increase in life skills among participants. (4) Conclusions: The LSTCP is effective in improving the life skills of participants. The LSTCP modules and processes can be used to further train youth and contribute to mental health promotion in the state.