The role of vocational education and training system (VET) in addressing the economic and social needs of vulnerable youth from low-income households can be significant. It enables economic empowerment, providing them with a pathway to sustainable employment opportunities; improving their overall well-being and sense of personal identity. This article presents qualitative and quantitative data elucidating different elements of employability issues faced by such youth. It distinguishes and divulges a vulnerable group out of a larger population thereby making a strong case for identifying and addressingtheirneeds. The approach is therefore not a ‘one size fits all’ training method. Students from urban Mumbai and New Delhi were mobilized from multiple channels such as self-help groups (SHGs), the National Institute of Open School (NIOS), distance education institutes, local government colleges, night schools and through direct community outreach. After carefully matching for demographic and economic characteristics, a group of 387 students in the age bracket of 18 to 24 years were selected and interviewed. This first set of data was generated for a range of personal, economic, and household characteristics. Data manifests structural barriers, poor human capital endowments and exclusion. To gain further insight into characteristics and to design a targeted intervention for a sub-group of 130 students from the total population, a second dataset is generated through a questionnaire and interview. Of this, two equal groups – an experiment group and a comparison group are formed as part of quasi-research. The third type of data is generated using a 5-point Likert scale questionnaire and personal discussions. A total of 2600 responses from the experiment (trained and skilled) and comparison (not trained) groups provides a basis for comparison of scores between the two groups pre-and post-intervention. The entire data collection process is practical, straightforward, and simple. Easy to explain - the dataset can be leveraged to generate evidence-based insights, and informed decisions on resource allocation, program design and strategies to mitigate risk factors. The multifaceted approach of data collection can be adapted to accurately identify vulnerable youth and create a newer framework for skill development and re-skilling. It can be used to develop measurement tools for employability by those involved in VET and in their efforts to create viable employment opportunities for high-potential yet disadvantaged youth.