Accredited Social Health Activists (ASHAs) are the essential link to healthy communities for Indian households. We present insights and findings of two focus group studies conducted with 16 ASHAs and 8 ASHA trainers across two health centers in Assam, India. We conducted two focus group studies to investigate challenges and opportunity areas in current health worker training ecosystem. Our objective was to identify insights that formulate design directions in order to develop technology solutions to train ASHAs effectively. We found challenges of poor training schedules, outdated information, inadequate contextual knowledge and field-based challenges, poor accessibility, and portability of the training material and low-confidence in communicating sensitive health information. We propose the need for technology intervention that supports practice-based learning, methods of role-playing and use of cultural songs and dance to increase engagement. We also propose the use of peer learning and sharing among ASHAs to increase adoption and acceptance. © 2019 ACM.