Explore the challenges and strategies of implementing an automation education program in this BSidesLV conference talk. Delve into the speaker's experience as a Security Analyst at Rally Health, focusing on yearly goals and program alignment. Learn about the program's objectives, including teaching Python to all participants and modernizing legacy Bash scripts. Discover the approach to creating a sustainable learning path through study groups, utilizing resources like "Learn Python The Hard Way," and incorporating LeetCode exercises. Gain insights on addressing short-term issues such as attendance and participation, as well as long-term challenges like maintaining motivation and accommodating diverse skill levels. Acquire valuable takeaways on initiating a program, securing buy-in, and aligning educational goals with practical automation needs in the security field.