The study explores enhancing elective course selection in Information Technology (IT) education within Estonian general schools by developing a pre-selection assessment tool. Aimed at aligning student interests and competencies with course offerings, the tool evaluates academic skills, prior exposure to IT, and personal preferences. Results from surveys conducted among high school and university students reveal significant disparities in preparedness and engagement levels, emphasizing the importance of early exposure to IT-related activities. Key findings include the strong influence of mathematics and digital safety skills on ICT interest, the value of hands-on learning approaches, and persistent gender disparities. The study highlights the potential of structured pre-selection processes to improve academic outcomes, reduce dropout rates, and address gender imbalances. However, challenges such as superficial evaluations and evolving student interests underscore the need for iterative tool refinement. Future directions include integrating AI-driven, adaptive assessments to provide personalized guidance, ultimately fostering equitable and inclusive pathways to ICT education and careers.