Advancements in state-of-the-art models and algorithms for chatbots have significantly driven the growth and evolution of human–computer interaction (HCI) in recent years. As a result, numerous authors are inspired to study the most effective interactive chatbot design that can maximize students’ experiences. Despite the fact that high school is one of the most critical stage in a student’s life, there is a lack of studies that focused on developing effective interactive high school advising chatbots. To address this current gap, this study aims to elicit the main effective features for high school advising chatbot. The authors in this study conducted a semi-structured qualitative interview with six high school students in UAE and the MAXQDA Analytics software—ver. 22.6.0 is implemented by processing the thematic analysis to study the findings. The results revealed that high school students recommended the same general interaction design characteristics that was derived from the previous systematic review with emphasizing more into accurate, reliable, and trustworthy short answers with having minimal conversational issues. In addition to that, emotions and empathic factors are less important for high school students.