This chapter presents a case study investigating the student experience with AI-assisted situational analysis using the SWOT approach in construction management education. The study focuses on third-year Bachelor of Construction and Graduate Diploma in Construction Management students enrolled in a “Complex Construction” course. The aim is to enhance students’ situational analysis skills by integrating ChatGPT for SWOT analysis tasks. The spiral of inquiry facilitated the data collection process by providing opportunities to gather data generated through demonstrations, presentations, group discussions, questionnaire surveys and evaluation of student work where relevant based on the nature of a given stage and its objectives. Findings suggest that AI-assisted SWOT analysis enables a broader understanding of a given topic relevant to the construction management domain and encourages critical thinking among students in collaborative settings. This study has implications for promoting technology-enabled teaching and learning in construction management education and industry readiness.