Retrieving semantically relevant documents in niche domains poses significant challenges for traditional TF-IDF-based systems, often resulting in low similarity scores and suboptimal retrieval performance. This paper addresses these challenges by introducing an iterative and semi-automated query refinement methodology tailored to Humber College's career services webpages. Initially, generic queries related to interview preparation yield low top-document similarities (approximately 0.2--0.3). To enhance retrieval effectiveness, we implement a two-fold approach: first, domain-aware query refinement by incorporating specialized terms such as resources-online-learning, student-online-services, and career-advising; second, the integration of structured educational descriptors like "online resume and interview improvement tools." Additionally, we automate the extraction of domain-specific keywords from top-ranked documents to suggest relevant terms for query expansion. Through experiments conducted on five baseline queries, our semi-automated iterative refinement process elevates the average top similarity score from approximately 0.18 to 0.42, marking a substantial improvement in retrieval performance. The implementation details, including reproducible code and experimental setups, are made available in our GitHub repositories \url{https://github.com/Elipei88/HumberChatbotBackend} and \url{https://github.com/Nisarg851/HumberChatbot}. We also discuss the limitations of our approach and propose future directions, including the integration of advanced neural retrieval models.