Artificial intelligence models such as chat generative pre-trained transformer (ChatGPT) are being increasingly used to inform treatment-related decisions. Among otolaryngology subspecialties, there is a paucity of literature examining the role of ChatGPT within head and neck surgical oncology. The utility of ChatGPT in addressing questions related to surgically relevant anatomy and lymphadenectomy procedures remains poorly understood. The primary pilot study objective was to determine the reliability of ChatGPT in answering neck dissection-related inquiries compared to expert head and neck surgical oncologists. Five neck dissection-related questions were presented to ChatGPT v3.5. Three fellowship-trained head and neck surgeons compared AI-generated responses to those of an expert head and neck surgeon. Raters, blinded to the author’s identity, evaluated the responses given based on a Likert scale ranging from 1 (strongly disagree) to 5 (strongly agree). The median level of agreement between raters for the ChatGPT responses was 1.0 (interquartile range [IQR]: 1.0, 2.5; minimum = 1 and maximum = 4), while the median level of agreement between raters for the surgeon responses was 5.0 (IQR: 5.0, 5.0; minimum = 5 and maximum = 5). The Mann–Whitney U test yielded a significance level of p=0.007 when comparing the level of agreement between ChatGPT and surgeon responses. Raters showed minimal consistency when evaluating ChatGPT responses (intraclass correlation coefficient = 0.05; 95% confidence interval: 0.0–0.88), in contrast to perfect agreement observed for the surgeon responses. In summary, ChatGPT is a promising tool in the acquisition of surgical knowledge. For neck dissection-related inquiries, a discrepancy between the reliability of ChatGPT-generated responses and surgeon expertise exists. Further refinement in AI models is needed to strengthen the utility of ChatGPT in head and neck oncologic surgery.