IntroductionLetters of recommendation (LORs) are a highly influential yet subjective and often enigmatic aspect of the residency application process. This study hypothesizes that LORs do contain valuable insights into applicants and can be used to predict outcomes. This pilot study utilizes natural language processing and machine learning (ML) models using LOR text to predict interview invitations for otolaryngology residency applicants.MethodsA total of 1642 LORs from the 2022–2023 application cycle were retrospectively retrieved from a single institution. LORs were preprocessed and vectorized using three different techniques to represent the text in a way that an ML model can understand written prose: CountVectorizer (CV), Term Frequency‐Inverse Document Frequency (TF‐IDF), and Word2Vec (WV). Then, the LORs were trained and tested on five ML models: Logistic Regression (LR), Naive Bayes (NB), Decision Tree (DT), Random Forest (RF), and Support Vector Machine (SVM).ResultsOf the 337 applicants, 67 were interviewed and 270 were not interviewed. In total, 1642 LORs (26.7% interviewed) were analyzed. The two best‐performing ML models in predicting interview invitations were the TF‐IDF vectorized DT and CV vectorized DT models.ConclusionThis preliminary study revealed that ML models and vectorization combinations can provide better‐than‐chance predictions for interview invitations for otolaryngology residency applicants. The high‐performing ML models were able to classify meaningful information from the LORs to predict applicant interview invitation. The potential of an automated process to help predict an applicant's likelihood of obtaining an interview invitation could be a valuable tool for training programs in the future.Level of EvidenceN/A Laryngoscope, 2024