OBJECTIVE: The study of expert performance provides a rich field for exploration in the surgical literature. This study aimed to examine the difference between expert and novice surgeons in their preparation for challenging cases. DESIGN: Expert (attending) and novice (postgraduate-year 2) surgeons were presented two cases of complicated cholecystitis and were asked how they would prepare, what they would expect to encounter intraoperatively, and how they would deal with these challenges. Their responses were recorded, transcribed verbatim and analyzed using thematic analysis. SETTING: Academic teaching hospitals. PARTICIPANTS: Two group of expert and novice surgeons. RESULTS: Nine experts and eleven novices from two academic centers participated. The majority of novices focused on patient history, work-up, preoperative optimization, anatomy, and anticipation of intraoperative challenges. In addition to the patient's presentation and preoperative optimization, most experts' thoughts were directed toward preparation for surgery (level of urgency, required skills in surgical team, case difficulty, and risk of conversion to open). Experts would involve the patient in the decision-making and were more likely to communicate with the operating room team. While novices attempted to predict challenges depending on gallbladder condition and intra-abdominal adhesions, the experts highlighted the importance of various elements of the operative field, the detail of the technique and possible challenges, and their troubleshooting plans. Regarding operative planning to address anticipated challenges, novices would tailor their plan to patient characteristics and verbalized an analytical "if-then" approach for all possibilities they might encounter. Experts would start with their standard technique regardless of case complexity and would deal with contingencies as they arise. Safety was a critical part of expert surgeons' plans. CONCLUSIONS: Novices mostly conveyed descriptive knowledge based on presented facts while experts demonstrated an ability to paint a richer mental image of possible future events by creating comprehensive anticipation of the operative field. Further studies are needed to validate the results of this study.