© 2018-IOS Press and the authors. All rights reserved. Background: Physicians working in a tertiary care injured worker clinic are faced with clinical decision-making that must balance the needs of patients and society in managing complex clinical problems that are complicated by the work-workplace context. OBJECTIVE: The purpose of this study is to describe and characterize the decision-making process of upper extremity specialized surgeons when managing injured workers within a specialized worker's compensation clinic. METHOD: Surgeons were interviewed in a semi-structured manner. Following each interview, the surgeon was also observed in a clinic visit during a new patient assessment, allowing observation of the interactional patterns between surgeon and patient, and comparison of the process described in the interview to what actually occurred during clinic visits. RESULTS: The primary central theme emerging from the surgeon interviews and the clinical observation was the focus on the importance of comprehensive assessment to make the first critical decision: an accurate diagnosis. Two subthemes were also found. The first of these involved the decision whether to proceed to management strategies or to continue with further investigation if the correct diagnosis is uncertain. Once the central theme of diagnosis was achieved, a second subtheme was highlighted; selecting appropriate management options, given the complexities of managing the injured worker, the workplace, and the compensation board. CONCLUSIONS: This study illustrates that upper extremity surgeons rely on their training and experience with upper extremity conditions to follow a sequential but iterative decision-making process to provide a more definitive diagnosis and treatment plan for workers with injuries that are often complex. The surgeons are challenged by the context which takes them out of their familiar zone of typical clinical practice to deal with the interactions between the injury, worker, work, workplace and insurer.