Background: Patients who undergo complex surgery (e.g., esophagectomy, liver resection) often experience substantial burden of health-related needs (medical, social, and behavioral health). A closed loop digital solution could facilitate the collection and resolution of health-related needs by care team members for patients who undergo complex surgery. A digital solution may facilitate adherence to a clear treatment plan and concomitantly reduce surgical complications and readmissions associated with unmet health-related needs, which remain persistent challenges across health care settings. Objective: To establish problems and gaps in the collection, integration, and management of health-related needs and identify a set of user specifications for a digital solution to collect and manage health-related needs, specifically medical, social, and behavioral needs for patients who undergo complex surgery. Methods: We applied the Double Diamond Framework and organized the study into two sequential phases: (1) qualitative methods to discover patients’ and care team members’ perspectives on health-related needs; (2) participatory design sessions to gain feedback and sentiment about ideal features of a digital solution. Both phases were conducted between December 2023 and March 2025. We supplemented both phases with analysis of electronic health record (EHR) data for patients who underwent complex surgery at our academic medical center (AMC). Results: Extensive themes emerged from interviews with patients (n=20) and care team members (n=24), capturing their health-related and surgical experiences as well as desired features for a proposed digital solution. Our swim lane diagram demonstrated four critical gaps in workflow: (1) heterogeneity in the approach to screening, monitoring, and managing health-related needs; (2) patients felt uncomfortable reporting health-related needs, particularly behavioral and social needs, to their care team; (3) lack of access to referral resources to resolve needs; and (4) the need for a closed loop intervention for patients and care team members. A subset of participants from Phase 1 (n=5 patients and n=9 care team members) provided feedback on preferred features, drawing from digital tools currently available in the EHR at our AMC. Among four existing EHR tools tested, there were notable variations in how patients and care team members felt about their potential use. Participants also provided extensive feedback for preferred components (e.g., goals and active plans) that should be available in an existing or custom digital solution to manage health-related needs. Findings from the qualitative interviews and design sessions were corroborated with EHR documentation. Conclusions: Digital solutions could provide a streamlined approach for collection and management of health-related needs in surgery, with the goal of addressing unmet needs and improving patient activation. This approach is critical to ensure patients, especially patients who undergo complex surgery, have positive health outcomes. We identified preferences for specific features in a proposed digital solution based on our systematic assessment that will inform future work.