Objectives: Depressive disorder (DD) is a complex disease, and the assessment of work ability in patients with DD is also complicated. The checklist depression (CDp) has recently been developed to support such work ability assessments and has been recommended for implementation in insurance medicine, starting with an analysis of the organisational and social contexts. The aim of this study was to identify the potential facilitators and barriers in the use of the CDp by insurance physicians (IPs) during work ability assessments of employees on sick leave due to DD. Methods: A qualitative research was conducted based on semi-structured interviews. The participants were IPs with at least one year of work experience in performing work ability assessments. The interviews were audiotaped, transcribed and analysed qualitatively. Results: Ten IPs (7 males, 3 females; mean 53 years) were interviewed. Important facilitators, which emerged for use of the CDp, were an oral introduction for colleagues and staff, support from management, valuing the increased transparency in work ability assessments with using the CDp, having adequate time for assessments as well as modification of the appearance (colour, plasticised form) and content (clarifying aspects of the examples) of the assessment tool. The fear of the loss of autonomy, lack of added value of the CDp, high workload, inadequate instructions and lack of time were mentioned as barriers. Conclusion: Adequate introduction to the use of CDp and the fear of the loss of autonomy of IPs need special attention in planning its implementation.