Background: Reversed total shoulder arthroplasty (RTSA) is an established surgery for many pathologies of the shoulder and the demand continues to rise with an aging population. Preoperative planning is mandatory to support the surgeon’s understanding of the patient’s individual anatomy and, therefore, is crucial for the patient’s outcome. Methods: In this observational study, we identified 30 patients who underwent RTSA with two- and three-dimensional preoperative planning. Each patient underwent new two-dimensional planning from a medical student and an orthopedic resident as well as through a mid-volume and high-volume shoulder surgeon, which was repeated after a minimum of 4 weeks. The intra- and interobserver reliability was then analyzed and compared to the 3D planning and the implanted prosthesis. The evaluated parameters were the size of the pegged glenoid baseplate, glenosphere, and humeral short stem. Results: The inter-rater reliability showed higher deviations in all four raters compared to the 3D planning of the base plate, glenosphere, and shaft. The intra-rater reliability showed a better correlation in more experienced raters, especially in the planning of the shaft. Conclusions: Our study shows that 3D planning is more accurate than traditional planning on plain X-rays, despite experienced shoulder surgeons showing better results in 2D planning than inexperienced ones.