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(1) Background: Individual adoption experiences represent important factors in implementing innovations. In the context of health systems, where the implementation of innovations aims to improve the quality of care, they provide an important basis for developing and adapting implementation strategies. (2) Methods: This study examines the adoption experiences of (tele-)medical experts (<i>n</i> = 13) using the example of telemedicine in the German healthcare system by means of a qualitative, guideline-based interview study. The interview guide, as well as the deductive–inductive analysis, is based on Rogers’ adoption theory. The transcription and analysis process was carried out according to Kuckartz. (3) Results: A total of 304 interview statements could be coded and assigned to the five main categories of persuasion, knowledge, implementation, decision and confirmation. More than half of all statements were coded under the main category persuasion, with its subcategories of convictions regarding the implementation of telemedicine (<i>n</i> = 89), international comparison of Germany’s development (<i>n</i> = 50), telemedicine as a way of optimizing resources (<i>n</i> = 22) and conviction to understand telemedicine as an overall system (<i>n</i> = 10). (4) Conclusions: This study provides insight into how the implementation of telemedicine in the German healthcare system is perceived by experts and allows for adjustments to the ongoing implementation strategy.