The importance of design as a source of value creation has been studied for decades. In the late 90s, however, a specific approach in the practice of design achieved a rapid diffusion across organizations: Design Thinking. This is a formal method for creative problem solving characterized by user‐centeredness, ideation, and iterative prototyping. The rapid diffusion of Design Thinking in practice has not been coupled with similarly rapid and robust development of its theoretical underpinnings. Most contributions have been inward‐oriented toward a confined community of scholars; therefore, the scientific discourse on Design Thinking has unfolded in a vacuum—often independently from other innovation management theories. The consequence has been that Design Thinking is often confused (especially among those new to the field) with the entire practice of design. Subsequently, we still lack an understanding on whether, why, and when Design Thinking contributes to innovation. In this editorial, we discuss the journey to the Special Issue “Design Thinking and Innovation Management: Matches, Mismatches and Future Avenues” that intends to critically reflect and enrich the scientific debate around Design Thinking. First, we aim at clarifying the distinction between “design” and “Design Thinking.” The former is a practice, to be studied; the latter is a paradigm, that is, a set of specific principles, methods, and tools to practice design. Second, we offer a brief overview of the community that has been investigating Design Thinking, a synthesis of the ten papers included in the Special Issue (distributed across this and the next issue), and show how they contribute to close the theoretical and empirical gaps with innovation studies. Finally, we suggest that the paradigm of Design Thinking is significantly contingent: its diffusion and success have been favored by the emergence of specific contextual conditions (substantially by the ubiquitous diffusion of digital technologies in direct interaction with users). As the context is dramatically shifting again, we wonder whether Design Thinking will keep its relevance and ability to support organizations in addressing the new challenges ahead? We address this question with the support of a contingent framework to position several design paradigms and suggest that the context ahead, where problems have multiple stakeholders and are undefined, will require the emergence of new paradigms characterized by a systemic (rather than user‐centered) and reflective (rather than ideative) practice. We therefore propose a few research questions that will hopefully encourage and shape future scholarly efforts into the study of the design practice for innovation in organizations.