This paper overviews an intensive 1:1 coach development workflow developed and used in U.K. performance and high-performance sport. The workflow has been field tested with over 60 coaches in mainly Olympic and Paralympic settings in a variety of sports. The workflow proposes six main stages: “beginning new relationships,” “seeking first to understand,” “preparing for reflective conversations,” “engaging in reflective conversations,” “working with difference,” and “supporting change.” The stages are tailored pragmatically to context, and the workflow does not suggest a fixed sequence. The application of the workflow requires adaptive expertise based on considerable coach development experience and a breadth and depth of coaching and coach development knowledge. The workflow suggests the need for coach developers to build and support trusting, collaborative, and supportive relationships with the coach, as a foundation for the coach development task. Coach development practices and the workflow are continually being developed and refined in a U.K. context, and future work will provide case studies, evidence of outcomes, and refinements to the work.