After a slow and challenging transition period, peer learning and improvement (PLI) is now being more widely adopted by practices as an option for continuous personal and practice performance improvement. In addition to gaps that exist in the understanding of what PLI is and how it should be practiced, wide variation exists in how the process is implemented, administered, how outcomes are measured, and what strategies are employed to engage radiologists. This report aims to describe lessons learned from our 20-year experience with the design, implementation, and continuous improvements of a PLI program in a large academic program. Since initial implementation in 2004, an oversight team prospectively documented iterative process improvements and data submission trends in our PLI process. Process data included strategies for engaging radiologists in the PLI process (fostering case submission, PLI meeting participation), steps for achieving regulatory compliance, and template content for facilitating the value and impact of PLI meetings (case analysis, review of contributing factors, identification of improvement opportunities). Submission trends, submitted case content, and improvement opportunities varied by clinical section. Process improvements that fostered engagement included closing the loop with participants, expanding criteria for case submission beyond interpretive disagreements (e.g., great pickups, near misses), minimizing impacts to workflow, and using evidence-based templates for case and contributor categorization, bias analysis, and identification of improvement opportunities. Implementing an effective PLI program requires sustained communication, education, and continuous process improvement. While PLI can certainly lead to process and individual performance improvement, the program requires trained champions, designated time, effort, resources, education, and patience to be effectively implemented.