Roadmapping is a well-established technique in the context of innovation and strategy, with the potential to support organizations address the complex transformative challenges facing humanity in the 21st century. This is enabled by its systems-based architecture and visual form of roadmaps, supporting communication and reduction of information asymmetries in complex sociotechnical systems. This paper focuses on an adaptation of the roadmapping method to support strategic planning for roadmapping systems in organizations, addressing implementation challenges. This represents a novel application of roadmapping to business processes and systems, demonstrating the flexibility of the roadmapping approach. A workshop template (‘R2’) and process for supporting the roadmapping of roadmapping systems is presented, developed and refined through a series of six industrial cases, and illustrated with an application example in the additive manufacturing sector.