Adaptation pathways approaches support long-term planning under uncertainty. The use of adaptation pathways implies a systematic monitoring effort to inform future adaptation decisions. Such monitoring should feed into a long-term collaborative learning process between multiple actors at various levels. This raises questions about who should monitor what, when and for whom. We formulate an approach that helps to address these questions, developed around the conceptual core offered by adaptive policy pathways methods and their notion of signposts and triggers. This is embedded in a wider approach that revisits the critical assumptions in underlying basic policies, looks forward to future adaptation decisions, and incorporates reciprocity in the organization of monitoring and evaluation. The usefulness and practical feasibility of the approach is studied for a case of the Delta Programme in the Netherlands, which incorporated adaptation pathways in its planning approach called adaptive delta management. The case results suggest that our approach adds value to existing monitoring practices. They further show that different types of signposts exist. Technical signposts, in particular, need to be distinguished from political ones, and require different learning processes with different types of actors.