Through a qualitative hermeneutic phenomenological study, I examined the intersection of document analysis, sensemaking and policy implementation, that revealed rich descriptions of situated policy contexts and nested working practices where policy actors from Ontario, Canada, and England, UK, translated and used career guidance policy documents. The different job roles of the study participants in Ontario and England influenced complex and differentiated activity during policy implementation, and underlined 25 very individual approaches to translating and using policy documents to support career provision decision-making in participating schools. Implications for future work include roles of all stakeholders as policy actors, opportunities for forming networks to source and access documents, and creating learning conversations to understand policy.