Purpose: The purpose of this paper is to develop a set of generic prompting principles and a framework of prompts that have the potential to foster learning and skill acquisition among adult novices when performing complex, ill-structured problems. Design/methodology/approach: Relevant research in the literatures surrounding problem structure, sensemaking, expertise, metacognition, scaffolding, and cognitive load were reviewed and synthesised in order to derive generic prompting principles and guidelines for their implementation. Findings: A framework of generic principles and prompts is proposed. Differentiation between prompts supporting cognition either within, or after an ill-structured problem-solving task was supported. Practical implications: Prompts such as those proposed in the framework developed presently can be designed into technology-enhanced learning environments in order to structure and guide the cognitive processes of novices. In addition, prompts can be combined with other learning support technologies (e.g. research diaries, collaborative discourse) in order to support learning. Empirical testing will be required to quantify the potential benefits (and limitations of) the proposed prompting framework. Originality/value: The prompts developed constitute a framework for structuring and guiding learning efforts in domains where explicit, actionable feedback is often unavailable. The proposed framework offers a method of tailoring the scaffolding of prompts in order to support differing levels of problem structure and may serve as the basis for establishing an internalised and adaptive learning approach that can be transferred to new problems or contexts.