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Cognitive skills are concerned with analysis, interpretation and decision making required for performing the procedural tasks. Since much of its process runs inside a human mind, the development of cognitive skill may largely rely on self-explanation as a mechanism for forming better procedures by clustering elementary operations and pushing them in to subconscious level. It is important for a tutoring system designer to consider acquisition of cognitive skills, particularly by life long learners who may not be learning in the traditional setting. The paper describes possible categorisation of learning resources to match the different phases of skill acquisition. It discusses an implementation of a cognitive apprenticeship-based learning environment and an independent feedback on its use in real classroom. It also touches very briefly on the far-reaching potential of such methodology when extended to the Internet.