Why and how is the Gestalt theorists’ concept of productive thinking particularly suitable for being applied to the educational question of how student motivation can be encouraged, thus providing an important condition for self-regulated, intrinsically motivated learning? An answer to this question has been sought using an approach to the fostering of text comprehension ability, based upon the features specific to productive thinking, originally identified by Wertheimer (1945) and Duncker (1935). Firstly, these specific features are dealt with and their educational implications compared with those deriving from the definitions of problem-solving used most frequently in educational research. Secondly, an analysis is made of the process by which the features specific to productive thinking are turned into the conditions for a kind of text analysis suitable for designing an instructional project aimed at enhancing text comprehension ability and, at the same time, encouraging intrinsic motivation and self-regulation on the part of the learner. Thirdly, an educational project centred on the thinking-aloud poor reader is described, where thinking aloud and reflection–response are combined in order to guarantee the maximum level of intrinsic motivation. In the concluding section, the most important features of the project are discussed in relation to reciprocal teaching and scaffolding.