The purpose of this paper is to give an account and a rational reconstruction of the heuristic advice provided by Aristotle in the Topics and Prior Analytics in regard to the difficulty or ease of strategic planning in the context of a dialectical dialogue. The general idea is that a Questioner can foresee what his refutational syllogism would have to look like given the character of the thesis defended by the Answerer, and therefore plan accordingly. A rational reconstruction of this (...) advice will be attempted from three perspectives: strategic planning based on the acceptability of Answerer’s thesis, strategic planning based on the predicational form of the thesis, strategic planning based on the logical form of the thesis. In addition, we will provide an illustration of the potential of this heuristic advice as we apply it to the interpretation of a fragment from Plato, presuming that, in a similar way, a reading of this kind might be more generally applicable in the interpretation of the Platonic dialogues. (shrink)