This contribution aims to offer some elements to study the problem of political advising in Renaissance political thought. The introductory section considers the Momus by Leon Battista Alberti, some letters by Marsilio Ficino and the chapters 22-23 of Machiavelli’s Prince. The focus then shifts to the fourth book of Castiglione’s Courtier, in order to analyze the relationship between the prince and the counsellor by clarifying its conditions of necessity, its internal structure and its conditions of possibility.