In this empirical study we analyse how children (aged four- to six-years-old) through communicative engagement with their teachers around their own drawings are supported in developing representational insight, that is, going from indicative sign-making to symbolic understanding. Theoretically, the analysis is informed by a sociocultural perspective, particularly Vygotsky’s work on concept development. The empirical data consist of approximately five hours of video observations of teacher–child communication in preschool. The activities analysed were designed by the teachers according to two different principles for facilitating discernment of the conventional meaning of symbols: contrast and induction. While one design is seen to be more powerful than the other in supporting children’s symbolic development, these patterns are, in the study and in everyday early childhood practice, intertwined with other communicative features such as establishing intersubjectivity. The implications for research and educational practice are discussed.