Methods and systems for providing rich semantic feedback to programmers by executing programs, or parts of programs, in data contexts relevant to the programmer are provided. According to one embodiment, software code associated with one or more of multiple programming building blocks is enabled to be concurrently edited and executed within a programming environment. A conversational programming agent of the programming environment receives (i) information regarding the programming building blocks and (ii) information indicative of a current situation relating to the programming building blocks. The conversational programming agent evaluates the programming building blocks based on the current situation. Then, detection of one or more logical errors in one or more of the programming building blocks is facilitated by the conversational programming agent proactively providing semantic feedback regarding those of the programming building blocks to which the current situation is relevant to the programmer based on results of the evaluation.