Questionnaires constitute a crucial tool in linguistic typology and language description. By nature, a Questionnaire is both an instrument and a result of typological work: its purpose is to help the study of a particular phenomenon cross-linguistically or in a particular language, but the creation of a Questionnaire is in turn based on the analysis of cross-linguistic data. We attempt to alleviate linguists’ work by constructing lexical Questionnaires automatically prior to any manual analysis. A convenient Questionnaire format for revealing fine-grained semantic distinctions includes pairings of words with diagnostic contexts that trigger different lexicalizations across languages. Our method to construct this type of a Questionnaire relies on distributional vector representations of words and phrases which serve as input to a clustering algorithm. As an output, our system produces a compact prototype Questionnaire for cross-linguistic exploration of contextual equivalents of lexical items, with groups of three homogeneous contexts illustrating each usage. We provide examples of automatically generated Questionnaires based on 100 frequent adjectives of Russian, including veselyj ‘funny’, ploxoj ‘bad’, dobryj ‘kind’, bystryj ‘quick’, ogromnyj ‘huge’, krasnyj ‘red’, byvšij ‘former’ etc. Quantitative and qualitative evaluation of the Questionnaires confirms the viability of our method.