In this descriptive-qualitative enquiry we discuss the linguistic modes of posing and answering questions as these are criss-crossed by the process of thought-provoking questioning. We adopt a language-centric approach to the relationship between asking and answering that enables us to place greater emphasis on the importance of the language choices made by both individuals asking and answering questions, especially in the context of cognitive well-being. We argue for the primacy of clear, concise and honest language in the question and answer dynamic as the approach most likely to promote trust and successful communicative exchange. We also argue for the “threatening” nature of clarity as something many may wish to avoid. Ambiguity and wilful deception frequently result from their recognition of the importance of trust and success in communication. It is our claim that any such communication is either undermined by, or appears even more threatening than, the absence of clarity in the words of a speaker.