Preparing a Subject for a Hard Question
Launch library · evergreen read

A brief, honest warning that a difficult question is coming, offered just before it is asked, often produces a more considered answer than the same question sprung without any notice at all. The warning respects the subject enough to let them gather their thoughts. That small courtesy costs almost nothing and is rarely forgotten by the subject who receives it.
Some interviewers worry that flagging a hard question in advance gives a subject time to construct a guarded or evasive answer. In practice, most subjects respond to the courtesy with a more thoughtful reply, since the warning signals respect rather than an attempt to catch them off guard.
The technique works best used sparingly, reserved for genuinely difficult territory rather than every question in the sitting. Used too often, it loses its effect and simply slows the conversation without adding the trust it is meant to build. Reserved for the moments that truly need it, the technique retains the trust it is designed to build.