Knowing When to Stop Pushing a Question
Launch library · evergreen read

Persistence can genuinely deepen an answer, but there is a clear point past which continued pushing stops producing new information and starts producing discomfort, defensiveness, or simple repetition of an answer already given clearly the very first time it was originally asked by the interviewer, however differently it might have been phrased on that occasion.
Recognising that point takes real practice and genuine attention to a subject's tone, not just their literal words, since a flat, repeated answer or a visible retreat into shorter responses is usually a reliable signal that the topic has reached its natural limit for this particular conversation.
Respecting that limit, and moving on gracefully rather than circling back repeatedly within the same sitting, tends to preserve the relationship for a future conversation where the same topic might eventually be revisited with genuinely more success, once the moment feels right for both people involved in the original conversation.