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Message: <blockquote data-quote="coolAlias" data-source="post: 7791023" data-attributes="member: 6998948">You can have one person asking the leading questions and another gauging the reaction - that's covered by the help action, granting advantage on any related ability check.Understanding what the other party in a conversation actually means / what their intentions are is part of communication, and that aspect of it is covered by Wisdom (Insight).Aside from just generally observing the person you're communicating with as you talk, which is assumed to be covered by the passive score, how are you going to search out a lie without doing something such as asking questions?I don't make my players actually come up with the questions - they can simply state that that is how they intend to try to detect lies or motive or whatever, and the roll determines how well they did / what they were able to learn, if anything.</blockquote>