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Message: <blockquote data-quote="Corinnguard" data-source="post: 9290923" data-attributes="member: 7033886">When in truth, a lot more goes into using diplomacy or intimidation to change someone else's way of thinking and doing things. A person using diplomacy is also going to be using Insight to see if their words have had any effect at convincing the other person. Insight is also needed to determine if the other person is lying (via a Deception check).  So it's not just a Diplomacy check, it's also an Insight check. A success in both skills could mean that they might have succeeded at convincing the other party. A success in one of them, but not in the other one could mean that there is still some more distance to go before the other party is convinced. And therefore, several Diplomacy/Insight checks will be needed. As for Intimidation, it depends if the person is using verbal threats or making physical threats against the other person. There is also the 'Good Cop/Bad Cop' approach which might require making Diplomacy, Insight and Performance checks if two members of the party are trying to get a stubborn someone to talk. Situations are not always one and done. The ones that aren't are probably going to be the more rewarding ones IMO. As they are going to be the ones where you really get to be in character.</blockquote>