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Message: <blockquote data-quote="iserith" data-source="post: 8725746" data-attributes="member: 97077">I think the optimal approach is to always describe what you want to do with reasonable specificity with an aim for automatic success, but to stick to tasks where you have some decent modifiers to the ability score or skill proficiency in case you have to roll. So in practice the rogue will tend to do rogue things, more or less, and the wizard will tend to do wizard things.Then if Inspiration is a tool that is used in the game, you keep that in your back pocket for when you do something you're not so great at and give yourself advantage if you have to roll. The incentive is basically then to portray your character well according to established characterization to be able to later shore up areas where you're otherwise weak or to try to ensure that the stuff you're good is way less likely to fail (again, if you have to roll at all).This creates a good feedback loop - I describe what I want to do and act like my character so that I can be more successful.</blockquote>