#dnd tip for DMs: as a storytelling game, many things are not covered in the rules that players want to attempt. Don't panic! In these cases use a few simple steps. Ask what they want to do, and how the character would attempt it. If it seems easily done, just let it happen.
— Shawn Merwin, incorporating aquisitions (@shawnmerwin) May 10, 2019
If the action is impossible even in a fantasy world, then just disallow it. For those actions that fall in between those two extremes, call for a check or die roll. Give the "terms" of success or failure, and make a reasonable consequence for failure.
— Shawn Merwin, incorporating aquisitions (@shawnmerwin) May 10, 2019
If possible, set three categories: total success, partial success, and failure. Give check results to match those three. For example, take this example of a character who wants to leap from a tree branch into a careening carriage passing nearby. You can say on a Dexterity (Athletics) check of 12 or higher, the character makes the dive into careening carriage from the tree. One a 7-11, the character misses the landing in the carriage but grabs onto the side, and is being dragged along, taking 1d4 bludgeoning damage.
— Shawn Merwin, incorporating aquisitions (@shawnmerwin) May 10, 2019
On a check less than 7, the character misses the carriage and takes damage from the fall. Let the players know and discuss this before the roll so everyone is happy. Let other players contribute. Then, after the roll, either you or the player can narrate the action. (And yes, I know that Strength is usually the attribute that does with the Athletics skill, but I personally love to mix it up to encourage different combinations and mitigate min/max effects on the game.)
— Shawn Merwin, incorporating aquisitions (@shawnmerwin) May 10, 2019
This sort of game play encourages communication, highlights unpredictability and die rolling while still relying on character attributes, promotes storytelling, and gets others involved even if one player is in the spotlight at the moment.
— Shawn Merwin, incorporating aquisitions (@shawnmerwin) May 10, 2019