DM guide: Running the Game: Resolving Outcomes Part: 2
Advantage and Disadvantage: Advantage and Disadvantage are among the most useful tools in your toolboxx. They reflect temporary circumstances that might affect the chances of a character succeeding at a task. Advantage is also a great way to reward a player who shows exceptional creativity in play. Characters often gain Advantage or Disadvantage through the use of special abilities actions spells or other features of their classes or species. In other cases you decide whether a circumstance would merit Advantage or Disadvantage.
Advantage: Consider granting Advantage when:
Circumstances not related to a creature's own capabilities provide it with an edge.
Some aspect of the environment improves the character's chance of succeess.
A player shows exceptional creativity or cunning in attempting or describing a task.
Previous actions improve the chances of success.
Disadvantage: Consider imposing Diadvantage when
Circumstances hinder success in some way.
Some aspect of the environment makes success less likely.
An element of the plan or description of an action makes success less likely.
Consequences: As a DM you can use a variety of approaches when adjudicating success and failure to tailor the game to your liking.
Success at a cost: When a character fails a D20 test by only 1 or 2 you can offer to let the character succeed at the cost of a complication or hinderance. Such complications can run along any of the following lines:
A character gets her sword past an enemy's defenses and turns a near miss into a hit but she then drops the sword. A character narrowly escapes the full brunt of Fireball but is Prone. A character fails to intimidate a Kobold prisoner but the Kobold reveals its secrets anyway while shrieking at the top of its lungs alerting other nearby monsters.
By putting the choice of success at a cost in the players hands and even letting them choose the setbacks you can give players more agency in crafting the story of their character's deeds.
Degrees of Failure: Sometimes a failed d20 test has different consequences depending on the degree of failure. For example a character who fails to disarm a trapped chest might accidentally spring the trap if the check fails by 5 or more whereas a lesser failure means the trap wasn't triggered during the botched disarm attempt. Consider adding similar distinctions other checks. Perhaps a failed Charisma (Persuasion) check means a queen won't help whereas a failure of 5 or more means she throws the character in the dungeon for such a display of impudence.
Degrees of Success: A successful D20 test can have degrees of success. For example, when characters participate in an archery contest you might decide that the more an attack roll exceeds the target's AC the higher the character's score. The archery target might have AC11, but it has 5 concentric rings indicating degrees of success. So, you could decide that an attack roll of 11 or 12 lands in the outermost ring 13 or 14 hits the next ring closer to the center a 15 or 16 hits the third 17 or 18 hits the fourth and a 19 or higher strikes the bull's eye.
Critical Success or Failure: Rolling a 20 or a 1 on an ability check or a saving throw doesn't normally have any special effect. However you can take such an exceptional roll into account when adjudicating the outcome. It's up to you to determine how this manifests in the game. One approach is to increase the impact of the success or failure. For example rolling a 1 on a failed attempt to pick a lock might jam the lock and rolling a 20 on a successful Intelligence (Investigation) check might reveal an extra clue. For attack rools the rules cover what happens on a nat 20 or a nat 1, Resist the temptation to add additional negative consequences to a nat 1 on a attack roll the automatic failure is bad enough. And characters typically make so many attack rolls that they're bound to roll dozens of nat 1s over time. What might seem like an interesting consequence like breaking the weapon used for the attack will quickly get tiresome.
Improvising Answers: With a little preparation and a lot of flexibility you can handle any curveball your players throw at you. One of the cornerstones of improvisational theater is called "Yes and..." It's based on the idea that an actor takes whatever the other actors give and builds on that. A similar principle applies as you run sessions for your players. As often as possible weave what the players give you into your story. An equally important principle is "No but..." Sometimes characters can't do what their players want but you can keep the game moving forward by offering an alternative. For example imagine the characters are searching for a Lich's lair. A player asks you if there's a mages guild operating in a nearby ciry hoping to find records that mention the Lich. This wasn't a possibility you anticipated and you don't have anything prepared for it. One option is to say yes and use the tools at your disposal to create a suitable mages guild. By doing This your reward the player for thinking creatively. Also the guild can become a great source for adventure hooks. Another option is to say no but a solitary mage in town might possess the desired information. This approach rewards the creative player while demanding less work from you.