These are relatively easy to write, so let’s try another Calmer GM. This time we’re calming down and cutting down Five Simple Rules For Dating My Teenaged Skill System.
Skills are often poorly handled in tabletop RPGs, which can lead to boring results and skills being viewed as an uninteresting and tedious means of conflict resolution. Follow these five guidelines, though, and your skill resolution will be much more interesting.
#1: Every Player Action Must Ask A Question Or Declare An Action
If a player asks if they can roll a skill at a situation without declaring a specific action or asking a specific question, ask them to elaborate on what they’re actually doing. If someone wants to roll Diplomacy at a guard, that’s probably fine, but ask them what they’re actually saying. A summary in lieu of a word-for-word statement will work, just as long as they are describing an action (or asking a question, like “what do I know about mind flayers?” which might call for an Arcana check or you might just tell them the information).
#2: Only Roll When There Is A Chance Of Success, A Chance Of Failure, And A Risk Or Cost To Failure
Almost anything is possible with a high enough skill roll, but many things are not possible with the skill bonuses that characters actually have. The Persuasion skill is not Dominate Person, and the Athletics skill is not a climb speed, so there are some people who cannot be persuaded to do certain things and some surfaces that cannot be climbed with a skill check that’s possible for playable characters. Do not bother rolling dice for situations where success is impossible even on a 20.
Likewise, do not call for rolls for simple tasks. A 5e character with expertise can have a bonus as high as +17 and will be unable to fail skill checks of DC 15, so there is no need to roll. A character attempting to tie their own shoes can’t really plausibly fail, so there is no need to roll. Less intuitively, a character who is trying to pick a lock and is under no time constraints cannot plausibly fail. If nothing stops them from trying over and over again until they roll high enough to succeed, then don’t bother rolling at all. A character who needs to pick a lock fast or quietly or without breaking their fragile improvised lockpicks needs to roll dice. A character who does not care about speed or noise and who is using proper thieves’ tools does not.
Side note: The “penalty for failure until you fail forever” is not a good solution. There is no reason a character should receive a -2 (or whatever) penalty to picking the same lock every time they try. If you don’t want a character to succeed automatically at lockpicking, put something on the other side of locked doors that will be other taken off guard by a quietly picked lock or have a readied attack waiting for the first person through if the lockpicking was noisy.
#3: One Roll Is Usually Enough
It is very rarely a good idea to require two rolls as part of the same task. If someone is trying to sneak by guards, one roll is enough, even if they need to sneak past two separate guard posts. If someone is trying to climb a tree to a bird’s nest before the bird returns, even if the nest is particularly high and the tree particularly tall, one roll is enough.
The guideline is usually for a reason, and exactly when it’s right to call for another roll is as much art as science. One fairly straightforward example is when the players can see the ticking clock. If they know the guards are getting closer and by how much with every failed lockpicking attempt, or they know the dark ritual is to happen at midnight, that it’s 11:37 PM now, and that each additional attempt costs one precious minute, then repeat die rolls remain interesting.
#4: Ask For Knowledge Checks At The End Of Description When Appropriate
If the party has broken into a sinister cult’s lair and found a mysterious symbol on the floor, you do not need to wait for one of them to ask if they recognize it. You can just go ahead and ask them to roll Arcana or Religion or whatever skill is appropriate. Consider also using passive knowledge scores the same way 5e uses passive perception scores. It’s more to keep track of, but it means you can weave which character knows what directly into description and players are not tipped off to the presence of unknown information by their failure to know it.
#5: Differentiate Approaches By Their Consequences
Consider a guard the party needs to get past. They have decided not to attack him, so we’re using skill checks. The obvious skills to use are Deception, Persuasion, Intimidate, or Stealth. You could just decide this guard is a DC 15 sort of fellow and let the party roll whatever they’re best at and hope for the best, but it’s more interesting to give different options different consequences. If you fail at Intimidation or Deception, the guard may become hostile. If you fail at Stealth, the guard will almost definitely become hostile. Trying to talk a guard you’ve never met into letting you through (Persuasion) is going to be much harder. You could add a bribe to bring the difficulty down, but now there’s the possibility that he’ll be angry if you fail, and if you succeed you have to actually pay a bribe. Even a relatively simple encounter like this can be much more interesting than just picking whichever relevant skill has the highest bonus.