In pretty much every fantasy RPG, every adventurer fancies themself a cut above the common folk. Whether we’re playing heroes, antiheroes, altruists, egoists, or any of the other possibilities on the adventuring-character checklist, the story of the game revolves around the idea that our characters are exceptional, both in their abilities and the things they do with those abilities. The barbarian is the ultimate battle machine. The rogue is the consummate confidence artist. The wizard is the master of magic that can remake the world.
So why is the GM asking my world-class adventurer to make an Athletics check to climb a rope? And does it serve any real purpose when a low roll on an ability check makes a character fail at a task that has no real consequences other than wasting time or looking kind of foolish? Is that really the best way to play the game?
The Hero Fast Track
D&D and every other fantasy RPG is a game of heightened and accelerated character progression. As people living in the real world, we’re all generally conscious that we’re not the same people now that we were five or ten years ago. We can look at ourselves and see where we’ve grown and where we’ve improved, even though the process of growth and improvement is often so gradual that we don’t see it happening.
Adventurers have an easier time of it. As a character levels up, the boons and benefits that improve their class features, skills, ability scores, combat prowess, magic use, and more are a benchmark of their growing expertise. Everything a character is good at feeds into experience or story milestones. Experience and story milestones feed leveling up. Leveling up feeds getting even better at things.
In real life, we often take our time getting better at things. But adventuring characters make self-improvement into a speedrun. Even in the grittiest, most low-magic, slowest-leveling campaigns, the math of advancement makes player characters exceptional. So don’t be afraid to embrace that idea by moving away from rolling dice when the characters undertake even challenging tasks, whether breaking down a door, gathering intelligence, deciphering lore, finding tracks, clambering up a wall, or any other of the activities of an adventuring life.
Getting Rolling with Not Rolling
Players and GMs have a number of different options for deciding when it’s the right time to allow characters to automatically succeed on ability checks, and how that can feed the narrative.
Skills, Tools, and Backgrounds
Establishing a baseline for automatic success is a good idea. Requiring that a character have proficiency in a skill is an obvious starting point, as is making sure that a task feels like something a skilled character could pull off under generally favorable circumstances. But in addition to skill proficiencies, don’t forget tool proficiencies. Because checks requiring artisan’s tools often come up less often than skill checks, allowing automatic successes on such checks can help make them memorable. Likewise, character backgrounds offer a rich array of possibilities for things a character should be able to pull off automatically with time and focus, from a sailor character skillfully untying a complex knot to a folk hero gathering intelligence in a city under the control of corrupt officials.
Automatic successes are a great fit for checks that extend from strategizing on the part of the characters and players. If everyone at the table spends time and effort thinking about the best way to get access to the headquarters of the thieves’ guild, give the rogue an automatic success on the check to open the secret exit in the back alley, or give the fighter an automatic success on breaking through the drain grate that gives the characters access to the guild’s cellars. Whenever the players are actively engaging in planning how to overcome a challenge, one or more automatic successes as they put that plan into action make a great reward.
The (Role)play’s the Thing
Automatic successes also make great rewards for roleplaying, whether social encounters or players fully digging into describing their characters’ actions during investigation, exploration, or even combat. If a bard has a great idea for dropping a chandelier into the middle of a ballroom to distract the duke’s house guards, with the player explaining in detail how they plan to make use of that diversion, don’t risk messing up the fun of that plan with a botched skill check to untie the rope that holds the chandelier aloft. Likewise, when the player of a bard sets up an elaborate scene of striking up a conversation with a local politician in an attempt to learn who’s bankrolling them, grant them an automatic success on their Persuasion check. Rewarding roleplaying in this way is a great way to encourage roleplaying — in contrast to having a great bit of roleplaying followed up by a failed skill check, which is a great way to make players wonder why they bothered with the roleplaying in the first place.
Setting Up Success
As the players and the GM get comfortable with automatic successes for ability checks, they’ll also learn to look for opportunities to allow one character’s success to feed the success of other characters. When the party needs to clamber up a cliff to reach the far side of a chasm, having the rogue make the climb with a breezy bit of narrative is undercut by having the Strength 8 wizard or the paladin weighted down by a hundred pounds of plate armor, weapons, and gear failing skill checks.
So let the rogue’s easy ascent extend into letting the rest of the party also climb up without difficulty, whether the climb lets the rogue mark out an easy route up marked by numerous handholds, or whether they drop down a knotted rope ladder conveniently hidden at the top of the cliff. Likewise, an automatic Intimidation success when the sorcerer challenges a guildmaster in a tense negotiation can spread to the other characters as well — perhaps not granting automatic successes on Intimidation or Persuasion checks of their own to deal with the guildmaster’s entourage, but with advantage on those checks.