Chapter III: Skill Challenges

There are always new, grander challenges to confront, and a true winner will embrace each one.
— Mia Hamm
While some challenges your heroes face may be resolved in a single attempt, most will be part of a larger goal or adventure. When this is the case, you use a skill challenge.
A skill challenge is a connected series of attempts. While climbing a short rope ladder would be a single attempt, climbing a mountainside is better represented by a skill challenge. Each success a hero has in the process of an hours-long climb plays into the next, making progress easier or more difficult. Similarly, haggling with a vendor over a sword can be accomplished in a single attempt while contracting with a ship's captain for a trade agreement would likely require a sequence of negotiations.
Skill challenges create a narrative of your players deeds. When multiple obstacles or difficult tests stand in their way, give them the opportunity to add to their story by building a skill challenge using the followin four steps.
QUICKLINKS
SUCCESS LEVELS IN SKILL CHALLENGES
Using success levels for each attempt in a skill challenge allows the attempt to be meaningful and evolve the challenge's story. You can determine the effect of an attempt's outcome or, even better, let the players describe how their hero's success or failure affects the rest of the challenge.
Critical Success: Use a critical success in a skill challenge to:
• Erase a failed attempt in the challenge of the same level.
• Gain two successes in the challenge.
• Grant advantage or reliability to the next attempt.
Major Success: Use a major success in a skill challenge to:
• Pass a rank bonus to the next attempt.
Limited Success: Use a limited success in a skill challenge to:
• Pass a rank bonus to the next attempt.
• Fail the attempt but don't count it as a failure.
Critical Failure: Use a critical failure in a skill challenge to:
• Cause two failures in the challenge.
• Apply disadvantage or unreliability to the next attempt.
Jump to a Chapter
STEP 1: DETERMINE THE OPPONENTS
In a fight, this might be three trolls and a dozen orcs. In a skill challenge to gain access to an heirloom needed to unlock a secret dungeon, it could be a baron, a baroness, their daughter, and an innkeeper. In a skill challenge to get a jewel out of the eye of an enormous monkey statue standing over a chasm, the opponent could be the jewel setting, the chasm, roving gnolls, and the precariousness of the statue.
STEP 2: DETERMINE THE TRIALS
Once you’ve determined your opponents, assign the trials connected to them. To gain access to the heirloom key, the baroness may require her husband be distracted with a new present, their daughter’s future ensured with a backup heirloom, and a present delivered to the matron of the local inn simply because the baroness wants to secretly see what her closest friend thinks of these so-called heroes.
For a skill challenge to retrieve the monkey’s eye ruby, one hero may need to climb the statue and engineer the jewel out while a second keeps their feet from slipping, a third keeps the statue's weight from toppling, and the fourth cloaks them from the gnoll patrols.
When determining the trials of your skill challenge, keep your players in mind. Just as you wouldn’t want to throw a hundred orc warriors at a 1st level party, giving only one player the only role in a challenge can have the same negatives as giving only one person a role in combat. Instead, involve every hero, leaning into their specialties or fears if possible.
STEP 3: DETERMINE THE REQUIREMENTS FOR SUCCESS AND FAILURE
After noting the trials, list the skill challenge’s requirements for success and failure. The rule of three is a good guideline. In the example challenges, three failures could mean a total failure of the challenge. In a larger skill challenge, failing two out of three branches of smaller skill challenges could result in overall defeat.
Victory should have its requirements just as clear. When the baron has his new destrier from the east kingdom, the daughter has her tiara from the antlion's den, and the basket of roses and honey are delivered to the inn, then the baroness will relinquish her gift. Likewise, when the jewel is pried out of the monkey statue, then the challenge to retrieve it is complete.
Requirements should be shared, either with the heroes, such as the baroness saying, 'Don’t bother coming back without a horse!', or with the players, such as stating that if there are three failures in trying to retrieve the monkey gem, the statue will fall. Clarity in the requirements for victory allows your players to plan their strategy and feel the thrill of being close to failure or success.
As with other encounters, you can mark triumphs along the way with rewards such as experience packets (for more information on experience, see Chapter VI: Rewards).
STEP 4: DETERMINE THE OUTCOME
The first step of determining the outcome is knowing the basic goal. I.e., the baroness hands over the heirloom key or the heroes take the monkey's ruby in hand.
However, just as a monster might flee a battle to warn its allies or a hero can die in a dying dragon's fiery breath, there can be shades of victory in a skill challenge. To set the success levels of a skill challenge, use the same levels you would with an individual attempt.
Critical Success: There were no failures in the skill challenge and additional boons come from the victory. For example, the baroness is so impressed with the group she names them her charges, granting them rights to the barony, while the statue might be robbed of its jewel and mastered in a way the party could use it as a trap.
Major Success: A lone failure in a skill challenge may result in a small positive beyond the goal. The baroness invites the heroes to call on her for a favor in the future while the monkey statue can also be dropped or defaced to create a desired effect.
Normal Success: With middling success, the goal of the challenge is achieved with nothing extra attached, perhaps by the skin of the hero's teeth.
Limited Success: With a limited success, a door is closed, but a window is opened. If the skill challenge is narrowly failed, the outcome might only be partially bad. The baroness doesn't relinquish the heirloom key but directs the heroes to a secret entrance to its catacombs, while the monkey statue topples but the gem falls out in the process and ends up a hundred feet down on the ledge of the cliff.
Failure: If three attempts are failed and the heroes weren't close to success, then the heroes hit a dead end. The baroness says no while the monkey statue tumbles with its gem over the cliff. While disappointing, make sure there is a new direction through which the heroes might triumph so as not to lose the party's enthusiasm. A seedy rogue could offer to steal the heirloom for a high price, or the gnolls could rush out to look upon their fallen statue in horror, offering the party a chance to vent some steam with an ambush.
Critical Failure: As with other critical failures, use a critical skill challenge failure to deliver memorable or humorous moments. If a skill challenge is failed with blisteringly bad luck or results, then heighten the repercussions. The baroness is so insulted, she demands the party be arrested or the statue crashes over the edge with the bard still clinging to it, and her shriek is so loud the gnolls come charging.

Other Considerations

SKILL CHALLENGES WITHIN SKILL CHALLENGES
In cases of larger skill challenges, such as quests that include sub-quests, using smaller skill challenges to focus the story can be to everyone's advantage. For you, this keeps the bigger picture manageable. For the players, their immediate goals remain clear.
In the example of convincing the baroness to relinquish her heirloom key, the sub-quests to retrieve the destrier, the backup heirloom, and impressing the innkeeper might each be their own skill challenge.
KEEPING THINGS FLEXIBLE
For player investment, it's important for skill challenges to have clear goals in mind. However, if the heroes pursue their desire a different way, do your best to accommodate them. New and exciting consequences can emerge from such decisions but more importantly, players are having fun when they get to play the way they want to play. Few players remember the story they were railroaded into, but almost all will remember the cockamamie scheme they pulled off to fly a reduced boulder over the hag's cottage and drop it on the unsuspecting villain within.

Social Skill Challenges

In exploration skill challenges, the skills, abilities, and outcomes utilized are usually clear. A wall needs climbing, a door needs unlocking, or a trail through the Swamp of Sorrows needs blazing. However, story situations can be less clearcut. When running a skill challenge focused on the story, or a social skill challenge, there are two tools to keep all the players' heroes involved and gauge their success.
IMPACT
When working with or against a creature, every hero will want to impact the challenge. Heroes who aren't charismatic can still contribute by providing information, either in argument to the creature or as ammunition for the party's chosen diplomat, or by proving their worth, at least for entertainment.
Entertainment: Sometimes a hero can assist in a social skill challenge by improving the mood of the creature. Acrobatics and Perform skills are perfect for this. In addition, Endurance, along with Strength, Dexterity, and Constitution attempts, can up the creature's respect: A hero lifts something heavy, shoots an apple off another hero's head, or walks across coals. Other movement skills, expertise skills, and even Handle Animal can be used when appropriate.
Information: A hero can assist in a social skill challenge by providing solid arguments or information as ammunition. Knowledge skills are perfect for this, as is Insight. In some cases, Survival may also prove useful. As a bonus, when a player's hero connects pertinent information to an argument, the player not only feels pride but will usually remember that information as well.
Diplomacy: Deceive and Persuade are often at the forefront of social skill challenges. Direct Charisma attempts to charm or impress a creature can be used as well. Either way, it can be helpful for the party to appoint a silver-tongued mouthpiece, or at least a hero that is easy on the eyes to negotiate a situation.
RAPPORT
When you want a skill challenge to determine a creature's feelings toward the party or a hero, you can use rapport. Rapport can be set or incremented by a skill challenge's results.
Love (Critical Success): The creature considers the hero in the best possible light in all situations.
Adjustment: Increase rapport three levels.
Friendship (Major Success): The creature considers the hero in a positive light and tries to see their side of things.
Adjustment: Increase rapport two levels.
Respect (Normal Success): The creature is willing to entertain arguments by the hero.
Adjustment: Increase rapport one level.
Indifference (Limited Success): The creature treats the hero no different than it would an unknown creature.
Adjustment: None.
Dislike (Failure): The creature actively dislikes the hero and views their actions and arguments in a negative light.
Adjustment: Reduce rapport one level.
Hatred (Critical Failure): The creature actively hates the hero and seeks to see hurt brought upon them.
Adjustment: Reduce rapport two levels.
Rapport is especially effective when applied to the party. Party rapport can only be increased once per hero until all heroes have increased the rapport level. This encourages all heroes to get involved in improving the creature's trust and allows heroes who don't like the creature to keep them at arm's distance.

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