The following is the version of skill challenges that I’m continuing to develop. There is a lot of borrowing going on here including, but not limited to WotC’s original work, and the Obsidian system by Travis Huston Dunlap.
Types of Skill Challenges
A Mental challenge lets the players using their minds and their senses to gain clues and to find their way around the world. DMs can use Mental Challenges to describe large scales of scenery and give players a chance to work out clues to obtain victory.
Examples: Finding your way through an old forest, determining the secret entrance to the underground city, solving the puzzle of El‐Karad, or finding the last ingredient for a ritual in an old library are examples of a Mental Challenge.
Standard skills for a mental challenge include:
*When dealing with anatomy or medical insights.
**Social skills can be useful to gain clues when other people are near the challenge site, such as using diplomacy to acquire help from the head librarian. Generally allow this only once per challenge per person.
***For navigating urban terrain or gaining information on the street.
Failure: Failing a mental challenge often means you arrive at a different location than the one you had intended, or that you obtain a piece of information…only to later find out it is incorrect.
Partial Victory: You gain some of the information you need, but need more. You successfully navigate the terrain, but are greatly delayed and it causes problems down the road.
Victory: You gain the information you need and solve the puzzle. You navigate the terrain quickly and easily, and perhaps find a treasure along the way.
A physical challenge often is the most versatile of challenges. It can include subtle stealth or outrageous stunts. Players are encouraged to describe their actions in detail.
Examples: Scaling a great cliff, sneaking past a group of guards, and crossing a raging river are good physical challenges.
Standard skills for a Physical Challenge include:
Knowledge (int or wis)**
*Social skills can sometimes be useful in physical challenges against other creatures. Using bluff to throw off a group of guards as you make your escape is a good example. Generally only allow this once per challenge per player.
**Knowledge skills can sometimes be useful in physical challenges that involve certain environments. Using nature in a chase scene that involves the jungle is one example. Generally only allow this once per challenge per player.
Failure: Failing a physical challenge usually involves physical fatigue and possibly great peril. The party might each lose two healing surges, or every person in the party loses ¼ of their hit points, and then is forced into a combat.
Partial Victory: The party has overcome the obstacle but may have created new obstacles in the process. For example, the party has to climb a rock wall in a way that leads to other hazardous terrain. Or the party completes the task but suffers fatigue in the form of losing two healing surges each.
Victory: The party overcomes the obstacle, fresh, strong and ready for the next one.
A social challenge generally involves talking and a large amount of role‐playing. Players are encouraged to use eloquent words, bold statements, and outright lies to win the day.
Example: A negotiation with the Duke, talking your way past the guards, and convincing an old hero to take up the cause once again are examples of social challenges.
Standard Skills for a social challenge include:
Knowledges * (int or wis)
*In some cases, some knowledge skills can be useful if they are particularly relevant to the challenge. Example: Using religion in a social challenge that involves a priest. Generally only allow this once per player per challenge.
Failure: The party does not get their desired help, and often the other group’s opinion of the party has dropped. If the opposing group was already hostile, it may result in combat.
Partial Victory: The party gets what they want, but the other group wants something too. Good examples are a rare treasure, some key information, or a favor. This could lead to another quest.
Victory: The party gets what they want. In many cases the other side will feel greater respect (or awe) for the party.
A skill challenge can be about almost anything including an abstraction of an epic combat. It can take place over the course of days or weeks, or it could be more immediate like disarming a complicated lock or trap during an exciting combat.
My players have commented that they dread hearing that they are entering a skill challenge. I think this is because Skill Challenges have been too mechanically rigid as we have interpreted them. “You must make a number of successes before a number of failures or you do not pass the challenge” I believe the skill challenge must evolve to be less about the mechanics of successes verses failures, and more about the roleplaying.
To help remove the contrived feeling associated with skill challenges, I don’t think a GM should ever use the words “Skill Challenge” until it is over. Until then all the players know for sure is that they are making skill rolls to guide and react to changing roleplaying situations. The effect is purely psychological, but it takes away the perceived formality of the skill challenge environment, and encourages creative thinking and roleplaying.
The time factor is easy to overlook in designing a skill challenge, and that's an error that can turn a compelling challenge into a rote series of die rolls. You know you've lost your group and messed up your design when the players are doing anything but playing the game. The best insurance against this lies in spreading a challenge out over multiple scenes, each allowing a different, general approach to the problem. By varying the environment and situation, you keep things fresh even when the group uses the same skills. There's a world of difference between the Diplomacy check against a drunken guard who mistakes the party's half-orc fighter for his best friend and the same check against the nosy shopkeeper who tries to shake down the PCs for a bribe. If you back up each scene with good roleplay and descriptions, the simplest skill challenge becomes an interesting, varied experience.
Extending a skill challenge over a longer period of time has an important benefit: it lets you plausibly inflict radical changes to the challenge without straining the players' sense of belief. It's ludicrous for the party to run into a long chain of NPCs, each requiring a different skill check to handle, during a 15 minute visit to the local pub. However, if that chain comes at the PCs during an entire day of scouring a city for information, the game makes a lot more sense.
Make the Players Active!
Placing the characters into the role of the aggressor simply means pushing your NPCs into a passive role as blockers, people who stand between the PCs and success and forcing the characters to serve as the catalysts for action.
For example, the characters need to escape from a group of pursuers. It's easy to default to have the PCs making Endurance or Athletics checks to see if they can stay ahead of the chase, but that pushes them into a passive role. The guards are the active party in that arrangement: they chase the PCs, and the PCs make checks to avoid capture. Instead, set up the challenge so that the PCs are the aggressors. They should make checks to foil the pursuit, such as by throwing obstacles in the guards' way, taking a path that discourages pursuit, sparking a brawl between two gangs, or starting a fire that serves as a distraction.
In this example, you might allow PCs to make checks to simply outrun the guards, but that should be one option amongst many. Even then, it's best to flavor that option with a sense that the PCs are the ones creating obstacles that the guards can't overcome. The Athletics check doesn't represent the PC simply running really fast. Instead, it allows a character to dodge through a crowded street with ease while the guards struggle to push through.
Placing the characters in the active role dramatically affects your design, presentation, and the players' engagement in the challenge. It forces the players to step up and make plans rather than sit back and react to your NPCs. It also pushes you to create multiple paths and options. When the PCs are the passive group in a challenge, it's too easy to allow logic to dictate that one, repeated skill check is the best way to plow through.
During a combat sequence, the actions taken by each character and monster set the stage for the next person's turn. In a good fight, the situation constantly changes, and this feeds back into the idea of the skill challenge as something that reacts and changes as the PCs take actions. The repercussions of skill checks must be more than modifiers or changes to subsequent skill DCs. They should be narrative events that change the situation and make the new conditions, options, and decisions flow into the game's story.
Going Off the Rails
Often players will come up with ideas that were completely unplanned for by the GM. For me this is where the fun begins. Suppose the challenge is to climb up a steep icy cliff and sneak past the guard post leading to the wizard’s tower, but when they get to that part the PCs merely walk up to the guards and hand them a sack of gold larger than they’ve ever seen. Hmmm. . . . Sounds like this challenge may have just ended regardless of how many successes the PCs have accumulated so far, and how many are still needed. This is the kind of quick creative thinking that needs to be rewarded. After handing the gold to the guards, don’t tell the players “that counts as one success,” and they still need three more! Tell them something like “the guards have just beat feet down the mountain, and didn’t even bother to take their swords with them!”
The structure is the nuts and bolts of building the challenge. How does the challenge begin? How does it end, and what happens in between? I like to break skill challenges into three sections, imaginatively titled the opening, the midgame, and the end. Each section requires about a third of the successes to complete the challenge to pass through it.
The opening sets up the skill challenge, makes it clear what the goal is, and lays the groundwork for the first few skills or options for the characters. This part is all about providing good description so they get ideas about how, and how-not to proceed.
The midgame is the actual process of moving through the challenge. The skills and obstacles the PCs face are determined by the path they choose and one or more random events I roll.
The final skill check depends on the nature of their destination and how the skill challenge has progressed so far. This part can be a GM’s nightmare to prepare for, because the PCs may have taken a path that was unforeseen.
Optional Random Events
To keep some repetitive skill challenges interesting, create a short table of random events for to spice things up. I like unexpected events at the table. They keep the players on their toes, and they keep me on my toes. For me, GMing is a lot more fun when I have no idea how a session might turn out.
A skill challenge will have limits of some kind. These could be limits to the number of checks that can be made with a particular skill, skills that are automatic failures, time limits, etc . . . . These limits should flow naturally from the idea.
Time Limit: Time-limited skill challenges are excellent opportunities for getting the whole group involved, since more people making checks means more checks get made in the limit amount of time available. Thus, when designing a time-limited skill challenge, try to throw in opportunities for a diverse set of skills.
Failure Limit (D&D recommends 3): Maybe they only have three Magic Orbs of Xinthos and each time the warlock fails an arcana check one of them shatters, or the prince will become infuriated and send them away after five failed diplomacy checks. A challenge limited by failures will probably only be attempted by the character with the best check in the relevant skills, and smart players will make judicious use of the aid another action. If you want to encourage multiple characters to contribute to the challenge, make skills limited so that they can only add one or two successes. It might also be a good idea to make the DCs a little harder and encourage PCs to use aid another if they’re not already.
Skill Check Limit: The PCs are trying to influence the ruling council, and get one skill check for each member. This approach works best for a challenge with levels of success and failure (see below). It also has many of the same features as a challenge with a limit on the number of failures, so all of that advice applies here as well.
No Limit: This works fine only if there’s an open-ended penalty for each failure, such as being delayed a day.
This is the most critical part. Decide what happens if the PCs succeed at every check, and what happens if they fail at every check. Depending on the circumstances, you might have a situation best served by a simple binary fail/succeed paradigm, in which case you’re done, or from there you might be able to branch out into degrees of success.
There must be the possibility of failure, and there must be a consequence for failure. In the most abstract terms, this means that the PCs are tangibly better off if they win than if they lost. This doesn’t necessarily mean something bad has to happen if they fail, though. For example, it might be that rather than something bad happening, something good doesn’t.
Six of one, half a dozen of the other.
Failure must be an option. Just generally good advice. If you ever find yourself planning something that the PCs simply cannot afford to fail at, then you’ve failed at planning. If there’s no possibility of failure, there’s no reason to roll the dice. If there’s no consequence for failure, there’s no reason to have the skill challenge in the first place. If failure isn’t an option, then you’re setting yourself up for having to choose between fudging things and railroading the PCs into what you need to happen or completely ruining your game.