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Traveling with Style: Skill Challenges

Skill Challenges

When I run a travel skill challenge, my goal is to give the players a chance to develop the story on their own terms, without me telling them “The weather was cold and overcast, but there were no monsters. Now you set up camp and take a long rest,” about seven times on the way from one city to another. I change up the flow of D&D (in which the DM tells the players what they perceive and the players decide how to react) and let players tell me what is going on in the world.   This is great for several reasons.
  • It lets me define the region they’re traveling through with a few simple statements, which I call parameters. More on that later. And then once my players have the parameters of the skill check, they do the rest of the descriptive work for me. By giving them narrative control within specific parameters, I let them tell me what they care about most at that point in time. Maybe they’ll focus on the natural world, or the travelers on the road, or the wildlife.
  • Once the players have set a scene, they’ll tie their character into the scene, describe what they do in order to resolve the scene they’ve described, and make an ability check to see if they resolve it successfully. If they don’t, I’ll ask how they fail spectacularly, because even failure can be fun if the person who’s failing can find the humor in it.
 

1. State What’s Happening

In a situation where you’re changing the flow of play, the single most important thing you can do is tell the players what’s going on. I tell my players, “We’re starting a skill challenge to describe how you get from [point A] to [point B].” If they don’t know what a skill challenge is, I describe it as follows:   “A skill challenge is a type of scene where the party needs to succeed on a certain number of ability checks before you reach a certain number of failures. We go to each person in turn, and you set up your scene yourself, describe how you try to overcome it, then make a check to see if you are able to succeed. If the party gets enough successes, you reach your destination safely. If the party fails the skill challenge, something bad will happen.   “Each person can only use a skill proficiency once. Once [character A] makes a Wisdom (Perception) check during this skill challenge, they can’t use it again until the challenge is over. You can still make a Wisdom (Insight) check, just not another Perception roll.”  

2. Set a Difficulty

I tell my players up front how hard the skill challenge will be. It gives them a tangible way to track their progress, and even raises the tension. Too much mystery can be a bad thing, as it becomes hard to know if the players are making progress. This is a small concession I make in immersion in order to increase fun—and it doesn’t break my group’s suspension of disbelief. In yesterday’s game, my players had to make a very simple skill challenge. It only required that they make three successful ability checks before they failed three checks. And I didn’t tell them this, but the DC of these checks were low: only DC 12.  

3. Set Parameters

I want to give my players free reign, but setting boundaries is useful for two reasons. The first is selfish, it lets me tell my players what parts of my fiction they absolutely should not break. I might say, “You’re traveling for four days across the desert to get from the City to the Oasis. The desert is prone to storms and filled with roaming packs of wargs, and the black sigil-stones embedded within its sands prevent the use of druidic magic.”   Now my players know what’s unique about this desert and can treat it differently from any other desert. Second, these boundaries give the players a starting point. Sometimes limitations breed creativity. If I tell the druid that they can’t just use magic to provide water for their party, maybe that will give them the idea to make a Wisdom (Survival) check to go searching for sustenance.  

4. Take Turns

Once these guidelines have been set down, each player can start contributing to the skill check. After every skill check, I like to intrude for a moment and describe the party’s progress as they travel. For instance, if character A just made a successful Wisdom (Survival) check to find a deer path that helped them move through the forest quickly, I might describe the party exiting the forest and passing into the plains north of the forest. This gives the players a sense of progress, and encourages them to keep going instead of getting bored and slowing down.   If I find that people are growing weary of the skill challenge, especially if there have been several failed checks in a row and it seems like they’re not making any progress, I will sometimes intervene and ask, “I have an offer for the next character. I have a scene in mind, and if you agree to play through my scene, you’ll get an automatic success on your next roll. If not, you can keep going as normal.” This lets me stay engaged in the process, and gives the players the choice to either keep playing their self-directed scenes or to hand narrative control back to me for a little bit.  

5. Conclude the Skill Challenge

Sometimes the players succeed. Congratulations! They’ve made it to their destination weary and weather-worn, but otherwise unscathed.   But sometimes they fail. Failure should have consequences, otherwise you’ve just wasted everyone’s time with toothless threats. More on that below.  

Difficulty and Failure

One of my personal hurdles with running exciting skill challenges is how to tune their difficulty. It takes a lot of trial and error, generally, and the number one rule you should remember is: you make the rules. The best skill challenges, like the best traps and the best combat encounters, serve the game, not the other way around. If they’re not fun and they’re not improving the story, find a way to bring them to a quick and satisfying conclusion.   In my mind, there are three elements to a skill challenge’s difficulty: Screentime, Difficulty Class, and Consequences.   A skill challenge’s screentime is how many checks it takes to succeed. In other words, it’s the “hit points” of the skill challenge. The more checks they have to successfully make, the longer the challenge will take, and ostensibly the harder it will be. My rule of thumb is to always require a number of successes equal to the number of characters in the party for long challenges, that number –1 for medium-length challenges, and that number –2 for short challenges. I never go below a minimum of 3 successful checks required, because it feels bad if the challenge ends before everyone in the party has at least a chance to attempt it. Then you’ve really wasted their time. Sometimes I’ll even fudge the numbers a bit to keep a challenge from ending before everyone in the party has a chance to participate.   I always have my skill challenges require only three failures to fail, because “three strikes, you’re out” is so ingrained in the American mind.   A skill challenge’s difficulty class is the DC needed for a character to succeed on an ability check. In other words, it’s the “Armor Class” of the skill challenge. I usually keep the difficulty class static throughout the entire check, but you can escalate it to create tension or lower it to make the challenge easier. The usual difficulty class guidelines apply here: a check of 5 is trivially easy, 10 is standard, 15 is hard, and so forth. Since a skill challenge involves many checks, you’re more likely to see average results, so plan accordingly. I try not to go below 10 on a skill challenge for low-level characters, 13 for mid-level characters, and 15 for high level characters.   A skill challenge’s consequences are what happens to the characters if they fail three checks before they succeed on enough checks to reach their destination successfully. Never say “you get turned around and wander back to [point A]. You can try the skill challenge again, if you want.” That’s a real waste of time. All that adventuring and, essentially, nothing happened! If you’re going to punish your players for rolling poorly, do it in a way that’s exciting. Here are some options:  
  • The failed skill challenge leads to a random encounter. Roll on your random charts, and then roll initiative! After overcoming the encounter, they are near their destination.
  • The failed skill challenge causes the party to get lost and waste several days trying to reorient themselves. The travel takes 1d10 days longer than expected, and each character must make a DC 15 Constitution saving throw or gain 1 level of exhaustion.
  • The failed skill challenge causes the party to take a treacherous route through the wilderness. They make it to their destination, but they emerge wounded and weary. Each character must make a DC 15 Dexterity saving throw, taking 27 (5d10) piercing damage on a failed save or half as much on a successful one. This can be scaled to the characters’ levels.
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