A skill challenge is an encounter-style framework for non-combat encounters. It has turn-based play, but no grid or minis.  D&D 4e formalized a structure for it, although I think they dropped it with 5e. The big draw about challenges for me was the idea of having game-style tactics and clear win/loss conditions like with combat, but applying to a broader range of situations that you have in an adventure: investigations, travel, politics, etc.

Unfortunately, the actual experience of skill challenges in 4e was a big let down for me.  It added a mechanical, encounter-style framework like I wanted, but didn’t add strategic complexity. In particular, everybody made their own skill checks, but there was generally just one optimized thing you could do in your turn, and there weren’t really situations where one person could set up another for a cooperative, combination play. So you ended up with half the overhead of combat encounters, but none of the tactical interest. Bleh.

Over time, my husband and I tweaked the skill challenge framework for our home games to allow for some cooperative play and to get some emergent tactical complexity.  You can take this same approach with any d20-style  skill system like D&D or Pathfinder, so feel free to steal the ideas below.

Establishing the Challenge Framework

So, our homebrew version of a skill challenge starts with the GM formally declaring that it’s starting, similar to how the GM starts a combat encounter. This lets the players know it’s time to switch out of freeform narrative mode and into encounter mode. For each skill challenge, the GM defines three variables:

• Allowed skills: We like to restrict each challenge to about 4-7 skills. You don’t have to restrict the allowed skill, but doing so prevents people from falling into patterns where they always try to do the same skills each challenge.
• Success & Failure Conditions: Typically the party wins the challenge if they get a certain number of “Breakthroughs,” and the party loses the challenge if they get a certain number of “Setbacks.” As soon as they either succeed or fail, the encounter ends.
• Skill Targets: In this challenge, skills aren’t just succeed/fail. Instead, they have 5 possible outcomes. Miss, Low, Medium, High and Exceptional. You need to tell the players, the check values they need to roll in order to get those outcomes.

Overall, a challenge declaration goes something like, “Okay, lets run finding the missing cacique, as a skill challenge. You’ll need to get five breakthroughs before four setbacks.  You’re allowed to use  Analysis, Influence, Deception, Perception, Stealth, and Thievery. The Low threshold is 16, Medium is 21, and High is 26.”

Establishing a Turn Order

Like with combat, play goes in turns and rounds. Everybody rolls a dice to determine the order of play. Unlike with combat, NPCs aren’t in the initiative order, it’s only PCs.

Also unlike with combat, players don’t add their initiative modifier to get their turn order. It’s a purely random roll.  The reason we don’t add initiative bonuses is to make sure that those at the front of the order aren’t participating more in challenges in general than the rest of the players. In-game it makes sense because the time scale of a skill challenge is a lot longer and more loosey goosey than in combat, so speedy reflexes don’t make a much difference.

Another difference from combat encounters is that you don’t want to allow players to skip their turn. If they could, then the optimal strategy would always be to determine which PC has the best skills and have them do all the work. So it would basically collapse into a series of skill checks by one person, which is something we’re trying to avoid. In combat, no one gets to entirely sit it out. Even if they’re not the best fighter, they’re in danger from the monsters and have to find a way to make an impact, even if it’s just helping set up a more combat-focused PC. We want to have that same dynamic here, so no skipping/delaying.

In theory, you could use a different style of initiative system.  In particular, I think a popcorn style would work well, where whoever wants to can go first, and then they choose who goes next and so on until everyone has gone that round. It would tend to get players talking and thinking about turn strategy, which may be a pro or con for you depending on your table. We stuck to a simple roll just so that the players didn’t have to learn two completely different initiative systems.

Player Turns

So, on their turn, each player makes a very specific type of skill check, using the allowed skills.  Here’s how it goes:

1. Describe the skill check in-game. They don’t necessarily have to be in-character, although they can if it’s fun. The reason you want to start with the in-game description is that the skill challenge framework is already an abstraction, so it’s easy to jump straight to the mechanics, but that really kills the immersion.
   
2. Declare skills. They choose the skill (or in our game, the two skill combination) they want to use from among the allowed skills. The GM may have to intervene if the description doesn’t really match the skills the chose. I like to give players a certain amount of leeway, but it’s always tempting to stretch the definitions of skills so that you use your better bonus.
3. Declare target. The player says whether they’re trying for an easy, medium, hard, or exceptional skill check. The difficulty of the check is the target.
   • Easy. Missing the check gives a penalty to the next player. Making the check gives a bonus to the next player. Either way, the next player must attempt at least a Medium check. So, it’s the safe choice because the threshold is lower, but you can’t have everyone making safe choices.
   • Medium. Remember me mentioning Setbacks and Breakthroughs earlier? Here’s where they come into play. Missing this counts as a Setback. Making this counts as a Breakthrough.
   • Hard. Missing this check counts as a Setback. Making this check counts as a Breakthrough and gives a bonus to the next player.
   • Exceptional. Missing this check counts as a Setback. Making this check counts as two Breakthroughs OR one Breakthrough and a bonus to the next player.
4. Roll. As the GM, I like describing what the results of the roll correlates to in-game, but you may want to leave that to the players.

So, a turn will sound something like this.

Player: “I’m going to go to the tallest lookout tower in the fort and carefully watch the traffic around the city. I want to watch for signs of the Cacique or the kidnappers or something suspicious. I’m going to go for a medium check using Analysis+Perception.”
GM: “Sounds good. Roll it.”
Player: “I made it! Breakthrough!”
GM: “In the distance, something catches your eye. It looks like some ruffians carrying a luxurious tapestry into an abandoned warehouse, but the tapestry looks like it’s moving. Your team has four Breakthroughs now. One more to succeed.”

If the player had failed, the setback could translate into the fort being taken over by some crazy militia, so they got into a brawl. Any hope of discrete surveillance from there was lost as well as time wasted.

Choosing Target Numbers

What time is it?  Math time!

Well, a little math, anyway.  Mathecito.

As I mentioned earlier, in our house, we use 2-skill skill checks, and so we have higher thresholds than what you normally see in a d20-style game system.  But I can walk you through developing your own table of target thresholds.  Here’s what you do.

First, you need to have a sense of what skill bonuses PCs have at the level for which you’re preparing. For example, let’s look at D&D 4e at level 1, since it’s something I’m fairly familiar with. I want to think about three cases.

1. Specialist. Think about a stereotypical Rogue.  How high is their stealth? Pretty high! They’re going to maximize it. They might have a +4 from their ability bonus and another +2 from their race and maybe another +2 from a feat and a +5 from training. So for example, a rogue might have a +13 overall in Stealth in first level.
2. Decent. Now lets think about a scholarly Cleric.  How high is their History? Well, they might have a +2 from their ability bonus if they made intelligence secondary, and maybe another +5 from training, but they’re not investing precious feats into it.  So, about a +7 overall.
3. Incompetent. Last, consider the Thievery of the Paladin. They’ll have a -1 ability modifier and a -1 as an armor check penalty, so you’re looking at around a -2.

You can do this same exercise at each level. In 4e, it’s pretty close to a linear progression.  The change is dominated by the half level modifier, although you do get some bumps where players get ability bonuses.  Plus, at higher levels, players may get feats and equipment that help, especially if they’re trying to be a specialist in a skill. But it’s pretty close to linear. And it’s good to mostly ignore those extra bumps anyway.  If you do so, the math makes it so that specialists go for hard and exceptional checks more often as they go up in level, but doesn’t really change much for the decent and incompetent PC cases. So overall it make the challenges play out a bit differently at different levels.

So if I’m creating thresholds, it’s useful to develop targets in terms of how often we want players to fail. Then the formula becomes:

Target = (Expected Bonus) + 20 x (% you want them to fail)

1. Easy: I like thinking of Easy as being something a decent PC fails about 15% of the time. Using our Cleric example from above, that means the target = 7 + 20 x (.15) = 10. As an extra reasonableness check, you can solve it in the other direction to see how often someone bad at something fails, which will tell you that a Paladin will fail at an easy Thievery check about 60% of the time. The specialist always makes it, because their bonus is higher than the target.
2. Medium. I like making the medium checks something that someone decent can do about 65% of the time. So, putting that into the formula gives a target of 14. The Specialist almost always makes it, but fails on a 1. The incompetent only succeeds 20% of the time.
3. Hard. I like making the Hard checks something that Specialists succeed at about 65% of the time on. So, putting it into the formula again, we get a target of 20.  At that, a decent PC will succeed about 35% of the time and an incompetent PC will never succeed.
4. Exceptional. I think they should be really hard to make at low levels, but start to become more practical for specialists at high ones.  So I like to peg it at about 35% for specialists, which translates to a target of 26.  With that, decent PCs succeed only on a 19 or 20, and incompetents really never succeed.

How it plays

So, we’ve been using this general approach to skill challenge encounters for years now, and I love it.  In practice, they run faster than combats, but still give you that everybody-is-working-together-on-a-coop-game feeling. Plus, it makes skills important to the min-maxers, because now you can put XP on the encounters and have clear wins and losses. It doesn’t replace the parts of role playing where you’re acting out a scene and making occasional checks, but it does give you more options as a GM to control the rhythm of the game and to have encounters and tactics without necessarily needing to make it about killing.

The only downside for me is that skill challenges can feel very same-y over time. Although the in-game situation may be wildly different each time, mechanically, players have the same few options each turn. If you’re designing a game from scratch, the best solution is to give PCs challenge-specific powers, just like they have combat-specific powers, but that’s a lot of overhead if you just want a quick framework to drop onto an existing game.

So,  after years of playing with it, we’ve learned how to incorporated variants which really shake things up and make different challenges play out differently from each other. Next up: Skill Challenges, Part 2, in which I cover variants. Plus, if you have questions, let me know and I’ll cover that.