Deeper Into Skill Challenges, Part One

A while back, I posted about skill challenges in D&D 4E. My thoughts at the time were that they were a good thing, but needed to be used appropriately. My opinion on that hasn’t changed, exactly, but it has evolved a fair bit, based both on Mike Mearls’s skill challenge articles in Dungeon (including the podcast he did about them), and my experience using them in play. Because of that, and because someone posted a comment asking for more about skill challenges, I’m going back to the well to talk about how I use them now, and what ideas I have for them.

When to Use Skill Challenges

First off, skill challenges represent people trying to do stuff over time. The timeframe may be a few minutes, a few hours, a few days, whatever. But if its something that takes very little time in the game world, I think its better to use a simple skill check rather than a full skill challenge.

I use skill challenges in fairly limited situations. Here’s my current list of when I use them:

  1. When players ask for them. Often times, my players will ask to do something as a skill challenge if they feel that it falls into one of the cases below, or if they feel that co-operation could overcome some inherent difficulty. So, rather than just say, “Hey, ranger. Find us a good campsite,” everyone will pitch in with Nature checks, Perception checks, History checks, or whatever else they think they can persuade me will be applicable. And I let them. Why? Because it fosters creativity in the players (“Hmmm. I suck at Stealth and Perception, so I’m going to use Athletics to help sneak through the woods by lifting fallen trees out of the way, then replacing them after we’ve gone through.”), it gets everyone involved, and it’s more interesting than just making the same sort of check for every character, every round.
  2. When success in an endeavour relies on a combination of different tactics. If succeeding at something requires the use of two or more skills for it to be believable, I might use a skill challenge. For example, finding the way through a magical maze of ice and snow might require Nature, Perception, and Arcana checks. Maybe even Insight, if part of the maze is illusory. I may set a minimum number of successes for the required skills for the challenge to succeed – maybe the party needs at least two Arcana successes and two Nature successes to succeed.
  3. When success in an endeavour could come about through a variety of different tactics. Sometimes, I can think of several ways that something could be accomplished. For example, chasing someone through a crowded city. When this comes up, I leave the how up to my players, and see what their creativity comes up with. So, using Athletics to run after the target, or Acrobatics to swing up to the rooftops, or Perception to keep track of the target, or History to know a shortcut, or… You get the idea. This lets the characters play to their strengths, stretch their creativity, and set the tone of the success – the conversation with the captured runner is going to go a lot differently if you tackled him in the street than if you persuaded him to stop by promising not to hurt him.
  4. When I want to create a montage feel in the game. Like the song says, “Even Rocky had a montage.” They can be a good way to gloss over hours or days of some fairly uninteresting task, while still letting the players put their own stamp on things. So, if the characters have two days to get a keep ready to defend against the advancing hordes, we don’t have to play through the whole two days. Set it up in eight-hour turns, say, and let everyone decide what they’re doing for that twelve hours. Some may drill the troops, some may reinforce the doors, some may dig trenches or lay booby traps, some may examine maps and plan strategy, whatever. Everyone again gets to play to their strength, you the game moves forward quickly, and what the characters do sets the tone of the following encounter. If the fighter spent sixteen hours a day training with the troops and the rogue spent sixteen hours a day digging pit traps in the approach, the fighter’s going to have a better chance at rallying the troops, even though the rogue may have a higher Diplomacy check.

Those are pretty broad categories, but they do impose some restrictions. For example, if the party comes up to a castle gate and wants to get in past the guard, I don’t turn it into a skill challenge using Bluff. Hell, I wouldn’t even let them use the Aid Another rules! Let’s face it – one character saying, “Let me in, because I am the Inspector General!” and everyone else nodding and going, “He really is!” does not sound like a viable way to convince the guards to let you past. If they’ve decided ahead of time that they’re going to use this tactic, then I might turn it into a skill challenge to build the cover identity, using Thievery to forge papers, Streetwise to bribe someone for information, Bluff to work up a disguise, whatever.

Basically, though, I don’t allow a skill challenge when the co-operation of the party would strain the credulity of success, is what I’m trying to say. I also don’t use one when the entire thing takes place in just a minute or two.

The other time I never use a skill challenge is when the result of it just doesn’t matter to the game. Here, I follow the advice from that great game, Dogs in the Vineyard: Say yes, or roll the dice. I just say yes. Want to see if you can seduce the barmaid? Yes, you can. Want to see if you amuse the peasants with your magic tricks? Yes, you do. No rolls involved, unless a player insists. Why? Because it’s a free way to give a player a bit of the spotlight, let them explore their character and have fun, without the potential for ruining the experience with a bad roll.

Success and Failure

So, if you succeed on a skill challenge, you get your objective, right? And when you fail, you don’t, right? Well, first off, the DMG recommends that, if a skill challenge fails, it shouldn’t end the adventure. Good advice, right there. If failing the skill challenge means failing the adventure, you should probably rethink it.

Also, given the fact that you’re accumulating successes and failures, it makes sense to me that the succeed/fail result be a continuum, rather than a binary state. What does that mean? Well, if you succeed, but rack up two failures, it shouldn’t be as complete a success as a success with no failures. In the same way, getting your third failure when you have all but one success shouldn’t be as bad as getting three failures right out of the gate.

I’ve implemented this idea in different ways in play. Sometimes, like in the “find the campsite” skill challenge that my Storm Point players love, I give them a bonus on remaining concealed based on the success vs. failure ratio. Sometimes, as in the “find the temple” skill challenge I ran in the same game, I impose a penalty for each failure – in this circumstance, every failure had them encounter a patrol of hostile humanoids.  And sometimes I just eyeball it and adjust on the fly – trying to find a goblin camp without alerting the goblins, I decide that no failures means the party gets a surprise round in combat, one or two failures means that there is no surprise round, and three failures (complete failure) means that the goblins have set a trap.

You may have noticed that I link everything to the failures, and nothing to the successes. This is because I already know what unmitigated success should look like (otherwise why have a skill challenge, right?), so I use the measure of the failures in order to temper the success.

Now, there’s a bit of a danger to this – it may prompt your players to resort to picking the character best suited for the challenge at hand, and then just using Aid Another to max out his chances. I haven’t had that come up, but I can see how it could. What do you do then? Well, my first instinct is to let them. I think that would make the skill challenge boring enough for them that they won’t do it too often. My second tactic would be to make them describe exactly how they’re helping – if it doesn’t make sense, they don’t get to aid. Combining the two should mitigate the problem.

But what about success? How to determine what success looks like? This is sort of glossed over in the DMG, and sort of assumed in most of the articles you read about skill challenges, but it may be the most important point to consider when designing one. What happens when the characters succeed?

I decide this by asking myself, “If nothing goes wrong in this situation, and everything goes right, what’s the best outcome that could reasonably come about based on the characters’ abilities?” The two key sections of that question are the “reasonably come about” and “based on the characters’ abilities.”

Let’s talk about the first point – reasonable. You don’t want to give away the shop. If you’re using a skill challenge to bargain with a merchant, it’s not reasonable to assume that he’s going to give you his stuff for free. So, let’s say you set a discount that they could reasonably hope to achieve – let’s call it 25%. More than that, and he won’t be able to feed his kids. See? Reasonable.

Now, let’s talk about basing the success on the characters’ abilities. If the characters are making their way through that magical maze of ice and snow I mentioned, they don’t get to cause the maze to vanish just because they made a good Arcana check – at least, not at heroic tier. Maybe at higher levels. But you can also colour the outcome based on the skills they used – relying on Arcana has them using mystical compass needles and runestones to pick the correct pathway, while relying on Nature has them watching the blowing paths of the snow to avoid invisible walls and crevasses, and relying on Athletics has them scaling the walls to follow a straight-line path to the goal.

Anyway, I think I’ve made my points here: success and failure can be used to make the skill challenge more interesting.

Level and Complexity

What level should the skill challenge be? How complex?

Well, as to level, I generally set all the skill challenges at the party’s level. The reason for this is simple: I can usually remember the target DCs for Easy, Moderate, and Difficult rolls for the party level, so I don’t need to look that up. It speeds things up in play, and lets me make impromptu skill challenges more often if I see the need.

If a skill challenge is meant to be an important, memorable event in the game, then I may set it a level or two higher, but this is rare – the DCs in the DMG are grouped by 3 levels: level 1-3, level 4-6, etc. That means that I may have to bump a challenge by up to 3 levels for it to make a difference to the DCs; easier just to shift to the Difficult category, or increase the DCs by one or two.

Complexity is a little trickier, appropriately enough. Most impromptu challenges I set at complexity 1, because I don’t want them to slow down play. In fact, I lean toward setting most skill challenges at lower complexities these days; it really distinguishes them more sharply from combats.

When I use more complex skill challenges, I try to instersperse the skill challenge rolls with other stuff: other encounters, role playing scenes, dealing with the consequences of failure, etc. This tends to make the whole thing a little less static and mechanical, adding variety and interest to the proceedings.


I was going to offer some samples of the skill challenges I use (or try to use), but I’ve already topped 2000 words, which is enough for one post. Tomorrow, I will post Part Two, where I will show you some of the challenges I’ve built, and talk about why I’ve done things the way I did with each of them.

Check back then.

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One Response to Deeper Into Skill Challenges, Part One

  1. Arashinomoui says:


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