A Thorough Look at Skill Challenges (Part 2: Analysis)

After my last face-meltingly long post compiling every variation on Skill Challenges (SC) out there, it's time to do a critical analysis of this concept. When I started this project, I was just imagining that I'd be making a simple pros and cons list. But after all that research, I have a lot of things to say.

So, this post will sorta have three main sections. Firstly, we can talk about Skill Challenges just, like, as a concept. Then, we can start reviewing each of the little variations on rules and deciding which ones are good and which ones are bad. Lastly, the results of this thinking, which ideally should be "the best version of how to do Skill Challenges for a D&D 5E game, at least in the style that Dwiz enjoys," but which is also the part where I note some things I feel like stealing for my OSR game Brave.

Are Skill Challenges good?

Justin Alexander once famously made a series of blog posts on game procedures. In it, he conjectures that you cannot create a truly "universal" procedure because so much of their depth is context-dependent. The closest thing we have is just the "basic cycle of play" procedure: the DM describes the scenario, the player declares an action, and the DM narrates the results. But anything with depth beyond that, from combat to hexcrawl to space travel and more, needs to be designed on a case-by-case basis with their unique qualities in mind, right?

Well, some have suggested that the Skill Challenge is actually a serious contender for fitting the definition of this "Holy Grail" universal game procedure.

Is it?

Alexander himself has countered this once, but I have a fair bit more to say. One of the things that makes this difficult is that, as I've shown, there isn't just one version of Skill Challenges that we can respond to. Justin Alexander was angry about how bad the rules for them were in the 4E DMG 1, but I wonder how his thoughts would change if he saw some of the later variations I covered in my last post. That said, I have some basic criticisms that apply pretty universally.

My main issue with SCs is that they ultimately abstract and systemize actions and challenges that, to me, would be more elegantly resolved through intelligent use of imagination and simulation-minded GM rulings. Which is to say, the more flexible, basic way to play the game. In my mind, I shouldn't have to play a minigame to interrogate an opponent or infiltrate a villain's compound or investigate a mystery. The GM should be able to just let me do those things.

Want to run an interrogation scene? Then let me verbally talk to the NPC, with each of us play-acting and making a roll here or there as the flow of the conversation dictates.

Want to run an infiltration? Then let me play through a dungeon with lots of armed guards and traps.

Want to run a mystery investigation? Then let me choose what locations to visit, clues to look for, NPCs to talk to, and ultimately just figure out the answer with my own brain.

As I've said many times before, the unique strength that TTRPGs have over videogames is that our "game engine" is just a human mind connecting with other human minds, which allows for an infinite possibility space that no videogame can touch. Something like Skill Challenges, in most of its forms, seems to be a rejection of that basic truth. It seems to reject the most simple appeal of what makes RPGs fun. 

...On the other hand... there is a comfort in having SCs around when you're running a crunchy modern game. I mean, what is a Skill Challenge if not just a reliable structure you can always fall back on when you aren't prepared to run an interrogation or infiltration or mystery investigation? It's a lot like how having a flexible core mechanic is one of the most important assets in supporting a "rulings over rules" style of play. It enables the DM to improv better if they can keep returning to the same foundations and adapting it slightly instead of starting with a blank canvas every time.

Here's the best thing I can say in defense of Skill Challenges: imagine that you're going to be DMing a game of 5E D&D. You know that the main attraction is the combat system because it is, after all, an action game. But you also know that 1) the combat system only really shines when you put some work into designing your encounters to be more engaging than just hack-n'-slash, and 2) if you never have interesting gameplay for non-combat activities, then your campaign won't feel like D&D and it'll suck. So you have a conundrum where most of your prep time is best spent making your combat scenarios a little spicier than the baseline, but where you also want to have, let's say, at least one badass non-combat scene to play through each session that everyone can get into.

The difficulty here is not in coming up with what those non-combat scenarios could be. That's easy. The difficulty is in thinking through how to design each one, knowing that you'll likely use them once or twice each, and that you also need to have time to still include a not-boring combat encounter for the same session. So you know what would be really, really great?

If there was already a conveniently-prepared library of "basic Skill Challenges" cataloging a huge range of common exciting non-combat scenarios, all formatted with a common game structure that's easy to understand, easy to teach, easy to run, and is usually pretty thrilling to use. I'll admit, such a library doesn't actually exist (to my own personal satisfaction), but we're still using our imaginations right now. And so I present you a list of SCs I imagine would be in that library:

1. Negotiation
2. Interviewing a witness
3. Chase scene (either as quarry or pursuer)
4. Interrogation (both as the interrogator and detainee)
5. Navigate the woods/swamp/wilderness
6. Doing research (remember how every episode of Buffy the Vampire Slayer had a phase after the team's initial encounter with the monster where they'd hit the books and spend a few hours reading medieval texts in the library? I love that trope)
7. Decoding a message/puzzle
8. Disabling a complex trap
9. Perform a magic ritual
10. Stopping a magic ritual
11. Solving a mystery
12. Navigating a maze
13. Get across a complicated natural hazard (e.g. cross a river, climb a cliff, cave system)
14. War summit
15. Fight a battle! Why not do warfare this way?
16. Infiltration (+ goal, like stealing something or sabotaging something)
17. Sneak past something
18. Escape
19. Compete in a tournament/sport
20. Race
21. Construct/forge/repair something big or complex (like a magic artifact or a spaceship)
22. Legal trial
23. Taming a creature
24. Piloting a vehicle through some rough terrain/a storm/a battlefield/whatever
25. Combat against a colossal creature that you can't defeat in the normal fashion
26. Complex performance/performing a play
27. Courting votes for a big decision

After having read through that list, tell me you wouldn't feel a whole lot more at ease prepping your imaginary 5E campaign knowing that you have this resource already packaged and ready-to-go. It's such an attractive approach to running the game that it makes me genuinely a little excited, like I might even actually try it myself.

No, I don't think that most of these options are as good as a more dedicated, thoughtful procedure uniquely tailored to that activity (e.g. running a heist as a proper high-security dungeoncrawl or running wilderness as a hexcrawl, etc.), but I do think that we could concede that this option is "good enough." If you used just one of these SCs per session, then that library would last you a whopping 27 sessions! That's a lot more than it probably sounds, and in reality you'll likely reuse some of them several times, too.

So yes, my bitter and jaded heart can see the appeal in relying on Skill Challenges as a fallback option to do a lot of heavy lifting. That hypothetical I just spelled out sounds nice and cozy to my exhausted, high-prep DM self.

What is the best way to do Skill Challenges?

Firstly, we're going to have to get past a few major problems that most iterations of SCs are still guilty of. Here are my big complaints:

1. Metagaming to the max

Most approaches to running SCs are, like, literally the definition of training players to look at their character sheet for answers instead of using their imagination. If you tell the players when they've entered a SC, they instantly begin to think within mechanical terms and earning successful checks, ceasing to conceive of the hypothetical situation as something analogous to real life.

We often claim that the ideal way to play is to think of your action in terms of the fiction, and then the DM will translate that into mechanics for you. We tend to instruct new players, "don't say 'I want to make a Survival check.' Instead say, 'I want to climb a tree to get a look around the surrounding geography' or something." But in practice, we often fail at this. Because the rules exist as a common language for us to use, specifically for the purpose of having a shared way to think about the world. And sometimes the rules are constructed in such a way that it's really, really difficult to ever speak in a language other than the mechanics.

Of course, many of the versions of SCs I looked at anticipate this problem and they try to subvert it. They would insist that you encourage your players to still decide their turn "fiction first, mechanics second" and that they should always just tell you what their character does rather than ever suggesting the specific skill being used... but then they shoot themselves in the foot. They'll have a rule saying something like, "you can't reuse the same skill as the last guy" or "you must be proficient in a skill to use it" or "you suffer a penalty for using a 'secondary skill'" or something like that. Constraints like these force the player to look at their skill list before deciding their action because now they have to limit themselves per the mechanics.

On the other hand, if you don't tell the players that they're in a SC, it becomes pretty easy for them to "break out" of the SC by not playing along with the scenario. Skill Challenges, even at their best, are still pretty contrived. Let me give you an example:

The villain flees from the scene, and the PCs can't let him carry out his evil plot. You expect a chase scene to follow, and have prepared a SC for this. If you announce that the PCs are now entering a chase scene SC, then they'll play along great and use each of their actions to do something which (hopefully) leads them closer to catching up to and capturing the villain. That's because you've declared the parameters of the current scene and set the expectation that, "we'll be using this structure until you either earn X successes or Y failures in terms of this goal I've given you." But if you don't tell the players that they're in a SC at all, there's a pretty good chance they'll instead say something like, "alright, let's let him go and then put a tracking device/spell on his vehicle so we can just let him lead us to his secret lair. Making him think he's being pursued will just cause him to start running, and why take that risk?"

"Womp womp womp woOoOoOomp," right?

Well, not actually, because that's a really good idea and the players should be rewarded for thinking of it. Hence why my preference still ultimately lies in just running the game in a more freeform fashion, and why my only concession towards SCs as something worth using is just for the sake of the DM who wants to occasionally say, "hey, I've decided that this is the next scene and we're using this structure to run it, dammit."

But I feel like there's a happy medium to getting past the metagaming issue.

Despite how I just made it sound, would you believe me if I said that, normally, I am much more in favor of transparency of rules and procedure to the players rather than those who prefer to "maintain the illusion"? I get that it can "break immersion in the fiction" but after many, many attempts at following that advice, all I've concluded is that it introduces far more complications than I care to deal with. Clarity and shared expectations are something I highly value at the table, so when I use a hexcrawl procedure, I tell my players and show it to them.

HOWEVER... the few times I used SCs (in Star Wars: Saga Edition) I actually did make them invisible. Of course, this was an early DMing experience for me, but it was informative. The first and third SCs were huge successes, but the second one didn't really work at all. See, the first and third ones were a chase scene and an interrogation, respectively, and I think that the players' actions mapped onto the SC structure so smoothly because the situations were so naturally well-defined and singular in their objectives and available strategies. The circumstances of that chase scene were such that it was really the only option my players felt they had, so my SC I prepped wasn't wasted.

But the second one was a prison break scenario where they needed to spring an important NPC from his cell, and my players did exactly what I warn you of: they didn't attempt any of the skills that the rulebook anticipated being used, or even an approach that I felt I could really systemize with "cumulative skill rolls." They didn't use acrobatics to crawl into ventilation ducts, they didn't use deception to talk their way past each guard, they didn't use stealth to pass under security cameras, and they didn't use hacking to exploit the facility's computerized security system. Instead, they pretended to be visitors scheduled to see their beloved imprisoned friend, chose the most common name in the Star Wars galaxy ("John Antilles" is the canonically correct answer, surprisingly) and prayed that a prisoner by that name would already be on today's list of scheduled visits. After introducing themselves to this very confused man, they then made him an offer: we'll spring you too if you go get our guy for us. They talked strategies with him and eventually decided on having him just go back inside like everything was normal, but then cash in on all of his favors with other inmates and guards on the inside to clear a path for the PCs to get to the target's cell and back with him in their possession.

Pretty cool, right? I sure was a big fan. But I also had to abandon the SC statblock pretty much immediately. That's the kind of problem-solving that I could only resolve through "playing it by ear." And if I tried to force the statblock's expectations on the situation, such as by putting a bunch more security obstacles in their path after they got their foot in the door, then it would feel like I was invalidating their good idea and failing to show that it had any positive effect at all. Not to mention drawing the session out.

Don't worry, about four years later they made the adventure I had in mind into an episode of The Mandalorian, so it all worked out.

So here is what I feel: I think 4E's advice goes too far in saying you should tell players what skills they need to use, but I think keeping it totally invisible is also too far. I think the ideal is saying "alright, we're doing a SC now. You need 5 successes before you acrue 3 failures" but then leave it at that. Let them feel out the rest, and cut most of the crunch that's going to cause players to make their decisions on the basis of mechanics that have no rational association with the fiction. It's good if the players understand the rules of the scene, provided that the rules in question are pretty simple and flexible to begin with. The sort of rules that won't really cause "metagame thinking."

2. Get'cho narrativist philosophy out mah damn game

Again, this is not true of every version of the SC I looked at... but it strongly defines most of them. Most importantly, it was the explicitly stated philosophy of both the 4E DMG 1 and Matt Colville's version.

When I first got into RPGs, I was really drawn to "story games," at least in concept. I thought that the storytelling potential of RPGs was by far their most interesting feature worth exploring, and I loved reading about games with dramatist mechanics. But as time went on, I just fell out of love with it. I found that the parts of the game I enjoyed the most and felt were the best use of my free time were those moments when we were using our noggins to think our way past problems where the answer wasn't obvious. Where we felt both challenged and yet very clever. And where I felt like I could truly immerse myself into the scenario and get right into it.

Many "narrativist" games and mechanics use what some refer to as a "writers' room" approach to gaming. Where each person at the table is explicitly taking turns as the one holding the "storyteller reins" and where you're not "playing your character" so much as "writing for your character." Everyone plays the game like they're a screenwriter, and their shared goal is to make things as dramatically interesting and satisfying as possible. You think in terms of arcs and themes and what makes for the best story. And always "for what audience?" I'd ask myself, since everyone else at the table is too busy focused on being the author of their own story. This is why so many game designers fixate on finding ways to mechanically "incentivise failure," as though players are incapable of ever unintentionally failing.

And this playstyle is really incompatible with the "challenge-focused" playstyle I enjoy and which I think the Skill Challenge should be best designed for. That's what happens when players are given the power to create new information. See, the "writers' room" is typically contrasted against high-crunch "system mastery" games when described by its proponents. "Unlike the powergamer's preference for video-game-y combat simulators fueled by feat lists and complicated action economy, our ambitious, intellectual, fiction-first, deep 'storytelling experience' is flexible enough to accomodate whatever fictional scenario you imagine."

And on the surface that sounds like it should appeal to my crowd. I also prefer a playstyle that similarly has open-ended challenges and freeform mechanics... but I don't like players having the narrative power to just add new info as they want. They're still merely players within my world, forced to work within the bounds of what info I've made available. That's where the challenge comes from: I give them a ton of detail, they leverage it intelligently to their advantage, them's the rules. There's no question: the DM is the author, the players are the audience. Yes, as interactive fiction they get more agency over the work than someone watching a movie or reading a book, but not that much agency. When you play Dark Souls it's still clear that FromSoftware is presenting a challenge for you to consume, and that's why their name is on the box and yours isn't.

And this bleeds into how a SC works. One of the reasons I linked Matt Colville's "Many Fail States" video last time is also because it's one where he explicitly declares this very philosophy. To paraphrase him, "It's a foregone conclusion that the awesome and heroic PCs will be successful. The dramatic question that remains is how they do so." 

And while I can recognize that this is a valid assumption to operate on while gaming, it also could hardly disinterest me more. Miss me with that.

To put it another way, I've always enjoyed acting and theatre and I've also always enjoyed playing sports, but when I was in high school I ultimately joined the robotics team instead. And my favorite part was getting the prompt for what our robot needed to be able to do, and then everyone working together to figure out a way we could build a robot capable of achieving that. Even better, once you're finally at the competition you get to see just how mind-bogglingly different each team's robot is, despite all being built for the same purpose.

So my ideal version of the Skill Challenge would be one where the DM has full control over what can happen, but more importantly, that the players never feel the need to just "make up a problem they can solve." Where the skill being tested is their problem solving abilities, not their creative writing abilities.

This is why I spoke so highly of both Saga Edition's advice to fill the SC with gameable details as well as DM David's alternate model of the "obstacle course." Rather than being a way to abstract challenges, a SC should have a pretty well-realized setup for exactly what the challenge consists of. What the SC system instead provides is a standard for the DM to measure progress and a format to follow for adjudicating actions and consequences in a rapidly-developing situation. All those parts I like, but I don't want to compromise the concreteness of the situation being simulated.

3. Not as flexible as you'd think

This is probably the main reason why I went through so much effort to catalogue every variation on SCs. Because each version of the rules is a different way of simulating a fictional situation, and can accomodate more or less possibilities depending on how well thought-out they are. The baseline rules for the 4E SC raise a lot of weird questions that will inevitably clash with any reasonable understanding of the underlying scenario the rules represent.

As Justin Alexander pointed out back during the 4E Beta, this means that Skill Challenges fall within a category we call "dissociated mechanics." If the rule is that you always need X separate successes before getting Y separate failures, then they only care about how much you've done to solve a problem, and rarely account for the actual details of what you've done. And this can be a problem if a player proposes an action that should be able to just totally secure victory or failure in one fell swoop. Sometimes adding those Rules Compendium advantages or situational conditions or the Saga Edition-style "Challenge Effects" can mitigate this problem, but it remains an important issue. And that's why I thought that comparing to things like ICRPG's "effort" system was a valuable contrast.

And much like how SCs only seem to care about the quantity of successes rather than the quality, there are also problems with the idea of how failures work. In DM David's series of blog posts, he made an astute observation: sometimes it makes sense that you can accrue both failures and successes, but sometimes it really doesn't.

For example, let's say you're trying to sneak into a vault. Well, we could interpret the rules such that "each success gets you closer to the vault, but each failure also raises the security level a bit." These both make sense to be progressing alongside each other, right? Contrast this, though, with 4E's favorite go-to example of a SC: "negotiating with the duke." So you're trying to persuade him for permission of something, right? Doesn't the success-failure dynamic here feel like it should be more of a tug-of-war zero-sum game? Wouldn't it be weird if you had 5 out of 6 successes but also 2 out of 3 failures, and the DM has to roleplay him as being incredibly close to both saying "yes" and saying "no"?

I guess my own personal issue is that most examples of SCs feel like the source of failure would, more logically, not come from failed attempts at contributing, since they oftentimes shouldn't make the situation any worse. Why should a player be afraid to "risk" making a knowledge check? How could their lack of knowledge harm things? Would a failure mean they accidentally misinform the party? Talk about killing the power fantasy.

To quote David:

Even worse, if a skill challenge lacks any clear marker of failure, running the challenge presents a problem. The first D&D Encounters season, Halaster’s Last Apprentice, included a challenge where the players seek to find hidden chambers in the Undermountain before they amass the three failures allowed by the rules. Why do three failures end this challenge? Is it because the players grow restless and are now all on their smart phones? The adventure suggests that rival groups might be seeking the lost chambers, but it fails to capitalize on this. The adventure follows the conventional advice by taxing each player a healing surge, and then saying that they found the crypt anyway.

“Why do we lose a healing surge?”

“Well, you know, dungeon stuff.”

Again, this is why I took so much interest in the alternatives. I really enjoy those Challenge Effects that offer a different source of failure, such as automatically accruing one each round or having them come from an opponent's own active efforts. Or how about the Obsidian rules, where you never earn failures and instead just have different thresholds of how many successes you got?

Thus, our version would have to be one which just has a bigger imagination than the basic model. The DM is empowered with simple tools to adjust the SC's structure as necessary to always fit the scenario, but without turning it into something unrecognizable.

Why, yes, this is what I look like when I write these posts.

So what's the best option to address each of these problems?

I think the right answers to nearly every question I have can be found somewhere in my last post, even if no single iteration has it 100% correct.

Detail: Some of the methods I read about require a lot of prep and forethought to make them good. Others are easy to improvise on the spot just in case your players surprise you with a plan that you didn't anticipate. Sometimes it's the little details in the rules that can allow for this. I would much prefer a system that can be easily improvised (like clocks in Blades in the Dark), but giving them any kind of nuance that accounts for the complications I just described above means that this might be tricky. Thus, I think the truly best answer is to make a library of "generic" options, not unlike the purpose served by the Monster Manual. Yes, good monsters in 5E are typically too mechanically complex to totally improvise, but it would also be too burdensome to meticulously craft a brand new one for each and every session. Thus, have a big collection of good ones ready to go for a variety of situations. It'd be the same thing for SCs. When playing the game, you may not have planned for the party to get into a chase scene, navigate a cavern, or defend a client in a criminal trial, but you can still run a mechanically dynamic encounter because you have one of those prepared in the archives.

But I also bet you I can make a useful "SC stablock" way shorter than the ones found in the 4E books or the Saga Edition supplement.

"Primary skills": All my favorite versions of the SC have no rules about which skills are preferred or have limits or anything like that. I actually believe in committing to letting the players be creative and rewarding it, and thus, being open to anything they propose. Thus, if a SC statblock mentions any skills at all, it would merely be for the purpose of naming some highly-expected skills and some extra considerations to make with each one. For example, let's say you're prepping a heist SC and you anticipate a player using Stealth: you might write down something like "the facility only uses CCTV security cameras, so merely jumping from blind spot to blind spot is enough to stay out of sight." This serves to better inform yourself of the concrete details of the scenario, which can be helpful while running it. 

And if you're going to include a list of expected skills, I think one of the more useful things you can do is include a consequence for each of those. That is, all this advice we've reviewed says you should create SCs that change each round and the PCs' actions should have immediate consequences, right? Well, I say that one of the better things to spend your energy brainstorming ahead of time rather than trying to improvise on the spot is an if/then effect for each obvious skill. "I expect my players to try X, so if they do X, then Y will happen as a result in addition to a success/failure."

Of course, I also only think you should do that in ways that still make sense. Matt Colville says that he thinks there should be one main consequence used after every failed check, which I'll admit is more simple. But I ask, why would failing your knowledge check result in you getting hit in the head by a falling rock?

Restrictions: I think too many versions of SC rules are terrified of allowing for outcomes that really aren't actually that bad. "What if the Wizard just keeps using Arcana each round of the magic ritual? Won't it get boring?" Eh, that's not actually so bad. If it really bothers you, then maybe instead of limiting the Wizard's options with no explanation, how about you make the SC have more complicating factors involved? Some of the sources I read would clarify to the GM, "ask yourself, 'does this challenge take multiple steps?' or 'does this take multiple people to solve?' about your challenge. If the answer is 'no' then you don't have a Skill Challenge." To that I respond, why not also require that SCs always have either multiple problems to be solved or multiple avenues of success to advance? The magic ritual requires someone to be continuously reading from the book, yes. But someone else needs to be draining themselves of blood, and another person needs to be maintaining negotiations with the spirits being channeled to complete the rites, and someone needs to be keeping the zombies from breaking through the walls and windows.

Thus, I do not want any rule that, totally regardless of context, explicitly limits:

1. How often you can attempt to use a skill,
2. How many successes a skill can earn,
3. How easy or hard it is to use certain skills,
4. If you need proficiency in a skill to use it,
5. or If someone else already used the skill.

I can imagine circumstances where some of those make sense based on the situation, but not as rules built into the system itself.

Oh, and I'm also 100% in favor of allowing non-skill contributions. Ability checks, saving throws, equipment checks, spells, class features, background features, racial features, etc. all seem like fair game to me if you can rationalize them. Which leads me to an important thing to emphasize:

The way the 4E DMG and most other sources phrase it, a DM creating a SC should come up with the challenge first, and then think of likely solutions second. But there's a possibly-better way to go about it: come up with skills and features you'd want to see used first, and then write in obstacles that would require those skills or features to solve. I once wrote a post about this sort of game design for 5E D&D, for which the second half is just a huge list of "non-combat challenges" to throw into your game inspired by character abilities. So maybe when you're fleshing out your SC, you could just go to that list and pick a few items that seem fitting. Don't worry, most of those ability-derived challenges have more solutions than just the one ability that inspired them. Your players will continue to show creativity.

Aid Another: When it comes to aiding your friend, I think that's a perfectly acceptable thing to contribute. Rather than applying a penalty or adding an additional requirement like proficiency, the only thing I would ask is, "how are you helping?" If you can't answer that, then you can't give any aid, and that's a good enough standard for me. The Dungeon Coach uses this method, and even lowers the DC by 5 for attempts to aid your ally, since the only payoff of succeeding on the roll is merely granting your buddy advantage rather than actually advancing progress in the SC. I kinda like that. But you know what I like better? In the 5E PHB section on "Actions in Combat," the "Help" action automatically works. You grant advantage to your buddy just for the price of spending your action on Helping, and no roll is needed.

Initiative: One of the most often abandoned features of SC in all the versions I found was rolling for initiative. I think too many people thought it made the procedure feel less fluid or more like combat. But all too often, they would introduce a replacement rule that could serve the same benefit but... worse. Because I will admit, the ideal SC is one in which everyone is participating equally and everyone is using a variety of their best skills. But while jamming in rules like, "you aren't allowed to be boring" is a bit ungraceful, including initiative (or something similar to it, as we'll see) will create this outcome naturally.

If you're using initiative order, then it makes sense why everyone would contribute a roll rather than just relying on the same guy again and again. Because the question can now be framed as, "alright, while the Wizard is doing her Arcana check, what is everyone else doing at the same time?"

And yes, I also think it's perfectly acceptable if you choose to "pass" on your turn. The correct answer wouldn't be to disallow that. It would be to make a harder challenge where players can't afford to sit things out. In particular, I'm a fan of SCs where the source of failures isn't failed rolls, but instead just something in the situation that is gradually getting worse and worse each round. And hey, if building a dynamic challenge is too hard for you, then you can also avoid the problem by coming up with lots of ideas for side benefits that a player could spend their turn doing. I can't blame a DM for presenting a fairly simple Negotiation SC where the correct path to progress again and again will just be some form of Charisma check, and I likewise can't blame the uncharismatic doofus PC for wanting to sit back and let the Diplomat work their magic. A system where everyone is forced to make a check on their turn risks causing the party to fuck up where they shouldn't have needed to, so if we instead always have some kind of option for characters to "Aid Another" or "gain insight" or "notice something" or whatever then that can be ideal.

Of course, I prefer the Saga Edition version where you don't roll for a set turn order, but instead just have to make sure that everyone gets a chance to go once before anyone can take their second turn. So technically, I also advocate an alternative to rolling initiative. 

Oh, and taking a note from the Obsidian rules, I actually quite like the rule of "the DM resolves all the party's actions simultaneously." That doesn't necessarily mean each action executes simultaneously, since sometimes the party is going to coordinate several actions to go "first A, then B, then C." But basically, the DM should practice the habit of going around the room, jotting down what each person says one at a time, then reviewing the whole picture all together at once and then narrating the collective result of the turn.

Success and Failure: This is definitely the trickiest thing to meddle with, because it's the core of what makes a Skill Challenge a Skill Challenge. Nearly every single version after the first draft in the 4E DMG 1 agreed on switching to the standard of "3 failed rolls = failure," but outside of that one major change I think this is typically one of the least-tweaked things in every version of SCs I could find.

The thing is that, every single version I found which modified this part had a good point to make. Sometimes it makes sense for a failed roll to result in a failure. Sometimes failure comes from a declining situation. Sometimes it comes from an opposing force. Sometimes there's just a time limit. And sometimes I even think it's fair to say, "basic success is guaranteed, but the SC determines how successful you are."

So to me, the answer is that you don't assume a default. Instead, part of designing a skill challenge is choosing the most appropriate option for this. I would call this the "source of pressure," and part of explaining the rules of Skill Challenges to new players is that you explain how pressure can manifest in a few different ways. And pretty much any form of pressure I can think of would benefit from being clearly telegraphed to the players anyway, so you can announce what the pressures are at the beginning of the challenge. And of course, the penalties inflicted by these sources of pressure can probably be logically inferred from what they are (e.g. "the dungeon is actively collapsing, so failure means getting crushed" vs. "the duke is also being advised by a villain, so failure means that the duke will be persuaded against you"). But by all means, return to the 4E DMG 2 for suggestions on this point (listed in Part 1).

And just as you should determine the appropriate source of pressure based on what makes sense for the scenario, you should "define success" in the SC. Do they have a checklist of problems to solve? Do they have one multi-part problem to all attack together? Do they just have to try for as much progress as they can towards a larger, ongoing goal? Sometimes they literally just have to move somewhere, and as long as they make it through without getting killed by the sources of pressure along the way, then that's success right there! One of my favorites is the "maze" rules from Graphite Prime, because the only source of pressure is just regular random encounters, and the way to "succeed" is to make a sufficient number of consecutive successful efforts. So you can attempt the maze, give up, return another day, and try it again as many times as you want, which is perfectly appropriate.

I actually quite like the 4E DMG 2's recommendations for "Progressive Challenges" and "Branching Challenges," as well as Obsidian's idea of "partial success" and Saga Edition's more interesting Challenge Effects. I don't think any of these options need be quite so formalized in the rules, but plunder away when designing SCs. And by that I mean, that's what I'll be doing when I make my library of pre-made SCs.

But of course, keeping in the spirit of what SCs are designed for, I would typically say that the best options for "defining success" are ones where you can find a way to squeeze multiple separate actions out of the party each round, for several rounds at least (whatever those actions may be).

And yes, I'm now complicating an element of SCs that was otherwise one of its simplest and most firm ingredients but instead saying, "there's a lot of possibilities, so you have to pick one on a case-by-case basis and explain it to your players." But I feel comfortable doing this because I've stripped out the little bits of crunch and complexity found elsewhere in the formula, so I think it evens out.

Okay, those were the core questions. Let's take a short detour into weirder trains of thought, more divergent than the base model SC.

How do you even determine successes at all?: "Hey, Dwiz, aren't you supposed to be one of them old school guys? Why we rolling so many dice?"

A fair question. It's something I thought about a lot.

That basic formula of "roll X successes before rolling Y failures" sounds solid to most gamers, yes. But that's because they take for granted that this structure is so reliant on your system of choice having some kind of die roll mechanic you can lean on... when we know that plenty of games actually don't. One that comes to mind is Ben Milton's Maze Rats, in which he renamed ability checks to "danger rolls." This is meant to emphasize his gaming philosophy that "rolling should only happen if you're doing something really risky" and that, ideally, a smart and skilled player will never roll their dice. To put it another way, "if you're rolling a die, you've already failed."

So in Maze Rats, the actual "default" way of resolving actions is to just describe what you do and have a solid idea. And I've always really enjoyed that. But, if you substituted the skill checks in the Skill Challenge with this method instead, then you'd get a couple funny results. Firstly, you'll discover that it breaks the original idea. The incremental actions need to have a risk of failing in order for the party to risk a total failure. How else would you know if the SC ends by some means other than success? But of course, we've already covered those alternatives.

A more interesting result: you'd accidentally reinvent the Free Kriegspiel method of "Three Reasons" as a means of task resolution. See, in lots of freeform, diceless FKR games, such as Chris Engle's Matrix games, the main recommended "mechanic" for resolving actions of uncertainty is for the player taking that action to provide three reasons why they believe it should be successful. And is that not the same thing as the player just saying, "here are the three things I'm doing that contribute to my success in this task"?

And honestly, I think that sometimes merely having a solid idea at all should count as a success. Imagine how unsatisfying it would be if a player was really creative and thought of a solution they could use, only to then fail the following skill roll they make.

On the other hand, maybe SCs being centered on skill checks is perfectly fine for games like 4E and 5E. I think there's an often-forgotten presumption that, if you're playing those games, then you must already enjoy having a skill system to begin with as opposed to a more old-school or FKR style of game that doesn't have them. And as long as you're playing a game that has them, then maybe you should be using gameplay structures like this that get the most out of them. As you'll see below, I wouldn't use this structure for my Knave hack... but I'm find using it with my 5E game because my players want to use their many proficiencies. Otherwise, what was the point of playing a system that required so much investment in the "build" of a PC? I am willing to validate that, as an alternative-but-not-inferior playstyle than the OSR style I also enjoy.

Are we gunna consider all those miscellaneous little rules throughout the last post?: "Hey Dwiz, aren't you the one who always says, 'the devil is in the details' and all that? Couldn't one of those small tweaks potentially be a game changer?"

Well, maybe. I did think about the things like "advantages" described in the D&D Essentials book or the Obsidian system's optional rules and so on.

I mean, I could judge each of these one by one if we wanted. I don't care for introducing "nat 20 criticals" on anything outside of attack rolls, designing the SC with a budget of "X moderate checks, X-2 easy checks, and X-3 hard checks," or really introducing any gambling mechanics. But there are two I'll address as pretty interesting:

From the D&D Essentials Rules Compendium: "However, after a character has used a particular skill to achieve a success against the moderate DC, later uses of that skill in the challenge by the same character should be against the hard DC." Meanwhile, from ICRPG: "after you fail a check, your next attempt at that check becomes Easy."

I think the first one kinda makes sense because, once you've already done that thing, how much more could you really get out of doing it again? And the second one makes sense because you've already "loosened the jar" and learned something from your initial failed attempt.

Then again, sometimes it makes sense not to allow another attempt after a failure. The question was not, "will you achieve success in the next 6 seconds?" but rather, "are you capable of achieving success at this task at all?" If it's that second question that we're really asking, and we find that the answer is, "no," then it'll stay "no" until something significant changes. But hey, I still think these two ideas are kinda solid in their rationale.

How do you actually make this "built for 5E D&D" in a meaningful way?: "Hey Dwiz, why do you always do an impression of the audience in your posts? Just let people comment on their own, man."

Shush. So here are some guidelines for how you design rules in a way that matches up with 5E's general design priorities:

1. Try to always use advantage/disadvantage rather than +/-X modifier or +/- DC.
2. Never ask the player to note the margin of success. In fact, rarely are there ever "degrees of success" like in a PbtA roll.
3. Do not add any steps requiring arithmetic beyond what's already there. That's already partially accounted for with the previous two points, but I mean it. Do not add a step where anyone has to mentally add or subtract. It goes d20 + modifier and that's it.
4. Cut the healing surge stuff. But don't shy from the skill system. Focus on proficiency as an indicator of what sorts of things make for good tests, even if you aren't going to limit things to proficiency like Matt Colville says to. Proficiency is a core ingredient defining 5E's particular brand of crunch.

In summation, the "Operatic Skill Challenge":

The DM confirms that the party is definitely about to enter into a situation that could be modeled as a Skill Challenge. If they have to... introduce a few extra complications that rule out alternatives then, hey, it's their table. They then announce that the party is about to enter a SC, then state the goal(s) and what variables are in play, which typically means communicating each obstacle to be solved (and thus, the number of successes needed) as well as any sources of pressure (e.g. countdown to doom, rival working against you, scheduled endpoint, unstable situation, etc.). Lastly, the DM gives the players an idea of the timescale of the SC, to set a standard for what amount of progress can be made per turn.

Then, each player takes turns declaring their action for the turn, which can be pretty much anything they can think of, just like in the rest of the game. They don't have to do it in any particular order, and can even coordinate their actions to be simultaneous. But the DM doesn't move on to the next turn until they've accounted for everything happening in the current turn, meaning that everyone gets a chance to do something. And of course, the players should prioritize explaining what they're doing rather than going straight for naming a mechanic they'd like to use. But by all means, negotiate with the DM to find a way you can apply a skill of yours. Sometimes the answer really is found on your character sheet.

The DM considers the results of each player action on a case-by-case basis, as this is the fundamental skill comprising their job anyway. But be prepared for lots of things to work automatically: the "cost" of most actions shouldn't be a risk of making things worse necessarily, but rather the opportunity cost of spending your turn taking that action and not knowing if it would have been smarter to spend it taking another (all the while, with some other variable keeping the pressure on).

When a check needs to be rolled, the DM should usually use the "Moderate DC" of the tier of play the PCs are currently in (is that even a thing in 5E? I think the answer is always "15"), and apply advantage or disadvantage per their judgment, taking into account situational factors that should have an effect on the outcome as well as possibly rewarding creativity from the players. PCs always have the option to use their action to Help an ally if they can describe to the DM a reasonable way in which they're providing aid, who may then grant advantage on whatever roll is being Helped.

To assist in running the SC, the DM will have a statblock in front of them with a few appropriate situational effects already included and some potential variables to throw in. For example, I can picture the "Basic Negotiation SC" statblock including a table of random "negotiation hurdles" to roll on/pick from 3-5 times, and could look something like this:

NPC isn't persuaded yet because...

1. They don't trust the PC(s)
2. They don't believe in themselves
3. They don't believe in the PC(s)
4. They are worried how they'll be perceived
5. They are worried about the price of failure/being wrong
6. They aren't convinced it affects them
7. They don't think they stand to gain enough from taking the PCs' side
8. They benefit from how things currently are
9. They are being pressured from another source
10. They believe falsehoods about the situation

Try to picture a similar table for each SC template, so that way not every single "jungle exploration SC" has the same 3 obstacles every time.

[EDIT: I decided to try making a full statblock so this post would have a little bit more nutritional value, so here's a sample "negotiation SC" statblock I've mocked up based on what I've described. The idea is that the DM could either pick out which options from this statblock are appropriate if the negotiation is one they've prepared, or they could roll/quickly decide on the spot if it was unplanned. Open to feedback. Formatting obviously subject to change based on what's optimal for whatever box it's being packaged in, since I doubt I'd ever publish something as just a raw Google Doc]

And that's it! I hope that's permissive enough while still helpful. Obviously, to complete the job I'd need to provide the library of SCs, but that's something I'll be writing as I prepare for my next 5E campaign. I'll upload all my DMing resources to the blog at that time. But as best as I can tell, this version retains the core virtues that make Skill Challenges worthwhile, but without...

1. Any dissociated mechanics forcing you to metagame in order to make basic decisions, or
2. Any rules that redistribute narrative control at the expense of the "sporting challenge" being tested, or
3. Any rules that limit the possibilities of what a SC could effectively simulate.

And I know that was an awful lot of hooplah to go through just to present a fairly simple variant of the rules, but the truth is that all this research was done ultimately in service to my Brave project. See, I've long had my eyes on Skill Challenges as something I might need to take a note from, despite how "anti-old school" they seem on the surface. And the reason for that has to do with the other kind of SC.

See, most of the examples we always use are things like negotiations and investigations and stealth. But something often left out in literature on the subject is that 4E D&D really emphasizes that you should try mixing this with combat. Imagine a boss fight where you also have to stop the magic summoning ritual or you also have to disable each piece of the big death trap or you also have to rescue each of the hostages. It's honestly a really good way to make any combat scenario much more interesting.

Meanwhile, I've long wanted to introduce a new procedure into Brave that also takes place on the "urgent" timescale like combat does (6-second turns), but which offers something else. I've tentatively called them "crises." These would be things like dealing with huge room traps, escaping a burning building, chase scenes, the trash compactor scene in Star Wars, and so on. Non-combat encounters that are nonetheless frantic and dangerous and complicated. I'm gunna be drawing on things like Runehammer's timer challenges, escape rooms, game show challenges like Legends of the Hidden Temple and Survivor, and other collaborative puzzle/task-solving stuff. I like when my games are tense and exciting and get your blood running but combat isn't always the solution. I don't actually love violence all that much, and it introduces a lot more complications than trying to, say, find a hidden treasure in a neighborhood that's about to be hit by a tornado.

And, naturally, I noticed that crises strongly resemble combat SCs. I'm glad I did all this work because I already have some ideas about how I'll be developing those rules. You have a lot to look forward to from me, even if this brings an end to this current phase of research.

-Dwiz