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The Challenge of Skill Challenges


June 2008. Wizards of the Coast releases the fourth edition of Dungeons & Dragons. They must realize that there will be some backlash to differences between this and previous iterations of D&D, but it becomes more divisive than they could ever imagine. The hobby splinters. While many switch to fourth edition, others stick with the previous 3.5, move to Pathfinder, or even take up bullshit indie games. Lo, the Edition Wars begin.


Kudos to Wizards of the Coast for learning from many of their mistakes and course correcting in the development process of fifth edition. (In case you can’t tell, I’m a bit biased against fourth edition). They spent over two years in an open beta getting feedback from the community and rebuilding the brand. Fifth edition did an incredible job of combining aspects from all previous editions and leaving out what didn’t work.


A lot of concepts introduced in fourth edition didn’t make the cut. However, there’s no reason they can’t be added back into fifth edition games. One of these add-ons I see talked about using more and more online is the skill challenge. Some people really like using them in fifth edition. I… have my own thoughts.


Skill Challenges


The fourth edition Dungeon Master’s Guide defines skill challenges as… Wait. It doesn’t really give a good definition. “When characters make a series of skill checks in response to a series of changing conditions, with success or failure being uncertain, they’re in a skill challenge.” Maybe it’s just me, but that sentence is crazy. Here’s something a bit more clear, but again, speaking only to the mechanics. "To deal with a skill challenge, the player characters make skill checks to accumulate a number of successful skill uses before they rack up too many failures and end the encounter.”


Does that make sense yet? Here’s an example from the book that hopefully makes it a bit more clear: "The PCs seek a temple in dense jungle. Achieving six successes means they find their way. Accruing three failures before achieving the successes, however, indicates that they get themselves hopelessly lost in the wilderness.”



The dungeon master comes up with a list of skills that would be useful in achieving the PC’s current goal (such as Survival, Nature, and History for the above example), but also allows for the players to come up with additional ideas. They tell the DM what they want to do, and roll skill checks until reaching the predetermined number of successes or failures.


In other words, the skill challenge rules were an attempt to make a game framework to be used in situations that would’ve been overcome in earlier editions more simply and organically. As with a lot of fourth edition innovations, I usually found this too abstracted and was taken out of the game. The book recommends needing up to twelve successes for especially complex encounters. It’s hard for me to imagine organically rolling over a dozen skill checks for a single encounter.


Any time I’ve tried to introduce skill challenges into fifth edition, it’s been met with a good deal of confusion. D&D is essentially divided into two modes of play: combat and everything else. This adds a third mode that seems indistinguishable from “everything else,” but all of a sudden has different, more arbitrary rules. Unless you commit to using skill challenges very frequently, it can make players freeze up.


This can be mitigated somewhat by, as the Dungeon Master’s Guide suggests, telling the players your list of useful skills. I hate this and take it as a sign that the system isn’t easily understood. Outside of the first couple sessions, the players shouldn’t need prompting from the DM like this.

Unsurprisingly, the skill challenge rules also pressure players to only use skills. I think this was the designers's intent, but part of the fun of D&D is never limited yourself to the obvious options. A paragraph in the Dungeon Master’s Guide does mention using other features and spells to count towards success, but I’ve seen even good DMs get blinded to only using skills. And if you’re not predominantly using skills to solve a skill challenge, what’s the point in using these rules?


So What Is This Good For?


I’m not saying that simple is always better. Here’s a terrible house rule for your D&D games: Give everyone a skill called “Fight.” We want classes to be balanced, so let’s set it equal to the level of the character. When the players encounter a monster, roll a d20+”Fight” and consult a table to see if they win or lose the fight. I’ve just balanced and streamlined D&D. 


That would be pretty lame, and yet it is what often happens outside of combat. Roll a single check to determine how things go. And this is why I assume people cling to skill challenges as an alternative. Yet I think it’s possible to have a multi-part noncombat encounter without adhering to the strict and arbitrary skill challenge rules. 


I suggest writing a scenario with multiple related obstacles that each have their own consequences. Then, introduce these obstacles just as you would any other obstacles! No need to stop the game and announce that it is skill challenge time. Instead of declaring that each obstacle requires X number of successes, just do what you do the rest of the time as a DM: listen to what the players want to do and then tell them the results.


For example, in the adventure I posted on Friday, the dungeon begins to collapse when the efreeti whose magic holds it together dies. This could easily be set up into three related obstacles: getting out of the dungeon before it collapses, finding a way down from the mountain after the bridge has collapsed, and making it through enemy territory without being caught. Depending on the actions of the players, consequences could include taking increasingly high damage from falling rubble, getting buried or stranded, taking some fall damage, and getting caught or killed by guards. Or, if they have a way for granting flight to all characters, maybe they just fly away. If it makes sense, allow it and move on.


That’s a lot of words to say that skill challenges have their “heart” in the right place, but make the rules too complicated and arbitrary. However, I’m sure some groups, especially ones that enjoyed fourth edition (you crazies) may like skill challenges. If it works for you, more power to you. I don’t recommend it to everyone, but I do recommend you think about scenarios that use a series of obstacles instead of just one.


P.S. If you’re not familiar with Matt Colville, he has a great YouTube series on running D&D and has a whole pro-skill challenge episode! I suggest you check it out as a rebuttal to my ramblings, as well as the rest of his videos. https://www.youtube.com/watch?v=GvOeqDpkBm8

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