One of the things heavily pushed in 4th edition Dungeons & Dragons was the idea of skill challenges. Even something like navigating a town and finding the bad guy turned into a skill challenge. When 5th edition was released, quite a few of the people I knew playing 4th edition switched over. When they did, however, a few of them took the idea of skill challenges with them. Due to this exposure, and coming across one recently when looking for free stuff to review on the Dungeon Masters Guild, I decided to talk about it a little bit. In particular I'll try to focus on what I felt worked, what elements are useful and what I felt didn't work.
What Is a Skill Challenge?
Put simply, a skill challenge was a method of determining if the players succeeded in a task by using multiple checks to achieve successes or failures. If enough failures were achieved, the players failed and if enough successes were achieved, they would succeed. They'd often allow different skills to be used and were heavily used in 4th edition Dungeons & Dragons adventures.
My issue with them in 4th edition was that I felt they were often overused. We get to a similar place as a result of regular play without the idea of a skill challenge. If a player wants to climb a wall and then try to jump from on top of the wall to grab a ledge, it can be easily handled by 2 different checks. Depending on which fails, the results could be different (misses the jump and landing back on the top of the wall, falling, or failing to climb at all). All of this is done without the introduction of a new mechanic.
One particular area that I liked skill challenges was for combat encounters. Having a short skill challenge (3 successes before 3 failures is about the longest I would try) where a player can use their skills to get a significant benefit often worked very well. Often it would force the rest of the party to protect the wizard while they tried to weaken a seal to let them advance, to prevent the summoning of an enemy later (such as a trap activation as they get closer to their objective), or breaking the magical and non-magical layers of protection of a sarcophagus. This forces another choice on the players: do we use our actions to try and do these checks or do we fight? If you have an Eldritch Knight with the arcana skill, does he keep the enemies off the wizard's back and let him concentrate, or do they both try to work on the portal to seal it, leaving the cleric and rogue to protect them? If something is complicated, it makes sense that it might take longer than one round to do.
Be Careful with Dispel Magic
What I've sometimes seen is a skill challenge like thing for something that dispel magic could do anyway. In these cases, I typically found a few different solutions. First, having a way to solve a problem without burning spell slots is not a bad thing so I don't mind it (at earlier levels they might not even have the spell or already used the slots). In others, such as trying to close a portal ripped into existence by a powerful being, you might decide that a skill challenge like thing on top of the slot is called for (you might want to provide a bonus based on the spell slot used though so it doesn't feel like they wasted a 9th level slot). There may also be some magic or some problem (old tomb defense, for example) that can't be so easily dispelled. Maybe it's not arcane but innate to the area, or after being dispelled it quickly reforms because the cause is not destroyed (the magic trap is just temporarily deactivated).
Let's Be More General
The thing about skill challenges is that they are really just a sequence of skill checks. I've always felt that treating them as such is far more effective and versatile. Instead of “failing” after 3 unsuccessful skill checks, you give 1d10 necrotic damage each time they fail. When they successfully make 3 skill checks, they succeed. Additionally, failing or succeeding any check that is part of a skill check can lead to other outcomes. Maybe because of how well the wizard was doing, the next check is made easier. Maybe since they failed, 1d4 skeletons come back to life and attack the party (they all drop dead after 3 checks, failures or not).
This more general version comes down to this: it takes multiple skill checks to succeed at something. Failing/succeeding a certain number of times might have a bad outcome, and so failing/succeeding one time might have a bad/good outcome. When I think about it, it makes sense that some things take more than one skill and/or more than one success to accomplish. Thinking about what makes sense in context will lead to skill checks that feel much more natural. It's just sometimes they might resemble what was called a skill challenge in 4th edition. However, there is far more you can play around with that wasn't included in the description of a skill challenge. I don't think we should miss out on those situations just because our tool didn't consider them.