Ill Met in Ylraphon uses a lot of skill challenges (or a similar mechanic) in its text. I didn’t discuss them in the review, but the skill challenge is a form of mechanic that I dislike intensely, mainly because most people use it so badly!
For those unfamiliar with the mechanic, the basic way is to describe a challenge as a sequence of skill checks, where the players can explain how they attempt the challenge, roll an appropriate check, and the DM narrates the progressive outcome, with the players trying to achieve X successes before Y failures. (The 4E version was before 3 failures).
This runs into several problems. The main one that afflicts most skill challenges is that the mathematics is lousy. Making a sequence of ability checks is *hard* when the DCs are 15 or higher, and they’re typically set too high.
(This was very true in 4E).
Another problem that afflicts them is that the interim states are rarely that interesting. A good example of a challenge resolved with ability (skill) checks is the chases in the 5E DMG; they have interesting interim steps that allow players to adjust tactics and see the changing situation.
Unfortunately, many skill challenge don’t describe interim states. Instead, they are presented as a simple mathematical challenge: Can you make X successful checks before 3 failures. There is no sense of progressing – either towards success or failure – except for the result of the roll.
As a result, the DM has to do a LOT of work to make them interesting. Not all DMs are up to the challenge.
Occasionally, they can be seen as a tool for creativity. The player describes an action, you work out what skill applies, and they make the check. That is nice when it works.
To run a skill challenge well, I feel it needs to create a narrative. For the players to feel the rising pressure from each roll – but, not only that, to know that their decisions are making an impact. If you are just rolling dice, then you’re not making decisions.
Ask yourself why you are making each roll. What do you hope it achieves? As the DM, I want guidance beyond merely “I make an Intelligence (Nature) check”.
If there isn’t a reason, then there’s not much creativity. And, in a lot of skill challenges as-written, it was “guess the right skill to proceed.” That wasn’t that fun.
Interim states! Interim states! I want to see the effect of every roll and know that it has made a difference to the challenge. When the situation changes based on how the players are going so they have to change strategies!
And, with that, you really don’t have skill challenges as originally designed and used for the majority of the time they were active. A very few did that – Journey through the Silver Caves comes to mind – but most read as basic rolling.
There’s a chase in Ill Met that doesn’t use the 5E DMG rules for chases, but it doesn’t suck (as the skill checks are out of the way pretty quickly). The “find the agent” challenge? That doesn’t work so well.
So, do you want to try skill challenges? Put some thought into interim states, and the reasons you are making rolls.