As the maintainer of the (now massive) Skill Challenge feature, I read quite a lot about skill challenges, no matter if they’re positive, negative, or somewhere in between. I think SCs can mostly be broken down into three main camps:
- Overt skill challenges. These are the ones that are mostly “by the book.” Announce what skills are usable as primary and secondary, and what they do in the challenge. (i.e. “You can use Theivery to try and repair the raft and that’s worth a success, or Perception to aid that attempt.”) I had surprising success using this method at the D&D Game Day for Monster Manual 2, probably due to how the skill challenge was written. Additionally, the skill challenges that you find in books and online, ready to run, are like this.
- Covert skill challenges. There’s a goal at hand that skills are useful for, but they aren’t explained by the DM. You ask what each PC does, and a skill roll is decided (either by the DM or the PC) and the DM decides what that counts towards. Success and failures are tracked invisibly (if at all) and the PCs may not even realize they’re in a skill challenge.
- Bad skill challenges. Dice are rolled, successes and failures totalled, and nobody cares. These may be the result of poor design or poor DMing, and can exist as a hybrid with the previous two styles. If you’ve been in a skill challenge where it seemed like you were just rolling your highest applicable skill and the end result didn’t matter (or worse, lead the game crashing to a halt) then you’ve probably been in this kind.
Obviously, #3 is to be avoided. But the first two styles both have their advantages and disadvantages. I know there’s a lot of scoffing of style #1 amongst experienced roleplayers, but it has the advantages of being really easy for a new DM and for players who aren’t able to come up with a unique idea on the spot. Instead of being frustrating for those players, it can allow them to just say “I can definitely help the party by doing this” or even better “this is the option my character would do.” Additionally, as I said, you can just grab a skill challenge ready to go (or perhaps with some DC adjustments). Players- no matter their experience level- will find a way to do something unexpected, and so you’ll still have to do some thinking on your feet to run one, but it minimizes the situation and (if you pick a good one to start with) ensures that a strong framework exists.
#2 is the option for DMs that are more comfortable. This method is most like previous editions, with the added benefit of some extra tools available for determining DCs and how long the challenge should run. Clearly, there are plenty of DMs with this level that can ignore skill challenges entirely, especially if that’s what your group is used to. For DMs that want to utilize it, but don’t have issues with thinking on their feet or players that get easily stuck, this can be an easy way to go. You’ll also find that players try to incorporate things that aren’t skills into this (like using powers) when it’s more wide open. Mike Mearls method (say that five times fast) of determing skill challenges on the fly is a big plus for this. This is also a good way to go for having a skill challenge that occurs unexpectedly but makes sense as one: “wait, they decided to negotiate with Demogorgon instead of running away! I didn’t plan for this!”
Either way, the key, as usual, is to know your group and your own limitations. One method might clearly be the way to go for your games, but I recommend trying to borrow liberally. If you run skill challenges as written, be adaptable. If you run open skill challenges, try stealing some ideas from the written ones.
Just try and avoid running a bad one. If there’s one thing that’s easy to pick up from the skill challenges critiques, it’s what NOT to do.