I’ve always felt that skill challenges were one of D&D 4th Edition’s most egregious failings, in large part because I was so excited for them. At Encounter-a-Day, I’ve tried to come up with ways to fix them by completely altering the framework of skill challenges.
The more I think about it, though, the more I become sure that the idea of a skill challenge is fundamentally broken, and needs to be put to pasture. The inspiration is absolutely wonderful, but the idea that you can make a single framework, no matter how flexible, apply to any situation is misguided at best.
Even worse, the mere existence of such a framework encourages you to try and shoehorn things into it.
That’s why I think the idea of a skill challenge should be struck from the gamers’ lexicon. But retain the inspiration, the idea that skills matter. Actively look for places to add skill checks into the game, particularly during combat. Mike Shea’s Circle of Protection encounter is a wonderful example of making skills matter.
My problem here is that if I were designing the same thing, I probably would have tried to make it a skill challenge, when it clearly doesn’t need to be. I’d try to fit the situation into the framework, rather than trying to design a new framework to fit the situation. There absolutely are times when the skill challenge framework is appropriate, but I think having that framework in your mind ahead of time is counterproductive.
So really what my advice boils down to is this: look for opportunities to test the characters’ skills, and design a framework that suits the situation from the ground up.