The 4E skill challenge rules were an okay framework, but they had some major flaws and depended heavily on the DM to flesh them out and make them interesting--if you ran them "by the book," the way you'd run combat, they were awful. I would do 5E skill challenges something like this (playtesting required to fine-tune the numbers):
SKILL CHALLENGES
In some situations, the PCs may need to resolve a complex situation by the use of ability or skill checks. You can run this situation as a
skill challenge.
During the skill challenge, the PCs need to earn some number of successes; if they don't reach the required number before the challenge is over, they fail. A skill challenge consists of a series of
passes, with each PC getting one opportunity to act during a pass*. The length of a pass varies, from as little as 1 round to as much as 1 day or even longer.
Each PC declares what he or she is doing during a pass. You then decide which of the following best describes each PC's action:
- Direct Contribution. The PC's action directly contributes to success in the challenge. The PC makes an ability or skill check of your choice. If he or she succeeds, the party gains 1 success.
- Risky Contribution. The PC's action is a gamble. It could help a lot, but it could also make things worse. The PC makes an ability or skill check of your choice. If he or she succeeds, the party gains 2 successes; if he or she fails, the party loses 1 success, to a minimum of 0.
- Support. The PC's action does not directly contribute, but helps another to succeed. The PC makes an ability or skill check of your choice. If he or she succeeds, one other PC gets advantage on one roll during this pass.
- Auto Success. The PC's chosen action takes advantage of some special opportunity. The party gains 1 or more successes with no roll required.
- Information. The PC is trying to gather information. The PC makes an ability or skill check of your choice. If he or she succeeds, the PC learns about an opportunity to gain an auto success.
- Unhelpful. The PC's action does not advance the party's goals in any way. Nothing happens.
- Sabotage. The PC's action actively makes things worse. The party loses 1 or more successes, to a minimum of 0.
PCs don't get to choose which skills they're using, though their chosen actions may suggest a skill. You may also call for some other type of roll if you feel it appropriate. The DC should be 10 for an action that is obviously relevant to the challenge, or 15 for an action which seems like a stretch or is unusually difficult. For example, during a tense negotiation with a hostile warlord, making a persuasive argument is obviously relevant and would be DC 10. Doing juggling tricks to put the warlord at ease
could work, but it's a bit of a stretch and should be DC 15.
If a PC tries to keep doing the same thing over and over, you may want to increase the DC or rule it Unhelpful after the first time. That isn't to say a PC can't keep using the same skill. Again using negotiation as an example, if the PC comes up with a series of persuasive arguments, you can grant a Persuasion check at DC 10 for each of them. But if the PC just keeps repeating
the same argument over and over, the second Persuasion check should be DC 15 and the third should be Unhelpful.
The number of passes depends on how much narrative weight you want to give the skill challenge. If you want to resolve things quickly and move on, 1 or 2 passes is appropriate. For something more dramatic, you can call for 3 or 4 passes. Suggested requirements for successes, assuming a party of 4:
- 1 pass: 3 successes required
- 2 passes: 5 successes required
- 3 passes: 8 successes required
- 4 passes: 10 successes required
You can reduce the required number of successes to make the challenge easier, or increase it to make it harder. You can also allow for partial victories or "stretch goals"--perhaps 8 successes will persuade the warlord not to attack, while 10 successes turns her into an ally.
[SIZE=-2]*Instead of having "X successes before Y failures," we have "X successes in Y passes" so that PCs without useful skills are not penalized for trying to contribute. For ploys that could backfire, use Risky Contribution.[/SIZE]