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In the DMG, it describes group skill checks as electing a lead character and the other characters aiding him. Would it work like this in a conversation (skill challenge)?.

  1. Lay out the primary and  secondary skills needed.
  2. Roll for initiative.
  3. Roll for a skill check for "Ben" (primary or secondary); the group aids the result.

This is a group skill check.

Sam rolls his skill check since he's second in initiative order. Could the group help him also, or does it just need to be the lead character — for this example, Ben?.

Also can the group aid the lead character next turn if the challenge isn't finished, so they can help the lead character more than once in a skill challenge?

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should mention that in the case of a conversation, it's probably better to let things flow organically rather than use intiative (only use intiative in combat, or in situations where character order/total involvement is an issue) –  wax eagle Dec 6 '12 at 16:24
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@waxeagle: I've found that in most skill challenges it helps with engagement to go around the table and include each player, requiring them to take some action in the challenge. I don't have them roll initiative, but requiring action prevents having the more diplomatic characters left bored during an environmental challenge and vice versa. tldr; I find that total involvement is always an issue. –  Gregory Avery-Weir Dec 6 '12 at 17:05
    
So can a group skill check Aid anyone or just the lead character? –  Luke Burgin Dec 6 '12 at 17:10
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up vote 2 down vote accepted

I say make an executive decision on this matter based on what makes sense.

If this were my game I'd say:

  1. make the players decide the order that they want to do the actions in. Ex. First tie up the villan (rope use) then intimidate her into revealing information.

  2. Let the character with the highest skill check be the lead (if and only if they don't insist doing something else at the same time) if Sam has the best rope use but says that he wants to search the room for treasure, don't let him be involved in the roll at all.

  3. I'd say the roll can be retried unless there is some kind of time crunch or negative result for failing. Ex. Villan is under a sleep spell for another 4 rounds and can't fight back, so I would let them make 4 rounds worth of checks (or until succeeding), at the point the spell wears off they'd have to contend with the awake villan and may not be able to try again. However for something like an intimidation roll if the group fails the first time then it is likely that the villan is just thoroughly unimpressed and rerolling isn't going to change that, unless they role play or come up with a creative solution. Ex. They discover that the villan is deathly afraid of snakes and they can somehow come up with a snake to use during the second attempt at intimidation.

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