As I said, they just went around the table rolling. It really didn't seem to add much, though I described as best I could the effects of each roll and how it added up to creating the kind of obstacle they wanted... or how a failed roll detracted slightly from what they were looking for.
How would you have run this skill challenge? I'm trying to get an idea for how to run them properly. I love the idea of skill challenges, but I guess I just don't "get" them.
Thanks in advance!
My first skill challenge experience (DDXP), as a player, was somewhat similar. Then I had a different DM and the difference was night to day. Since then I've run probably over 80 skill challenges and my player experience with that second DM is what I've tried to emulate.
First, give the players a clear understanding of the goal. What are they trying to achieve with this Skill Challenge? If the goal is to find a path through the jungle and survive the horrible environment, describe it in detail. If they don't understand what they are trying to achieve they will be confused. Optionally you can tell them which skills are primary, though that adds a level of metagame that steals away the immersion.
You can have them go around the table or roll initiative. In the above example the find a path goal would probably be attempted by some only, but the survive the weather extremes needs to be attempted by all (maybe a once a day roll or once an hour of travel roll.) Also describe in detail.
When a player is going to roll, don't just have them roll. Let them tell you what they are going to attempt. That gives you a chance to determine if there are any bonuses or penalties. It also allows others to hear what is going on and attempt to assist.
DM: Okay, you guys find yourselves in a triple canopy jungle. The heat and humidity is overwhelming. You are sure that this heat will affect you unfavorably as you travel. Your quarry has escaped and you will have to find a way back to the coast on your own. Okay player 1, what would you like to do?
Player 1: I'm going to roll Perception.
DM: Describe to me what your character wants to do. How is he going to use perception and for what?
Player 1: Well, I'm going to climb up a tree to see if I see a path.
Player 2: Oh, I'd like to assist him in getting up the tree.
DM: Okay, Player 2 how do you plan to assist.
Player 2: I'll throw a rope over one of the high branches and use it to haul him up.
DM: Okay, Player 2 roll an Athletics roll to get the rope there.
Player 2: My athletics is +0 but my Acrobatics is +5 can I try it with that?
DM: Well, I can see how you could use your agility instead of your strength to get the rope there. However it is a ways off so make the roll with a -2.
Player 2: I rolled a 17 with the -2 a 15.
DM: Very well, you send the rope skirting through the air easily avoiding other branches. Player 1 with the assistance of Player 2 you are able to get to a much higher vantage point so Add +2 to your Perception Check.
Player 1: Okay, I'm also going to use that spyglass that we found in the hut.
DM: Okay add and additional +2.
Player 1: I rolled a 12, with the +4 I get a 16.
DM: You see the beginnings of a path that leads to the north. That is one success.
Player 1: I'll let the group know where the path is.
DM: Player 3, what do you want to do?
Player 3: I'd like to use Nature to follow the path?
DM: Very well, describe what you'd like to do.
Player 3: I'd like to get one of those machetes we found in the hut and use it to clear the path for everyone to follow.
DM: Roll your Nature or Perception to follow the path. Since you are clearing some of it with the machete add a +1 to your roll.
Player 3: I rolled a 14, with the +1 that's a 15.
DM: You clear a bit of the path and notice that it veers to the north but quickly changes to the west. There are some tracks on the path but you can not identify them. That is one success. Player 4 what would you like to do?
Player 4: Can I use perception to know what the tracks are?
DM: Nature or dungeoneering, or even Arcana with a -2 penalty might give you a better understanding of the tracks.
Player 4: Okay, I'd like to check the tracks with Arcana. I rolled a 19.
DM: With the -2 that is not enough to identify the tracks, but this is neither a success nor failure because it does not directly impact the goal of getting to the coast. Player 5, what about you?
Player 5: I'd like to identify the tracks. I do have Dungeoneering.
DM: Very well make your roll.
Player 5: Ha, hah. Nat 20. That's a 27.
DM: Okay, you identify the tracks as those of a Rage Drake. You also know that it seems like it was heavily burdened. However, the tracks are old, maybe more than a week. There are no other tracks here so you think your quarry did not follow this path. Okay, player 6 what would you like to do?
Player 6: I'd like to use Insight to determine which path our quarry might have most likely have followed.
DM: Okay, that task will be difficult, but it is an inventive way of determining that. Go ahead and roll Insight. If you are able to give me one or two facts that you remember about the quarry you might get a bonus.
Player 6: I rolled a 17. I remember that he mentioned having family in Karbundum. He was also of Olinian descent and he was very knowledgeable of this jungle as he got us here without a hitch.
DM: Okay, that counts as a success. With that roll and your information you are able to determine that....
So you see the Skill Challenge actually work best when you let the players be a big part of the free-form. Sometimes you are just going to have to "force" them to describe what they want to do instead of just letting them roll.