DM Tips: Organic Skill Challenges

There comes a time in all good roleplaying games where we must take a step back from combat and accomplish something that does not require swinging a sword or firing a crossbow. There is always a cliff face that needs climbing or an outraged paladin that needs to be talked down. In Dungeons and Dragons 4th Edition, you can complete such tasks with a Skill Challenge. But, a lot of people find that the Skill Challenge itself is a mechanic that needs not exist. They say it "kills roleplaying".

There has been much debate on the subject and many attempts at "fixing" the problem. There are those that say you should announce when a Skill Challenge presents itself. There are those that say you should abolish the whole idea and just make a skill check when appropriate. I, for one, use a third, more organic, option.
Before I elaborate, we will need a quick review of the Skill Challenge. The Skill Challenge is not meant to replace how skills function in Dungeons and Dragons, nor does it count as a full encounter. The Skill Challenge mechanic is there to help clarify exactly how much experience points you have earned for your efforts, based on difficulty and complexity.

As a Dungeon Master, it is your job to create and drive the narrative. It will definitely destroy the immersive nature of the game if you suddenly declare "SKEERR CHARRENGE STARTU!!" (That's Skill Challenge Start for those of you that can't read Engrish), however that does not mean it cannot take place.

When the moment comes for a Skill Challenge to take place, let it occur naturally, and without the player's knowledge. For example, Player A says he wants to talk to the King about getting gold to fund their quest:

"Your majesty, in order to remove the Goblin Armies from the land, we will need funds to fuel our quest."

The DM then calls for a Diplomacy check. The check succeeds, but the DM needs at least 4 successes from the player before declaring the situation solved.

"I am listening, but why is it that I should offer coin from my own coffers for a quest that will take place far from my own lands?"

Player B interjects, asking for any Historical information on the subject of the Goblins. Making the check, which does not count towards the final four, he is able to make his own Diplomacy check with a +2 bonus.

"Over the years, the Goblin Armies have been moving steadily Westward. This will bring them straight at your kingdom in less than a year should we not do something."

The Diplomacy check succeeds, creating their second success. The DM responds in kind.
"That is most unsettling. But how can I be convinced that you will not simply run off with my gold and do nothing to solve this problem?"
Player three attempts his own check using Diplomacy.

"We are noble in spirit and true of heart, your highness."

The check fails. The DM marks it on his notes and then they retcon what was said.

".......because?"

"Because? You will have to do better than that before I freely give my coin to you lot."

And so it goes until they reach a minimum total of 4 successes before 3 failures.

"Eh, why not? You'd just try to steal all the gold anyways."

As the example dictates, the conversational Skill Challenge can flow organically. Of course, to make it a little more organic, the player can wait to speak until AFTER the roll has been made to determine exactly what to say.

How about an example of a longer Skill Challenge:

The PCs are attempting to cross a vast volcanic wasteland to get to a mystical land on the other side. We have our starting point and our goal. As the DM, create several pathways through the wasteland with two endings. Other than the main goal, the second ending should be what happens when they fail. Because of the severe nature of a longer Skill Challenge, the punishment for losing should be big. In this scenario, I suggest that it takes them to a location within the wasteland that will take the remainder of the game session, if not the next one as well, to complete. You should also plan out what rolls lead them where. The more failures they have, the more lost they become. The more successes, the more everything looks like they are on the right track.

Fill the Challenge with multiple types of checks. Call for Athletics to climb a steep cliff wall. Have them roll Nature to find a passable trail. Maybe they could use their Dungeoneering to find safe cave mushrooms to eat. If it would help you, create a grid based map of the area to show where they are in their Challenge, each grid representing a different challenge.

You could also go old school with a hex grid!

If you keep the Skill Challenge organic, moving it in a logical direction, not only can your players possibly manage to gain more experience than with a fully written out Challenge, but it will feel more natural for your players. A more natural feeling game, the more enjoyment you will find in the roleplaying.