Skill challenges are a strange beast. Either they are really fun or they are a painful, awkward experience. When I first started running skill challenges, I attributed this to bad writing or poor gamemastering. I no longer think this is the case. The skill challenge system is just clunky. The underlying principle is sound. Reward players for non-combat related encounters. But the mechanics get in the way of the gameplay.

Consider 4th edition combat. Pull that one piece out of the game. Stuff it in a box, shrinkwrap it and put it on  the shelf at the local gaming store. That’s essentially the D&D miniatures skirmish game, albeit with much more complex rules. As a board game, the combat system holds up very well on its own. I would purchase that game.

Unfortunately, the skill challenge system does not stand up on its own very well. Imagine extracting it from the rules and trying to produce a game out of it. It would not be something I would be interested in playing.

I realize you cannot make a direct comparison between the skill challenge and combat systems. They are very different animals. The skill challenge system is more like a mini-game than a full fledged game. If these imaginary products were created, the combat game would be comparable to a board game like Descent and skill challenges would be more akin to a card game like Slamwich. You can hold them to the same standards of fun though. Is this a fun game in its own right? In the case of skill challenges, the answer is no.

My problems with skill challenges are several. The goal of the skill challenge makes little sense. You must achieve X number of successes before 3 failures. In life, we often learn as much from our missteps as our triumphs. The number of failures is pretty low if you consider the winning condition in most published adventures is usually all or nothing. If the challenge has a scale of outcomes, it makes a little more sense.

The actual gameplay of the skill challenge is repetative. The players with the highest bonus always performs the same skill checks. This is how people interact in the real world. I am not trained in dentistry. Whenever I have a dental problem, I always let my dentist do the heal check. So why wouldn’t the wizard with a +12 bonus perform all the arcana checks? A strong team of players might even collude to spread out their skill bonuses insuring they will almost never fail a skill challenge. They tried to address this somewhat with the updates in Dungeon Master’s Guide 2 with group and secondary checks, but I’m still not happy with it.

I most often hear people talk about enjoying a skill challenge when they didn’t even realize they were in a skill challenge. Dungeon Master’s Guide 2 attempts to codify this invisible skill challenge. My theory is that a skill check takes you out of the game for a moment. Since skill challenges basically consist of five minutes of furiously rolling skill checks, your players are repeatedly being cognitively removed from the fantasy. I think that is the source of the problem. You should demand skill checks from your players sparingly. If they perform a difficult action or it increases the drama, have them roll.

I admire the designers and the concept of skill challenges is sound. I think the goal was to boil down roleplaying elements to a one page statblock that a gamemaster could easily digest and didn’t require hours of preparation. Mission accomplished, but it’s a really difficult task to shoehorn that concept into a set of rules that are fun to play.

Here’s the method I use to run my skill challenges. First off, keep a notecard with your players skill bonuses in an easy to read format. If you have been gaming with your players for awhile, you probably won’t even need notes as you already know what their strengths are. Next, read the skill challenge in its entirety. The text is like a freeze-dried narrative. Add a little water and expand it in your head into a story.

Now, you’re ready to run the skill challenge. Glance at the skill challenge to refresh your memory while running it, but do not feel slavishly attached to the skills required as written. Describe the scenario to your players and let them tell you what they want to do. Try to keep rolls to a minimum. For example, your wizard sees a portal and says he would like to do an arcana check. Glancing at your skill bonus notecard, you see the wizard would easily succeed the check. Don’t bother with the roll. Kindly ask them what they would like to know about the portal and mark it down as a success. If a roll has a dramatic effect, definitely ask for the check. An easy example is disarming a trap. It’s much more dramatic to roll that thievery check to disarm a trap as everyone expectantly watches the d20 wobble across the table. Life or death may hinge on that roll.

When you have a difficult check that requires a roll and the player is unsuccessful, you may not want to automatically mark that as a failure depending on the circumstances. Let’s say the aforementioned thief accidentally sets off the trap. Giant spikes shoot from the ceiling and clang against the floor in the next room. After a moment, they slowly recede back into holes in the ceiling. While the thief did fail to disarm the trap, he has gained new knowledge of the way the trap works. Perhaps there is a gap in the spikes in a certain place that would allow the party to cross the room without even having to disarm the trap. Let these details flow naturally from the players’ actions or think them out before hand. Like the players, you may too realize you like skill challenges best when you don’t even realize you’re in one.