I really like running Skill Challenges. I like how dynamic and different they are from normal combat encounters. I love how they represent a story complication rather than Yet Another Battle. I love how much role-playing goes on during one, and how players come up with new and creative ways to use their skills ("I'm going to use my Thievery to try and 'steal his heart.' Kay?"). They get players invested. They get players thinking. Most importantly, they're fun.
They also a ton of fun to write. Trying to think about how a particular skill may relate, especially skills that are peripheral to the challenge, is an interesting mental exercise for me. For instance, in Social Encounters, I've come to reorganize Intimidate in my head. It isn't just about scaring people; I mean, it's really good at scaring people, but that's not the whole of it. Where diplomacy is about the art of persuasion and bluff is the art of conversational jujitsu, Intimidate is about force of personality. From now on, Intimidate is the skill I go to for performance, for stealing a crowd, for being a force of nature that people just cannot ignore. I expect that, as I delve deeper into the system, I'll begin to do likewise with other skills as well.
Part of the problem in dealing with a skill challenge, though, is coming up with new and interesting penalties for skill checks. DMG2 gives us some ideas for penalties on a failed skill check, but they're pretty narrow, really. Coming up with a penalty for failing the whole challenge is actually pretty easy ("That thing you wanted, you don't get it."). Making each skill check hold different weight in the challenge is pretty important. It makes failure carry a consequence beyond being one step closer to failing the encounter.
I've been trying to come up with a list of penalties for failure that I can throw into a challenge as I'm writing them. Below, you'll find what I have so far.
From the DMG2
The first set of penalties I want to look at are the ones covered in the published material already. The second Dungeon Master's Guide goes into pretty deep detail on skill challenges and how they can fuck with your players, which is nice. On page 87, they talk about "stages of failure," which is something that I think should be in every skill challenge forever. They suggest the following as ways to penalize players during a skill challenge:
Lose a Healing Surge: This is pretty intense. This is what made me fall in love with Skill Challenges during D&D Encounters. I mean, I'd used them, but I didn't make them nearly as important as I have in recent adventures. The basic idea is that, if a character fails the skill check he or she is attempting, he or she takes damage. That damage is healed with a Healing Surge, so we're just going to do damage directly to the Healing Surges.
Spend Time or Money: So you failed at a thing you were trying to do. You went down the wrong path, talked to the wrong bookie, took an hour examining runes that had nothing to do with what you thought they did, or just hit up the wrong sheriff for information. Now you're going to need to backtrack, maybe grease some palms, and get back on track.
You Broke the Skill: For the rest of the encounter, no one can try to use that skill. You broke the last beaker in the lab, used the last of the gauze, none of the drug dealers will talk to your crew anymore because they think you're a bunch of snitches, whatever.
Take a Status Ailment: This is usually for in-combat skill challenges; you're dazed or immobilized or stunned or helpless or blinded or something. You fucked up, and the thing you fucked up fucked you up even more.
Take a Penalty: You screwed up, and the fact that you screwed up makes the next attempt at the skill even harder. You pissed off the mayor and now you're going to have to convince him to like you again, you sprained your ankle on that last somersault, you pulled a muscle in your arm and still have to lift this thing, your attempt at stitching your buddy up made him bleed more, etc.
My Own Additions
Now, these are pretty solid, but I like a little more variety in the ways I fuck with my players. So I'm going add to this list the following:
Extra Failure: When you fail at this skill check, it counts as two failures against the skill challenge. This effectively cuts the number of possible failures in half, assuming they try (and fail) this skill multiple times. I usually use this on a "limit 1 success" secondary skill, but it's still scary when you lose an extra failure.
Time-Delayed Failure: Failing doesn't actually count against the skill challenge, but the next time you fail a skill check, you accrue an extra failure. If you don't fail again, there's no downside. If you do, it becomes extra-devastating. Again, I usually put this one on secondary skills that normally don't count against the skill challenge when you fail.
Everyone Takes a Pentalty: Rather than just fuck things up for yourself, your failure at this skill check fucks with everyone. Nothing makes people hate you faster. ^_^ This one I usually reserve for primary skills that you can succeed on a few times, with a pretty low DC. It gets frustrating if it's used too much, but it's fun to watch players squirm when they give all of their friends a -2 on their next skill check.
Defense Penalty: For the rest of the day, you take a -1 challenge penalty to your AC, Fortitude, Reflex and/or Will. Failing this skill weakens you, slows your reactions down, frustrates you, and makes you more vulnerable to attack. This lasts until your next Extended Rest.
Speed Penalty: Until the end of the day, you take a -1 challenge penalty to your speed. You have honey on your shoes. You're moping. You're lost in thought or caught in a crisis of faith, and you're just not moving as quickly as you normally do.
Initiative Penalty: As above, except that instead of hindering your mobility, you're just not reacting as quickly to danger as you usually do.
Lose a Daily Power: Daily powers are massive feats of awesome. Sometimes, when you screw something up, it shakes you to your core. Your awesome isn't there, you just can't call on it to get the job done. If you fail this skill check, lose one of your daily powers as though you've used it (and hit with it, in the case of Reliable daily powers).
Lose an Action Point: Like most of the resource-deprivation penalties I've listed here (and that's pretty much the theme of these penalties; you're losing access to a thing you're usually able to rely on), this one steals something from you for failing. In this case, it's an Action Point. If you do not have any Action Points to steal, it will take a Healing Surge instead. I feel like this one should almost always be attached to Arcana for some reason.
Attack Penalty: For the remainder of the day, you take a -1 penalty to hit. This is devastating, people. Don't over-use it. Probably related most often to Acrobatics or Athletics. You've hurt yourself trying to do that cool parkour thing you saw that guy do the other day, and you just aren't as good at hitting people as you could be.
Grant Combat Advantage: For the rest of the day, you grant combat advantage. To everyone. I have a feeling that this one should be attached to Stealth and Streetwise. You've failed to be sneaky, and now the sneaky people are taking advantage of that for the rest of the day.