Let’s talk skill challenges. I used to be a fan. For the short time I ran 4e, I loved them. I don’t anymore. It’s not so much the structured approach to resolving conflict. It’s not the way they tie in with the game’s story/event based elements. It’s the shitty DMs.
Some background: skill challenges are based on the concept of a leveled skill system. 2e introduced proficiencies. They were based solely on stats (with a constant modified depending on how difficult the skill is to learn/employ). 3e went from proficiencies to skills and gave points to spend on improving them (awarded every level). 4e replaced points with a flat level-based modifier and a flat bonus for being “skilled” or “trained”. 5e… well, I’m not really sure. I think it’s the same as 4e? Whatever, doesn’t matter, because we’re talking about skill challenges.
4e gave us the concept of a skill challenge which is a structured approach to resolving a conflict through the use of skills (as opposed to hitting it with your axe). But all of this is dependent on the concept of a skill roll (and, to a lesser degree, training in a skill) as a necessary means to achieve a win-condition in the game. No skill system, no need for skill challenge rules.
But this is where I have a real problem: in a skill challenge, the DM defines the win. Which is the opposite of how the game should work. When the DM defines the win, the game needs to play out according to that requirement. Players don’t want to scale the wall or talk to the guards? Fuck you, you can’t get into the castle. Only two can get over the wall? Sorry, you needed to get everyone over. You suck, no reward for you, start over.
And I know the despondent opposition will proclaim: “That’s not how it works! If the players think of something clever, the DM just assigns a skill, a difficulty and a result, and adds the success/failure to the running total.” Well fuck you, voices from the internet æther, because you’re looking at it from the wrong angle. The problem isn’t whether or not the DM is capable of responding to something unexpected. It’s the fact that the DM defined the win for the players.
Players define the win. When swords are drawn and initiative is rolled, what’s the win-condition? It’s whatever the players want it to be. The monster might fight to the death; it might run away; it might be willing to parlay; it might take some food and wander off. But in no case should the situation be dictated by the DM such that only a few outcomes can count as a win. The players decide how to engage a monster and how to go about getting what they want. And the rules are designed to encourage certain behaviors, such that, more often than not, a win occurs when the players kill the monster and take its treasure (and earn XP). Want to encourage different behaviors for a different kind of game? Create a reward structure that supports your concept. But don’t define the win for the players.
Just… just stop. Let the players decide what their goals are. Let them choose what a win looks like and let them decide how to go about getting it. You, as the DM, need to worry about defining the rules that govern your world. “Skill challenge” resolution will happen naturally.