Man, I have such a ridiculous write-up on this topic if I thought it would ever percolate and become something.

TL;DR,

As a general rule, skill checks should influence how much information you get and how much information (true or not) you provide right now. They should rarely directly influence the outcomes of events; outcomes are determined by the successes and failures of activity and the choices you make. You make decisions based off of information. Decisions bear fruit far enough down the road to where a save would most likely be irrelevant.

Situation 1:
1. A druid is about to kill a kid right now.
2. Kid says im not horrible!
3. You, thinking kids shouldn't be killed, makes a persuasion check to save their life.
4. You fail, kid dies.
*Clippy shows up* Uh oh! It looks like you are trying to make a skill challenge! Most DMs use those only to heighten the drama of a larger event that is unfolding, not determine the outcome!

Situation 2:
1. A druid is sentencing a kid to death, to be executed the next dawn - i.e., in the future. She says this child is horrible and must be killed.
2. Almost everything in the conversation after this is irrelevant to the outcome, as the decision to free the kid or not is decision, and the outcome determined later as this is an overall game event. However, the rest of the chat is information

The time in the grove is spent spinning plates and getting info. Persuading here, stealing there, planting something here. Towards the end of lots of smaller quests and events the totality of all of the things you chose to do over the last 2 hours start bearing fruit. some are surprising, some are funny (I had a feeling hiring that madman to pretend he was an arch druid wouldn't go well...), and they overall build the DC for an impassioned speech or create enough of a distraction where you put the girl in a sack of potatoes and sneak out.

The overall structure of so many of these challenges is that of a Bang Bang Play.

What is a Bang Bang Play in Football? A bang bang play involves multiple events occurring at once or quickly, one after another. Because bang bang plays are used to describe a play that happens so quickly, they often lead to difficult calls being made and challenge flags being thrown to argue such calls.

The concept of a challenge in the game is fundamentally flawed. Its pivoted orthogonally to how events play out in D&D.


What is the problem you are solving? Does your proposed change solve the problem? Is your change feasible? What else will be affected by your change? Will your change impact revenue? Does your change align with the goals and strategies of the organizations (Larian, WotC)?