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You can find great tools by looking to older editions of Dungeons & Dragons. 4th Edition introduced skill challenges, which are an interesting way to run a narrative event (such as a chase or an escape from a collapsing building). The party is pitted against a series of challenges that can be solved with a skill check. They are required to amass a certain number of successes before failures, or face the consequences. If you want to learn more about how to run skill challenges, there’s some great videos out there by Matt Colville and Dungeon Dad.
When I started planning a skill challenge, it was easy to come up with events that would narratively fit a skill check. However, I had no idea how to plot these beats, how high to set the Difficulty Class (DC), and how many failures to accept. Basically, I was shooting in the dark with how hard the skill challenge would turn out. I knew I could adjust on the fly at the table, but there’s always a concern that lowering the final dramatic DC will not fit the narrative. You don’t want a DC 10 Athletics check for jumping off a cliff onto a dragon.
Wanting to know how skill challenges really work, I made a calculator.
How To Use
When planning, I assume that the player with the highest skill bonus will attempt the challenge. This doesn’t always happen in practice, but it is reliable for planning skill challenges that utilize the different skillsets of the party members.
While this is a useful tool in planning, it’s even better in practice. Players may find advantage in places you did not anticipate. Or, if they’re ahead of the game, you can check on whether throwing disadvantage on a particular roll will throw the whole skill challenge off the rails. If you want to see the odds update live as the skill challenge progresses, you can add each success as an acceptable failure. Knowing the odds gave me the comfort level to adjust DCs in situ. I hope it works for you!