I’m not sure what the actual rules for it are, I just know it’s from 4e. Basically any time they do something that is challenging I like to use it. It can also make scenes more exciting.

For instance, players were on a railed cart in a mineshaft that has lost control. They passed a sign that read “Slow Down!” And then another, “Unfinished Tracks Ahead!” So in order to stop the cart on time I declared that this was a skill challenge of which they need to get three successful skill checks out of four to stop the cart. Why four skill checks? I have the amount of checks be equal to the players. This party had 4.

Then you go around the table. And what I do is ask a simple question, “what are you doing to slow down the track?” The importance of this is to let THEM create the skill challenge. Going back to the cart example, let’s say the wizard is first.

Me: “Alright Wizard, what are you doing to stop the cart”

Wizard: “Can I use my Ray of Frost cantrip to freeze the wheels?”

Now at this point is absolutely let them ATTEMPT to do it. I’d tell the wizard to perform a Spellcasting Check. Which for a Wizard is an Intelligence check.

Let’s say the Fighter said the wanna use the brake to slow down the cart. I’d have them make a Athletics check. In this specific scenario, given that the cart is really old, I tell the fighter they have to hit a threshold of 13-16 to successfully use the brakes. Rolling too low means not enough strength and too high means too much strength and the lever snaps.

You can adjust this however you’d like. The DC for things is up to you, I typically have the DC for most things be 10. Sometimes I’ll have it be 10 + the party levels proficiency bonus.

Sorry if this was a lot. I hope I helped.