Examples

Example:
Situation: Rocky the dwarf and Wispy the Elf are blown over the cliff by a gust of wind.
The PCs are level 4, so the base DC is 9. There are 5 PCs. (Rocky, Wispy, Barb, Izard, Roguely)

Barb the Barbarian: I drop my weapons and reach out to grab Rocky. result: Athletics 17

DM: Hrm, you gotta be there first, but good reaction, make an Acrobatics check, with advantage for being quick on your feet.

Barb: result: 13.

Izard the Wizard: I use mage hand to throw my rope from my pack to wispy.

DM: Sounds good, give me an Survival check.

Izard: damn, 6.

DM: Ok, so as the two are tossed over the cliff the rest of the party reaches out. Roguely what are you up to?

Roguely: I figure that Barb can handle the weight of the dwarf, so I reach for the rope.

DM: That makes sense, give me a Perception check to make that decision quickly.

Roguely: 22. Bamn.

DM: Ok, barb has a solid hand on Rocky and Roguely has take the weight from Izard's rope.
(mechanical: That was the setup phase. The PCs got 2 successes out of three checks, so start them at moderate. Meaning a DC of 11 and 4 checks. Given that this is a simple situation, I'll drop the number of successes by 1. So the PCs need to make 3 DC 11 checks to get them up.)

(Plot: Decide the outcome. In this case the pcs don't fall to their death, instead they are dropped to a ledge below. This can either cause limited damage 1d6 or 2d6, or perhaps delay a chase. In this case I decide there is a cave below with a monster guarding treasure. They will take damage but see the glint of gold.)

DM: Alright, who's taking the first action?

Wispy: Acrobatics to climb back up.

DM: What does that look like? Otherwise a flat check is at disadvantage.

Wispy: Right. Wispy thinks back to the time she fell off a huge tree and remembers putting her fingers into the roots of tiny plants to gain traction.

DM: Sweet. Make a check, or tell me a quick story for advantage.

Wispy: It was during her training, her mentor wanted to push her and knocked her off the cliff, ready to cast feather fall should she fail.

MORE HERE

Escaping thief

CR3 challenge 700 xp

A thief flees into a busy market. Roll 3 : perception(watch the crowd), investigation(guess where they are headed), intimidation(quickly ask people where the thief went).

Usable skills: Acrobatics, Investigation, Insight, Perception, Intimidation.

Example responses:
Acrobatics, pass : As you chase the thief you see an empty stretch behind some carts, you slip into the open space and gain some ground.
Insight, pass: Your eyes scan the crowd looking at faces. You hear a small child start crying, as if started by a stranger.
Intimidation, fail: You approach a guard and ask which way the cloaked figure went. Sensing trouble the guard tells you to slow down and walk calmly or else there'll be trouble.