Hey gang, I wanted to provide a real life example to help convey what Skill Challenges can feel like, and how they're perhaps best used by you as a player.
I feel like i neglected in my rules description to mention exactly how much SCs are really an opportunity for you guys to take a lot of control as Players (something D&D doesn't necessarily do too often outside of combat), of the narrative and the mechanics.
It's supposed to be an opportunity for you guys to create a narrative, and create realities in the game world, that weave an exciting and interesting scene of your choosing, while using the Skills that your characters are best at, all to shine as a player and character.
Summary of actual gameplay:
Situation was, the party has just fought their way through a town suffering from a zombie apocalypse-style invasion of undead. And defended the townhall from a prolonged zombie siege.
We played through that all in "normal" scene to scene, round to round, gameplay. Lot of combat. By the end they were beat up and depleted.
Well, then I used a Skill Challenge to play out an escape from the town, because zombies were just continuing to appear and swarm.
There was a big horse drawn cart, they had a couple dozen townsfolk they loaded into it, and the Challenge was to escape with as few townsfolk dying as possible.
Success meant no one died, the sooner the failure meant the more townsfolk died.
We kick it off and the Druid is like, "I use Animal Handling to keep the horse calm and drive the wagon."
Fighter is like, "I use Athletics to boot zombies off the wagon as they try to crawl up it's side as we ride by!"
Sorcerer is like, "I use Deception to keep the townsfolk calm - everything is fine here folks nothing to worry about! :D"
Rogue is like, "I use Stealth to throw a blanket over everyone and try to keep us low profile as can be... in a wildly racing wagon..."
DM: "Heh, well, the less flesh that is showing, the less excited a zombie might be about your cart. I think that helps!"
Ranger is like, "I use Survival to shout directions to Druid for the fastest way out of town!"
Warlock be like, "I use Eldritch Blast???"
Me, a DM: "Noooo! No attacks remember? I know this is hard for you."
Warlock: "Ok, well... I think the townsfolk are starting to lose it, despite Sorcerer's cajoling, so I'm using Intimidation to shut them up - CAN IT peasants or I will send you to my Infernal Lord for sup!"
DM: "Ok, that's on-brand, yea."
And so on...
They gave more narrative than that with each scene ofc, and there was more interaction between us all, being like, "Oh that's good!", and laughing and wincing at failures, and cheering success, but for the sake of not typing out an entire book, I paraphrased.
But, so, point is: I didn't ever tell them the horse was skittish, or that their were zombies trying to clamber onto the wagon, nor that the townsfolk were scared, or that they needed directions, or needed to hide, or that the townsfolk were getting scared again.
They made up all of those realities themselves, based on the narrative situation and the things that they reasonably saw happening in such a situation that their particular Skills could really help them with in overcoming it.
That's what Skill Challenges are for, for you all to flex your creativity as a storyteller and to use your best ranked Skills to show how you overcome a broad challenge.
Skill Challenges are there for you to create exciting stories and to shine.
You have A LOT of agency in Skill Challenges and it really shines as a mechanic when you use that to the fullest. Use your best Skills. Tell the version of the story your character shines in. Make the whole thing what you want it to be.
Does that make sense and/or help you guys picture the ways in which you could be using this opportunity?