5 Persuasion Skill Challenges for 5E D&D

Salutations, nerds! This series touches on each of the skills on the fifth edition Dungeons & Dragons character sheet and lists off five flash encounters for each of them. The idea is you can drop these into your game at any point without them taking up too much time or serving as longer plot hooks. These are single scene skill challenges, beginning to middle to end, right there. They exist if you need to stretch the action for a moment or give spotlight to a 5E D&D skill heavy character. Right now we’re talking about getting people to do what you want them to through Persuasion.

5E D&D Persuasion skill challenges

Wagon Problem

A wagon has broken down on the path. There’s a roadside inn not far from here with a carpenter who knows how to fix their busted wheel but the people on the wagon don’t have any money to pay the carpenter and perhaps they belong to a group the carpenter is iffy about.

This doesn’t have to be a situation like, “The carpenter doesn’t like elves.” Maybe the people on the wagon are puppeteers and the carpenter thinks puppeteering is a waste of time or they’re heading to the city for a festival and every year people on their way to this festival come into the tavern and cause a big fuss and so the community just really isn’t into them.

The object of the challenge is to persuade the carpenter to fix the wheel.

Use When. You need an event between Point A and Point B to break up the monotony of travel or you want to tease how there’s going to be a festival in the next town.

Result of Failure. Some poor merchants are going to have to wait for more help to come along. Or the adventurers will cast mending or use their own repair skills to help. Let them. There’s more than one way to fix a wagon wheel.

Door Guard

The adventurers already need to get in somewhere and there’s a guard on the door who doesn’t think they should be there. You can use this practically any time you want whether the characters are supposed to be there or not. This is a case of mistaken identity and a stubborn guard digging in their heels.

Use When. You need to stall for time or you want characters to be a little bit frustrated when they get in where they’re going. A guard on the door says, “This place has security and they think they are important.”

Result of Failure. If you really need them to get inside then the owner can pop their head out and be like, “Nah they’re cool,” or possibly the adventurers beat up the guard. You can also keep asking them for proof and keep giving them rerolls. After all someone who was really Xena, Warrior Princess would have her famous chakram, right? And be able to do unnecessary backflips?

Hey Kid, Let me Borrow Your Bike!

This one has to sort of already be in the cards. A character needs something they don’t have in order to finish doing something they’re trying to do. A rope to scale a wall. A bicycle to chase down the bad guys. Something. An NPC has it and the character has to persuade them to let them borrow the item.

This turns, “I forgot I used the important item doing this other thing and now we don’t have it” into a fun little bartering aside as this kid really doesn’t want to let the character borrow their bike.

Use When. Someone doesn’t have something they need but you want them to have it and feel it was earned.

Result of Failure. I certainly hope characters won’t punch out a kid for their bicycle but honestly let them bribe the person. Let them keep trying and make it funnier every time they fail. This isn’t a high stakes challenge.

Traffic Ticket

Adventurers come out of a tavern to find a city guard writing them up a citation for where they tied their horse or something similar. Listening to characters talk their way out of minor inconvenient legal trouble is comedy gold.

Use When. You want to offer some comedy relief for the adventuring party.

Result of Failure. A small fine. Legitimately a couple of silver pieces at most. This shouldn’t be something for adventurers to get arrested over unless they escalate. You know whether or not the characters in your game are going to start a fight with the guards.

Dear Princess Celestia…

There are two friends (or maybe siblings) having an argument and characters need to convince them to make up with each other. This probably isn’t any of the party’s business at all really but I promise you the second one NPC says, “I am so mad at my brother I could scream,” and the brother says, “Did she tell you I was being the jerk? Let me tell you!” They aren’t going to be able to help but get involved because this reeks of side quest.

Use When. You’re trying to humanize the townsfolk. If you’re planning on threatening this town later then the adventurers will likely feel more attached to people they’ve helped out in the past than random strangers and feel it more when those people are in danger.

Result of Failure. The brothers continue fighting. Maybe the adventurers get to try again later or have to find something to prove that their argument is stupid like find the actual copy of their father’s will or something. But this is really beyond the scope of the skill challenge.

That’s all I have for 5E D&D Persuasion. Hopefully I’ve rolled high enough to get you to try some of these out and if you do I’d love to hear about it in the comments. As always, stay nerdy!