Okay, before I get into this huge megapost about social rolls let me explain what I think about rolling for social actions:
I think rolls for social skills are good. A player might not fit a GM’s assumption of a “convincing” or “charismatic” person, but their character might be just that. Not letting the player who’s spent their character resources on getting that sweet proficiency bonus and expertise on Persuasion and a huge Charisma bonus is just bad form.
Having said that, there’s a false dichotomy that usually pops up when the idea of rolling for social actions is brought up. That social rolls are simply used to fast forward through role-playing. That is not what I’m proposing.
Having run and played lots of PbtA game I’ve tried to bring the principle “to do it, do it” over. You first describe what your character is doing, then you roll the dice. You don’t say “I roll to Persuade,” because that does not describe what you’re doing. In doing that you’re skipping an important step.
There’s no need to get overtly verbose here either: some players enjoy speaking with the voice of their character, assuming an actor stance; others prefer to describe their character’s actions in broad strokes from the third person, in a directorial stance. Either way is perfectly fine to me. “I say, ‘What ho watchman, wouldst thou grant us passage?” is equally valid as “I request the guard for passage.” Now, in my mind neither of those would warrant a social roll yet. You’ve just described your intent. The GM might say that the guard grants you passage, no need to roll. Or the GM might describe the guard telling you that his orders are not to let anyone in, at which point the negotiation starts.
So, now that it’s clear what you want and it’s time to make your case, how do we go about making a social roll?
Simple: you describe what you do or say to convince the person. The GM sets the difficulty, the player rolls, and then we see what happens.
This is usually when things get messed up. The player might have rolled poorly and now you’ve just put a roadblock on the way of the players: like a locked door, only requiring a Charisma check to get through instead of using Dexterity to pick the lock or Strength to break down the door.
In some cases a failure at a social roll might have very clear and immediate consequences arising from the nature of the attempt being made: a failed Intimidation check might result in the guard calling backup, turning the social scene into a fight scene. But most of the time it doesn’t really make sense to just escalate things because of a failed social roll.
The words “No, but” are your friend here. “No, I won’t grant you passage, but there’s something you might do for me to make me look the other way.” Failure might mean paying a bribe, doing a favor, or having some other cost. Failure shouldn’t mean a roadblock: it should represent a new branch in the action.
Now let’s talk about setting the DC and other such stuff.
If the players know the person in question wants something or has a particular vice or desire, that might be worth Advantage if the player weaves that into their roll. If the player doesn’t know any such thing, an Insight roll can be used to get a read on a person. If the person is a drunkard, making a distraction by offering them a drink might work, represented by Deception with Advantage. If the person has a noble streak, arguing that letting you through in spite of their orders would be in service of the greater good might allow for Persuasion with Advantage. If the person has some person or thing they really like, using that as leverage might allow for Intimidation with Advantage.
If you haven’t thought of an NPC personality trait in advance, here’s the perfect opportunity to put all those random personality trait charts you have to good use. Heck, you might even want to roll on an appropriate Background chart almost as if you were rolling for a PC’s Traits, Ideals, Bonds, and Flaws randomly.
So, how do we set the DC? Well, the baseline DC should be 15. In a system adapted from Strike!, the DC will move up or down based on two things: the person’s attitude towards you, and whether the thing you’re asking from them is in their interests.
NPC attitude might sound familiar, because it’s a holdover from previous editions that makes sense even in the context of 5e: Hostile, Unfriendly, Indifferent, Friendly, and Helpful. The baseline DC of 15 assumes an Indifferent person, and every step towards Helpful decreases the DC by one step (all the way down to Very Easy for Helpful NPCs) and every step towards Hostile increases the DC by one step (up to Very Hard for Hostile NPCs). Whether the thing is in their interests or not is a simple thing: either the thing you’re requesting is in their interests (decrease DC by one step), it’s against their interests (increase DC by one step), or it’s not really something they’re actively for or against (DC stays the same).
So you might get the DC all the way up to 30 if you’re asking a Hostile NPC to do something against their interests, which is fine: the player should still be able to roll, albeit with a high chance of failure unless they’ve really pumped all their resources into that thing, in which case they deserve their success.
But what happens when you ask someone Helpful to do something in their interests? Well, then we hit the Secret DC That Nobody Wants You to Know About. DC 0.
DC 0 is rarely used because it’s one of those “You really shouldn’t even be rolling for this” things. For an example, walking around would be a DC 0 check. You don’t ask for players to roll for walking around, because even by the rules of Passive checks they really can’t fail no matter how low their Dexterity is. It’s not an explicit rule in the game, but it’s one that I’ve taken as an implicit thing.
In most cases a DC 0 check is an automatic success: most characters won’t have enough penalties where they might even fail such a roll. But in the rare case that a Charisma 3 character tries to negotiate, even though all the odds are stacked towards them, there’s still a chance for failure. Why? Because just like we want to reward the player who spent all their resources on being the best at negotiaton, the character who has dumped their Charisma has to feel the effects of their low Charisma should they run into a situation where they have to negotiate.
If you’d like to plug in one more thing from Strike! that I like, you could take into account Reputations. A single character in the group or the whole group might have a Reputation. A Reputation is either specific to a certain faction or location, but they might become broader in play.
Reputations shift specific NPC attitudes by one step. The three reputations are:
Famous: Treat Indifferent people who your Reputation applies to as Friendly.
Feared: Treat Unfriendly people who your Reputation applies to as Neutral.
Admired: Treat Friendly people who your Reputation applies to as Helpful.
Black Leaf the Rogue has spent a few adventures in a city. She’s already got her future advancement planned and wants to become a Mastermind, specifically a criminal mastermind with a globe-spanning criminal empire. To this end she’s already looking to make some contacts and find out about the local Thieves’ Guild.
Black Leaf spends some downtime looking for a beggar she knows has ties to the Thieves’ Guild and is about to ask them for the basic scoop on the Guild. The beggar is Indifferent towards Black Leaf, but since Black Leaf has already gained quite a reputation within the city’s criminal underbelly for a few heists she’s pulled she counts as Famous, so the beggar is treated as Friendly. However, giving information to strangers about the Guild is against the beggar’s interests, so the DC is still a 15.
Black Leaf doesn’t like those odds (with her +2 proficiency bonus and +2 Charisma it’d be an even 50/50 split) so she decides to try an Insight check to get a read on the beggar. Successful, she gets a read that the beggar’s Ideal (determined randomly on the spot by the DM) is “Redemption: There’s a spark of good in every one.” Black Leaf spins a yarn about how she used to be a bad person who stole only for her own gain and she now wishes to put her skills to good use stealing from the rich and giving to the poor, and she thinks the Guild might be the way to do it. She thus gets to make a DC 15 Deception roll with Advantage.
Note: Edited some things; while writing the example I apparently decided in the middle of it to change the name of Black Leaf the Rogue to Sheila the Thief because my pop culture references are a strange mess.
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