In the "OSR" space and related environments, social skill rolls are generally viewed with distaste. This isn't without reason—resorting to simple d20 skill rolls to resolve all social interactions is stultifying, and verbal conversation is one of the few in-game activities where the events of the fiction and the actual experience of play can align near-perfectly. I'm generally in agreement with this orthodoxy, but I don't think it's fully accurate.
I contend that there's an invisible social resolution mechanic often used in OSR games—the use of the Reaction Roll outside of the context of immediate first impressions—and that, while it's a perfectly serviceable solution, I think some improvements could be made by dragging this invisible system out into the light and dressing it up into a proper procedure.
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The simulation of conversation can never be fully perfect because the GM is being asked to take on the role of many different sentient creatures, each with their own complex inner lives, and to accurately determine how they would behave in unusual and challenging situations. This is an impossibly complex task. We rely on heuristics to get us partway—you write down that this NPC has a mien of "grumpy" or that this Ogre is "food-motivated," and sometimes that's enough to resolve a whole encounter—but in the end of the day every GM is going to eventually reach a point where they just don't know how a fictional person will react to a particular proposition. While I imagine there's a wide range of responses here, in my experience the most common solution is to look to a trusty old pal, the Reaction Roll, as an oracle.
The problem here is that the Reaction Roll, at least in B/X and its derivatives, is clearly designed for a fairly specific purpose: to determine how a potentially-hostile monster will react when encountered in the depths of a gloomy labyrinth or expanses of a rugged wilderness.
Since you're presumed to have no preexisting relationship with the monster you're encountering, there's no real provisions for any modifications except from Charisma, and even that presents the thorny problem of whose Reaction modifier ought to be used. The only explicitly affirmative result is a 12, which is only a 1-in-36 chance; if you try to use this as-written to resolve a proposition you'll probably end up in a loop where most positive outcomes are "considers offers" and you go back to square one. Usually a Reaction Roll of this sort will mostly just give the GM a 2-12 number which they will then interpret based on vibes alone, which isn't a terrible system (OD&D does it that way, afaik) but can definitely be refined.
Now, there is another Reaction system recorded in B/X: the Retainer Reaction system.
This is certainly a better fit for the purposes discussed. It doesn't presume hostility or unfamiliarity, it contains provisions for your offer actually being accepted on something other than a maximum result, and it doesn't assume that they will violently attack you if you flub the roll. On the flip side, it also gives pretty much any proposal a base 50/50 chance of passing (assuming you read "roll again" literally and not "come up with a better offer and then roll again," which would also be perfectly reasonable) and it leaves all the bonuses and penalties up to the GM, which ends up in the same place as the original "roll 2d6 and eyeball the results" territory.
I propose a new procedure, intended to give a consistent way to adjudicate these kinds of situations without removing the benefits of skillful play.
Persuasion
- ...add or subtract any Reaction adjustments that you already have with that NPC.
- ...+1 if you present a coherent case for why cooperating is in their best interest.
- ...+1 if you present a coherent case for why cooperating will screw over someone they dislike.
- ...+1 if you present them with a substantial piece of new information that changes the situation.
- ...+1 if you present them with a substantial bribe or gift.
- ...+1 if you present them with a credible threat (be it physical or reputational).
- ...-3 if going along with the plan is personally risky to them.
- ...invert the above modifiers if you try to invoke one of them but get it totally wrong (i.e. telling somebody "you should go along w/ this plan because it'll make your boss look like a chump," not knowing that this person is actually their boss's secret gay lover).
Deception
- ...+1 if you have a reason for them to want the lie to be true.
- ...+1 if you have a reason for them to fear the lie being true and them not acting on it.
- ...+1 if you have a sense of urgency.
- ...+1 if you have the imprimatur of authority.
- ...+2 if the person is especially gullible.
- ...+2 if you are a Thief-type of considerable talents, or some other gifted liar.
- ...invert the above modifiers if the opposite is true in some exceptional way—if the mark is particularly sharp, if they have some strong reason to want to disbelieve the lie, &c.