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D&D 5E Need Advice for Running Social Skills

I make sure there are multiple ways to achieve the same result, in the same way that there are multiple options to get through a dungeon. eg. if you come to a locked door, the party could pick the lock, kick down the door or go find a key.

Similarly, if the queen has horses to offer, make sure there are several ways to acquire them. The PC's could ask directly (a single persuasion roll with a DC set depending on why the queen might give them horses), the PC's could impress on the queen the urgency of the situation that leads to her offering horses (a deception or intimidation roll perhaps) or a reason for the queen to want to be rid of a certain animal (insight to notice the prince has been thrown several times from the same horse)

It's best if multiple skills could be used, in the dungeon example Athletics, Thieves Tools and Perception would be used for each option respectively. It's a little harder to spread checks across ability checks in social situations, but INT and WIS both make a lot of sense. I also find being a little loose with what counts as intimidation helps vary things a little. eg convincing the queen that the threat is urgent could be an intimidation tactic rather than a second choice of persuasion. Intimidation doesn't HAVE to be a direct threat of personal violence.

I find this way engaging the players with more than; "Can you roll a die." <Clatter> "The queen offers you horses as well." It puts the ball in their court to come up with the idea's. They have to ask, or think to raise the issue of urgency.
 

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Something else that can be done is a variable effect based on the roll (rather than a straight DC). For example, with a neutral NPC:

<1 NPC refuses
1-4 NPC disagrees (-10 on next check)
5-9 NPC hesitant (-5 on next check)
10-14 NPC interested (+5 on next check)
15-19 NPC swayed (+10 on next check)
20+ NPC agrees

This allows for a series of roll to convince an NPC, requiring the players to put forward several reasons for the NPC to agree. One bad roll shouldn't cause immediate failure (without penalties), but a lucky roll might sway the NPC right away. This system might make social interactions take a lot longer, however, with a lot of die rolling.
Using the above as a start. face man rolls against Hobson horse manager of the queens stables gets a 9 total. Now all players roll social check of their choice. Results
Thief 20 War horse in his color. max hit pts
Wizard 15 match result riding horse.
Cleric Fail Nag for glue factory.
Barbarian big fail. Magical war horse. Aka Sway back mule.
 

This is stated in a few different ways, but I'll throw my wording into the ring...

As with any situation in which there might be a roll, you as the DM determine if a roll is actually needed.

1. If the success is guaranteed OR necessary for your story to continue, then just say Yes and move forward
2. If failure is guaranteed OR necessary for your story OR the request is just stupid, then just say No and move on
3. If the story will be more interesting whether the PC succeeds or fails, call for a roll at a DC that you reveal to the players (or not). The skill could be your call (e.g. "Please give me a Persuasion check") or you could give the player some options (e.g. "Roll me a Charisma based skill of your choice" or "Give me a skill check and explain what skill you'd like to use and why")
If it is the "Explain what skill you'd like to use and why" option, consider rewarding exceptional creativity with Advantage sometimes. Or, if the particular skill simply doesn't mesh with that particular NPC, have the roll done at Disadvantage or hike up the DC accordingly. It's really up to you as the DM.

For option 3, and this seems key to me, there needs to be Consequences for failing. You can set this to be a binary "Yes or No" or graduated. Here's what I mean by graduated: if the PC barely fails, maybe the queen agrees to loan the horses but makes them leave a sizable deposit or swear some oath or she sends along a trusted NPC to keep an eye on them. If the PC fails miserably, maybe the queen gets offended for some reason and does not offer the horses, and maybe they've lost an ally or worse...
Similarly, for option 3, you could have bonuses for success, if you want. Barely succeeding just gets them the horses. Succeeding by a lot gets them the horses plus an escort or the use of a special magic item (which they are expected to return). You get the idea.

You can expand on these ideas from time to time with prior-edition-style Skill Challenges, which are excellently explained by Matt Colville here:
https://www.youtube.com/watch?v=GvOeqDpkBm8

Have fun and make those social rolls meaningful!
 

For me, it helps not to divide encounters up by category. Thinking of an encounter as a “combat encounter” or a “social interaction scene” or a “skill challenge” just leads you as a DM to subconsciously limit yourself. Once you decide “this is a scene where the players fight some goblins”, that’s what’s going to happen, unless the players really fight against your expectations to circumvent it. Likewise, when you decide “this is a scene where the players try to convince the queen to supply them with horses”, convincing the queen ends up being the only option you present the players with for how to secure horses. I find it more useful, therefore, to think about encounters in terms of what the players’ goals are, and what obstacles are preventing them from achieving those goals. Then “combat”, “social interaction” and “skills” become possible means of resolving the central conflict of the encounter.

So, to use your example, the players’ goal is to acquire horses. In order for this to be an encounter, there has to be a source of conflict - an obstacle preventing them from getting the horses. In this case, the queen needs a reason she doesn’t want to provide the party with horses (let’s say, she doesn’t trust them because they have yet to complete a task she had sent them on previously). Then that reason is the source of conflict, and social interaction becomes one method among many of resolving that conflict. Another method might be violence - maybe they kill the queen and try to take the horses, now it’s a “combat encounter”. Or maybe they try to sneak into the stables at night and steal the horses. You just provide the players with a goal and an obstacle in the way of achieving it, they’ll work out how they want to resolve the situation.

Now, assuming the players decide that the way they want to go about resolving this conflict is by convincing the queen that they are trustworthy. Now we can start to see why resolving this conflict by social means might be more complicated than a single Charisma (Persuasion) roll. They’re going to have to provide her with reasons to trust them, or convince her that her reasons for not trusting them are misplaced. If you want a mechanical framework for resolving this, you could do worse than 4e’s “X successes before Y failures” skill challenge mechanic. When the players offer inscentives to the queen, consider her reasons for distrusting them, and if what they’re saying would alleviate her concerns or exhaserbate them. Treat it just like any other task - is there a chance this might help resolve her misgivings? If no, mark a failure. If yes, is there a chance what they’re saying would worsen them? If no, mark a success. If yes, ask for a Charisma check, and allow the players to apply a relavent skill based on their approach, and mark success or failure based on the results of the roll.
 
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I've used essentially the same system for 30 years.

D&D is an RPG - a Role Playing Game. Characters play a role in a story. You want to make it a good story.

Have you ever tried watching a movie on streaming only to have it buffer ... constantly ... at ... a ...
...
... ...
good....
...
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spot?

It really hampers the story to have the flow of a great scene, especially a great conversation, broken up. As such, my key rules are aimed at having the flow of an encounter progress without many, if any, disruptions to roll dice or look up stats during the encounter. In fact - I don't really 'roll dice', but instead just have a spreadsheet printed out with random numbers from 1 to 20 that I can reveal to myself slowly to generate the 'rolls' to make sure everything moves quickly.

Trivial Social Encounters: A trivial encounter is an encounter in which there is communication, but no significant story elements of the game are progressed and the PCs are unlikely to communicate with the NPC often in the future. For these encounters, I roll nothing. I know the PCs social skills well enough that I can translate what they're trying to do through the filter of their character's capabilities. If an eloquent player playing a PC with a -1 Persuasion tries to seduce a guardsman to let them have a look in a store window, I have them describe what they're trying to do and then I ask myself how it would have worked had I tried to pull off the line. In general, if there is no real impact, it is fine to use passive social skills to determine success and failure. It makes sure the PCs feel like they have (or do not have) the skills they have (or do not have).

NPCs in these situations usually have one dominant characteristic, like most minor characters in books do, but little depth to their personality. They're caricatures more than characters.

These encounters flow smoothly without disruptions for dice and stat checks. Essentially mechanics of the game set the stage, but we can just move ahead with the story fluidly.

Minor Social Encounters: A communication based encounter that has a reasonable possibility to make a meaningful change in the campaign, but not a major one. Perhaps it is buying a magic item, or trying to persuade a guardsman to let the PCs get away with a minor crime. For these encounters, I roll one die before the encounter begins and then apply it to their social skills throughout the encounter to determine how effective they will be at communicating. There are usually flat DCs to determine how hard it'd be to do something as opposed to any opposed skill checks.

These types of NPCs are generally a bit more fleshed out - my trick is to pick a person or character and try to mimic that character. A shop owner might be based upon Giles from Buffy, or a Silver Dragon might be Maui from Moana.

As the only dice rolled are rolled before combat, it is easy to keep things flowing smoothly here and keep the story going. When I use the sheet of random numbers and a reference sheet for character ability scores, I can just keep the story going and not break up the storyline with pauses for mechanics.

Major Social Encounters: A communication that can change the course of a campaign. Negotiating with the warband chief to prevent an attack on a city, or navigating through the social hierarchy of a major city at the event of the season to gain access to a King. Here, I'll generally roll a few dice for each PC, but I'll do so before the situation begins. One die will reflect the start of their social endeavors. Another will reflect a middle phase of what they're doing. The final will reflect the last third of the social endeavor. Sometimes I will break the social encounter up into only two phases, while others could have four or five. I determine how many phase there will be by looking for natural breaks in the social situation. For example, if the PCs are attending a banquet in which they hope to gain access to the King and persude him to do something, the first role might reflect what happens before dinner, the second would address events during dinner, and the last would address after dinner. Then I'll have 1 or 2 additional dice rolled that I'll reserve for the 1 or 2 key moments where you want to have a dramatic die roll determine success or failure. I may or may not use them for each PC. In my banquet example, the PCs might use one of these dice when the PCs try to gain access to the King, and another when they try to persuade the King.

The key players in these encounters are usually based upon a person or character as discussed above for minor social encounters, but I try to pick central characters that have more depth, and I'm not afraid to modify them substantially to suit my needs. However, there are often a large number of folks involved in these major social events, and non-key players are often caricatures with no real depth.

In this model I do break up the encounter a bit for mechanics - but they feel like the right time for a dramatic pause.
 
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