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Ok, so the title is a bit of hyperbole. But my party has recently been using persuasion abilities (backed with RP) to turn otherwise combat encounters into social ones.

To be clear, I have nothing against this kind of play.

But, I don't know how to challenge the player(s) who are doing the persuasion.

I don't simply want to turn up the DC on persuasion checks. That's not challenging, and defeats the purpose of the player who built his character to persuade. How can I challenge this PC in a way that feels satisfying to the PC, without reducing it to "roll to defeat entire encounter in 1 check".


As an example: (spoilers for the Lost Mines of Phandelver module)

In the Redbrand encounter in town, the social PC (a half-elf warlock) attempted to persuade/bribe the Redbrands to join them in their attempt to overthrow Glassstaff and take over the Redbrands.

Not wanting to trivialize what was the only combat encounter of the night, I made the dwarven NPCs racist against the half-elf PC, so that they would not choose to work for him (the module has been modified to sit inside the dwarven kingdom in my homebrew world).

In hindsight, this was a mistake, and it took away what was a smart play for the PC in exchange for giving the rest of the party something to do. At the time, I felt the need to give the rest of the party something to do.


We are using 5E, so any 5E specific solutions are appreciated, but I suspect the solution is a system agnostic one.

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    \$\begingroup\$ Is this style of play something the whole table agrees on? Is everyone contributing in some way to the encounter when it goes this route or is one player with heavy social skills more or less getting a chance to shine? \$\endgroup\$ – Pyrotechnical Oct 23 '17 at 18:52
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    \$\begingroup\$ Related reading about treating social interactions like encounters. Be warned, mild NSFW language. \$\endgroup\$ – JAD Oct 26 '17 at 13:55
  • \$\begingroup\$ Could you not have the combat encounter anyway, but make it harder so that convincing those Redbrands to join them seems worthwhile? \$\endgroup\$ – Kapten-N Jan 23 '18 at 9:30
  • \$\begingroup\$ @Kapten-N, I'm not sure I understand your point, but if you wish to put it into an answer, I'm happy to give you some rep for it. \$\endgroup\$ – Shem Jan 23 '18 at 14:38

13 Answers 13

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To begin, some general advice on the nature of social skill challenges:

First, skill rolls are not, mechanics-wise, a substitute or a parallel system to combat. You as the GM are under no obligation to let the players swap out skill rolls for combat, simply because you're under no obligation to rule that the skill rolls have any meaningful chance of success. It's like a player insisting on making a strength check to lift a two ton boulder-- sure, you can let him make the check for the sake of show, but without some extenuating circumstance, there's no reason to let him succeed even if he rolls a twenty. Some social rolls, like some strength checks, are simply non-starters.

Should they all be non-starters? That's probably too harsh and verges on rail-roading. But allowing infinitely malleable and persuadable and deceiveable NPCs is also problematic.

Second, even if you decide that a certain situation is amenable to this treatment, you are under no obligation to have it resolve in just one roll. The 4e notion of the skill challenge is a highly useful model, even if the math needs to be adjusted somewhat for the situation. There, the core idea is that multiple rolls, preferably used against multiple skills in concert, are necessary to achieve large results.

Third, related to this, you are under no obligation to allow the player to control the pacing of this kind of extended skill challenge. As the GM, you are in control of the pacing, and if you decide that it would take several lengthy units of time (either in-game time several days, or RPG-time of several sessions) to accomplish this goal, that is your prerogative. I would try not to be arbitrary about it, but it is in your hands.

Fourth and finally, you are under no obligation to treat this as a binary pass/fail where the players either succeed and have a new band of minions, or fail and have no consequences. It should be possible, for instance, for the players to screw up so badly they are even worse off than before (somehow) or for a partial success to occur, or for something weird and unforeseen (relatively speaking) to happen that no one planned on.

To continue, some concrete suggestions for this encounter:

Disclaimer: I've never had my players try to take over a band like this, but I have had them on numerous occasions try to influence a large number of people, and I have used the skill challenge motif, and I have this advice to give:

First, even if it takes you a few minutes to settle your mind, make some notes about how many successes and failures are necessary before the outcome is decided, and what sorts of skills are helpful. I wouldn't treat that as etched in stone (especially if the players have a creative idea) but I have found it helps keep me objective, and prevents me from falling into an overly adversarial role.

Second, if you are going the extended skill challenge road, it is critical to give your players feedback about whether they are doing well or not. My early failures in this regard happened because I knew the players needed (say) four successes, and had achieved three, but I failed to communicate a sense of success or progress, so they gave up.

Third, it sometimes helps to personalize this sort of thing by casting it as a two sided conflict: The PCs, say, vs the Redbrands' leader and top lieutenants, where the prize is the course of action or the loyalty of the rest of the group. This increases the drama (the opponent has a face) but also gives a lot more scope for reactions, role-playing, and understanding why the group is not amenable to persuasion. (Say, because Lieutenant Thuggy McThuggerson pointedly reminds everyone what happened the last time someone tried to tell Captain Brute what to do-- that would be the existing leaders' own intimidation or persuasion roll.)

Fourth, on the idea of non-binary results, consider carefully what a total catastrophe might look like, or what a partial success might look like. Are the thugs so regionally scary that they could put a bounty on the PCs' heads? Could the PCs peel off a quarter or a third of them and start a gang war? Could the local authorities exploit that? Complexity is the friend of the GM.

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  • \$\begingroup\$ If a persuasion roll could make things worse by leaking secrets. For example, "Resistance is futile. We are immune to everything but cold iron."... "Thanks for the tip. I knew I kept this old rusty thing for a reason" \$\endgroup\$ – gmatht Oct 26 '17 at 8:09
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Treat difficult social encounters like combat

Any encounter shouldn't be finished in one roll. The bandits guarding the bridge aren't going to roll over and let the party pass just because you asked nicely once, but you may be able to persuade them to not be initially hostile, deceive them into thinking you've got nothing worth stealing, then with some sleight of hand, prove it.

Or, to use your example, the Redbrands aren't going to simply turn against their leader with a single persuasion check. A deception check might be able to instill some doubt within some of them that their leader may not have their best interests at heart, an insight check might reveal that they're simply mercenaries, and their only real motivation is money, and then players might be able to persuade or bribe them to mutiny, in order to get back what they're owed.

Other systems can manage this a fair bit easier than 5e can, such as Fate in this example from Reddit. Here, we see Spiderman and Aunt May having a heated exchange in which they trade verbal blows and emotional guilt, resulting in Peter conceding to working in a soup kitchen on the weekend, rather than being Spiderman.

To model the same thing in 5e, however, we can exchange some of the skills for similar ones in D&D, but model the encounter much the same way. Rather than assigning aspects, just describe how the scene changes as a result of the actions of the party, for the better or for the worse. Allow some back-and-forth too.

Don't be afraid to roll back against the party, and have your bandit chief intimidate players, presenting himself as an imposing force that should not be lied to, or your Redbrands push back against the persuasion as loyal soldiers who will not abandon their leader, and narrate how that changes the arena as well.

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    \$\begingroup\$ And this is why I like Dogs in the Vineyard as a system so much. You can escalate from Guns to Talking (assuming the conflict started somewhere other than Talking) bringing more dice to your arsenal (its a bidding system: dice are rolled once and then you spend their results until someone runs out of dice). I've never found a good way to handle that sort of thing in a d20 system, but this answer comes so close...and Novak's answer. \$\endgroup\$ – Draco18s Oct 24 '17 at 5:26
  • \$\begingroup\$ blogpost with an example of treating social interactions like encounters. Be warned, mild NSFW language. \$\endgroup\$ – JAD Oct 26 '17 at 13:59
  • \$\begingroup\$ I really like the last paragraph about having the leader of the NPCs try to intimidate and counter the persuasion. When reading the title, I was thinking "just ambush them", but that didn't fit the text of the question. Having the NPCs begin the interaction with an intimidation roll would definitely act as an "ambush" style of social interaction. Put the party on the defensive immediately. Maybe add some extra intimidators to set up disadvantage (perhaps just the size of the NPC group?). \$\endgroup\$ – krillgar Oct 26 '17 at 21:26
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    \$\begingroup\$ +1; the first two paragraphs in particular made me favourite this question, just so I can remind myself of this (since my group like finding alternatives to combat and in particular when I'm DM I would like to remember this). \$\endgroup\$ – NathanS Oct 30 '17 at 11:44
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Preface

I have never played 5e, but I agree that much of the answer will be system agnostic so I address it that way.

Make a social victory come at an interesting cost

It will rarely fit in the fiction that you can get everything you want by being persuasive, instead you gain an upper hand in negotiations. So, instead of entirely avoiding the encounter, successful persuasion should usually instead offer more options, though normally on favorable terms. Those other options, if structured right can help move the spotlight for a bit onto other characters.

For instance, assume the group's goal is to make an ork tribe stop harrassing a village. The traditional DnD answer is to go kill most of them until the rest flee the region for good. This can be an option, but another might be negotiation. But even the most persuasive person (barring supernatural influence...) is likely not going to get the tribe to just up and move without anything in exchange. Instead, the Ork's might agree to move if the thing which drove them here in the first place is defeated, and might even give the adventurers an added reward for doing it. Now, your party has a choice. Attack the Ork's anyway because they don't want to go clean up the Ork's homeland, or go on a bigger quest to free the Ork's homeland which can result in other fighting.

Or they might agree to move if the adventurers find them a new homeland that meets their criteria. This is purely negotiated and might avoid fighting entirely, but now it shifts away from your persuasive character onto your best explorer to lead the team in exploration.

Make one social victory lead to other encounters

Alternatively, they might get an occasional complete social victory, but one that leads to the next encounter instead of ending it. Sticking with the Ork's, maybe the adventurers really are so persuasive that they convince the tribe to just leave with nothing further. They might later learn that doing so disturbed some nefarious power's plans, and now that power wants vengeance. This power, being motivated by vengeance, cannot be negotiated with, so they have to fight. The persuasive character gets to overcome the first challenge and gets credit for doing so, but the rest of the party gets their fight, only slightly later.

Inspiration

If you play video games and want inspiration, take a look at the Witcher, especially The Witcher III. There are lots of challenges that can be overcome either by barrelling through with swords or by talking, but talking rarely entirely ends the challenge it just converts it into something requiring investigation or exploration or some other challenge instead of straight fighting. And however you solve the challenge, there is often fallout from it later.

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    \$\begingroup\$ Or "orc", what with this being D&D and not Warhammer :) \$\endgroup\$ – mattdm Oct 23 '17 at 22:48
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    \$\begingroup\$ about video games, there is also the example of Thea: The Awakening, which is radically different on how it tackles the issue. \$\endgroup\$ – Anne Aunyme Oct 24 '17 at 8:49
  • \$\begingroup\$ If its not too off topic, can you mention a bit about Thea? I've never heard of it. \$\endgroup\$ – TimothyAWiseman Oct 24 '17 at 18:23
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    \$\begingroup\$ +1 players doing stuff like this generates more story for free, always a bonus in my book :) \$\endgroup\$ – Rob Oct 25 '17 at 7:55
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    \$\begingroup\$ +1 for using persuasion to add a quest hook, that is more fun then the original quest. \$\endgroup\$ – Garret Gang Oct 26 '17 at 16:19
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So there are a few ways to go about this and for the most part, it comes down to individual DM styles.

As a general rule, 'defeating' an encounter requires multiple opposed checks. The most common type of check could be in the form of combat, the rules for which are thoroughly detailed in the PHB and DMG. You'd typically consider this to be a combat encounter. This tends to take a fair bit of time and involve a lot of dice rolls, which is usually fun for the players since they get to flex their skills. Consequences for failing could be death, capture, retreat, failing the mission objective.

Alternately, the encounter could be survival related. For example, suppose the group needed to scale a mountain, that would likely require a bevy of checks for Athletics, Nature, Survival, and anything else the players can think of that might aid their survival. 4e generally considered these to be skill challenges, but the same mindset works in 5e. Again, this tends to take a fair bit of time and involve a lot of dice rolls and now the players get to utilize skills that might be underappreciated. Consequences for failing climbing the mountain could be a substantial delay, falling off it, perhaps worsening the path to the point that an alternate method needs to be utilized.

The same mentality can be utilized for extended social encounters. While getting a discount at a shop probably doesn't need more than a single Persuasion check, trying to persuade a group of goblins to let you in to see their chieftain is probably going to require at least a few checks. Perhaps the players can use their History skill to relate recent events in the area to justify their presence, the party Rogue sneaks away using Stealth and makes a distracting noise nearby with their Deception skill to suggest that danger is fast approaching and it's imperative that the guards permit passage quickly, and the party Bard pushes his Persuasion skill to make the whole story make sense. Success on the challenge lets the party avoid a combat, failure could cause the guards to become wary and run for help, or perhaps it triggers combat immediately.

Overall, the best encounters (regardless of whether combat is involved or not) usually involve multiple checks. But don't let skill checks get in the way of story. If you want the players to talk with a king and gain his favor, you may want to base that more off of what the players say and how they approach him in-character and less on what the dice dictate.

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    \$\begingroup\$ The last sentence might could use a bit more emphasis or elaboration; good answer in any case. \$\endgroup\$ – KorvinStarmast Oct 23 '17 at 21:26
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I have recently adopted an approach to skill challenges that I find works well for encounters like this. (I'm sure I'm not the first, but don't have a name for it)

Anytime PCs want to accomplish something that's in the realm of a skill check, but too complex for a single check, I set both a DC and a number of successes required. (Also, usually a fail condition, such as a time limit, or max failures) The encounter becomes roleplay heavy, and anytime the PC(s) do(es) something that could help the scenario, they get a roll.

For the bandit example, you could roleplay as one or two bandits speaking for the group, and just talk to the players as you would. Any time any player makes a compelling point, they make the appropriate check. (The bard might persuade that the PC's pay better, while the Barbarian intimidates that its really in the Bandit's best interest, and the Wizard could bluff that he's more powerful than he looks)

Since you know the motivations of the Bandits, you should bias certain actions accordingly. If something offensive is said, no check is needed, and you can count a fail. Likewise, if the players say something VERY compelling, give them an automatic success. Nat 1's and 20's can also count for double. (Because everyone loves getting crits!)

Not relevant to this question, but this system can be used for any slew of skill checks, from diplomacy, to crafting, to animal handling, to ritual magic.

By pulling one check out into many, the "encounter" still feels full-bodied, with a more natural ebb and flow. The whole party is able to participate, and players are rewarded for creativity and good role-play.

Additionally, as the challenge progresses, make sure to give clues and ques as to how the party is doing. Subsequent successes should cause a change in the NPC's demeanor, while successive failures should eventually provoke hostility.

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    \$\begingroup\$ Can have a success without rolling. +1. Refreshing to see this approach. \$\endgroup\$ – KorvinStarmast Oct 24 '17 at 15:07
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    \$\begingroup\$ @KorvinStarmast Absolutely! Rolls should only ever happen if an outcome is unknown. A DM should never be afraid to deny a role for something that's impossible, and shouldn't bog down the game with rolls for anything trivially easy. (I've seen that mistake made a LOT) \$\endgroup\$ – ThunderGuppy Oct 24 '17 at 16:07
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    \$\begingroup\$ @ThunderGuppy "I hand the shopkeeper some gold" "OK, make a dexterity check" "Natural 1" "You try to hand over the gold, but instead drop it on the floor and slap the shopkeeper" \$\endgroup\$ – Luke Oct 25 '17 at 6:06
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    \$\begingroup\$ @Luke I do that ALL THE TIME in real life, and lemme tell you, its totally embarrassing! \$\endgroup\$ – ThunderGuppy Oct 25 '17 at 16:25
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The purpose of diplomacy (in real life as well as in games) is to convince the other party that their goal align with yours. But it is very rare for someone to have a single goal, and even more unlikely for a group of people to be completely united in their goals.

If the NPCs are not perfectly in agreement about what they want, then you can throw all sorts of wrinkles at your PCs as they try to convince them. For example, perhaps they convince the leader of a group, but that leader's ambitious second-in-command takes the opportunity to declare that the leader is a traitor and needs to be killed.

Or in your example above, if you had made only half the NPCs racist then the PCs' diplomacy check would have succeeded in part - but they would have then been attacked by the racist portion of the NPCs. But the racist NPCs are the friends of the 'friendly' NPCs, so if the PCs wish to secure the aid of the others then they will have to defeat their friends without causing permanent harm.

More generally, there's a plotting technique that I've seen described as Yes-but, No-and that may be useful for consideration. The general idea is that every action the protagonists take changes the plot in some way. Either they succeed in what they were attempting BUT that success causes a complication that changes the plot or they fail AND the consequences of that failure change the plot.

Either way, something unexpected has happened, directly influenced by the decisions that the characters made, and in either case there are additional conflicts to deal with.

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The other answers here are great, but there is one more thing to keep in mind.

One big concern that seems to be being raised, as mentioned well by @THiebert , is that the party is trying to replace combat with one or two rolls for success or failure.

Don't allow just a Persuasion check, or a Deception check, etc. to substitute for a combat. Require the PC's to roleplay their social engineering activities and (as mentioned elsewhere on this site with regards to non-social skills) use rolls only once you have verified that the PC's plan seems reasonable. You can even set the required rolls based on how much the PC's proposal fits in with the social realities that you envision for your NPC's. Tricking a bunch of orcs into abandoning their base in search of a fictitious convoy to raid might require an easy roll, while tricking them into thinking that the PC's party is twice its actual size and run away in fear might be a harder roll. Tricking a powerful wizard into thinking that you are an even more powerful wizard (when you really are not) might require an even harder roll, and tricking the king into thinking that you are actually a jelly donut would probably be deemed so hard that the DM wouldn't even allow a roll ("You fail, there's no way he would believe that.").

If a player says "I try to persuade." or "I try to deceive.", ask them how they are going to do this. Here are some ways:

  • Tell lies. (What kind?)
    • Realistic?
    • Plausible but a longshot?
    • Wild?
    • Practically impossible?
    • Mathematically impossible? Perhaps the target's INT could come into play here to determine how likely they are to recognize the impossibility.
  • Use flattery.
  • Make a demonstration of power. Show off some shiny weapons, cast some impressive spells, etc. Perhaps burning through some valuable spell slots might be necessary! Here's an interesting way to "use" them outside of combat!
  • Quote notions of duty and honor. ("We saved your people five winters ago, so you owe us a favor or two.")
  • Wave shiny status symbols, important-looking documents, etc.
    • Were these symbols obtained 'legitimately'? Were they looted? Fabricated? Did whoever forged the symbols know what they were forging? What kind of expert would be required to identify them as fake? Do the NPC targets have access to such an expert? Could the PC's combine this with some kind of Intimidation to convince the otherwise skeptical NPC's to forgo investigating the symbol's provenance?
  • Try to get the NPC's to pity them (e.g. "we are all orphans" a la Gilbert and Sullivan's Pirates of Penzance) and cut them a break or offer them charity.
  • Preach religious or political doctrine and try to get the NPC's to convert to the PC's side.
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This is a very interesting topic in my opinion, first, because most people tend to play d20 in a combat focused manner, something which gets really boring over time.

There are a lot of good answers here that will surely help you to create a better game experience, I will try to complement.

That being said, I have been playing/dming for over 14 years now, and the best way to fix this problem, is to build a little more personality in the NPCs. This will not be easy, but you don't have to do it with everyone, just with the ones you feel should be a challenge for the players. A well-built NPC, with beliefs and rules they follow, would not be so easily convinced, and it may just require interaction from the other players, sometimes a bribe is not enough, the fighter would have to intimidate them as well. And even if they succeed in turning the NPCs, who is to say how many will turn and if they won't turn back later on, remembering the power of their leader in this case?

Create interesting conversations, do not depend exclusively on the rolls, allow the rolls to persuade, but as you are putting effort in your characters, demand effort in the interpretation and wording of your PCs, if they are lazily building speeches, heighten the difficulty of the test and explain it to them.

This may seem harsh in the beginning, but it will enhance their relationships with their characters.

The system is designed to allow for quick problem solving, differently from storytelling and a few others, this is why it seems hard to fix these situations.

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Make some combat encounters happen anyway, but modify them to balance against whatever benefit the players have gotten through social encounters.

Your players don't know what you have planned. If you have an encounter coming up you could alter it on the fly.

If the players manage to convince some NPCs to join them in the fight, then you can add more enemies, or make them stronger, to make the fight more difficult. That way you can make the players feel like they made the right decision by convincing the NPCs to join them.

You don't have to trivialize the combat encounters just because the players choose to go a social route, even though trivializing the combat encounters is probably be the goal of doing that.

Balancing the combat encounters on the fly like this will both make your social players feel like they did a good job while also letting your combat players shine. It shouldn't upset them, since they won't know you're doing it.


Of course, you don't have to balance the encounters. Sometimes it's enough to let them happen anyway. For example, the players manage to convince the main bad guy to surrender, but the main bad guy's lackeys won't have it and they start combat anyway.

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I'm just copying-and-pasting a bit from the homebrew stuff I'm working on that I think has relevance to this (obviously not 5E specific).

An example of a bad challenge might be one where the objective is to “convince the king to give us his sword”, and the characters are expected to continually make diplomacy checks until they have successfully convinced him. This sort of challenge is both narrow (it only allows for a very limited set of skills to be put to use) and shallow (convincing someone to do something is fundamentally a “yes or no” type situation - it should be modelled by a single check, not a dozen of them). It will result in only a small subset of the party (the social characters) being able to contribute, and even for them, it will be repetitive and dull.

It’s boring because it is intensely focused on a simple objective, that cannot really be broken down into steps. What we need to do is expand the challenge by broadening its scope beyond a single discussion. The party still needs the king’s sword, but the king has a counsellor who has his own eyes on the sword, and the party needs to overcome his various machinations - blackmail, threats, poison, sorcery - and expose his corruption before the king will consider their request.

Our skill challenge now has width. Instead of just being about diplomacy, it can incorporate skills around deflecting blackmail, resisting threats, detecting and treating poison, unravelling spells, reading people, investigation, stealth and diplomacy. At the same time, it has become deep - the situation provides enough obstacles that each success progresses the party past one, and into another. The GM can reply with something like “after successfully foiling his attempted blackmail, it appears the counsellor has turned to other means to counter your influence with the king - roll a perception check to see if you notice the poison in your breakfast.” instead of “the king looks one-sixth more convinced”.

I'm not really familiar with the Redbrand encounter, but reading between the lines, it seems like it's the sort of thing (winning over an entire mercenary band as allies) that is unlikely to be the result of a single Persuade roll. If the party (the whole party, not just the social character) agrees to pursue the social solution to the situation, it should result in a significant challenge for the whole party, not just a skill check for the Persuade monkey.

Divide the Redbrands into factions - one pro-party and one anti-party. Invent named NPCs to represent both factions. The party needs to woo one, and thwart the other. Think of curve-balls that the anti guy will throw in to the situation, and get the party to improvise solutions to them. This can be hard to throw together on the fly, but if you have some time, it can make a challenge like this much more believable, and enjoyable for everyone (instead of just the one person).

If the whole party doesn't agree with the social solution, well, it's hard to persuade people to be your friends while your other friends are trying to impale them on various pointy things.

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One thing I haven't seen mentioned much in the other answers is that you don't have to allow a social encounter to completely replace a combat one. It's not (usually) a binary situation. For example, you might have the NPC leader be unpersuadable, but some of his followers are willing to listen, and then a pre-combat social encounter doesn't completely avoid the combat but makes it substantially easier (you fight the boss, but not the underlings; maybe they even help out). Or perhaps one underling takes a swing at one party member; the rest of the party can now decide to resort to total violence, subdue the one attacker and press the negotiations more firmly, or try to get the NPCs to handle their own enthusiastic comrade. Alternatively, with a multi-part encounter / recurring hostile force, you might force a combat initially, but - if the party beats it by force of arms - allow them to persuade further enemies that combat is unwise.

You can also keep combat as an element by having one side demand a duel or tournament, say between champions, or within a given proving ground or even trial by combat. This is especially valid as an option if the party tries to convince the NPCs of their military prowess ("Join us, and together we can defeat him" / "Are you really so eager to die today? We've killed far tougher opponents than you lot") or needs to demonstrate a particular type of ability (such as mounted combat, archery or other ranged combat, submerged combat, etc.). It can be proposed by either side (as DM, think about situations where the NPCs might be in a position to make such challenges, or interpret what the PCs say as such a challenge). The duel might have rules (no lethal blows, for example, or 1v1 fights only), and of course an enemy (or less-than-honorable party member) might sometimes break the rules; this should have consequences (good and/or bad) for the rest of the encounter and possibly the rest of the campaign.

A few tips:

  • Successful social encounters should, in general, at least substantially reduce the difficulty of an associated combat (where they don't eliminate it), or perhaps somehow improve the rewards afterward or let the players gain some other benefit. However, it's fine to occasionally turn this tactic against the players, for example by having somebody who has no intention of negotiating in good faith use the talking time to set up a trap. Let the socially-optimized player have a chance (or several chances) to detect such deception, which might trigger combat as usual, but if they fail at that it might make all their other social successes in that encounter come to naught.
  • Keep the other players occupied, whether there's an actual fight in the offering or not. Give them a chance to notice one of the other NPCs deciding this talking stuff is a waste of time, or rely on them for things like knowledge rolls that the party face hasn't specialized in.
  • If there is a combat, make sure it keeps the other people involved. Don't have your hobgoblin leader challenge the party face to single combat (at least, not if this is a combat the social-focused PC is likely to win), have him and his lieutenants challenge the most combat-oriented party members, or at least have him challenge the barbarian.
  • Keep any part of an encounter that only involves one PC - be it a parley, a duel, or a drinking contest - short and flavorful, so the other players can enjoy spectating and not get bored.
  • Don't be afraid to have a player's reputation for a silver tongue or an imposing stature get ahead of them, and cause problems (or just become a less-effective way of solving problems) down the road. Force them to adapt or improve if they want to continue succeeding at social encounters that would otherwise be combats. At a minimum, the same approach shouldn't work every time.
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I generally make the PCs roleplay the actual negotiation, and then have them roll persuasion at the end, or at major junctions of the discussion for longer negotiations. The roleplaying determines what argument they're making or deal they're offering. The persuasion check determines how eloquently they made it.

If the deal is good enough, it won't take much persuasion to get the NPC to agree. But if they're asking everything and offering nothing, the best check in the world won't help them. Most of the time, things fall in the middle: the better your persuasion skill, the easier it is to offer a deal that benefits the PCs a bit more than the NPCs.

Say they're trying to motivate NPC soldiers to join a battle. The soldiers mainly just want to be paid more. If the PCs offer cash, but a bit less than the soldiers wanted, the roll's fairly easy. But the PCs instead argue that there's glory to be won in the fight. The soldiers don't really care about glory, so the PCs need to make their case eloquently if they want to convince anyone. That's where the roll comes in. Roll horribly and the phrasing will be something along the lines of "Come on, dudes! It'll be awesome!" Roll well enough and they channel the St. Crispin's Day speech.

(Having a fixed DC with Advantage or Disadvantage depending on the quality of the argument instead of variable DC might work well in 5th ed. I haven't played enough 5th to say for sure.)

Since finding a good argument can be as important as making it well, it gives some roleplaying opportunities before the discussion: learning enough about the other group to come up with a good argument. And since a specific agreement is struck after the negotiations succeed, instead of it just being "The PCs get everything they wanted", the specifics of the deal should give some ideas as to what comes next. In both cases, there will be opportunities before and after for all the players to do stuff. (Even during the negotiations, they can all chime in; it's just assumed that in-character, they're suggesting deals to the chief negotiator, who in turn decides how best to present it.)

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Make your NPCs seem more complex, so that persuasion attempts may work for some, but not all, and it will seem more realistic.

In addition to the great suggestions here, one other suggestion (inspired by this post on reddit) is to come up with a pre-built list of goals/motivations for your important NPC's, and to have on-hand a short random list to add onto random NPCs that the PC's choose to talk with.

To summarize the post (you really should go read it): create "instincts" and "obligations". Then allow your PC's to determine these through checks and play off of them to convince the NPCs to act how the PCs want them to.

Instincts are things like greed, courage, arrogance, etc... Random NPCs should have 1-2, important NPCs (content gates) should max out at 3-4.

Obligations are more complex, but range from "I owe my loyalty to X person/group for them doing Y" to "Telling a lie is unbecoming of a member of the royal guard". Similar limitations to Instincts should apply.

Players should be able to determine their instincts and obligations either through your roleplay of the NPC, or through successful insight checks. You can then set the DC of the persuasion/deception/intimidation checks based off of how the PCs are leveraging one or multiple of the NPC's instincts or obligations. Convincing an NPC to do something against their instincts and obligations is likely impossible, leveraging one against the other may be challenging depending on the relative strengths of their instincts and obligations, and appealing to both should make the persuasion almost guaranteed.

This encourages the PCs to persuade the NPCs to do things other than exactly what they want. If encountering a guard who has strong loyalty, but also crippling debt may allow you to leverage him to stay out of the fight, but will likely not allow you to convince him to join you. A mobster's minion who is hedonistic and under-valued by his boss may very well be able to be convinced to switch sides. It can also provide side-missions, as the PCs may have to promise to assist the NPC in some other way (gather rare materials, rescue a loved one, exonerate their family member, etc...) in exchange for their assistance. This exchanges making the current encounter easier with having to have more encounters later.

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