I'm a relatively new DM - I ran some games back in the early 80's, basic dungeon crawls and we had a great time. Today, I'm starting with some of the intro 5e campaigns. I'd like to get an opinion on this scenario:

My party is doing well with talking to NPC's using persuasion and intimidate and moving the story along by obtaining all the necessary information. They will be coming upon a rather strong adversarial NPC that where they will use the same techniques (instead of killing) and will likely convince this powerful NPC they are friends.

The NPC has a treasure chest with a key item to the story that can easily be handed over. The treasure chest also contains some nice items that the party would benefit to have. If the party and NPC are on friendly terms, what (if any) method or role play should be used for the NPC to hand over the other items (assume no killing)? The NPC is friendly, but, he certainly wouldn't hand over his magic items or the sum total of his wealth in gold pieces.

The NPC is initially very adversarial and will fight if necessary. Assuming the players roll intimidation and succeed, then, the NPC will be intimidated and not fight. Not friendly per se, but, willing to talk.

Once discussion begins, the NPC will give them an item to move the story along. There is nothing necessary for the story in the treasure chest, just all "nice to have".

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    \$\begingroup\$ Oh and Welcome to RPG.SE! Take the tour if you haven't already and see the help center or ask us here in the comments (use @ to ping someone) if you need more guidance. Good Luck and Happy Gaming! \$\endgroup\$
    – Someone_Evil
    Apr 7, 2020 at 14:29
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    \$\begingroup\$ Neat, I added the appropriate tag and a touch of editing to make it easier to read (long, blocky paragraphs makes it easy to go cross-eyed). Some further clarifications I think would be useful: What is the nature of this NPC relative to the party? You start by calling them adversarial and then say they are friendly which seems like a contradiction. Also, is this an item the party needs for story reasons or just a cool/useful item. \$\endgroup\$
    – Someone_Evil
    Apr 7, 2020 at 14:48
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    \$\begingroup\$ Thanks!! I made additional clarifications in the original post. Thanks for the formatting as well! Definitely just cool/useful items in the chest. \$\endgroup\$
    – Davey
    Apr 7, 2020 at 15:45

4 Answers 4


This is a nice system-agnostic question, but I'll open with a quote from Dungeon World. If you ignore the small amount of mechanics in it, it essentially answers the question:

When you have leverage on a GM Character and manipulate them, roll+Cha. Leverage is something they need or want.

On a 10+, they do what you ask if you first promise what they ask of you. On a 7–9, they will do what you ask, but need some concrete assurance of your promise, right now. Parley covers a lot of ground including old standbys like intimidation and diplomacy. You know you’re using parley when you’re trying to get someone to do something for you by holding a promise or threat over them. Your leverage can be nasty or nice, the tone doesn’t matter.

Merely asking someone politely isn’t parleying. That’s just talking. You say, Leverage is anything that could lure the target of your parley to do something for you. Maybe it’s something they want or something they don’t want you to do. Like a sack of gold. Or punching them in the face. What counts as leverage depends on the people involved and the request being made. Threaten a lone goblin with death and you have leverage. Threaten a goblin backed up by his gang with death and he might think he’s better off in a fight.

So, you are right that they wouldn't just hand over the treasure. They need to get something in return.

That could be something tangible (here is some money). That could be the lack of something (hand it over and we won't smash your face in). Something based on a lie (the dark lord Zzzz'Zxxxx will rise and burn the town down and we can only stop them if you give us the item).

The trick is convincing the NPC that the deal is worth it.

If you leave aside the "persuasion and intimidate" options that the players are fond of, as well as ruling out killing, then that leaves you various forms of theft.

Sneak past them as steal it.

Render them incapacitated (without killing them) and steal it.

Use magic to steal it from a distance (I don't recall any spell that D&D has which would do this, so it would likely require something custom).

  • \$\begingroup\$ Thank you for the suggestion. Thinking about it as leverage is how I was leaning. Either the NPC can say "bring me what I want and I'll reward you" or, the players can demand the items and then promise to deliver what the NPC wants. I'm just not sure my players will think to demand to see what is in the chest. \$\endgroup\$
    – Davey
    Apr 7, 2020 at 16:00
  • \$\begingroup\$ Note that the question is now tagged as being about/for D&D 5e. You may want to update your answer accordingly, if applicable. \$\endgroup\$
    – V2Blast
    Apr 8, 2020 at 3:33
  • \$\begingroup\$ @Davey If you specifically want your players to try to find out the contents of the chest (or to actually try to retrieve the items), just make a point of bringing it to their attention. When you describe their surroundings, make sure to mention the ornate chest in the corner of the room; that the NPC keeps trying to put himself between you and it, as if to try to hide it. Maybe even outright say that the NPC notices a player scanning the room and quickly throws a sheet over the chest. Any one or several of those will draw attention to the chest. Let your players take it from there. \$\endgroup\$
    – Doc
    Apr 8, 2020 at 4:29

One of the things that makes pen and paper RPGs unique is the vast array of ways you can solve the same problem. As you have pointed out, there are at least two ways of getting the quest item from this NPC, fighting or negotiating. Both strategies are equally valid. That does not mean they need to have equal outcomes. It is ok if the party gets less material rewards for talking to the NPC than fighting them. The group is making choices and different choices have different consequences.

The real situation to deal with here is how to make sure having a "better" outcome for violence doesn't encourage "murder hobo" behavior and is fun for a party like yours that enjoys negotiating. Here are a few things I have found that encourage more diverse play styles.

Adversarial NPCs are not just obstacles to loot

Whenever you have an adversarial NPC think about their role in the world. By giving them connections and motivations, there are reasons they can have value to the players when kept alive. One of the easiest ways to do this is with information. They might be willing to share what they know about the Big Bad Evil Guy, or the location of other treasures, or even just the name of a guy in town who will give them a good price for their loot. This can be as part of a trade, but if there is no direct conflict of motives it can also just be part of a conversation.

Another possible option is a willingness to do favors and build relationships. Maybe they are a spellcaster who is willing to cast some cantrips for the party; what do they care, it doesn't cost them anything. Maybe if the party maintains a relationship they can even ask for bigger favors. The last campaign I was in developed a whole subplot where the goblins we were supposed to kill in the first chapter started a trading relationship with the human village, with the party serving as negotiators. It was one of my favorite parts of the campaign.

The PCs gain a reputation

As the players continue in the campaign doing progressively more and more notable feats, people will have begun to have heard of them. If they gain a reputation for "murder first and ask questions later" then if NPCs hear they are in town they might do things to stop them before they cause trouble. This doesn't just have to be adversaries, if the town leader hears trouble makers are around, they might send guards to keep an eye on them.

On the other hand, if they have a reputation for talking things out, they may find that people start offering them information or bribes. Maybe some of the minions aren't 100% thrilled with the bad guy's plans and are willing to share secret weaknesses in exchange for leniency. Maybe the bad guy himself might want to see if they can resolve the conflict peacefully with the help of such a diplomatic party.

Since these things aren't immediate, it is a good idea to seed these kinds of ideas slowly rather than bringing them in all at once so the party doesn't feel "punished" for things out of their control. Have some NPCs early on who are skeptical of "murder hungry adventurers" and they'll be keeping an eye on them. Have other NPCs try approaching them with information to trade because they seem trustworthy. Generally seed the idea that people have preconceptions and those preconceptions can change.

Not all conflicts have the same "best strategy"

The other thing to keep in mind is that your party is playing this game for many sessions and not just one offs. It is ok if in some sessions the party come out objectively worse for having negotiated rather than fought so long as in other sessions they come out better. Maybe in this session the party might lose out on all that loot because they decided to talk and the NPC doesn't have any worthwhile information the party gains. Just make sure there is some later session where diplomacy will get them more than if they had just killed everything in their path. This type of campaign tends to be a lot of fun for many players as they can try to figure out the best approach for each situation and it rewards different play styles at various points in the campaign.


This is a age old question: How much (if at all) can you overcome/avoid a combat challenge with social skills?

You are aiming for "overcome completely", to the point where he actually hands over all the treasure. But you fear social is only - for lack of a better word - valid for "overcome partially", i.e. him handing out only the quest item, but not everything else.

The simplest way would be to just declare he hands it all over. If they get only "partial loot" from Social defeating (and can propably see it clearly in this case), that would just incentivise the good old murder-hobo behavior. You do not have murder-hobos right now, wich is something many GM's aim to get.

If you want him to hand everything over, you can just declare he does. You are the GM, you can declare that kind of stuff. Of course, it should not be trivial or risk free to get everything either. If it was either of those, it would become quickly boring. It would be easiest if there was some form of social conflict/combat System you could fall back on. On a "total defeat" he would hand over everything. This group clearly seems to indicate you could use one. Unfortunately I do not have any for D&D, but I hope they have one in some ruleset.

A possible workaround: Move the chest/the loot from "behind the NPC" to "behind whatever that key opens"? That way getting the key gets the full loot either way. This would even work if you plan to hide "loot" behind a animal. It just guards the key (not understanding what it is).

  • \$\begingroup\$ You may be interested in reading up on the Fate system, where you can use words to attack my social defences while I use weapons to attack your physical ones. The encounter ends when one or the other of us takes enough hits, either physically or socially. \$\endgroup\$ Apr 8, 2020 at 0:08
  • \$\begingroup\$ @JoelHarmon I know of at least 1 other System like that. "Spaceport Adamant", IIRC. But a old version of Warhammer Fantasy had a intersting System for it too (making it a tug of war with limited tries). But as I do not actively GM and am not exactly a social master in RL, it is not really for me. \$\endgroup\$ Apr 8, 2020 at 10:48
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    \$\begingroup\$ While the GM certainly can declare that the NPC hands everything over, the OP seems to be looking for something with a little more verisimilitude than "Oh, hi, stranger! Can I have your life savings and everything else you own?" "Sure, you seem like a nice guy. Here you go!" \$\endgroup\$ Apr 8, 2020 at 12:37
  • \$\begingroup\$ @DaveSherohman That ship sailed when he allowed the to defeat him using social skills, rather then combat. And without something specific like a specific social combat system, we can not really add anything. | Also, my workaround could easily work by splitting the loot between "behind door" and "behind NPC". \$\endgroup\$ Apr 8, 2020 at 16:38

Follow the Rules

There is a section in the DMG on page 244 titled "Social Interaction" which covers this exact situation. I recommend you read it, but I'll provide two summaries here.

Short Short version

Tailored to your case: Roll a Charisma (Intimidation) with Advantage against a DC 20. If the PC succeeds, the character hands over the item. If not, tough luck.

That is based on your question implying the item is moderately important to the character, the character starts off neither actively hostile nor actively helpful, and the party is working together to intimidate the character. See below for details.

Short Version

Below is a summary of the full DMG rules, with some notes on how it applies to you.

Starting Attitude

There are three categories this character could start as:

  • Friendly - will go out of way to help party
  • Indifferent - will not do much either way without persuasion
  • Hostile - will go out of way to harm party

Based on your description, the character starts off rather neutral toward the party. They aren't actively opposed but they aren't going to volunteer, either. They could be persuaded, which leads nicely into


This is the role playing portion. It's possible to shift the character's attitude in either direction by appealing to its ideals, bonds, and flaws. This shift may be temporary or permanent.

To determine those characteristics, the party may already have good clues based on previous world building or the current conversation. They may also attempt a Wisdom (Insight) check with a DC you set. A particularly poor roll (10 below DC) might give the party the wrong idea.

However it pans out, it's largely the DM's call on how the character reacts.

Charisma Check

Depending on the party's approach, and at an appropriate point in the conversation, you call for a Persuasion, Deception, or Intimidation roll from one of the participating PCs. The check can be aided by other characters who make contributions to the conversation, giving the roller advantage. Gaffes may impose disadvantage.

There are some tables for the results. Most likely applicable here:

  • Friendly, DC 10: minor sacrifice
  • Friendly, DC 20: major sacrifice
  • Indifferent, DC 20: minor sacrifice

Any other results don't point to the party getting the item, but they may end up getting advice or other information.

It may also be possible to repeat the above steps if there are multi-part requests. In your case, you could have them roll once for the macguffin and again for other assorted items, information, social connections, or direct combat assistance.

Final note

Don't forget the rule on Inspiration, if it's something you choose to use and the players earn it.


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