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I've checked the books and can't find an answer by RAW other than the DM decides, so I'd like to know the best way to handle this in my games.

What happens if a thug tries to intimidate/persuade the PCs? Do I roll vs the character's skill (and which one) or set a DC based on how difficult I think it is?

Most of the time I just describe the monster's/NPC's actions and let the players tell me how their character's react, but the monsters have those skills listed in the Monster Manual for a reason.

How can I best handle these checks in order for the monster to be effective and have the same failure chance as the PCs, while avoiding slowing down play or making the players feel cheated?

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Preserve Player Agency in Role Playing Games

While "DM decides" is a standard tool to keep play moving, removing player agency for what players decide to do can turn role playing into roll playing (letting the dice drive everything) and lead to low player satisfaction. The best way to deal with this is to role play the situation.

Ability checks are not saving throws.

You are right: most players will feel cheated if they are forced to do something they didn't choose to do (player agency) that isn't the result of a failed saving throw. Ability checks are similar to, but not the same as, saving throws. (DMG p. 237 and p. 238).

Saving throw fails can lead to players doing things against their will, but they are being influenced by some sort of power ... something like magic.

Examples:

  • The Fear save (failed) due to a Dragon's power to instill fear causes the character to flee rather than fight.

  • Failing to save versus the Umber Hulk's Confuse power can lead to characters running off, standing around, or even attacking someone in their party.

Ability check is a test to see whether a character succeeds at a task that he or she had decided to attempt.

Note that it is the player initiating something: player agency in action (which may fail anyway).

Compare that to a Contest (p. 238)

A contest is a kind of ability check that matches two creatures against each other.

If two NPC's are in a contest, the players can watch it play out as part of a scenario. Rolling for the result is an option you have ... or you can play out the scenario based on how you want to set up the follow on challenge for your players.

PC to NPC contest? As your question suggests, is it because the player initiated action, or a course of action, or is it a result of a DM initiated course of action? If the latter you are already driving the narrative: why roll? If rolling dice helps you get a feel for how strongly the NPC reacts, then the dice help you role play. If it is to create a saving throw for a social interaction that forces a character to act in a certain way, you may be headed to the railroad station.

What happens when a thug tries to intimidate a PC?

The DM's role playing skills come to the fore. If you set the conditions where the PC feels that she needs to choose a course of action, or feels threatened because of what the thug can do, or who his friends are, then role play the thug and the setting, then let the player choose. Otherwise, you can end up in a situation like this:

DM: "You feel intimidated."

Player: "I go ahead and do it anyway, he doesn't scare me."

DM: "You can't, you are intimidated, he won the intimidation roll."

Do you want to be the engineer on that railroad?

  • Scene: the PC bard is meeting a thug in a warehouse near the river docks. She is following a lead, and has been told to "come alone." (The wizard's bat familiar is flying high cover while the wizard hides/remains invisible at the extreme end of range.) Thug arrives with two associates, both of whom have heavy crossbows loaded. Thug's line of conversation is that bard is messing with stuff not her business, and she needs to buzz off. Bard (player agency) tries to role play a diplomatic quid pro quo deal with the thug, offers information, help, services, cash, something. Here, a social skills check for Persuasion makes sense: you want to gauge how well the NPC receives this unless you have already decided that he's not interested, in which case no roll matters.

Let's say the persuasion check fails.

  • The thug now threatens the bard with something more than harsh words if she doesn't mind her own business. (A passive Perception check about now to see if she or the wizard/bat detect the other three armed ruffians hiding behind some crates of mining equipment would be timely. Picking up on that is further intimidation, or a sense of threat).You don't need to roll for whether or not the bard feels intimidated: she'll either take the hint or not. Once again, her player agency is preserved, and you set the conditions for her to operate. What she chooses will determine whether or not there is a fight, or she gracefully bows out and looks for other leads. (If you want to roll for your own benefit, to see how aggressive, scary, or intimidating the thug's trying to be, that's something I did for years as a DM: let such rolls help me with flavoring the role playing. )

Social interactions between the PC and the NPC need to be in the hands of the player as much as possible. The NPCs are your tools for creating the environment and the challenge.

On pages 244-246 of the DMG, "Roleplaying Interactions" walks you through starting attitudes of NPC's, Conversation/Interaction, Charisma checks, and role playing. The details includes reactions and DC's based on the creature's initial status: Friendly, Indifferent, and Hostile. It also provides advice on how to use your body language and voice in enrich the encounter.

In Summary

The DM role plays these interactions, rather than relying on dice since this isn't a saving throw scenario. You can let the dice help you shape the role play of the NPC.

Why?

  1. It's part of the fun.
  2. Preserve player agency wherever you can.

Coda

I had a DM years ago whose theory on dealing with players was "give them enough rope, they'll hang themselves." He was mostly right. We got ourselves into all kinds of scrapes on our own volition by making decisions regardless of the signals he was sending us. Player agency to the limit, and immense fun.

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While I partially agree with KorvinStarmast's answer when it comes to preserving player agency, you don't have to make social skills useless in the hands of NPCs to do so. Simply not allowing an NPC to affect a PC with a skill like Intimidation or Persuasion because the PCs don't like being told what to do is utterly preposterous.

NPCs have social skill bonuses for a reason.

  • Thug (MM page 350) has a +2 bonus to Intimidation.
  • Spy (MM page 349) has a +5 bonus to Persuasion and Deception.
  • Priest (MM page 348) has a +3 bonus to Persuasion.
  • Noble (MM page 348) has a +5 bonus to Persuasion and Deception.
  • Gladiator (MM page 346) has a +5 bonus to Intimidation.
  • Cult Fanatic (MM page 345) has a +4 bonus to Persuasion and Deception.
  • Cultist (MM page 345) has a +2 bonus to Deception.
  • Bandit Captain (MM page 344) has a +4 bonus to Deception.
  • Assassin (MM page 343) has a +4 bonus to Deception.

Even monsters such as the Mindflayer (MM page 222) and the Medusa (MM page 214) have bonuses to social skills. If NPCs were intended to not be able affect PCs with social skills, the aforementioned entries in the Monster Manual would not have bonuses to social skills. Obviously, rule zero applies and the DM is free to rule according to his or her own philosophy in this regard. But arguing that PCs are intended to be immune to social skills by default is at a minimum intellectually dishonest.

Translate failed social contests into temporary circumstantial penalties.

The only fair way to solve this conundrum without making social skills worthless in the hands of NPCs while simultaneously not railroading the PCs is to translate failed social contests into temporary circumstantial penalties for the loser of the contest.

Let's say a thug is trying to intimidate a PC. The thug tells the PC to mind his or her own business and leave before things get bloody. You resolve this as an opposed social contest between the thug (Intimidation[CHA]) and the PC (Insight[WIS]), and the thug wins. You don't want to force the PC to actually leave because that would remove player agency, but you don't wan't to make the PC immune to the consequences of failing the social contest because that sends the message that PCs can ignore social skills without any repercussions.

Apply a temporary circumstantial morale penalty to actions that deviate from the thug's command. The PC wants to press forward despite the threat and ignore the fact that they have been successfully intimidated? Fine, but he or she takes a -2 morale penalty to any attack rolls, ability checks, or saving throws against the thug for the remainder of the scene/encounter due to shaken nerve. The penalty is the consequence of the PC failing the contest against the thug. This only applies to the characters who fail the contest; other PCs or hireling/henchmen NPCs wouldn't be affected unless they also failed the contest. They might notice that the PC taking the penalty has had his or her nerve shaken, but that would require a separate roll on their part (Perception or Insight are good choices).

Note that this is well supported by the rules. Specifically, see page 7 of the Player's Handbook regarding step 2 of the core mechanic - the D20:

Apply circumstantial bonuses and penalties. A class feature, a spell, a particular circumstance, or some other effect might give a bonus or penalty to the check.

A DM is well within his or her authority to assign a circumstantial penalty to any D20 roll.

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    \$\begingroup\$ @Dyndrilliac - join the ongoing discussion if you want to push your claim that I'm wrong. Considering this only addresses when a PC fails a roll, it's very telling that the roll is on the PC's side of the table, and not the other way around. However comments are not for debate, so please, join us in the chat: chat.stackexchange.com/rooms/27035/… \$\endgroup\$ – Lino Frank Ciaralli Aug 19 '15 at 16:19
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As a DM, this is how I handle it:

  1. Pick an arbitrary DC, based on what the PLAYER was last doing. For instance, if the player is confronting the NPC because he's bored and wants a fight, then the DC to intimidate him might be 12. If it's because he's desperate to save his dying sister, then he's a lot more motivated and harder to intimidate - so maybe an 18.

  2. Roll the dice, and tell the player how they feel about it.

e.g. I roll a 1, I might say:

He's stares at you with a constipated expression, and waves his sword randomly. You think he might be trying to scare you but he seems more likely to cut off his own ear, and you have to resist the urge to laugh.

If he rolled a 20, I might say:

You feel a chill run down your spine at his vicious glare. [NPC] leans towards you intimidatingly, and you suddenly feel certain that you'll be lucky to get out of this alive, never mind with all your limbs attached.

  1. The player now knows what the situation is, and can role-play an appropriate response.

Remember, skill checks like diplomacy and intimidate affect perception. What someone - including an npc - rolls, affects how they are perceived. So to represent the result of a roll, just let it influence your description of the scene. An NPC who gets a good diplomacy roll is "charming and friendly". Someone who rolls badly "looks like they are up to no good".

Additionally, be aware that as the DM, you are responsible for everything that is out of the players control - and that includes involuntary actions. There is nothing wrong with controlling something minor in a case like this. For instance, say the NPC and the player are trying to stare each other down. I'd have them roll opposed intimidate check, and then say, depending on the result,

You flinch, and take an involuntary step back. Looks like he's scared you.

or

He flinches, and takes an involuntary step back. Looks like you've scared him.

And the player can then continue role-playing from there. If the player wants to, he can do whatever he wants here, completely ignoring the results of the roll - but at least you've set the scene.

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    \$\begingroup\$ Yes, use the roll to decide if you as DM should actually intimidate the players or not :p \$\endgroup\$ – GMNoob Aug 16 '15 at 14:20
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First off I'd think about, what are rolls for:

  • Decide conflicts, that can't be decided otherwise.
  • Determine if a PC is able to do something.
  • Decide how good/bad something ends.

In your case it's about a conflict and the question is: can it be decided otherwise? If a monster tries to intimidate or seduce a PC and the player decides that his PC falls for it, there is no need to force a roll. The Player can describe his PC's reaction and you can play on from that.

There are some situations where I'd think about letting the situation be decided by a roll:

  1. Some players just ignore social skill and decrease them for more points in combat skills, but when it comes to social interactions they still play them as though their PC is great in that, because they can play it out and get through it. In that case I'd force a player that can and does play his PC's social skills way better than his scores and abilities represent to make some rolls in social situations.
    The main reason for this is so that players who put points into social skills are not punished for that choice. In each case the decision highly depends on the situation.
  2. Sometimes players try to take a "my PC backs away cause he's intimidated" to not suffer from harder results of a social skill situation. In that case it might be fitting to let a roll decide the situation, to ensure that a PC could be hit by the full spectrum of results.
    This is mainly applicable if a Player tries to get out of social interactions with taking a "small loss" on a regular base. In that case a GM should talk to him outside of the game to see what's up with that, and how they want to deal with it at the table.
  3. Some Players are not that comfortable with playing social interactions. Even though they might think about their PC in these situations a lot, and have a clear idea on how their PC would react in it, they just can't play it themselves. In that case I'd give them the possibility of a roll to get a result without having to play it. I had some newer players that weren't so comfortable with roleplaying yet that were happy to let a roll decide a situation. In the long run you shouldn't let this become the common thing, but you can use it in situations where the player can't find a better way for a solution and then try to create a better situation ne next time.

The overall thought process in a social situation is:

  • Does it hurt to get a solution without rolling?
  • Does any player benefit from a roll?
  • Could the situation be improve the next time around?
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Preserve Player Agency by sharing DMing with the player

This is a system that I use both for monster vs. player rolls, and player vs. player rolls.

Essentially, when it comes to a social skills check, I let the target be the DM for a moment, giving them control of one iteration of the game loop, i.e.

  1. The player describes their character.
  2. Monsters/players describe social actions they want to take.
  3. The player describes the outcome, possibly having decided using dice rolls.

They then get to decide what the possible outcomes of the check are, including if the check is irrelevant.

I've found that this works well because if a check does occur, it's the players choice, and they also get to decide how much they are affected by it. This allows them to both maintain control over their character's agency, but also let the dice help them decide what their character does if they want.

Further, if they really strongly don't want to be affected at all, they can effectively opt out of the check. This is a useful release valve to avoid circumstances that would really damage that player's enjoyment of the game; but in practice I've found it almost never used, including in PvP checks.

In practice I never use this for persuasion checks, but there's nothing to stop it from being used in that way.

In more detail:

  1. Monster or Player 2 role-plays some social interaction with Player 1.
  2. They want to socially affect Player 1.
  3. I hand over the reins to Player 1, asking them "Is there no chance of success or no chance of failure to e.g. persuade your character here?"
  4. If they say that one outcome is certain, the game continues.
  5. If they say it's uncertain (which we have agreed beforehand means they are willing to let the dice decide how their character reacts to some degree), I ask them to secretly (a) set a DC or series of DCs for uncontested checks (e.g. persuasion), where I give them some priming examples like "DC 10 = a ~50/50 chance that an average person could persuade you here" or (b) set levels of success (e.g. "beat, beat by 5, lost by 5") for a contested check (e.g. deception vs. insight). The option to set more than one outcome allows them to say their character would be affected in a stronger/different way by a big success than they would by a small one.
  6. Checks are rolled.
  7. I ask Player 1 how their character seems to react, and they describe it.
  8. The game continues.
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  • \$\begingroup\$ Letting the player set the DC is a really smart way to handle this. I'm curious why you have them do it secretly, though. \$\endgroup\$ – Mark Wells Jul 4 at 14:38
  • \$\begingroup\$ @MarkWells Thanks! There are 2 main reasons: (1) It lets them keep some mystique around their character's motivations and triggers, leaving a player who tries to e.g. persuade them to have to work those out more on the role-play level than the mechanical level over the course of many interactions, and (2) It gives them the option to not actually "set" an explicit series of DCs, but just eyeball it once they see the result; which I think is a reasonable (and often faster) way of doing it too (indeed, that is what I often do as DM when NPCs are targeted with social checks). \$\endgroup\$ – Vigil Jul 4 at 16:01
  • \$\begingroup\$ I like how you approach this. I will try it out next week with our Thursday group. Thanks and a +1. \$\endgroup\$ – KorvinStarmast Sep 4 at 14:16
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In order to maximize immersion, I always favor minimization of meta-gaming. Roll-play is one aspect of metagaming - it's about dice on a table, not about orcs in a forest. So:

  1. Roll the social skill, be it intimidation, diplomacy, whatever in secret.
  2. Describe accordingly.

This:

The huge thug bulges over you, his combat prowess evident in every minute movement. "Your gold or your life" he grunts calmly.

vs

The bandit steps closer. As he utters "Your gold or your life" his pupils dilate slightly, he scans past you.

appeals to me far more than this:

The bandit rolls successful intimidation against your character, act accordingly.

or even the worse:

The bandit rolls successful intimidation against your character. You give him your gold pouch with trembling hands.

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