In the current urban campaign I'm running, the party is getting into the habit of interrogating people. Nothing too violent yet, but mostly the Teifling using Thaumaturgy to change his eyes color and give some spooky wind flow that he threatens the person being interrogated of having his soul committed to some demon if they do not talk. It seems like after a few intimidation checks; the party gets what they want out of the person.
I think I'm doing this wrong because what is the point of making checks if the party is not going to relent on the subject until they get the answers they want or accept.
I thought, why not ask the hivemind how they run interrogations? Maybe there is something I can learn from or take a homebrew approach to the subject.
So, I wonder if this falls into the same category of the 'convincing the guard they killed the NPC with persuasion' trope?
It always annoys me when I see skits like that on comedy D&D vids. Fact is the NPC knows they didn't kill the person, simple persuasion won't change that. Neither would intimidation with just words. Now, if the party have got something on that NPC (their family's lives, or evidence of infidelity etc) then that might get the NPC to falsely confess. Otherwise, no sane person is going to confess to something they didn't do.
So in that same vein it would seem to be about the character themselves. How loyal is this NPC to the person they've got information about? There's a huge difference between a guard who doesn't have a family, a guard who has a family, and the head guard of a castle. The guard with no family ties, hasn't got anyone outside of themselves to protect so their death is likely to be something that would frighten them beyond anything. That character might spill the info on the secret entrance to the castle under duress. The guard with a family might be less afraid of their own death and instead realise that being known as the person to reveal the secret entrance is treason, for which his family might get exiled...so no amount of simple intimidation or persuasion is going to result in success for the party. Blackmail, or threats against their family on the other hand...that's different. Then there's the chief of the guard. Utterly loyal to their core, and fanatically dedicated to their country and Queen. They will, under no circumstances reveal information. They may even have had training to resist torture.
In short, a player could roll a nat 20 and still fail to elicit the info they are looking for because the fear of death isn't stronger than their loyalty or other motivations. It's why so many DMs make it clear that a nat 20 isn't always going to be a success.
Then you can take a real life example. People lie and tell the interrogators what they want to hear under duress. I'd actually class what your players are doing here as torture. And under such duress people do lie. Generally that lie is in the form of telling the players what they want to hear. 'Yes there is a secret entrance, it's here'. Maybe that entrance leads into the guards' quarters. Maybe once the party have let this person go free they're going to find a way to organise the guards into a position to trap and arrest the party. Either way, just like real life interrogators, they won't always be able to tell the difference between a lie under duress and the truth...this is why people have confessed to murder in police interrogation rooms in the real world.
More than that, long periods of interrogation often shut people down in real life. They begin to become unresponsive or worse still erratic. Their answers begin to contradict each other. There's tons of fascinating psychology on the matter if you're that way inclined.
On top of that you as DM decide how long to ride the check for. If they rolled intimidation, and failed...that check could easily apply to the whole intimidation attempt by that PC. So, I would respond with something like 'no matter how hard you try, how many questions you ask or threats you make, the NPC just doesn't believe your threats...you're unsuccessful'. Sure they might decide they want to try a different tack, but sorry, it doesn't work that way. You decide when the dice are rolled and when a check is made, not the players. Now if said PC wanted to instead try a new approach entirely...maybe trying to persuade that NPC, well guess what? That's at disadvantage. He already is hostile to you and didn't buy your intimidation, that's going to make it harder to persuade them.
All of this is part and parcel of the basic rule set so no homebrew required. I truly think it comes down to knowing your NPC. If you have made one up on the fly...and how many times have we as DMs done that eh? Then when the player tries to intimidate take a moment while the PC is describing how they are trying to intimidate to think about who the NPC is. You could even call a quick break for refilling of drinks, toilet etc, and during said break come up with that stuff. Then you know and can respond from a place that is grounded in who the person they are interrogating is. That's how I'd approach it anyhow.
If they rolled intimidation, and failed...that check could easily apply to the whole intimidation attempt by that PC. So, I would respond with something like 'no matter how hard you try, how many questions you ask or threats you make, the NPC just doesn't believe your threats...you're unsuccessful'.
Yeah this is how I do it. You make a check and it works or it doesn't. If it doesn't, you don't just get to reroll it again.
If you really wanted, you could allow them to try again tomorrow, letting the prisoner stew for a while. Of course, that opens up possibilities of a prison break that night... Somehow the situation needs to change to warrant a new check.
Yeah, multiple intimidation checks as the same PC changes up tactics is a bit silly. If you want to go "round the horn" with the whole party with each one getting a crack, you could do that. Or assume the "round the horn" approach means the lead interrogator character gets advantage and there's one check.
But an NPC "intimidated" does not necessarily mean the NPC will cooperate with the investigation. As pointed out intimidation is basically making someone feel threatened. In the context of an interrogation/interview that mindset puts many personalities into a fight/flight "say anything" mode and the credence one should give whatever is said in those contexts should be cautious. The "bullied" or "beaten" confession you see in cop and secret agent TV is a fiction of TV timescale and misunderstanding of what such techniques' goal are among IRL cops and operatives. Beating a confession out of someone is not about getting to any unknown truth. It's forcing the subject of the interview to conform to a preconceived theory of the interrogator or otherwise play "guess what I'm thinking" in order to satisfy the interrogator. Clearly, not best practices.
So yeah, battlefield interrogations where there's gun to the head sort of questioning or waterboarding etc. Those do nothing but give a pretext of "confirmation" for a group to act on "intelligence" they think they already know. The long form custodial "enhanced interrogation" torture programs are also problematic in that the torture is there to break down the mind of the subject so analysts can sift through fragments. Imagine the mind as a book in a locked box, a torture program is designed to blow up the box so you can read the bits of paper that might have survived the blast, and if you blow up enough boxes, you might have the story.
Effective interrogation is actually more often called interviewing. It's persuasion intensive and requires a rapport between interviewer and subject which can be challenging because of the likely broad range of differences that put the interviewer and subject in adversity. You need a very performative personality in the interviewer spot to bridge that gap to convince the subject they're valued in a way they want to be valued, which is often very different from the value the subject's knowledge actually holds for the interviewer.
Basically, in game, treat significant sources of information like puzzles, design them as social puzzles. As a foundation use the standard motivation for people who become sources in espionage: money, ideology, compromise, and ego (compromise in this context means the subject is a proverbial "hard place" and needs to work something out with the folks that got 'em) play the social puzzle to determine the best way to roll the subject into compliance. Depth of puzzle depends on depth of information. You can also plant "traps" in the puzzle where the subject will misinform the PCs.
In other words, it's not "I roll itimidation or persuasion" to interrogate, the PC needs to articulate the play they're making that the skill check represents (by which you can set the DC).
While writing this I started to like the idea of Iron Shadow Hobgoblins having been through something akin to SERE school, and having a captive Iron Shadow behaving like Denzel Washington in Safe House.
Rollback Post to RevisionRollBack
Jander Sunstar is the thinking person's Drizzt, fight me.
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
May I ask why you allow them three checks? Is there a gameplay or storytelling benefit to allowing them a second shot at the same check?
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
May I ask why you allow them three checks? Is there a gameplay or storytelling benefit to allowing them a second shot at the same check?
I cant speak for the OP but from my perspective if you think about a real life interrogation scenario it is unlikely that the first round will reveal anything. The subject is fed, watered, only recently been caught and feeling cocky. Over time they will slowly break down, so 3 checks indicates a longer period of time needed to get the information, but also after 3 failed checks the target of interrogation has basically said, either kill/hurt me, or let me go I am not telling you anything
In the current urban campaign I'm running, the party is getting into the habit of interrogating people. Nothing too violent yet, but mostly the Teifling using Thaumaturgy to change his eyes color and give some spooky wind flow that he threatens the person being interrogated of having his soul committed to some demon if they do not talk. It seems like after a few intimidation checks; the party gets what they want out of the person.
I think I'm doing this wrong because what is the point of making checks if the party is not going to relent on the subject until they get the answers they want or accept.
I thought, why not ask the hivemind how they run interrogations? Maybe there is something I can learn from or take a homebrew approach to the subject.
So mechanically you are applying the rules in a way that works, but, letting the players do the same thing over and over again can get boring both for them and for you as a DM. intimidation and threatening during Interrogation can be a famously bad way of getting information in the moment, especially if there is no legal backing to the process. Sometimes my players will do that and I will purposely give them a ton of false information they can't check in the moment. I once sent a party on an 8 session wild goose chase after they tortured a guy who knew nothing and int he end told them what he thought they wanted to hear. They learnt from that as characters that sometimes honey is better than salt.
The key thing for you to consider is "does this character actually hold information I want the party to have to progress the story", If they do not and the characters don't believe them, then consider what they do know that they can embellish, lie about etc that the party will believe and then stop what they are doing and move on. if the character then knows they lied then consider what they do afterwards. Also consider the risk reward, if the character knows something, but telling will see the big bad kill them, then having his soul committed to a demon in the distant future when he dies might be more acceptable to having the bbeg kill him now. have a character call the players bluff, maybe have them interrogate someone who has already signed a pact with a demon or devil. Or who understands that isn't how it works anyway. Don't just pander to your party, as a DM it is perfectly acceptable to metagame and pre empt what the party always do to make them think differently.
Now if they do hold information you want the party to have then never make the recovery of that information be reliant on a dice roll, it is like presenting a locked door to the party that is the only way through the continue the quest, if they fail the dice rolls to get through what do you do. Have the players make the necessary rolls but, the success becomes about how long it takes to get the information, not if it succeeds or fails, and tell the players that, if they roll a nat 1 tell them that they spend 5 days interrogating this individual and he finally lets slip a name and a location. They have now lost 5 days to this scene but they have the information you needed to give them.
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
May I ask why you allow them three checks? Is there a gameplay or storytelling benefit to allowing them a second shot at the same check?
I cant speak for the OP but from my perspective if you think about a real life interrogation scenario it is unlikely that the first round will reveal anything. The subject is fed, watered, only recently been caught and feeling cocky. Over time they will slowly break down, so 3 checks indicates a longer period of time needed to get the information, but also after 3 failed checks the target of interrogation has basically said, either kill/hurt me, or let me go I am not telling you anything
Oh that certainly makes sense if time is passing, or if the PCs are trying a different tack as I mentioned. But if those rolls are happing almost immediately...that's got to be a no go. The situation you outline, we're talking about hours if not days in general.
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
May I ask why you allow them three checks? Is there a gameplay or storytelling benefit to allowing them a second shot at the same check?
I cant speak for the OP but from my perspective if you think about a real life interrogation scenario it is unlikely that the first round will reveal anything. The subject is fed, watered, only recently been caught and feeling cocky. Over time they will slowly break down, so 3 checks indicates a longer period of time needed to get the information, but also after 3 failed checks the target of interrogation has basically said, either kill/hurt me, or let me go I am not telling you anything
Oh that certainly makes sense if time is passing, or if the PCs are trying a different tack as I mentioned. But if those rolls are happing almost immediately...that's got to be a no go. The situation you outline, we're talking about hours if not days in general.
In game that might be several seconds or mins of rolling, but my party understand that in game a lot of time has passed
I'd take a couple steps back before making checks.
1) Does the NPC know anything of any use? What exactly do they know?
2) Do you want the players to obtain the information for plot purposes? Will having the information help or hinder running the ongoing content? Are the players likely to choose the preferred direction when given the information.
Interrogating NPCs from the DM perspective is all about plot advancement OR giving the characters something cool.
3) What is the NPC like? Would they under any circumstances share information and would it be truthful?
Once the DM knows these things - interrogations become easy.
1) Give the characters whatever specific information you want to give them. Give them additional checks as part of the process as they come up with alternate strategies. The only reason you allow multiple checks is because you plan to give the characters this information anyway and role playing them working for it can be fun. Alternatively, if you don't want to role play it you can narrate the intense interrogation and the information the NPC eventually gives up.
2) If the NPC has optional information and you whether the characters receive it or not isn't crucial then have them describe their attempts and make one roll, possibly with advantage if they come up with good ideas. Succeed and give them the info, fail and they won't be able to get it.
3) The NPC won't give up the information no matter what. Regular interrogation won't work - characters will need to resort to Zone of Truth, Detect Thoughts, Telepathy and other techniques of finding out what the creature is thinking rather than what they are saying. Regular interrogation techniques either are just narrated failure or the characters roll and no matter what is rolled the DM says it does not succeed even if the character rolls a 20. A 20 is not an automatic success at an impossible task.
Finally, never reward torture. Some characters can take a very dark path when trying to obtain information and this never ends well. Torture is not an effective technique since the victim will often just say whatever they think the torturer wants to hear. In addition, if someone is being tortured, telling the truth isn't likely to save them or cause the torture to end, so any information obtained this way is far from reliable and could well just be a trap. A DM should feel free to give false information leading to a deadly encounter for characters who want to employ this type of technique.
I wouldn't allow more than 1 intimidation check. The characters get all of their little tricks and strategies together, and if its convincing enough, give them advantage or a lower DC but not multiple attempts.
If they fail the first check the victim is obviously not intimidated. It's very hard to threaten someone who isnt intimidated.
Dont tell them what the DC is. Have them tell you what their result is. Then simply have the interrogated NPC tell them something. They wouldn't know if it's the truth or not until they investigate it. If they roll low, lie to them, or have him/her repeatedly deny knowledge. But dont tell them they failed the check.
Now, if your players decide to move from Intimidation to Torture, that's a completely different thing. Torture often ends up with the NPC saying what he THINKS they want to hear.
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In the current urban campaign I'm running, the party is getting into the habit of interrogating people. Nothing too violent yet, but mostly the Teifling using Thaumaturgy to change his eyes color and give some spooky wind flow that he threatens the person being interrogated of having his soul committed to some demon if they do not talk. It seems like after a few intimidation checks; the party gets what they want out of the person.
I think I'm doing this wrong because what is the point of making checks if the party is not going to relent on the subject until they get the answers they want or accept.
I thought, why not ask the hivemind how they run interrogations? Maybe there is something I can learn from or take a homebrew approach to the subject.
So, I wonder if this falls into the same category of the 'convincing the guard they killed the NPC with persuasion' trope?
It always annoys me when I see skits like that on comedy D&D vids. Fact is the NPC knows they didn't kill the person, simple persuasion won't change that. Neither would intimidation with just words. Now, if the party have got something on that NPC (their family's lives, or evidence of infidelity etc) then that might get the NPC to falsely confess. Otherwise, no sane person is going to confess to something they didn't do.
So in that same vein it would seem to be about the character themselves. How loyal is this NPC to the person they've got information about? There's a huge difference between a guard who doesn't have a family, a guard who has a family, and the head guard of a castle. The guard with no family ties, hasn't got anyone outside of themselves to protect so their death is likely to be something that would frighten them beyond anything. That character might spill the info on the secret entrance to the castle under duress. The guard with a family might be less afraid of their own death and instead realise that being known as the person to reveal the secret entrance is treason, for which his family might get exiled...so no amount of simple intimidation or persuasion is going to result in success for the party. Blackmail, or threats against their family on the other hand...that's different. Then there's the chief of the guard. Utterly loyal to their core, and fanatically dedicated to their country and Queen. They will, under no circumstances reveal information. They may even have had training to resist torture.
In short, a player could roll a nat 20 and still fail to elicit the info they are looking for because the fear of death isn't stronger than their loyalty or other motivations. It's why so many DMs make it clear that a nat 20 isn't always going to be a success.
Then you can take a real life example. People lie and tell the interrogators what they want to hear under duress. I'd actually class what your players are doing here as torture. And under such duress people do lie. Generally that lie is in the form of telling the players what they want to hear. 'Yes there is a secret entrance, it's here'. Maybe that entrance leads into the guards' quarters. Maybe once the party have let this person go free they're going to find a way to organise the guards into a position to trap and arrest the party. Either way, just like real life interrogators, they won't always be able to tell the difference between a lie under duress and the truth...this is why people have confessed to murder in police interrogation rooms in the real world.
More than that, long periods of interrogation often shut people down in real life. They begin to become unresponsive or worse still erratic. Their answers begin to contradict each other. There's tons of fascinating psychology on the matter if you're that way inclined.
On top of that you as DM decide how long to ride the check for. If they rolled intimidation, and failed...that check could easily apply to the whole intimidation attempt by that PC. So, I would respond with something like 'no matter how hard you try, how many questions you ask or threats you make, the NPC just doesn't believe your threats...you're unsuccessful'. Sure they might decide they want to try a different tack, but sorry, it doesn't work that way. You decide when the dice are rolled and when a check is made, not the players. Now if said PC wanted to instead try a new approach entirely...maybe trying to persuade that NPC, well guess what? That's at disadvantage. He already is hostile to you and didn't buy your intimidation, that's going to make it harder to persuade them.
All of this is part and parcel of the basic rule set so no homebrew required. I truly think it comes down to knowing your NPC. If you have made one up on the fly...and how many times have we as DMs done that eh? Then when the player tries to intimidate take a moment while the PC is describing how they are trying to intimidate to think about who the NPC is. You could even call a quick break for refilling of drinks, toilet etc, and during said break come up with that stuff. Then you know and can respond from a place that is grounded in who the person they are interrogating is. That's how I'd approach it anyhow.
DM session planning template - My version of maps for 'Lost Mine of Phandelver' - Send your party to The Circus - Other DM Resources - Maps, Tokens, Quests - 'Better' Player Character Injury Tables?
Actor, Writer, Director & Teacher by day - GM/DM in my off hours.
Yeah this is how I do it. You make a check and it works or it doesn't. If it doesn't, you don't just get to reroll it again.
If you really wanted, you could allow them to try again tomorrow, letting the prisoner stew for a while. Of course, that opens up possibilities of a prison break that night... Somehow the situation needs to change to warrant a new check.
My homebrew subclasses (full list here)
(Artificer) Swordmage | Glasswright | (Barbarian) Path of the Savage Embrace
(Bard) College of Dance | (Fighter) Warlord | Cannoneer
(Monk) Way of the Elements | (Ranger) Blade Dancer
(Rogue) DaggerMaster | Inquisitor | (Sorcerer) Riftwalker | Spellfist
(Warlock) The Swarm
Yeah, multiple intimidation checks as the same PC changes up tactics is a bit silly. If you want to go "round the horn" with the whole party with each one getting a crack, you could do that. Or assume the "round the horn" approach means the lead interrogator character gets advantage and there's one check.
But an NPC "intimidated" does not necessarily mean the NPC will cooperate with the investigation. As pointed out intimidation is basically making someone feel threatened. In the context of an interrogation/interview that mindset puts many personalities into a fight/flight "say anything" mode and the credence one should give whatever is said in those contexts should be cautious. The "bullied" or "beaten" confession you see in cop and secret agent TV is a fiction of TV timescale and misunderstanding of what such techniques' goal are among IRL cops and operatives. Beating a confession out of someone is not about getting to any unknown truth. It's forcing the subject of the interview to conform to a preconceived theory of the interrogator or otherwise play "guess what I'm thinking" in order to satisfy the interrogator. Clearly, not best practices.
So yeah, battlefield interrogations where there's gun to the head sort of questioning or waterboarding etc. Those do nothing but give a pretext of "confirmation" for a group to act on "intelligence" they think they already know. The long form custodial "enhanced interrogation" torture programs are also problematic in that the torture is there to break down the mind of the subject so analysts can sift through fragments. Imagine the mind as a book in a locked box, a torture program is designed to blow up the box so you can read the bits of paper that might have survived the blast, and if you blow up enough boxes, you might have the story.
Effective interrogation is actually more often called interviewing. It's persuasion intensive and requires a rapport between interviewer and subject which can be challenging because of the likely broad range of differences that put the interviewer and subject in adversity. You need a very performative personality in the interviewer spot to bridge that gap to convince the subject they're valued in a way they want to be valued, which is often very different from the value the subject's knowledge actually holds for the interviewer.
Basically, in game, treat significant sources of information like puzzles, design them as social puzzles. As a foundation use the standard motivation for people who become sources in espionage: money, ideology, compromise, and ego (compromise in this context means the subject is a proverbial "hard place" and needs to work something out with the folks that got 'em) play the social puzzle to determine the best way to roll the subject into compliance. Depth of puzzle depends on depth of information. You can also plant "traps" in the puzzle where the subject will misinform the PCs.
In other words, it's not "I roll itimidation or persuasion" to interrogate, the PC needs to articulate the play they're making that the skill check represents (by which you can set the DC).
While writing this I started to like the idea of Iron Shadow Hobgoblins having been through something akin to SERE school, and having a captive Iron Shadow behaving like Denzel Washington in Safe House.
Jander Sunstar is the thinking person's Drizzt, fight me.
If my PCs make multiple attempts at intimidation, I typically ratchet up the DC for each failed check, letting them know that it's getting harder and harder to intimidate this person. The most I typically allow is 3 checks, after that I let them know that this person will not be affected anymore.
May I ask why you allow them three checks? Is there a gameplay or storytelling benefit to allowing them a second shot at the same check?
DM session planning template - My version of maps for 'Lost Mine of Phandelver' - Send your party to The Circus - Other DM Resources - Maps, Tokens, Quests - 'Better' Player Character Injury Tables?
Actor, Writer, Director & Teacher by day - GM/DM in my off hours.
As a PC, my rule is, "If they haven't voluntarily failed the save against zone of truth, they're lying."
I cant speak for the OP but from my perspective if you think about a real life interrogation scenario it is unlikely that the first round will reveal anything. The subject is fed, watered, only recently been caught and feeling cocky. Over time they will slowly break down, so 3 checks indicates a longer period of time needed to get the information, but also after 3 failed checks the target of interrogation has basically said, either kill/hurt me, or let me go I am not telling you anything
So mechanically you are applying the rules in a way that works, but, letting the players do the same thing over and over again can get boring both for them and for you as a DM. intimidation and threatening during Interrogation can be a famously bad way of getting information in the moment, especially if there is no legal backing to the process. Sometimes my players will do that and I will purposely give them a ton of false information they can't check in the moment. I once sent a party on an 8 session wild goose chase after they tortured a guy who knew nothing and int he end told them what he thought they wanted to hear. They learnt from that as characters that sometimes honey is better than salt.
The key thing for you to consider is "does this character actually hold information I want the party to have to progress the story", If they do not and the characters don't believe them, then consider what they do know that they can embellish, lie about etc that the party will believe and then stop what they are doing and move on. if the character then knows they lied then consider what they do afterwards. Also consider the risk reward, if the character knows something, but telling will see the big bad kill them, then having his soul committed to a demon in the distant future when he dies might be more acceptable to having the bbeg kill him now. have a character call the players bluff, maybe have them interrogate someone who has already signed a pact with a demon or devil. Or who understands that isn't how it works anyway. Don't just pander to your party, as a DM it is perfectly acceptable to metagame and pre empt what the party always do to make them think differently.
Now if they do hold information you want the party to have then never make the recovery of that information be reliant on a dice roll, it is like presenting a locked door to the party that is the only way through the continue the quest, if they fail the dice rolls to get through what do you do. Have the players make the necessary rolls but, the success becomes about how long it takes to get the information, not if it succeeds or fails, and tell the players that, if they roll a nat 1 tell them that they spend 5 days interrogating this individual and he finally lets slip a name and a location. They have now lost 5 days to this scene but they have the information you needed to give them.
Oh that certainly makes sense if time is passing, or if the PCs are trying a different tack as I mentioned. But if those rolls are happing almost immediately...that's got to be a no go. The situation you outline, we're talking about hours if not days in general.
DM session planning template - My version of maps for 'Lost Mine of Phandelver' - Send your party to The Circus - Other DM Resources - Maps, Tokens, Quests - 'Better' Player Character Injury Tables?
Actor, Writer, Director & Teacher by day - GM/DM in my off hours.
In game that might be several seconds or mins of rolling, but my party understand that in game a lot of time has passed
I'd take a couple steps back before making checks.
1) Does the NPC know anything of any use? What exactly do they know?
2) Do you want the players to obtain the information for plot purposes? Will having the information help or hinder running the ongoing content? Are the players likely to choose the preferred direction when given the information.
Interrogating NPCs from the DM perspective is all about plot advancement OR giving the characters something cool.
3) What is the NPC like? Would they under any circumstances share information and would it be truthful?
Once the DM knows these things - interrogations become easy.
1) Give the characters whatever specific information you want to give them. Give them additional checks as part of the process as they come up with alternate strategies. The only reason you allow multiple checks is because you plan to give the characters this information anyway and role playing them working for it can be fun. Alternatively, if you don't want to role play it you can narrate the intense interrogation and the information the NPC eventually gives up.
2) If the NPC has optional information and you whether the characters receive it or not isn't crucial then have them describe their attempts and make one roll, possibly with advantage if they come up with good ideas. Succeed and give them the info, fail and they won't be able to get it.
3) The NPC won't give up the information no matter what. Regular interrogation won't work - characters will need to resort to Zone of Truth, Detect Thoughts, Telepathy and other techniques of finding out what the creature is thinking rather than what they are saying. Regular interrogation techniques either are just narrated failure or the characters roll and no matter what is rolled the DM says it does not succeed even if the character rolls a 20. A 20 is not an automatic success at an impossible task.
Finally, never reward torture. Some characters can take a very dark path when trying to obtain information and this never ends well. Torture is not an effective technique since the victim will often just say whatever they think the torturer wants to hear. In addition, if someone is being tortured, telling the truth isn't likely to save them or cause the torture to end, so any information obtained this way is far from reliable and could well just be a trap. A DM should feel free to give false information leading to a deadly encounter for characters who want to employ this type of technique.
Thanks, everyone! I appreciate all the feedback. This is great and give me some new perspectives to manage interrogations.
I wouldn't allow more than 1 intimidation check. The characters get all of their little tricks and strategies together, and if its convincing enough, give them advantage or a lower DC but not multiple attempts.
If they fail the first check the victim is obviously not intimidated. It's very hard to threaten someone who isnt intimidated.
Dont tell them what the DC is. Have them tell you what their result is. Then simply have the interrogated NPC tell them something. They wouldn't know if it's the truth or not until they investigate it. If they roll low, lie to them, or have him/her repeatedly deny knowledge. But dont tell them they failed the check.
Now, if your players decide to move from Intimidation to Torture, that's a completely different thing. Torture often ends up with the NPC saying what he THINKS they want to hear.