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Glazius
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When the output of a scene is "does the kenku stay YES or NO" you can very easily find yourself in this situation, where you don't want to say NO but the dice aren't saying YES, but this is a false dilemma. If you have a concept of failure that's more meaningful than just NO, you can compromise to less than just YES when the dice say failure but the setup for the roll seems really good.

It's alright, you don't really get taught well how to deal with itframe a dice failure in that way. The main thing dice come out for is combat, where failing your roll just looks like "nothing happens", but actually that's just from one combatant's perspective. What happens is you pay a price for failure and that price is "everyone else gets a go before it's your turn again", but that price lives out in the order of combat, not on the roll itself, so no one ever tells you to think of it like that.

The key hereto framing a failure you can compromise with is that in a believable world, everything exists for more reasons than just to interact with the player characters. You don't have to get thumbtacks and string and plot out your entire NPC roster on your bedroom wall or anything, but if you're bringing someone in as the focus of a non-combat scene, you should know what they want. When you know what they want, you can give them what they want on a hard failure and compromise with what they want when the dice say failure but the setup for the roll seems really good. You can fail forward.

Now, you don't always need to have a particularly progressive concept of failure - if you're already moving in one direction for a scene and your players try to play out a way around it and fail, you'resometimes it's fine to just keep going the way you're going, especially if the players are acting on their own initiative to e.g. try and get some free armor out of the blacksmith. As long as you know what your NPCs exist for more than to interact with the player characters, -- what reason they have to keep doing what they're doing -- you can just have them keep going the way they were, the player argument very good but not stronger than their own motivations. (Future's looking grim, blacksmith's gotta eat, there is no "smiling bard" discount, if you won't buy it at this price there'll be someone else along who will.)

Now, exactly what the NPC canin this case should do is something you're much better equipped to answer than I am. It's going to depend on all the campaign prep you haven't shared and which would probably be too long to share.

If the kenku wants to make a deal, a way this can work to the PCs' detriment is if they make a bad deal for the PCs - like, depending on how the scene goes, the PCs have to pick some number of the following onerous conditions (but you can claw that number back as a compromise for a good setup):

  • On a total failure, they would call in the squad and try to fight their way out. Unless the PCs don't fight back they'll at least have a few captures of their own to learn something from.

  • OnAs a less total failurecompromise for a good setup, they panic and call in the squad accidentally, then beg for forgiveness and hide. The fight is easier, but the squad will fight to rescue them. (Oh, now they're saying they don't want to be rescued? Obviously they were charmed, and they can fix that back at base.)

  • On an outstanding success? Maybe they offer to call in the repo squad and suckersmack them to hand the PCs an easy win.

When the output of a scene is "does the kenku stay YES or NO" you can very easily find yourself in this situation, where you don't want to say NO but the dice aren't saying YES, but this is a false dilemma.

It's alright, you don't really get taught well how to deal with it. The main thing dice come out for is combat, where failing your roll just looks like "nothing happens", but actually that's just from one combatant's perspective. What happens is you pay a price for failure and that price is "everyone else gets a go before it's your turn again", but that price lives out in the order of combat, not on the roll itself, so no one ever tells you to think of it like that.

The key here is that in a believable world, everything exists for more reasons than just to interact with the player characters. You don't have to get thumbtacks and string and plot out your entire NPC roster on your bedroom wall or anything, but if you're bringing someone in as the focus of a non-combat scene, you should know what they want. When you know what they want, you can give them what they want on a hard failure and compromise with what they want when the dice say failure but the setup for the roll seems really good. You can fail forward.

Now, you don't always need to have a particularly progressive concept of failure - if you're already moving in one direction for a scene and your players try to play out a way around it and fail, you're fine to just keep going the way you're going. As long as you know what your NPCs exist for more than to interact with the player characters, you can just have them keep going the way they were.

Now, exactly what the NPC can do is something you're much better equipped to answer than I am. It's going to depend on all the campaign prep you haven't shared and would probably be long to share.

If the kenku wants to make a deal, a way this can work to the PCs' detriment is if they make a bad deal for the PCs - like, depending on how the scene goes, the PCs have to pick some number of the following onerous conditions:

  • On a total failure, they call in the squad and try to fight their way out. Unless the PCs don't fight back they'll at least have a few captures of their own to learn something from.

  • On a less total failure, they panic and call in the squad accidentally, then beg for forgiveness and hide. The fight is easier, but the squad will fight to rescue them. (Oh, now they're saying they don't want to be rescued? Obviously they were charmed, and they can fix that back at base.)

  • On an outstanding success? Maybe they offer to call in the repo squad and suckersmack them to hand the PCs an easy win.

When the output of a scene is "does the kenku stay YES or NO" you can very easily find yourself in this situation, where you don't want to say NO but the dice aren't saying YES, but this is a false dilemma. If you have a concept of failure that's more meaningful than just NO, you can compromise to less than just YES when the dice say failure but the setup for the roll seems really good.

It's alright, you don't really get taught well how to frame a dice failure in that way. The main thing dice come out for is combat, where failing your roll just looks like "nothing happens", but actually that's just from one combatant's perspective. What happens is you pay a price for failure and that price is "everyone else gets a go before it's your turn again", but that price lives out in the order of combat, not on the roll itself, so no one ever tells you to think of it like that.

The key to framing a failure you can compromise with is that in a believable world, everything exists for more reasons than just to interact with the player characters. You don't have to get thumbtacks and string and plot out your entire NPC roster on your bedroom wall or anything, but if you're bringing someone in as the focus of a non-combat scene, you should know what they want. When you know what they want, you can give them what they want on a hard failure and compromise with what they want when the dice say failure but the setup for the roll seems really good. You can fail forward.

Now, you don't always need to have a particularly progressive concept of failure - sometimes it's fine to just keep going the way you're going, especially if the players are acting on their own initiative to e.g. try and get some free armor out of the blacksmith. As long as you know what your NPCs exist for more than to interact with the player characters -- what reason they have to keep doing what they're doing -- you can just have them keep going the way they were, the player argument very good but not stronger than their own motivations. (Future's looking grim, blacksmith's gotta eat, there is no "smiling bard" discount, if you won't buy it at this price there'll be someone else along who will.)

Now, exactly what the NPC in this case should do is something you're much better equipped to answer than I am. It's going to depend on all the campaign prep you haven't shared and which would probably be too long to share.

If the kenku wants to make a deal, a way this can work to the PCs' detriment is if they make a bad deal for the PCs - like, the PCs have to pick some number of the following onerous conditions (but you can claw that number back as a compromise for a good setup):

  • On a total failure, they would call in the squad and try to fight their way out. Unless the PCs don't fight back they'll at least have a few captures of their own to learn something from.

  • As a compromise for a good setup, they panic and call in the squad accidentally, then beg for forgiveness and hide. The fight is easier, but the squad will fight to rescue them. (Oh, now they're saying they don't want to be rescued? Obviously they were charmed, and they can fix that back at base.)

  • On an outstanding success? Maybe they offer to call in the repo squad and suckersmack them to hand the PCs an easy win.

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Glazius
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You need a more productive concept of failure, so you can compromise with it.

This is what's tripping you up:

some of which would have ended with the kenku fleeing if the social encounter had gone sideways

When the output of a scene is "does the kenku stay YES or NO" you can very easily find yourself in this situation, where you don't want to say NO but the dice aren't saying YES, but this is a false dilemma.

It's alright, you don't really get taught well how to deal with it. The main thing dice come out for is combat, where failing your roll just looks like "nothing happens", but actually that's just from one combatant's perspective. What happens is you pay a price for failure and that price is "everyone else gets a go before it's your turn again", but that price lives out in the order of combat, not on the roll itself, so no one ever tells you to think of it like that.

The key here is that in a believable world, everything exists for more reasons than just to interact with the player characters. You don't have to get thumbtacks and string and plot out your entire NPC roster on your bedroom wall or anything, but if you're bringing someone in as the focus of a non-combat scene, you should know what they want. When you know what they want, you can give them what they want on a hard failure and compromise with what they want when the dice say failure but the setup for the roll seems really good. You can fail forward.

Failing Forward, As In Motion

You might have a concept of "fail forward" that amounts to "say YES but be wibbly about it" but what "fail forward" means is that things change as a result of failure. In your scene, if the kenku panics and bolts, nothing has changed. You went through all that trouble for the kenku to steal a phone and set up a meet, but at the end of it all, things are just where they were before - the Evil Organization exists, and the PCs have no inroads to it.

(This is probably another reason why you don't want to say NO, because you set up this entire scene and demanded your players participate in it, and after all that what's it going to feel like to get nothing?)

Now, you don't always need to have a particularly progressive concept of failure - if you're already moving in one direction for a scene and your players try to play out a way around it and fail, you're fine to just keep going the way you're going. As long as you know what your NPCs exist for more than to interact with the player characters, you can just have them keep going the way they were.

But when your first impulse is to set up a YES or NO scene, how do you come up with a failure that changes things? Once again, consider what the NPC exists for, and how that can do something to negatively impact the PCs' lives, more than just wasting their time to do nothing.

Potential Ways Out

Now, exactly what the NPC can do is something you're much better equipped to answer than I am. It's going to depend on all the campaign prep you haven't shared and would probably be long to share.

But, looking at just what you've provided -- the kenku wants to make a deal with the PCs but is paranoid and easily spooked -- here's how I'd use either of those as inspiration for a failure that changes things that I can compromise with.

If the kenku wants to make a deal, a way this can work to the PCs' detriment is if they make a bad deal for the PCs - like, depending on how the scene goes, the PCs have to pick some number of the following onerous conditions:

  • "An unbroken watch, for security." One PC must keep a constant watch over the kenku while they sleep. Whoever does gains a level of exhaustion.

  • "I must have these wards, for protection." Every day the PCs have to burn some modestly powerful spells on the kenku.

  • "They are too easily compromised." The PCs must break off relations with another useful NPC they have been working with.

  • "You need some skin in the game." (Extremely scenario dependent and this should count for 2/only come in on total failure.) A PC must be captured by the Evil Organization (and their player can run someone else in the meantime) so the kenku knows the PCs will get serious about stopping them.

If the kenku is paranoid and easily spooked, they have an extraction plan - a repo squad on call to help them escape.

  • On a total failure, they call in the squad and try to fight their way out. Unless the PCs don't fight back they'll at least have a few captures of their own to learn something from.

  • On a less total failure, they panic and call in the squad accidentally, then beg for forgiveness and hide. The fight is easier, but the squad will fight to rescue them. (Oh, now they're saying they don't want to be rescued? Obviously they were charmed, and they can fix that back at base.)

  • On an outstanding success? Maybe they offer to call in the repo squad and suckersmack them to hand the PCs an easy win.