Questions from a Yugoloth

[Nidgit]

In our home game, the party has just encountered a bound Arcanaloth that will shortly be freed as soon as the party gets a MacGuffin they need for other reasons. The Arcanaloth bears the party no particular ill will and has actually won some cautious sympathy through their dialogue, so they're looking to make the best of the situation. In exchange for statblock information on the current BBEG, the party has agreed to answers two more questions truthfully and to completion, with the caveat that neither question can be about any of the party. What kind of thing does the Arcanaloth ask?

The Arcanaloth has been bound in an empty tomb for a millenia and is naturally curious about the world, but won't ask anything too simple because they're about to be freed anyway. She has a grudge against an Ultroloth but has no reason to believe the party knows anything about this rival or the Lower Planes (and they don't). And she can't ask anything about the party in front of her, though it's just a verbal agreement and she might be able to wheedle some information out anyway.

Ultimately this is just about building further trust so the Arcanaloth can get the party to trade favors for additional aid, but she still wants to maximize her gains. As a DM, I want the party to feel a little uneasy at what she's learning but not so much that they're unwilling to keep talking to her. So what type of questions would you ask if you were playing an Arcanaloth in this situation?

[lall]

Is it hot in here, or is it just me?

Could you point me to the nearest restroom?

[Unoriginal]

In our home game, the party has just encountered a bound Arcanaloth that will shortly be freed as soon as the party gets a MacGuffin they need for other reasons. The Arcanaloth bears the party no particular ill will and has actually won some cautious sympathy through their dialogue, so they're looking to make the best of the situation. In exchange for statblock information on the current BBEG, the party has agreed to answers two more questions truthfully and to completion, with the caveat that neither question can be about any of the party. What kind of thing does the Arcanaloth ask?

The Arcanaloth has been bound in an empty tomb for a millenia and is naturally curious about the world, but won't ask anything too simple because they're about to be freed anyway. She has a grudge against an Ultroloth but has no reason to believe the party knows anything about this rival or the Lower Planes (and they don't). And she can't ask anything about the party in front of her, though it's just a verbal agreement and she might be able to wheedle some information out anyway.

Ultimately this is just about building further trust so the Arcanaloth can get the party to trade favors for additional aid, but she still wants to maximize her gains. As a DM, I want the party to feel a little uneasy at what she's learning but not so much that they're unwilling to keep talking to her. So what type of questions would you ask if you were playing an Arcanaloth in this situation?

Question 1: Who among the powerful people in the current world would be in need/want of an arcane advisor and open to hiring a Fiend?

This keeps the Arcanaloth's image as an underdog who just wants to start over, while also teaching the Arcanaloth about the PCs (namely, their level of connections with the currently powerful people and their willingness to engage with Fiend-friendly people) without directly asking about them.

Question 2: Who will the Arcanaloth need to avoid once they're out of the dungeon, to avoid troubles?

Again, this plays on the sympathy the PCs feel for them, while being a reasonable question, but it teaches a lot about the PCs to know who they know, who they consider dangerous, and who they are willing to describe as a threat to the Yugoloth.

[sandmote]

I'd expect something that only technically counts as a single question and lets her learn about the people in front of her without asking about them.

Ex: "What are the political status, position, and goals of each of your closest employers or political patrons outside any in this room?"

Not sure for a second question, but she might want to fake being tricked into an easy or irrelevant question (an "and what does he desire?" type thing) to make the party feel they might be able to trick her going forward. Depends on how much she can get out of the first question though.