Your story
The personal ones. Sounding rehearsed hurts you most here.
The role & your thinking
Where she's testing judgment, not knowledge.
The classic ones
The behavioral staples. Have a real answer so these never catch you flat.
The practical ones
Raised gently, usually late.
Questions to Ask Her
In a warm, casual chat your questions are the impression you leave — more than your answers. Pick 3–4 that feel like you, ask them, then follow the thread; the follow-up (“say more about that”) is where it gets real.
- “When you picture this role really working, what's the first thing that gets easier for your team — the close, the forecast, or the endless ad-hoc ‘why did this move' questions?”Makes her name the actual pain in her own words — and tells you exactly where to aim first.
- “Where has AI already let you down in finance — something that looked great in a demo and then didn't survive real data?”Invites candor, and signals you know the demo-to-production gap is the whole game.
- “What's your team still doing by hand that they'd be almost embarrassed to still be doing in two years?”Surfaces the highest-toil work — your best first target — and it's a fun one to answer.
- “How do you personally draw the line between ‘AI drafts, a human approves' and letting something run on its own — and where would you never let it cross?”Her governance philosophy is the make-or-break of this role, and it mirrors your whole thesis.
- “If you had to bet — is the bigger unlock better forecasts, or faster and cheaper ones? Where's the pain actually worse?”Forces a real opinion, and her answer reframes what you'd build first.
- “What would a tool have to do for you to trust its number enough to put it in front of the CFO?”Hands her your exact wheelhouse and lets her define the bar you'd be building to.
- “Anitha mentioned you're building in a similar space — I'd genuinely love to hear where you've landed, and where you're still wrestling.”Collaborative, not competitive — positions you as a peer comparing notes, never one-upping her.
- “You're closer to this than almost anyone — what do you think most people get wrong about applying AI to FP&A?”Flattering and revealing — her “what people get wrong” is a window into her whole philosophy.
- “Is this a builder embedded inside finance, or a finance-literate person on an AI team? Honestly, the best version of me looks a little different depending which.”Shows self-awareness and gets you the single most important scoping fact.
- “Six months in, what would make you look back and say ‘that hire was clearly the right call'?”Her success criteria in her own words — echo them for the rest of the chat.
- “What's kept you at eBay?”People love answering it, it's genuine, and it ends things on warmth.
The listener: “Based on everything you've said, the thing I'd be most excited to get my hands on first is [the exact pain she described] — is that where you'd want me focused early?” Proves you listened and shows you already doing the job.
The brave one (optional): “Is there anything about my background that gives you pause? I'd genuinely rather hear it now than have it go unsaid.” A confident move — invites the objection so you can answer it. Only if the rapport's warm and you've time to respond well.
- Ask 3–4, not all. A firehose reads as a checklist; a few you actually dig into reads as a conversation.
- The follow-up is the skill. Her first answer is the setup; “say more about that” is where you learn something real.
- Avoid: anything Googleable (revenue, org size), comp this early, and yes/no questions she can escape in one word.