“So — tell me a bit about yourself.”
“So what are you working on these days? And — honestly — why would you leave that to join a team?”
“So — why finance? You come from more of an AI/builder background.”
“And why AI — what got you into building this stuff?”
“You don't come from a finance background — what do you think would be hardest for you here?”
“Why this role, and why eBay?”
“Where would you point AI in our FP&A function first?”
“How do you get finance people to trust an AI tool?”
“Tell me about something you've built.”
“What's the biggest risk of AI in finance? What keeps you up at night?”
“How would you measure success?”
“You're technical — how do you work with a finance team?”
“Where does this go in three years?”
“What would you say your greatest strengths are?”
“What's your biggest weakness?”
“Tell me about a time something you built didn't work out — and what you learned.”
“Why should we hire you?”
“What are you looking for in your next role?”
“How do you handle it when someone pushes back on you — say a finance expert who thinks you've got it wrong?”
“Where do you see yourself a few years from now?”
“One thing I want to be upfront about — you'd be on your own here in Toronto. I'm in the UK, and the rest of the team is in India. Does that give you any pause?”
“Do you have a sense of what you're looking for, comp-wise?”
What gets easier first — the close, the forecast, or the endless ad-hoc “why did this move” questions?
Where has AI let you down in finance — great in a demo, then didn't survive real data?
Your line between “AI drafts, a human approves” and letting it run on its own — where would you never cross it?
Bigger unlock — better forecasts, or faster/cheaper ones? Where's the pain actually worse?
Anitha mentioned you're building in a similar space — where have you landed, and where are you still wrestling?
Is this a builder embedded inside finance, or a finance-literate person on an AI team?
Six months in, what would make you say this hire was clearly the right call?