InterviewCaddy

I've sat on both sides of a lot of interviews and some questions still puzzle me.

"Are you a leader or a follower?" is my pick. It's a false binary with an obvious right answer, so nobody says "follower" and the interviewer learns nothing. Good people are both depending on the situation, which is the one answer the question doesn't leave room for.

Curious what other people have run into. The ones with no right answer, the brainteasers that measured nothing, the questions that only tested how well you'd rehearsed. Or the opposite, if you've ever been asked something genuinely good that told them something real about you.

I've been building in the AI-for-finance space, and I've noticed the real barrier isn't whether the models are good enough. They're getting scary good at reading documents, reconciling transactions, spotting patterns a human would miss. The barrier is trust and specifically, the gap between AI that reads your finances and AI that acts on them.

Here's the line I keep bumping into: people are surprisingly comfortable letting an agent categorize expenses or summarize their spending. But the moment it wants to do something file the taxes, move the money, recommend a five-figure decision the comfort evaporates. And I don't think that's irrational. The cost of a wrong email is an awkward apology; the cost of a wrong financial action is real money or an audit.

What's interesting is that the same person will draw that line in totally different places depending on stakes and reversibility. A $40 miscategorization? Whatever, fix it later. A mistimed refi or a missed deduction? Now trust matters enormously.