Every senior product hire I've been part of has taught me the same lesson twice. Experience is easy to verify. Judgement is not — and it is judgement you're actually hiring for.
The interviews that work are the ones that stop asking what a candidate did and start asking why they didn't do something else.
The three questions I never skip
One: tell me about a decision you now regret, and what you would trade for the information you were missing. Two: describe a room where you were the least experienced person, and how you added value anyway. Three: what is a strongly held belief about product that you've changed your mind about in the last two years?
The best senior operators aren't the ones with the cleanest résumés. They're the ones who can still be surprised.