The best interview questions reveal how people think

What questions should I have asked you? I've been using that one forever, whether I am interviewing somebody or being interviewed, because the person is an expert in themselves.

When I interview a growth PM or analyst, I will always ask, 'What is a experiment you launched that has a very unexpected result? And what did you do after that?' So first of all, they have to be launching a lot of experiments to get very unexpected answer... Secondly, I want to know just why it's unexpected. That reveals the deep, deep level of their thinking, how deep they are thinking.

Think about one of the biggest mistakes you've made, truly, the more painful the better. And tell me what the mistake was... and tell me actually how you actually think differently now, work differently as a result.

What's the hardest you've ever worked to get something done and why? And that does differentiate a lot of people, a lot of people don't actually have a great answer to that.

"Colombo questions" refers to asking seemingly simple, open-ended questions that reveal deeper insights, like the detective character Colombo who solved cases through deceptively basic inquiries.

When I interview, I always do Colombo questions. What would you do your first 14 days as VP of product here? And they don't want to visit customers. Don't hire them.

I do like to ask people what the most complex thing they ever built was. I just love to understand mostly, what do they gravitate to? Is there something you gravitate to? And two, are they able to simplify it?

I ask, what's the hardest thing you've ever done? And I ask that because working at Ramp is hard. I want to understand what hard means for them.