Hilary Gridley

Product leadership is the type of role where if you are not in control of the voices in your head, they will eat you alive.

What is much more helpful than understanding what your CEO thinks is, I think understanding how your CEO thinks.

Anytime you find yourself tempted to ask an open-ended question to somebody whose brain you're trying to understand, stop yourself and say, 'Let me just say that. Let me say as a statement what I think,' and then try to calibrate based on their reaction.

I would really love it if more people were like, 'Screw it. I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well.'

Your job is to understand what the CEO's vision is and what they care about, again, sort of how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product.

When I approach these conversations, I always try to think of them as, even if I don't agree with the feedback, if I don't agree with the decision, what is the insight that I'm missing? How am I wrong about this?

There's always a shot clock. When you're working, especially on a zero to one product, I think it can be very easy to feel like you have the luxury of time, of just like, we got to take the time to figure this out and get it right and that's what's most important. But the sort of build versus buy question is always live and it's always fair.