I think his response meant in situations where you just need to figure out which project management tool they use so you can log in for the first time, binary questions are the right tool for the job (information gathering). But I mostly agree that, in the big picture, the broad questions are more helpful for solving the complex problem you’re facing.

and nobody is going to say it’s not raining when it’s hailing outside… but I understand if that was just a metaphor. You’re probably asking that question to figure out what kind of clothes to wear, and they would probably infer that. It’s so contextual though.