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.
Ask for reactions, not opinions
Craft → Analytical Sense
I generally value the reference check over interview signals. If I had to stack rank in interviews, what is the best signal? The reference check is the top of the list. Those people, they worked with this person sometimes for years, their knowledge, what you're going to get out of 30 minutes of artificial scenarios it's just like never going to compare what a good reference check will give you.
I think a pretty first principles driven approach for this, which is to think about how long does it take me right now to get to the reaction I'm looking for from my recipient? If it takes a bunch of back and forth and a bunch of friction, then that's my baseline. And once you start practicing some of these communication skills, how does that speed up?