[2C64]

Exactly this. Context is king - and as someone else stated below knowing how to get to the actual ask vs. how the ask is being phrased is something that comes with experience.

That said, it should also be the role of the more senior technical leadership to involve junior technical staff in the process so they have the opportunity to grow. For example, CEO asks CTO how long it would take to add X feature so CTO loops a junior engineer into the conversation and demonstrates how to get to what the CEO is actually asking (which may or may not be X) vs. just providing a time estimate for X feature. Hopefully the CEO learns something here too but ymmv.