“The benefit from asking a stupid sounding question is small in most particular instances, but the compounding benefit over time is quite large and I’ve observed that people who are willing to ask dumb questions and think "stupid thoughts" end up understanding things much more deeply over time.”
The naive question often exposes that the obvious answer is wrong. Most people never ask it, because looking smart in the meeting matters more to them than understanding the problem. The cost is a few awkward moments. The payoff compounds for a whole career.