This was a delightful essay by Dan Luu. In my experience, especially in a meeting dynamic, most people are unwilling to ask questions that might make them look stupid. Those are the most important questions to ask.
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. Conversely, when I look at people who have a very deep understanding of topics, many of them frequently ask naive sounding questions and continue to apply one of the techniques that got them a deep understanding in the first place.
Source: Willingness to look stupid