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.

when I was talking to Gary Bernhardt, he told me a story about a time when he was chatting with someone who specialized in microservices on Kubernetes for startups and Gary said that he thought that most small (by transaction volume) startups could get away with being on a managed platform like Heroku or Google App Engine. The more Gary explained about his opinion, the more sure the person was that Gary was stupid.