alt Hacker NewsNever be afraid to ask stupid questions. As someone who spent years doing penetration testing, I can assure you that when stupid questions don’t have an obvious answer, someone isn’t thinking properly.
Also never be afraid to question people who answer quickly. We spend way too much effort training smart people to answer quickly rather than deeply, and there’s almost always a tradeoff between the two.
Replies
> I can assure you that when stupid questions don’t have an obvious answer, someone isn’t thinking properly.
Once you start asking stupid questions on the regular it's quite an interesting experience how often you can ask "stupid" questions to rooms full of senior engineers and sort of get back confused silence. In my experience there's a lot of really important but "stupid" questions that often just gets half-ignored because imagination and prioritization is hard.
I love and struggle with the second point. It's taken me half my career to realize that people would very much prefer the complete and right answer slowly or later than the '90% sure' answer right now. Being quick doesn't make you look smart
I disagree. Asking stupid questions, even if in good faith, can be mean being banned from communities or losing participation privileges. Such as mathoverflow or stackexhcange.
> Never be afraid to ask stupid questions.
Unfortunately that's the kind of black-and-white advice that seldom applies in the real world. Would you want to see your surgeon asking stupid questions? The pilot of the flight you're on?
You wouldn't, because part of your psychological comfort depends on your perception that people like this -- people whose decisions really matter -- actually know what they're doing.
ETA: By "stupid questions", I don't mean "basic but obviously important questions". I mean questions that reveal that you don't know something that other people expect you to know, that signal to them (rightly or wrongly) that they may have overestimated you.