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A worry junior engineers and new hires frequently have is that they ask too many questions.

The most common advice I've heard is to try to figure it out yourself for 30 min, and if you're still stuck, ask. This is reasonable advice, but I don't think it's actually very good.
One nuance that gets wiped away by the 30 min rule is the wide variety of question-asking situations.

I've gotten stuck on something important after mere minutes, and then unblocked after a 10 second conversation with a coworker. (the files I couldn't find had legacy names)
Sometimes I gradually work things out myself in over 30 minutes.

Sometimes I have questions that aren't essential or urgent. I batch these, ask them together at convenient times, and learn a lot of cool things.

There is so much variation!
There is a skill of knowing when and how to ask questions, and this skill can be learned.

Moreso, I think many people are already pretty good at this! Many of my friends tell me they're *worried* they ask too many questions, and few have been told they *actually do*.
My preferred method for building the skill of asking questions is the same as for reducing worry: allow messing up.

Learning from failure is underrated.
If you asked questions you could have figured out yourself, now you have examples of ways to improve. If you asked too many questions, now you know what too much is.

And you can stop worrying about doing it wrong - because doing it wrong is *expected* as part of the learning.
Learning from messing up does NOT come for free.

You need psychological safety, where people feel safe messing up. This is largely the work of senior engineers, managers, and leadership.

And to learn, people need to know they made mistakes! There has to be fast feedback!
tl;dr instead of telling people to wait 30 minutes before asking questions, encourage curiosity and allow people to actually ask too many questions. Provide a psychologically safe place to mess up, and provide useful and timely feedback when they do.
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