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But sometimes I don't know why it's a bad idea ahead of time! That doesn't mean I'm wrong -- often time reveals what it was I was subconsciously worried about.

That's what expertise is sometimes like: an accurate gut feeling, impossible to articulate clearly.

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In that case one must be assertive. Speaking this way does not come naturally especially to engineers.

You don't have to articulate it clearly, you don't have to know why you are making the estimate you are making. It's ok for management to push, in fact it is their job.

I suggest this book. https://www.amazon.com/dp/B004IK8Q22

I agree, sometimes it is just a gut feeling, but a lot of times expertise means knowing where the gut feeling comes from and being able to explain it.

If nothing else, management will be more trusting in those situations if you give good and accurate estimates the rest of the time and are able to justify them.

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