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I find this anecdote fascinating because, while I identify completely with the new head of engineering, his requirement really only makes sense if you interpret it as a commitment to build at a certain level of quality, business be damned. Which is fine, but then he folds at the first test of this principle! Didn't even let the business sweat for a day!

This could be a lesson for us engineers to be a little less glib and a little more introspective, especially as you gain more power and influence in an org.

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I think in this case it was more a plea to have his judgement valued when he said "dude, if the qa team has found this many bugs this is only going to harm our reputation with the client, and we are going to be the ones doing emergency bugfixes at midnight". but also the company had a pretty toxic culture where the CEO knew how to manipulate people to get his way. he definitely managed to guilt trip me into working overtime when he told clients we already had features that we didn't in order to close a sale, basically "we've worked so hard already and we really need to close this sale, can't you just work up a basic version of it over the weekend?"
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I wonder if the better approach would have been to lead engineering with a similar reliance on bending rules and "what you can get away with". This is where multiplying estimates by PI comes in, I think. And possibly some creative division of responsibilities to make it harder for a CEO to officially bully engineering. Totally different job than most engineers would (or could) want to perform- the guy probably wouldn't have taken the promotion in this case!
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Doubtful. I suspect the CEO was the one doing the estimating, so any number you give him is ignored in favour of what he provides instead.
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you are indeed correct
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