Wow, lots of great opinions here I'll look forward to reading and learning from. My very brief take is: Estimates should be for "making the best decision now"

Wow, lots of great opinions here I'll look forward to reading and learning from. My very brief take is: Estimates should be for "making the best decision now" and not judging performance. Those are orthogonal concerns. It's very fair for the business to need to weigh "well if X takes 10 days and Y takes 20 days, and X makes more money, of course we'll do X". That is what estimates are for. However, if X ends up taking 15 days, the business (CEO, product, even CTO depending on their closeness to the solution) shouldn't/can't decide if that is a performance issue--only the engineer/the engineer's manager/etc. can make that call. And maybe it is, maybe it isn't. Granted, pulling this off is really hard; tangentially I'm now working in the construction industry which has the very same problem: this home should take 9 months. It took 10! Who's fault is that? Well, that's the wrong question. The right question is how could we have known that delay sooner/better, and mitigate it if possible this time and more importantly next time. If you're interested in working on a "humane" project management system (I just made that term up and it's super early, so disclaimer/etc), reach out </shill>.