When did estimates turn into deadlines?

So when those times have occurred I've (we've more accurately) adopted what I refer to the "deer in the headlights" response to just about anything non-trivial. "Hoo boy, that could be doozy. I think someone on the team needs to take an hour or so and figure out what this is really going to take." Then you'll get asked to "ballpark it" because that's what managers do, and they get a number that makes them rise up in their chair, and yes, that is the number they remember. And then you do your hour of due diligence, and try your best not to actually give any other number than the ballpark at any time, and then you get it done "ahead of time" and look good.

Now, I've had good managers who totally didn't need this strategy, and I loved 'em to death. But for the other numbnuts who can't be bothered to learn their career skills, they get the whites of my eyes.

Also, just made meetings a lot more fun.

I worked at a place where this management insanity was endemic, which lead to everyone padding all estimates with enough contingency to account for that. Which lad to the design team, and the front-end team, and the backend team, and the QA team, all padding out their estimates by 150 or 200% - to avoid the blame storms they'd seen for missing "deadlines".

Then the Project managers added those all ups and added 150 - 200%. Then the account managers and sales teams added 150 - 200% to the estimated costs before adding margins and setting prices.

Which ended up in literally around 1 million dollars a month to maintain a website which could _easily_ have been handled by a full time team of 8 or 10 decent web and full stack devs. Hell, apart from the 24x7 support requirement, I reckon I know a few great Rails or Django devs who could have done all the work on their own, perhaps with a part time of contracted graphic designer.

That all lasted a handful of years, until the client worked out what was going on, and my company management flew the whole thing into the mountain, with ~100 people losing their jobs and their owed entitlements (I was out about $26K that day.)

And the only cure is instead building a company that's tolerant of mistakes while still aspiring to excellence.

The one I've worked at which got the closest had a corporate culture that failures were atrributable to processes, while successes were atrributable to individuals/teams.

Of course that had its own negative side effects, but on the whole it made the company a lot more honest with itself. And consequently got better work out of everyone.