When did estimates turn into deadlines?

I've gone through times when management would treat estimates as deadlines, and were deaf to any sort of reason about why it could be otherwise, like the usual thing of them changing the specification repeatedly.

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.

In my experience, super large estimates don’t make you look good in the long run, they make you look incompetent. The engineers who are most likely to be under-performers are also those who give super inflated estimates for simple tasks.

Maybe this is a good strategy for dealing with people who aren’t going to judge you for delivering slowly, or for managers who don’t know what the fuck is going on. For managers who do, they will see right through this.

So many bold claims in this comment and little to no justification.

For what it's worth I've seen pretty much the opposite. I don't know about competent vs. incompetent engineers. But when it comes to experience, I've seen the inexperienced ones giving super low estimates and the experienced people giving larger estimates.

I think general problem on HN is that you can't say something "bold" without people going "nuts" - especially when it comes to estimating work.

In my experience (been hacking since the '90's before it was cool) great developers are great at estimating things. And these are not outliers, all except 1 great developer I've had pleasure of working with over these years has never been "off" on estimates by any statistically significant margin. but you say anything like that here on HN and it is heresy.

My general opinion is that developers LOVE making everyone believe that software development is somehow "special" from many other "industries" for the lack of a better word and that we simply cannot give you accurate estimates that you can use to make "deadlines" (or better said project plans). and yet most developers (including ones raising hell here and downvoting any comment contrary to "popular belief") are basically doing sht that's been done million times before, CRUD here, form there, notification there, event there etc... It is not like we are all going "oh sht, I wonder how long it'll take to create a sign-up form."

I think we have (so far) been successful at running this "scam" whereby "we just can't accurately estimate it" because of course it is super advantageous to us. and WFH has made this even worse in my opinion - given that we can't provide "accurate estimates" now we can simply pad them (who dare to question this, it is just an estimate, right? can't hold me to the estimate...) and then chill with our wifes and dogs when sh*t is done 6 weeks earlier :)

It really depends on what you are working on. When I did agency type of work, building things you have built before, from scratch, it's easy to estimate. E.g. some sort of e-commerce website from scratch. On the other hand, working in a large corp, with massive legacy systems, unknown domain knowledge and dependency on other teams, it becomes near impossible. What might have been a 2 hour task in agency, might either be completely impossible during our lifetime unless the whole company was built from scratch or take 2 years. You might need 6 other teams to agree to make some sort of change, and you first might have to convince those teams, and then 2 teams will initially agree to it, then pull out in the last moment, or realize they can't do it.