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 :)

You can't make accurate estimates that can be used for deadlines for non-trivial work. You can make educated guesses on how long specific things will take, and it might be a pretty good guess if you've been keeping metrics on your past work, including things like vacation days and other similar disruptions as well, and keeping a team together long enough to have solid institutional knowledge on your code-base. And you can respectfully lay these numbers out to a manager in the form of, "This will probably take 1 to 3 days," or for bigger stuff, "2 to 3 weeks", and so on. And the manager can take the sum of all this and say, "The soonest it can probably be done is 3 months, but most likely it'll be 4, with a small chance of a bit longer", or whatever, you get the idea. And then the mangers can set the deadline as they see fit. Now, for some reason, many managers just look at the first number and are done - that's the due date. And then after that they get deer in the headlights treatment, so the worst case becomes the best case. That's on them. If they don't understand that software estimation isn't an exact science they're in the wrong field.

As for software development being special, I really hope that what I've described above is like other engineering disciplines, and we're not special. I don't want to be special, I want to be an engineer, like those who work with aircraft or bridges and what not. I feel like in those fields the concept of estimation is a little more respected. But I'm probably wrong. :^)

I'll mention I've been a professional software developer since the early 90's, not that experience equals veracity. But I've had good success using the system above, and even though the bad managers to good managers was pretty even during that time, the company experienced outstanding success during my tenure (20 years!). In the end, bad managers never last. Good managers, who take reasonable estimates to their superiors, succeeded, where managers who brought "It'll be done July 1st" got doubted because their superiors know it really doesn't work that way.

your comment is exactly what I am talking about. you actually CAN make accurate estimates for non-trivial works. try to envision this - I hand you a non-trivial assignment to estimate with a condition that if you meet your estimate -/+ 5% you get 7-figure bonus. alternatively if you do not you get fired. after working 30 years in the biz you tell me which of the two is happening for you?

I worked at two places that gave huge bonuses when deadlines were met (based on “estimates”) and wouldn’t you know it sh*t always got done on time and people got paid.

in the short term, people will work crazy hours to hit a date if it's the difference between a 7 figure bonus and getting fired. if the estimate is based on devs working reasonable hours, that's a lot of slack built in. I'm sure they hit the date more often than not in your scenario, provided they control most of the dependencies, but it's not a sustainable approach for delivering features.

"provided they control most of the dependencies" is a pretty important caveat by the way. many times I've seen people get the rug pulled out from under them by partner teams at the last second. it doesn't matter how clever you are or how hard you work. if you depend on something owned by a team far away in the org chart, they can always blow up your project with little consequence.