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've seen the inexperienced ones giving super low estimates and the experienced people giving larger estimates

I have the same anecdotal experience with a possible explanation:

Inexperienced engineers often don't see the greater picture or the kind of edge cases that will probably need to be handled ahead of time. I've often had the following type of conversation:

Engineer: "I think that would be a day's work"

Me: "This will need to interact with team X's package. Have you accounted for time spent interacting with them?"

Engineer: "Oh no, I guess two days then"

Me: "Will this account for edge case 1 and 2?"

Engineer: "Ah yes, I guess it would be three days then"

Me: "Testing?"

Engineer: "Maybe let's say a week?"

On the other hand experienced devs might have their judgement clouded by past events:

"Last time we did something with X it blew out by 3 months" - Ignoring the fact that X is now a solved issue

> "Last time we did something with X it blew out by 3 months" - Ignoring the fact that X is now a solved issue

This is software though, if X has actually been done before then it doesn't need to be done again. It is already done.

Task X clearly had the potential to blow out by 3 months, and they are now working on task Y that is similar to X. It is a reasonable position to assume that there are other as-yet-unknown issues that might cause it to blow out by 3 months until someone has demonstrated that all the unknown unknowns are also resolved by doing it quickly. That is just basic evidence based planning.