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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.

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bdangubic 6 days ago | parent [-]

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.

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leetcrew 6 days ago | parent | next [-]

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.

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bdangubic 6 days ago | parent [-]

I honestly do not think it is about working crazy hours. perhaps my example can be misunderstood in a sense that if you give someone 7-figure bonus they will inevitably work 20hrs/day if necessary to get there which of course would not mean that they estimated correctly but were off by 12hrs/day :)

as things stand what is my incentive to provide an accurate estimate? if no one can question my estimate and hold me to it (well perhaps they can question it but we as industry have successfully been able to convince everyone that these are just estimates, nothing else...) what is my incentive to be accurate? If like one of the commenters above can say "it'll be 2 to 3 weeks" there is an INSANE difference between 2 and 3 weeks, 33% difference. it's like coming to buy a house and agent says "this house is $200k or $300k but you sign here on the bunch of dotted lines and we'll tell you all about it eventually before you have to cut a check." It is good to be in this industry (and especially if you WFH) - say 2 to 3 weeks, finish in 2 and get a week of working on your wellness (or another job :) )

	▲	yetihehe 6 days ago \| parent \| next [-]
		> it's like coming to buy a house and agent says "this house is $200k or $300k but you sign here on the bunch of dotted lines and we'll tell you all about it eventually before you have to cut a check. Not really with price, but when I've had my house built, the date was overshoot by about 30% too, because of various reasons, like having to stop for winter because some supplies were late by a week several times or my builders had to help teams at other places from time to time (because other teams were late too), not doing anything at my house sometimes for days. So even when building homes (something they do again and again) you can't really put exact estimates.
	▲	6 days ago \| parent \| prev [-]
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redleggedfrog 6 days ago | parent | prev [-]

That's an interesting scenario you're proposing.

To answer it personally, which of the two, 7 figure bonus or being fired, it'd be I'd quit. If someone is structuring the development of software based on this premise, then they are going to need a different kind of person than me. But I admit I'm probably an outlier here. I don't really work for the money, and my salary is enough, and I don't like undo pressure.

For arguments sake let's say the 7 figures is $1,000,000. To offer that kind of bonus the project is likely going to be a larger one. And I'm assuming my estimate is determining the deadline, so of course I'm making sure it's something I think I can achieve.

But then there are other significant problems with this structure and the likelihood of meeting the deadline, and, more importantly, generating good code and user experience.

- +5% (in ignoring the -5% as no one cares if you're early unless it creates some sort of QA burden) implies a narrow window. On a 6 month project that is ~6 days. Enough that personnel changes or other uncontrollable factors could lead to a missed deadline. One person getting fed up and leaving would be a huge problem.

- The specification would have to be really clear and agreed upon, since there is much at stake.

- Any changes, scope creep, customer requests, could change the development time, and you'd have to have some sort negotiating buffer built in since there is now so much at stake. Otherwise you're going to get literally everything rejected by the developer as they drive towards the deadline (maybe that's what you want, though).

- Is the result worth having? A focus on a deadline, in my experience, tends to shortchange quality. But maybe the deadline is more important than quality.

- And lastly, if that deadline is missed, or worse, something changes the scope of the project and the bonus is not awarded because that led to the deadline being missed, you're going to have some super pissed developers that will not trust such an arrangement in the future.

I suspect you're talking about situations beyond my pay-grade. I've been a meat and potatoes programmer working in e-commerce and integrations mostly, and we don't see 7 figure bonuses. We certainly have had can't miss deadlines that we mostly didn't miss, but mostly those deadlines were due to external factors (API deprecation mostly), or financial considerations, or lastly, arbitrary deadlines set by management. On the latter, those mostly got missed. But that was to be expected as they were not tied to reality.

And I'd second leetcrews comment below of, "...but it's not a sustainable approach for delivering features". Maybe this scenario works once or twice, but it seems like a terrible way to develop software.

But still, an interesting thought experiment.