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The only thing I've ever seen work (and I've seen it work well) is to avoid estimating based on time. Instead, you estimate things relatively and then empirically measure how long things take (known as the "velocity" in agile parlance). So the programmer doesn't have to think about the 1001 things that they have to do in order to complete a task, or all the distractions or BS or overhead they'll have to deal with, they just need to think: is task A about as hard as task B, or is it twice as hard?

There are a key pieces to making that work. First of all, you give your estimates in terms of "points", not hours or days. Secondly, you estimate tasks relatively to one another, not absolutely: a 3-point task is about 3-times as much work as a 1-point task. Third, you have multiple people give the estimates, often using something like "planning poker" (where everyone on the team selects their estimate and reveals them simultaneously, then discusses if they're different), which ensures they're more reliable. Fourth, you measure the velocity of the team (not individuals, the team) over time. It often takes a while for it to get anywhere close to stable, as people get used to the project, the technology stack, each other, and so forth.

That's the only thing I've ever seen work, and it can actually work pretty well. It prevents the developers from having to account for all the non-coding things: you don't have to think "Well, this will take 2 hours of coding, 2 hours of test-writing, 1 hour of debugging, 1 hour of docs . . . but I also have 2 hours of meetings a day, and I get pulled off to firefight customer problems periodically, so really it'll take 4 calendar day." You just measure all that stuff empirically: if you have a bunch of meetings or firefighting, your velocity slows down, but your estimates don't have to change to account for it.

It also avoids wishful thinking, especially if you're rigorous about what counts as something being "done". It's harder to lie about whether or not you're going to hit your dates if your measurements say you're going too slowly; it's far easier to be in denial when all you have are time estimates, since those are easier to fudge than relative estimates of difficulty or empirical measurements of velocity.

(Of course, as with any measure of productivity, it's subject to abuse by idiots. But as a scheduling and measurement tool, it can be invaluable.)




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