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I’ve seen concerns and FUD over getting lost in too many tasks. How do you manage the overhead of 20 4-hour tasks against 2-3 high level tasks?

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Well, they're just checkboxes inside the main tasks. You just think through how you're going to perform the task (which you'll anyway have to do when you get close to actually doing it), and note down the sequence of steps. Then you try to estimate each step. Sounds simple, but it works.

Why bother estimating? you have the checkboxes, now just get to work. If the pace of checking those boxes is slow then you can start cutting things out. Estimates are for managers, much better to just ship it already.

Because if you haven't built it yet, you can't ship it already.

But you are right that estimates are for managers. Managers should watch their reporter's progress and use that as evidence to build evidence. If the first task of 20 took 1 week, it's a 2year project. Update estimate as time and progress and work remaining increases.

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