I have recently been spending a lot of time with two different "project management" applications: FogBugz and Team Foundation Server. FogBugz originally attracted my attention because I read Joel Spolsky's blog, Joel on Software, and he's the CEO of Fog Creek Software which makes FogBugz. TFS attracted my attention because it includes a new Source Control system which is a-w-a-y better than Visual Source Safe. I have been evaluating these products and trying to figure out which I'd rather use, its a harder task than it sounds.
The new version of FogBugz, 6.0, mainly consists of Evidence Based Scheduling. I have to be totally honest and say that EBS is not only very cool but makes total sense and I believe it would totally work. However it requires two things: 1) time tracking and 2) work item estimates.
Joel Spolsky recommends keeping your estimates under 16 hours, anything longer than that doesn't stand a chance of being accurate. That means you need a lot of very detailed tasks entered in the system (ex: develop function foo). Once you have estimates at this level you can start to get good predictions of when you'll ship AND you can start to pick and choose what tasks you want to do based on how much time you have left.
TFS doesn't really have any scheduling. It has Remaining Work and Completed Work fields (but only on the Task work item type, not on the Bug work item type...), but no reporting, no nice views, and no nice way to enter time (you have to subtract from the remaining work field manually when you add Completed Work...). The TFS developers seem unconvinced that estimating work at the level Joel recommends is at all worth while. Witness these articles on the Teams WIT Tools blog.
Personally I think estimating how long a task will take is a great idea. I think creating a list of tasks at that detailed level would not only help a developer think through what they're going to do before they dive into it but also help them get an idea of "where they're at" with all their work. I think it would make managing work loads a lot easier too. Not to mention the fact that the ship date estimates would make it possible for you to determine when your initial "blind" estimates were wrong or when scope creep is starting to get the best of you.
My question for all of you is, what do you do at your work? It doesn't even have to be programming work. Do you estimate work? At the detailed task level, or at a more abstract level? Is it helpful? And if you don't estimate work, do you wish you did?
UPDATE: I've posted a follow up post, Managing Projects