Planning is very difficult. We are not naturally good at estimating our own future, and many cognitive biases exacerbate the problem. Group planning is even harder. Incomplete information, inconsistent views of a situation, and communication problems compound the difficulty.
Agile methods provide one framework for organizing group planning–making planning visible to everyone (user stories), breaking it into smaller chunks (sprints), and providing retrospective analysis so you get better at planning. But finding good tools to support these practices is proving tricky.
What software tools do you use to achieve these goals? Why are you using that tool? What successes have you had with a particular tool?
Best Answer
OmniPlan
Mac OS X planning tool.
Pivotal Tracker
Useful even if you aren't doing "agile" development.
FogBugz
Incredibly useful and featured issue tracking.
I use these in conjunction. OmniPlan is great to lay out all the tasks that need to be completed and divide them among your team. You can setup critical paths (things that must happen for completion) and breakdown overall effort. Also great visually for management.
Pivotal is excellent for keeping up your development pace. If you fully subscribe to agile methodology it's excellent, but still very useful to track features, dependent components, and currently active status.
FogBugz provides an easy to use interface for non-programmers to submit bugs or feature requests and monitor progress. Issues that come in are evaluated and logged in Pivotal. Then they get moved into OmniPlan if it becomes a larger task with multiple components.