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?