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We have a project that has multiple tasks and we are trying to show a roadmap / project plan. The challenge is that each task is very "long tailed", meaning that most of the task will get done in, let’s say 2 months, but then there is 5% of that task that will take much longer to close out (let’s say 9 months before every final bit is closed out) due to the complexities of some exception cases.

If I treat the whole thing as a single item going out 9 months, it doesn't reflect that breakdown. If I put 2 months, then it ignores that fact that it really won't get fully closed out for 9 months.

What is the best way to represent this type of task on a roadmap, project plan?

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Break your work down into its components. That is what the WBS is for, to break your work down into more manageable chunks or elements. And the rule as to how far down you break your work is: until these kinds of questions are answered, i.e., break it down until you are comfortable with your ability to manage it. (The further you break it down, your admin costs climb but your insight into the work grows; find your balance and ignore others' rule-of-thumb inputs.)

If you break it down just one more level and show the first package duration as two months, you can load your resources--both materiel and human--into it and show the budget at completion to be 95% of your total. You next package will span seven months with a finish-start dependency to the first, loaded by the proper resources that will exhibit 5% of your total budget. If you chose to break the work down further, sequence and load and strike your baseline. You can even split a package to show passage of time where no work or labor is being burned, e.g., waiting for concrete to cure.

Your BCWS (budget cost of work scheduled) or PV (planned value) will be properly laid out if you were doing earned value. Your gantt chart will exhibit the waterfall schedule. And most importantly, you can manage to it properly.

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Can you create a series of milestones that show the edge cases?

Sept 1 - code complete except for 7 edge cases.

Nov 1 - edge case 7 complete

Jan 1 - Edge case 2 complete

etc.

and perhaps even have go-nogo meetings along the way to see if it makes business sense to resolve these edge cases?

The idea is to front-end load the display of business value and completeness, so you can show progress, then partition the other things. Perhaps they'll even be done by a different group.

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As David said, you haven't broken it down (decomposed) enough yet. It seems you're saying 'task' when you mean 'deliverable'.

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