I am not aware of any method or add-on that could provide an automated method to achieve a multi scenario approach or best to worst case timelines; but for a manual approach you can look into setting up Multiple scenario planning, and in each of the scenarios adjust the weighted items of the scheduling factors (i.e. rank, estimates, capacity, dependencies, etc...) to get the varying level of comparison, best to worst on the plans layout, and after reviewing commit the one that looks to be the most achievable.
Using this approach as your primarily looking at the Release variable you could set up one scenario with a "As early as possible" start date and a "dynamic" release date and the second with the optimal fixed dates and the third with a conservative fixed dates to compare the three variable plans and see if there are any conflicts in the schedule on each scenario.
Also check out the documentation for "Scheduling behavior" that goes into more detail on how the item weighted items are calculated.
Hi community, I’m Roi, a product manager working on Advanced Roadmaps for Jira. While Advanced Roadmaps is a powerful tool to plan and track work at scale, we know it can be challenging to get star...
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