When I was in a large organization, the upper management roadmap was based on quarters and year. Like Q1 2020 Q2 2020. That's a very large granularity of 3 months.

This had the benefits of ignoring the usual variations of software planning. Any development task could take 1 week or 4 weeks (if it goes well or not). This stops being an issue when the planning is quarterly because few weeks of jitter doesn't matter.

The question is then, do we have time to do this task next quarter, as well as the other 3 tasks we scheduled there? otherwise we'll plan it for the quarter afterward.