The limitation isn't really our tools, to some large extent it's our brains and our ability to wrap our head around the whole pyramid. In a tiny startup that mi

The limitation isn't really our tools, to some large extent it's our brains and our ability to wrap our head around the whole pyramid. In a tiny startup that might be manageable, but even at 20-30 people you have to start abstracting. When you choose to use JIRA for something, you are giving up an organizational dynamic where you previously depended on judgement, and you are now handling it with process. Judgement is adaptable but very hard to scale, process is rigid but maybe too easy to scale by fiat (whether it's a good process is a different question). To be clear I don't mean that your PM's become mindless drones the moment you standardize on JIRA. I mean that where previously your 1-week projects and your 6-week projects would use custom planning processes, now with weekly sprints the 6-week project has to subdivide itself. There may be good reasons to subdivide longer projects, but I think this is an example of the class of problems that come from reality slipping through the cracks of processes. When you look to JIRA or any other tool for the answer, you have to make sure you are not implicitly giving up the role that judgement plays as the safety release valve for procedural red tape. In that sense it's not even the tools' fault, because you can't blame them for trying. It's that the organization has to see the tool as "just a tool".