[zerzar]

One way we try to solve this problem in our paid product is by prioritizing more urgent meetings (marked ASAP in our tool) and dynamically moving flexible ones (marked "This Week / Next Week / etc.") around if possible to free up space. If the meeting is scheduled manually via Outlook/GCal, we assume it is high priority and don't move it. We experimented with more complicated priority systems but ultimately that required too much work from the user

[nogabebop23]

Aside from everyone marking their own meetings as IMPORTANT! you could also delete all meeting requests that are "flexible" or deemed not critical - why are they being held in the forst place?

[zerzar]

We think of priority based on time sensitivity - not importance. For example, if I have a 1:1 with my direct report, it is very important but not time sensitive. This allows us to move that 1:1 if needed to accommodate a more urgent meeting