In order to fully take advantage of the workload portfolio view, you’re required to have estimated times associated with tasks on relevant project boards. However, there seems to be no way to automate this entry with rules. When trying to create a rule, you can leverage custom fields with dropdown options but neither a custom field with number format nor the Asana-created field for estimated times can be used for a triggered action. This is prohibiting accurate visibility of team capacity as it relies on individuals manually inputting these times themselves (which doesn’t happen).
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I agree. There is an opportunity here to help create the proper habit.
I believe forgetting to add time estimation or to start a timer is probably now one of the biggest bottlenecks for more accurate time and workload tracking. i.e., the fact that we are human is the bottleneck. 
I thought it would be great if a rule could be set to remind people to add time estimates if the field is empty, maybe with one click from My Tasks, kind of the same frictionless UX developed for adding the Time Tracking Custom Field.
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Just replying to add more weight to this. Seems kind of crazy to not be able to create a rule that enforces users to add estimation in a Task/ Story or it won’t be allowed in To Do. For those (like me) that operate this way that is.