Currently, you need to manually keep track of features and what status they are in, to know whether an initiative is in progress, at risk etc. Could there be some analysis by the product that suggests an appropriate status or adds a to-do to review status based on what is happening in it's related features?
Thanks for the idea. Please see the example workaround shared by Suzanne in the comments. Reports are an excellent way to put together custom visualizations to provide greater insights into Initiative status.
At this time, we don't have plans for automatic status updates between features and initiatives as there are many complicated factors which may contribute to a status change. The suggested workaround would be to leverage the saved report and manually change initiative statuses based on all of the key information at hand.