As an example of something I personally struggle with: what's the best way to have the rest of the company know what all of our teams are working on without A) going into too much detail B) being obtuse C) opening ourselves up for miscommunication to customers or deadline promises D) giving ourselves room to fail, because not everything will work out.
The current iteration is a fortnightly newsletter that I curate between product and the engineering managers in the department and it gets sent around, but making everyone happy with it is /so/ hard.