When the context of “keep me in the loop” is between manager and managed, things might be a little different. After all, the whole purpose of a staff is to make sure that a boss has the information, knowledge, and insight she needs without being burdened with having to figure it out for herself. In a world of information flow built around the distribution of atoms, it made sense that the staff made the decisions on what the boss should see, based (of course) on what the boss said she wanted to see.
When information flow is based on bits, when working out loud is (can be) the norm, when the boss can see what she wants to see when she wants to see it instead of waiting for a meeting or the email with the monstrously huge PowerPoint file, she can keep herself in the loop.
Working out loud goes both ways; it is just as important for managers and leaders to understand how to work out loud as it is for their employees.