This is great! I would love to shadow the CEO like this and understand what they do and how they do it. However I fail to understand how this gives the CEO nay feedback about their own job as mentioned in the post.
I interpreted that as the shadow and CEO spoke with each other sometimes, and the CEO asked for the shadow's thoughts (it would be odd if they didn't talk with each other?).
And a bit from the shadow updating the online docs, but maybe that's not for the CEO.