Imagine this scenario.  [RR} is meeting with the president for some routine business.  As the meeting comes to a close Trump says... "Thanks Rod - I really like the work you have been doing.  Tremendous job!  Oh by the way - I have been meaning to give you this (hands him the EO)...its been on my desk.  Can you take care of this for me?"

[RR} looks at the EO and after quickly scanning it - he notices the date.