I really like the attention to taking the analogy much further. It is a great thought experiment to drive the point.

One of the questions that comes away for me is "how do we make sure to take the right amount of time and effort explain the right amount of the rules?" Sure when the size of a company is small it is easy as you pointed out, but growing bigger than that it starts to get complicated. Is on-boarding for a 100 person company 6 days, 6 weeks, or 6 months? And how do you know when your current on-boarding process isn't working? You aren't able to observe every team and what they are doing continuously. Are there specific clues you look for?