Ask HN: How to shadow a CEO?
Set the habit from the beginning to do quick debriefs (a few minutes) after each meeting. The most interesting thing when shadowing very senior people is to see why they do certain things.Try to have 1 question ready after each meeting/call/... Why did you agree to the terms? What was the most important thing about this call? Why did you handle it like that? What did you try to get out of this meeting? How did you know they were going to say X? Try to get a sense of why they make certain decisions, how they think about it.