[ghufran_syed]

"You learn by doing and putting skin into game not by watching or listening random CEO advice." Perhaps you meant: "you learn MOST by doing and putting skin into game, COMPARED TO JUST watching or listening random CEO advice."

I did this kind of shadowing as part of an MBA and it was super useful. Senior managers are often flattered that someone would want to do this, and they often find the discussions (including naive questions) with the "shadow" useful in providing an alternative perspective. So it's not only beneficial to the "shadow". One of the tasks we were asked to complete, in addition to general observation, was to make a note every 5 minutes or so on what kind of task was being performed, and (of possible to judge), the level of the task e.g tactical (day-to-day / week-to-week) concerns vs strategic (months - years). Tabulating that and writing a short report for the CEO afterwards is helpful for the shadow in order to consolidate and organize what you learned, and very helpful to the CEO, who almost always end up spending most of their time on tactical issues ("firefighting") rather than strategic issues, even though they know they should probably be spending more time on the latter than they currently are.

[vvanders]

Yeah, we find each new hire pretty valuable in the first few months because they provide a perspective on pain points that we may have internalized and disregarded.