Hi Selil,
On most of what you said, I agree. I will, however, beg to differ with you on your final point.
I certainly agree that this is the most effective way of transfering contextual knowledge. Where I would disagree with you is when you say "formalizing concepts like this will rarely succeed".
A highly formalized model of how to organize this type of knowledge transfer exists and has for quite a while. The problem with knowledge of the model is that it comes out of a rather obscure part of Anthropology and the core theoretical texts are written in a manner that would make any manager throw up her hands in disgust.
If you're interested, the model is the classic "Rites of Passage" model produced original by Van Gennep and modified by Victor Turner, Edward Bruner, Charlie Laughlin and some others. Operationally, the model tends to be poorly understood and misapplied outside of Symbolic Anthropology and, to a lessor extent, Performance Anthropology. The reason I disagree with you is that the model was built based on observations in the field of how many cultures actually formalized this type of knowledge transfer.
There are, however, several rather serious operational problem with the model - at least in terms of applying it in large organizations. First, the model relies quite heavily on the use of certain types of ritual structures that have been banned by law in most jurisdictions (it's not drugs, it's a form of psychological manipulation). Second, in order to do it properly, it is both time and person intensive.
Marc
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