In an absolutely fascinating opinion article, Adam Grant opined that "those who can do, can't teach." I laughed as soon as I saw the title. It was pretty clear to me where he was going. Grant argues rightly that the greatest experts in a subject are not necessarily the best teachers. My usual way of getting to this issue is to tell an entry-level person that the best coach will never be more than two levels above you. Beyond that, the expert will be highly abstract, assume the unassumable about you, and won't be able to put the skills in a concrete package.
But Grant's way of going at the issue is so very useful, it needs to be added to your toolkit for coach selection.
First, pay attention to how long since the teacher studied the material. Ignore the top universities' boast about how most of their classes are taught by top faculty. The best teachers are probably grad students who just learned the material and know what it's like to be a beginner. In my post-doc work, I signed up for a course in adult learning and was initially disappointed that it was going to be taught by a teaching assistant, a grad student in his last year of PhD. From the start, he surprised me with his thoroughness. Later in the semester the top prof in the field subbed for his grad student when he had a bad case of the flu. Wow, was I glad the TA was teaching. The expert couldn't get the cookies on the bottom shelf for us no matter how many questions we asked...
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