The other day I was talking with the interesting Brad Grossman, who shared a bit of his experience as a "cultural attaché" for producer Brian Grazer, described in this New Yorker article as the following:

This person would be responsible for keeping Brian abreast of everything that’s going on in the world; politically, culturally, musically. . . . They’re also responsible for finding an interesting person for Brian to meet with every week . . . an astronaut, a journalist, a philosopher, a buddhist monk. . . . There is LOTS of reading for this position! Grazer may ask you to read any book he’s interested in. You’ll probably get to read about 4 or 5 books a week and you may be required to travel with him on his private plane to Hawaii, New York, Europe—teaching him anything he asks you about along the way. . . . You will also be provided with an assistant. . . . Salary is around $150,000 a year. . . . You will be to Grazer what Karl Rove was to Bush. 

There's an interesting bit of the history around those kinds of roles in the article, but the below in particular caught my attention:

Grazer has had one bad attaché experience. “A few years ago, I hired this really smarty-pants Harvard guy,” he said. “He was just remarkably lazy. If he didn’t get the Wall Street Journal on his desk, it was like it didn’t exist.” Still, he said, the experience came with a lesson: “Under no condition can you teach curiosity.”

The thought that "under no circumstances can you teach curiosity" is particularly interesting to me. It's something I've thought on quite a bit, ever since first being a part of this world of planners/strategists - all my best conversations about what it means to be insightful in these kinds of roles ultimately end on the idea of curiosity. 

 
I too tend to get to the point where I feel it cannot be taught; I sometimes think that this is in part because it requires the willingness to expose oneself to things that critically invalidate one's own (present) worldview. I think of this as a spectrum ranging from having a solid identity and perspective of how things should be, to being curious and understanding of the world but without any solid, unchanging core perspective.

The reason curiosity cannot be taught is because this is a tradeoff not everyone is willing to make.

I drew a quick sketch of this once, come to think of it:
Understanding_vs_justification
 
That said, I think it might be better to say that curiosity cannot be taught, but it can in fact be fostered. This would be something like fostering the idea that there are lots of ideas out there in the world (lots of perspectives), and they don't so much hold objective right or wrongness as much as they hold measures of value in terms of how they impact other people. 
 
Perhaps that counts as "teaching."