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The greater the knowledge component in work, the more leadership of that work resembles philosophy. Probably the only way to ‘lead’ a bunch of research mathematicians (besides actually doing pioneering math yourself) is to write zen poetry or something.
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Thinking more of philosophy in a lay/informal sense, not academic. I don’t regard either as particularly philosophical, though they are leaders of knowledge workers for sure. And pg has in particular repudiated philosophy explicitly.