Here’s my stab at the guide Tyler and his producer mentioned near the end of the 2021 retrospective show. The goal is to give the uninitiated listener essential context. (They mentioned a 10-point guide, but I only need 8.)

1. These are not debates. Tyler will make his point and move on. He will let the interviewee do the same. Nor are they wrestling matches: one neither needs to pin down the opponent for some length of time nor see a scoreboard get incremented. (So, just because Tyler doesn’t mark the occasion specifically, don’t think he doesn’t take himself to have just decisively refuted an entire Nobel Prize-winning body of research.)
2. Why talk as in (1)? One reason is efficiency. Never forget that this is part of Tyler’s moonshot project, one core of which is for him to process as much information as he can. Always think of Tyler trying to maximize his own intellectual progress per minute.
3. Again, why talk as in (1)? Think of Tyler as committed to the view that things have explanations (perhaps several) and as a realist about explanations. In particular, sometimes explanations are, in fact, simple–which is not to say “easy.” Here I think of the way (the philosopher) David Lewis often seemed to believe things based on very short lines of argument (e.g., here), or the way Reid Hoffman values simplicity in decisionmaking. (This is one way Tyler is working in philosophical traditions; see below.)
4. If you are a realist and a pluralist about explanation, you ought to care how these explanations coexist. And Tyler does. So, e.g., he presses Robin Hanson on levels of explanation. And for guests with thrilling empirical results (e.g., Raj Chetty), he tends to ask “but what’s the causal mechanism here?” Such questions are deeply unfashionable in some circles these days, and it’s striking how much his guests vary in the quality of their answers here.
5. I view Tyler as working in a Socratic/Platonic tradition. (Explanations exist; they’re domain-relative; their domain-relativity does not undermine their reality; the real natures of things are very hard to understand, usually too hard for a single human mind; etc.) More generally, whether or not he resembles an academic philosopher, and whether or not you want to think of his work as philosophy, think of him thinking of his work as philosophy.
6. If you still don’t understand why Tyler is asking something, think about comparative advantage. He views his guests as having uniquely benefited from some lifelong course of study (see (2) above) and attempts to extract as much insight as possible from the intellectual tools they’ve uniquely developed.
7. And if you still don’t understand, think about cultural background. Tyler thinks that things tend to have earlier roots than is generally recognized: that includes individual people’s intellectual output. He’s not asking about someone’s childhood to be polite or to humanize the guest: he probably suspects that their work on cancer research (or whatever) truly grows out of their being a cultural product of Topeka (or wherever).
8. Some, but only some, teachers-on-the-Internet (1) remember that you have pause and rewind buttons and (2) take you to know how to use them. Tyler is one of them.