In order to truly understand a text, the reader must actively engage with the material, must connect what they know, understand, and have experienced with the material, and then must go through a progressive series of reflections and interpretations that eventually allow them to collapse all of the complex pieces into a coherent, integrated understanding of the whole. Most people read the text and that is it. When we expect students to come prepared to have deep philosophical conversations after a single reading, we are being unrealistic. We have to structure and scaffold their reading so that their brain has time and process to do all that expanding necessary to allow them to explore the potential implications of the text and relationships between them, and then the collapsing down to essential points, then the re-hydrating the dehydrated version so that it occupies a three-dimensional place in the brain's long-term filing cabinet.
The same is true of conversations with people. The same kind of thinking is required. Some people bring faster processing speed, more connections, more background knowledge, greater flexibility when it comes to leaping across categorical boundaries, so they can "get there" (to a synthesis) faster—especially if those with whom they are speaking are slower at accomplishing all of those things, or if the topic of conversation is something they have already spent a lot of time considering, but I suspect that the process is the same for both sets of people. "Intuition" plays a role in the process as well—speeding things along even faster for those who understand how to connect that pipeline of truth so that it flows into their other "ways of knowing."