Reminds me of when I was training truck drivers. I normally was in the right seat, but once in a great while we had to do a bit of a "team" drive. There were times where I would be back in the sleeper with the curtains closed for four hours, and then yell to my trainee "Hey, you just missed your exit!" and they'd yell back "HOW THE **** DID YOU KNOW THAT?"

After a while, you just know every curve, bump, and smell for a large portion of the country. In most of the Midwest and Northeast, and some parts of the rest of the country, I can still know where I am by looking at the roads below without even looking at a sectional.
But yeah, the instructor knows better than you do, OP. That isn't to say that he's doing what Jesse is talking about for sure, but have you looked at what he's doing on the phone exactly?