I started reading a book called Brain Rules last week, and in the fourth chapter on attention the author slipped in a recommendation to start explanations with an overview of the concept, then break it down into lower level details because that's how people learn best. The author seems pretty scientifically rigorous and this was presented as a blanket generalization, so I was surprised. Mostly because my brain is completely unlike that.
I work terribly with high-level overviews of systems when I don't know the details. Actually, I'm pretty sure that I'm always terrible with high-level overviews of systems. There have been a couple of very memorable moments in my life where I learned enough rules about something that the entire system and how it worked suddenly became clear. Choir-of-angels-singing-from-the-heavens moments, truly. The most memorable of these was the day that I finally understood math--some piece of knowledge fell into place in high school calculus, and all of a sudden everything that I'd learned prior made perfect, wonderful sense. Before that moment I'd hated math. Then I ended up at college majoring in computer science and spent three years as an Algebra TA.
After thinking about it more, I realized that the high-level stuff was actually discussed, usually in the first week or two of a new math class. I vaguely remember analogies being presented about functions and derivatives, but without anything concrete this all went in one ear and out the other. I would have greatly benefited from having the analogies/overview explained to me AFTER learning the mechanisms and details, but that never happened.
Looks like the way my brain works might be in the minority--most people that I've talked to about this genuinely prefer the overview-before-details approach to learning. I wonder how it breaks down as a percentage of the population, but I'm having trouble locating actual research on the subject.
I've definitely made mistakes in the past by assuming that everyone's brains worked the same way that mine does. Instead of explaining a system or concept in a generic way, I've tried to introduce it by assigning people concrete tasks, assuming that after working with the system in a few different ways, they would develop an internal model of the system on their own since this is how I learn best. I heard the question that's the title of this post asked by a coworker who was explaining a system to a new employee a few weeks ago. I'll definitely steal this question for use in future instances where I have to explain a complex system and tailor my explanation based on the answer from now on.