The historical Buddha taught in different ways for different audiences. Of course, what he taught was, in many ways, radically different from anything the people of his time had heard before. He knew that much of what he had to say might sound like nonsense.
So, rather than preach over people's heads, in his sermons he built upon the capacities and assumptions of the people in front of him, listening to his words. In effect, he met them where they stood, in a thicket of illusions, and gave them as much instruction as they could handle so that they could find their way out of the thicket. To do this, he had to be skillful at sizing up the audience.
"Sizing up the audience" is something we all have to do sometime. At Nyoho Zen, Koun Franz writes about playing with his three-year old son, and about misunderstanding his son because he failed to see the world through his eyes. He writes,
"So much of teaching is putting oneself in the place of the student, anticipating that person's difficulties and addressing them. That's the start of skillful means, and it's hard to remember it sometimes, much less to get it right. For some reason, I have the hardest time standing in my little guy's shoes. I'm so busy celebrating for him (and congratulating myself) that I lose sight of what he sees, which is a world made of high walls, impossible dexterity tests, and cruel oral exams."
Do read he whole post; it's very sweet.
Elsewhere I found someone's account of liberating a lizard from his bathroom. The lizard needed to be outside where she could find things to eat, but she scampered away whenever the human tried to catch her. Only when the human began to consider how the lizard experienced things was the human able to guide her outside.
I've found that when giving people instructions it is sometimes helpful to tell them only so much at once. For example: I've been voluntarily assisting a jukai class in sewing new rakusus. A rakusu is many little pieces of cloth sewn together in a very exacting way, and there are infinite ways to make mistakes or for the thing to turn out lopsided. Making one is a challenge for an experienced sewer, never mind a sewing newbie.
At one point I was explaining the next two or three steps to someone, and I saw panic in her eyes. It was too much at once. So I said, forget that. Just do this one thing, and when that's done we'll go on to the next thing. And then all was well.
When the Buddha taught, he didn't explain everything at once. Often he was addressing just one thing that was most perplexing his listeners. And because his audience lived with a whole different set of cultural assumptions and perspectives, some parts of the sutras may need skillful re-contextualizing to be accessible to modern students.
Today, people often pick up one or two "things" about Buddhism and build an entire Grand Theory of Dharma around those things, not realizing that what they've learned is one step, not the whole ladder. This is why it's important to stay open to expanding one's understanding.
It's also good practice for all of us, as we communicate with anybody about anything, to try to put ourselves in the place of the person we are talking to. At the very least, we'll be bringing a little more clarity to the world.