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When we read the account of the Buddha’s last night, it’s easy to sense the importance of his final teaching before entering total nibbāna: “Now, then, monks, I exhort you: All fabrications are subject to decay. Bring about completion by being heedful.” These words call attention to themselves because they were the last he ever said.

That may be why it’s so easy to overlook the importance of what the Buddha did right before saying them. In a gesture extremely gracious—given that he had been walking all day, had fallen severely ill along the way, and now was about to die—he offered one last opportunity for his followers to question him. He even made the offer four times to show that it wasn’t just a gesture. He seriously wanted to clear up any remaining doubts in their minds before closing his mouth for good.

Then the Blessed One addressed the monks, “If even a single monk has any doubt or indecision concerning the Buddha, Dhamma, or Saṅgha, the path or the practice, ask. Don’t later regret that ‘The Teacher was face-to-face with us, but we didn’t bring ourselves to crossquestion him in his presence.’”

When this was said, the monks were silent.

A second time… A third time, the Blessed One said, “If even a; single monk has any doubt or indecision concerning the Buddha, Dhamma, or Saṅgha, the path or the practice, ask. Don’t later regret that ‘The Teacher was face-to-face with us, but we didn’t bring ourselves to crossquestion him in his presence.’”

A third time, the monks were silent.

Then the Blessed One addressed the monks, “Now, if it’s out of respect for the Teacher that you don’t ask, let a friend inform a friend.”

When this was said, the monks were silent.

Then Ven. Ānanda said to the Blessed One, “It’s amazing, lord. It’s astounding. I’m confident that in this community of monks there isn’t even a single monk who has any doubt or indecision concerning the Buddha, Dhamma, or Saṅgha, the path or the practice.”

“You, Ānanda, speak out of confidence, while there is knowledge in the Tathāgata that in this community of monks there isn’t even a single monk who has any doubt or indecision concerning the Buddha, Dhamma, or Saṅgha, the path or the practice. Of these 500 monks, the most backward is a stream-winner, not destined for the planes of deprivation, headed to self-awakening for sure.” — DN 16

It’s possible to read this passage simply as a rhetorical flourish, indicating how special the assembly was that had gathered to witness the Buddha’s passing: Only those who had had their first taste of the deathless were privileged enough to be present. But the passage goes deeper than that, showing how the Buddha had brought them to that taste. Instead of enforcing an unquestioning acceptance of his teachings, he had resolved his students’ doubts by being open to their questions. The fact that this incident is placed right before the last teaching is a measure of how central this method was to his teaching, and how important it was to his followers who assembled the Canon.

Other discourses emphasize this point as well. AN 2:46 [§73], for instance, notes that the Buddha trained his followers in cross-questioning, with the result that, “when they have mastered the Dhamma, they cross-question one another about it and dissect it: ‘How is this? What is the meaning of this?’ They make open what isn’t open, make plain what isn’t plain, dispel doubt on its various doubtful points.”

The central role of questioning in the Buddha’s teaching may be connected to the fact that his teaching starts not with a first principle but with a selfevident problem: how to put an end to suffering. And instead of trying to argue from this problem back to first principles, he stays focused on the immediate question of how to solve it. As he noted, suffering gives rise to two responses— bewilderment and a searching question: “Who knows a way or two to stop this pain?” To help put an end to that bewilderment, the Buddha presented his teachings as responses to the many questions deriving from that primal, searching question. Thus questions formed the primary mode for organizing what he taught.

But even though the Buddha ordered his teachings around questions rather than first principles, he did not set out to answer every controversial question that came his way. He focused solely on questions related strategically to the end of suffering, i.e., questions that would actually help in attaining that goal.

For this reason, he classified questions—as they related to this focus— according to the response-strategy they deserved, and he arrived at four sorts: those that deserved a categorical answer, those that deserved an analytical answer, those that deserved to be cross-questioned before being answered, and those that deserved to be put aside. This fourfold classification is the theme of this book, for it provides important insights into both how and what the Buddha taught about the way to end suffering.

To understand the importance of this classification, and why the Buddha formulated it in those terms, it might be useful first to reflect in general terms on what it means to ask and answer a question based on a desire to attain a goal. A helpful way to begin that reflection is with a question that, in Western thought, is first stated in Plato’s Meno:

When youre looking for something but dont know quite what it is, how do you know when youve found it?

In the Meno, Socrates uses this question as the departure point for his doctrine of memory from past lives: You know what you want because you knew it in a previous lifetime. But from a Buddhist point of view, a more fruitful approach to this question is to look at the psychology of how people go about setting up a problem and solving it in the here and now: You know when you’ve found the knowledge you were seeking because the desire that sparked your search had already given it a function and a shape. You wanted knowledge that would perform a desired function, and you wanted it to make sense, to fit in with what had worked with similar problems in the past. When you’ve encountered something that, when put to the test, meets both specifications— the function and the fit—you know that that’s what you wanted. (Ironically, even Socrates himself would set up a problem and test the proposed solutions in precisely this way.)

The questions aimed at determining the fit and function of your answers operate on three levels. The first level aims at giving your ignorance a shape, to define your felt need and why the need makes sense. The second and third levels determine if the answer actually functions as you want it to, with the second level establishing tests for checking the actual performance of whatever potential answer seems to fit that shape, and the third setting standards for measuring whether an answer has actually passed the tests.

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