I want to further explain my misgivings about Ryle's account of knowing-how (see here). Ryle's positive view of knowing-how is embedded in his arguments against intellectualism. As Jason Stanley noted during his "meisterkurs," these arguments are targeted against a number of different positions at the same time, and Ryle lumps them all together under the banner of "intellectualism." First there is the notion that all knowledge is knowing the answer to a question. This is the position Jason wants to defend. Ryle is also arguing against the view that the intellect is the defining feature of the mind: that to be a person is to have a mind, and to have a mind is to have an intellect, where the intellect is defined as that which considers and grasps propositions, or truths. I think Jason wants to defend this position, as well; and it may very well be entailed by the first position. Along with these views is the view that, in order to act intelligently, one must perform a unique act of grasping a proposition. Jason rejects this view, claiming that it is just manifestly absurd to think that one has to perform a unique act of engaging propositional content in order to apply one's propositional knowledge. An issue here is how we understand propositions. For Ryle, one can follow and understand rules without grasping propositions, because Ryle thinks of propositions as sentences. Jason rejects this view of propositions, and so rejects Ryle's view of propositional knowledge. While Ryle argues that the following of a rule is logically prior to the grasping of a proposition, Jason thinks these amount to the same thing. (I think there's an interesting question about whether or not rules can be considered propositions, but I won't get into it here.)
In The Concept of Mind, Ryle says that training involves lots of "sheer drill." Yet, at the same time, he also says that "drill dispenses with intelligence, training develops it." This means that training both develops and dispenses with intelligence. To avoid the contradiction, we might say that Ryle just misspoke, and that training doesn't really involve drill, though this seems empirically false. Training does often involve drill. So perhaps Ryle meant that only drill without training dispenses with intelligence. When drill is part of training, intelligence is developed. The problem then is how Ryle wants us to conceive of the difference between drill as part of training and drill as such.
Ryle appeals to cases where rote learning is supposed to be obviously distinguishable from active learning. He contrasts the memorization of multiplication tables or the alphabet with learning how to read maps or play chess. But, as he says, even these cases of supposedly active learning entail rote memorization. And even in the relatively simple cases of learning the multiplication tables or the alphabet, one is still susceptible to Wittgenstein's rule-following dilemma. We might suppose that, as he said back in 1946, even to learn how to follow the basic rules required for mere drill, we must use intelligence. And therefore we no longer have a coherent distinction between drill and training.
Ryle does not seem to have presented a coherent account of knowing-how. One response to this fact is to say that Ryle was never trying to do that in the first place. Ryle is not doing metaphysics. He's not an epistemologist, either. He does not commit himself to the view that knowing-how is a natural kind. This does not mean Ryle is a fictionalist about the mind. Ryle does not say we are only speaking figuratively when we talk about judgments, learning and so on. He seems to want something like what Daniel Dennett develops in his work on the intentional stance: a view of the mental idiom as a predictive strategy. Indeed, Dennett no doubt was influenced by Ryle on that count.
Ryle says that, when we attribute mental capacities we are issuing ouselves "inference tickets." We license ourselves to make various explanatory-cum-predictive assertions about people's behavior. Thus, when we call something a judgment, we are not referring to any intrinsic properties--no special features which define it as such--but rather to the way it is situated with respect to other things. Similarly, when we call a performance "intelligent," or the exercise of a skill, we are not referring to any intrinsic properties, but only to the way the performance is situated with respect to other things.
On this view, Ryle is not trying to identify a natural kind. He's just trying to map out the logical space of a particular idiom. Ryle even refers to it explicitly as an idiom. If our common sense distinction between drill and training breaks down upon closer inspection, so much the worse for the common idiom. Thus, what appears to be a contradiction in Ryle's thinking is just a contradiction in the way people normally think about human behavior.
That answer might be plausible, if it were not for the fact that Ryle's aim is a metaphysical one: to overturn the intellectualist view of minds and action. Furthermore, Ryle seems to take the distinction between rote repetition and active learning, between drill and training, as a very real one. If Ryle believes that there is no intrinsic difference between these things, then he does not believe there is an intrinsic distinction between single-track and multi-track dispositions. But Ryle seems committed to there being an intrinsic difference here. That, I think, is Ryle's greatest error. He doesn't leave himself any conceptual space to make sense of any sort of intrinsic difference. He tries to finesse the problem by saying that the difference is just in the way the performances are carried out. I don't see how this can be read, if not as an assertion about intrinsic properties of action. And, as it must be, he does not give himself room to provide a coherent account of ways.
One of Ryle's main points is that the difference between an intelligent performance and an unintelligent (or non-intelligent) one is not the occurence of some extra operations, but rather just in the way the performance is executed. This is Ryle's metaphysics of the mind: Minds are not special places or sorts of mechanical processes. They don't exist in the same logical category as causal states or events. Minds are dispositional. Thus, the difference between a mentally engaged process and a mentally inert process is not a difference in causal features, but a difference in dispositions. So, an intelligent performance cannot be distinguishable by its causal properties. We cannot locate any special operations or states which define "active learning" or "using critical judgment." We have to view these dispositionally. And yet, these dispositions are manifest in the ways people perform. So what are ways?