Kevin Dettmar's recent lovely ode to an editor put me in mind of my own readers. Like the art of praise, the art of giving useful feedback is a delicate one.
Although I've been trying for years to cultivate a detached attitude toward my writing (as all writers do), I still find it frightening to show writing in its early stages. It is always bad. A bad version of every essay must be written, often multiple bad versions. There is no point in trying to save time by skipping the bad version; there's no skipping it, because without the bad version there can be no good version.
The bad draft is bad because we write our anxieties. If we feel hemmed in by a previous critic's argument, then we ramble on about how very wrong that critic is. If we feel insecure in our understanding of a philosophical point, we will attach multiple lengthy footnotes to the section in which we explain it. If we're not quite sure what we mean by a phrase, we will say it repeatedly. At least for me, a first draft is a record of my anxieties about the ideas about which I'm writing. Only later can the bloom of anxieties be cleared away, and the ideas themselves emerge, blinking.
A good reader helps the ideas emerge by taking for granted that they are there (somewhere). She assumes that you know what you're about, gives you the benefit of the doubt, and responds to the smartest version of what you could be saying. She tells you not only when you're being unclear but also how. Instead of naming deficiencies, she asks questions and offers suggestions. She notices patterns in your writing that you didn't see yourself. Above all, she tells you what she sees, which is usually different from what you think you said.
Like praising, giving feedback is a skill I learned informally. I had a dissertation group for a year or two, and that was crucial in helping me see how to respond to others' writing. (I was also teaching composition continuously during this period, which made for some startling revelations.)
The dissertation group made me realize that good feedback is not only a response to writing but also to a writer. Some people have particular habits that need remarking. Some people's relationships with their dissertations are so fragile that suggestions must always come in the form of praise, lest the writer despair and stop writing altogether. And often, too much feedback--high quality or otherwise--is so overwhelming that it shuts the writer down. The point of feedback is not to be exhaustive but to be useful.
I've had many good readers, and there's something exciting (also scary) about receiving feedback from someone for the first time. It's a special kind of favor that scholars do for one another, one that I've always deeply appreciated. Just as there are certain things only family and friends can do for you, there are certain things that only a scholar can do. Likewise, it's an honor to be asked to read a colleague's work in progress. (I say this with a little guilt, knowing that I still owe someone a response to an article.)
In addition to these, I have two truly exceptional regular interlocutors, one an advisor, one a peer. Both of them are exceptional first of all because I trust in their scholarship. Both do me the honor of engaging deeply and frequently with my work, even in its bad phases. Of the two, the more senior is perhaps the better respondent to my writing; he's a master of the distilling phrase. It's my peer, however, who's the better respondent to me as a writer; she knows my work in all its forms and can detect latent concerns before I do. Because of these two readers, writing is never not collaborative to me. Even when I reject all of their suggestions, my thinking changes, and therefore so does the writing.
There is also an art of taking feedback. But that's another topic.