Sunday’s Master Class on profile writing with Mark Singer and Susan Orlean was the best event I saw all weekend. The talk was structured basically as Singer grilling Orlean, in a friendly way, on the process of writing profiles, while Orlean would occasionally turn the tables. As the have been friends for decades, their shared references made it a powerfully informative, probing, and intimate session. The two writers were both so genuinely curious about the other’s process, it was as if the audience were not there at all. It was a truly remarkable session.

What follows is a more or less unstructured selection of observations and quotations.

It was fascinating to observe the many things Singer and Orlean have in common (curiosity, thoroughness, mad typing skills) while approaching very similar projects quite differently. Orlean is warm and seeks emotional connection with her subjects; Singer is more detached, calling his a “deadpan approach.”

Singer prefers to do exhaustive research before meeting the subject; Orlean prefers to learn about the subject in a more haphazard way. Singer made a great point about questions, saying that you should never ask a subject for information that you could acquire independently. In other words, don’t ask “Where were you born?”—ask what it felt like to grow up in Sheboygan. The former is publicly available; the latter is what you’re hired to find out. Orlean saw this differently; as she said, “I write a profile the same way I would go about making a friend,” and you would certainly ask a budding friend where she was born.

More than you would think, a lot of the process of writing these profiles occurs before it’s even agreed that there will be a profile at all. There’s a great deal of negotiating with the subject about access, and many profiles never end up happening at all. Some of Singer’s more interesting stories had to do with unwritten profiles. Since profiles at that stage are so amorphous, the process, later too, is necessarily infused with self-doubt—is this a subject? why would people read this? What am I doing here? And so on.

To counter this, a good profilist needs a compensating sense of worth: As Orlean said, “You have to have the confidence to say, as a writer, that somehow the choices you make are, in and of themselves, justifiable.” A simple and yet elusive point—as the example of a profile she did for Esquire about “the typical ten-year-old boy” demonstrates. She had to assume, on some level, that she was, of necessity, capable of “proving” to the reader that this material worth reading. “I love seducing readers,” she said, starting with a subject that seems of doubtful interest and then winning the skeptic over. She observed that Tina Brown, someone who would normally suggest very well-known people for profile subjects, could never really understand how Orlean achieved her effects (the two women have an abiding friendship nonetheless).

On the subject of editors, both writers were unabashed in their praise—indeed, awe—of David Remnick’s reportorial skills. As Singer said, “He is so good that he can spend a week in Israel and write a ten-thousand-word piece on the flight home,” a process for which the two panelists and most of their colleagues presumably would need far longer, on both the data collection and production sides. That had come up as a tangent on the subject of notes—both Singer and Orlean take copious notes, but Orlean insisted that the writer should be able to tell the story of the piece entirely out of her head, as it were. Until you’ve gotten immersed to that extent, you’re not ready to write. She compared the process to that of telling an anecdote at the dinner table. If you say, “I heard about this car that got stolen, but the owner’s dog was still inside,” your dinner-mates will likely not wrest the floor from you anytime soon. The same dynamic is in play with a successful profile. (That anecdote was the basis for an actual profile Orlean wrote, by the way.)

Orlean raised the question of tape recorders. Singer said that he has used them but hates them, “because then you have to listen to it.” As many people do, he detests transcribing as well as the sound of his own voice. Rather surprisingly, to me anyway, Singer likes to bring his laptop along as often as possible, and will often transcribe conversation with his subjects on the spot. Singer said the best course he ever took was typing, and Orlean laughingly bragged that she types exceedingly well, even better than the well-known Meryl Streep incarnation of her .

I did not know that Orlean did profiles for Rolling Stone for a long time. She explained that the material for a Rolling Stone profile is usually gathered an hour or less, in a hotel room with the subject, a process so truncated that the writer must, of necessity, invest random utterances and actions with absurd significance. (Singer: “The best approach in those situatons is just to shoot yourself before the interview.”) In addition, “nut grafs” are a Rolling Stone requirement: “The Fugees are important right now because …” At The New Yorker, unsurprisingly, things are different. Writers are encouraged to come up with a form and approach that fit the material, even if it means spending weeks with the subject. Singer said that the process is often so attenuated that subjects frequently question whether he is competent, wondering how on earth anyone could ever make a living this way. Orlean offered that she is always grateful that she can spend three weeks not apparently accomplishing much while she gets a sense of the subject at hand.

On the subject of form, Singer referred to his “cinematic” understanding of content, which leads him to use “scenes” to help him structure the material. As he said, “You have to have a really great reason to abandon chronology,” something that Orlean does more often than most. Singer observed that it is very difficult to write profiles about very funny people. There is a constant temptation to reproduce shtick, which never comes off nearly as good in print; such pieces are always threatened by a “you had to be there” quality that is death to a good profile.

Orlean once did a kind of mental tally of the geographical origins of New Yorker employees, concluding that the staff was “overwhelmingly midwestern” (I pass on the information in the interests of sociology). Singer and Orlean agreed that in a city like New York, many good profiles arise out of a kind of restless, pavement-pounding inquisitiveness. See an odd shop? (Orlean’s example was a shop specializing in ceiling fans.) Talk up the proprietor, you’ll likely discover a hidden expert in some arcane subject: “Everybody’s more intensely whoever they are in New York.”

I could easily go on for another ten paragraphs, but I won’t. Clearly, this material fascinates me in a big way. I’ve read a great many profiles in my time, and now I have at least an inkling of how they are put together. For that I am thankful. —Martin Schneider