If Darwin’s theory of evolution holds, humans will develop a set of nimble, styluslike digits to work with our electronic devices—and fast. Too late, of course, for me to avoid embarrassments like the one I recently suffered, when I fat-fingered the following Blackberry message to legendary editor Daniel Menaker: “hey Dan: see by 11 or so? I have a plumbee here now but should be done by soon. Today stull work for you?” But as mortifying as it was to have just assaulted one of the publishing world’s great wordsmiths with a foul sentence, that mangled e-mail turned out to be a great conversation starter.

Admit it,” I say, “when you got my e-mail, didn’t your heart sink a little?” Menaker laughs. Humor—a good start. “No,” he says, good-naturedly. “I didn’t take exception to that.” Within seconds, we move from my poor typing to the English language and technological upheaval. Changing subjects: excellent. “Our language is like silly putty,” Menaker observes. “It accommodates. It can’t be misshapen.” What about teenagers and their entirely new lexicon born of text messaging, I ask? Ah, curiosity. “Fascinating to me,” Menaker replies. “I learn from it. I have no objection to writing 'U’ instead of 'you,’ for example. What I would hate, though, is for English to lose its subtlety and nuance. If that is an outgrowth of all of this, then I would be upset.” He launches into a detailed explanation, something about the Hawaiian language, and how consonants tend to be dropped over time because, well, because... uh oh, boredom.

“What if I had included one of those little smiley faces in my e-mail?” I interject. Menaker raises his hand. “No,” he says. “Now that I strongly object to.” Thank you, impudence.

Okay, so ordinarily I don’t sit around checking off a conversational scorecard, but since reading Menaker’s A Good Talk: The Story and Skill of Conversation (Hachette/Twelve), I find I can’t stop deconstructing my conversations. The book brims with examples and analyses of conversation and amusing anecdotes from Menaker’s fabled 26-year career at the New Yorker and his 12 years in publishing. “I’m not an expert or a specialist, but I’ve been around for a long time and the more I researched the subject the more interesting it became,” Menaker says, when asked how he came to write a book about conversation. “And it amused me. I’d written a lot of humor for the New Yorker, and I thought I could write an amusing book, as well as an enlightening, possibly useful one.”

Amusing, and useful. Not only have I been great at parties lately, last week, in fact, this reporter put the book’s lessons to work on a phone call with a computer company’s lackluster customer service department. I’ll spare you the transcript. But I prolonged the conversation long enough to score a $100 credit—no question, just to get me off the damn phone. With Web 2.0 merging conversation and literature into new and exciting forms, PW caught up with Menaker for a good talk about his new book, his new, new-media gig consulting with the B&N Nook to deliver humor pieces to the e-reader’s fledgling Grin & Tonic section, and the publishing business then, now—and in the future.

So I’m feeling a little extra pressure to be a good conversationalist today. Do you have any pointers for me?

You’re feeling extra pressure. How about me? What have I done to my social life? For starters, you should avoid responses like the one I just made. One of the worst habits some talkers have is to immediately refer any comment from another person to themselves. One person says, “Sonia Sotomayor is disappointing me,” and the response is, “yeah—you know, I applied to law school, but I decided not to go.”

I guess mainly I would say to anyone, cultivate your curiosity. And if you like the person or people you’re talking to, meet candor with equal candor.

The book offers some insightful and very funny conversational examples from your career, especially from the New Yorker. Is there a connection between good conversation and good literature?

It seems clear to me that books originally grew out of oral storytelling, so, yes, there are of course correspondences between conversation and literature. They are both made out of words, after all. And both, when they’re good, have layers—they linger, and resonate after they’re over. The main differences are that literature is at the beginning entirely one-sided, and conversations are not only plural-sided but verbally looser and less demanding, more recreation than concentration. Still, every now and then we meet people who can tell a story so good and so well that it is in fact oral and aural literature.

What was it like to be at the New Yorker in 1969?

It was a lunatic asylum. A wonderful magazine, but a cult of personality focused around William Shawn, the editor at the time. I started as a fact-checker and worked in a small room with six other people, and everyone smoked. I knew I was in a truly strange place when about two weeks after I started work I answered my phone and a little voice on the other end said, “Mr. Menaker? This is William Shawn.” I said, “Hi, Mr. Shawn, what can I do for you?” As we talked, I noticed everyone staring at me. After I hung up, I asked the person who worked across from me why. “You don’t say 'hi’ to Mr. Shawn,” she said. “You say 'hello’ to Mr. Shawn.”

You were shaking things up already?

Trouble wasn’t my middle name at the New Yorker, it was my first name. I was once asked to leave. I remember it started over a line from a Charles Reich piece after The Greening of America that read something like, “after all, it’s our constitution, not theirs,” meaning government officials. To me that just didn’t sound right. It’s a resounding line, sure, but sounded like a Jacobin rebellion. I questioned it, politely, and was told I was out of line. So I decided to write a 1,000-word piece about the false premise of that statement. I gave it to William Shawn, and two days later the executive editor came in. “What do you think you’re doing?” he said. “You’re a member of the junior editorial staff.” I’ll never forget that. To this day, no diminutive has ever sounded smaller to me. A few days later he told me to look for another job. But I hung on. I wasn’t fired, and William Maxwell, perhaps the most eminent fiction editor of his time, took a liking to me. Shawn was said to be an iron hand in a velvet glove, but I think his hand was velvet, too, because nobody made me leave. And that turned out to be a good lesson in management—you should always look at the talents of people who give you trouble before you just tell them to go away.

You eventually went to Random House in 1995. How did that move come about?

I feel certain that Tina Brown asked her husband [Harry Evans] to give me a job. She might dispute this, but she took me out to lunch one day, and said “Dan, what do you think of Bill Buford?” I said, “There goes my job.”

“Oh, don’t be silly,” she said. “I’m not going to hire him.” About three months later, Harry Evans made me the offer at Random House. “You’ve been at the New Yorker for six or seven years now,” Harry said. I said, no, 26. I went back to Tina and said, “As you know, your husband just offered me a job.” She said, “Yes, we’d hate to see you go.” Well, that’s it, I thought—I’m gone.

Did you have any idea what you were getting into with book publishing?

No, not really. [Former Holt publisher] John Sterling was the only person to advise me to think twice about taking the job. “You do understand that you are going into a sales job,” he said—and there was some merit to that. I didn’t even know what a marketing meeting was. I remember Ann Godoff took me into her office and asked me if I could do a P&L, and I said, “What’s a P&L?” Ann was great. She walked me through the whole thing. How many books do you think this project will sell? What will the returns be? I said, “What’s a return?” It was like the old Bill Cosby routine about the kids in kindergarten: “Two plus two make four. Yeah... what’s two?” That was the level of my ignorance. But I learned by doing, and either I was good or lucky—probably both—because the first 10 or 12 books I published did very well. The first novel I published was Primary Colors, which was a #1 bestseller and sold over a million copies in hardcover.

Did you think, hey, the book business is pretty easy?

No, I thought it was completely hard. I was glad it was working out, but it was difficult. The most difficult thing was the meetings. The meetings drove me crazy. They were largely ritualistic and repetitive. When I went into book publishing, the ratio of editing to other stuff flipped from 75/25, even at Tina’s New Yorker, to 25/75. And now I was dealing with 400-page manuscripts.

In December, you published a pretty sobering assessment of life in the book business, Redactor Agonistes, in the B&N “Review.” What motivated that?

Why did I write that piece? Good question. Publishing is a noble profession. But I think there is great tension between seeing publishing as a cultural enterprise and seeing it as a commercial enterprise. I think these kinds of pieces happen cyclically, as people leave publishing in greater or lesser bitterness. Whenever I speak to a high school class, I’ll hold up a book and say, “Tell me all the things that go into this.” They’ll begin talking about jacket and flap copy, what does this barcode mean, the author bio, page layout, who decides the price, how do you get these things out? They begin to see what’s involved in the manufacture of a book. It is an incredibly complicated process to manage for someone who thinks of himself more purely as an editor.

Why did you decide to leave Random House?

I think both sides tried to renew my connection in a good faith way—we simply failed to come to terms. When I look back at it now, I realize it was inevitable. There were other things I wanted to do. But I think a fair amount of time for an editor or an executive to prove himself or herself is five years, and I just don’t think publishers have that kind of time anymore. I think they’re caught. Financial returns have to be managed almost quarterly now, and the pressure is so great within the large media conglomerates that corporate accounting systems may no longer be able to brook the very severe ups and downs book publishers have, because shareholders are looking for sustained growth. I think with the Internet’s arrival, the already difficult fit between publishers and their parent corporations has become even more difficult. People are buying fewer books, there’s a fragmentation in attention, and if there was a literary or book culture it is being broken up by the Internet. Yet the imperative to have big sales grows stronger. The pressure for big sales was always there, of course, but publishers used to be okay with a 5% profit margin. That doesn’t wash anymore.

How did you become involved with Barnes & Noble and the Nook? Did you consider other publishing jobs after Random House?

I had some offers. If someone had come along with the right offer, I might have taken it—to some extent Barnes & Noble did. Mike Skagerlind [head of digital content at Barnes & Noble] told me he was looking for someone to manage a humor feature on the Nook called “Grin & Tonic,” and asked me if I knew anyone who would be interested. I said, why not me? I’m not an employee, I’m a consultant, but I really like it, and the dot-com world really is different. For the first “Grin & Tonic” piece, Dave Barry, to his assistant’s astonishment, gave us a fabulous piece called “How to Use Your Nook.” I thought, I can do this, this is fun. In this age of upheaval, one of the responses people have is humor, which is why the Onion has thrived, and the Daily Show. I think with such technological anxiety, this is a good time to be doing this.

Now that you’re involved with the Nook, how do you feel about digital reading and e—readers?

I don’t really know, but I think in 10 years there will probably be as many e-readers as there are digital cameras when you go into a store. There will also be devices that are e-readers along with everything else they do, so it may be that e-readers like the Nook and Kindle are transitional. I think book-length texts will probably get shorter, as they have in printed books, though of course there will still be 500-page door-stops, too, and that we will see a very rapid evolution. I think that in 10—15 years at least 50% of book-length texts will be read digitally, probably more, and printed books will shrink down to a special, almost boutique market. And then, they may expand again, because it’s not only geezers who like books. The book is a wonderful device. Also, I think that there is something about an electronic text that makes it harder to become immersed in. Pixels move—even though you don’t see them move. I think there is an unconscious awareness of their lack of physical realness.

As someone who started at William Shawn’s New Yorker, you’ve seen a lot of change in the literary scene over the years. Do you think publishing and literary culture will survive the digital transition?

I think digital is good for literary culture—and I think it is bad. I think it is good because more people will have more immediate access to more texts than ever before. But I think it’s deleterious, too, because it is decentralizing. I think it is good to have a nation or a culture with a literary center, and I think that’s going to be harder to come by with the fragmentation electronic delivery brings. I think the book industry is having a hard time trying to come to terms with this. If I owned a publishing company, god forbid, I would try to get 10 bestselling writers together to publish their books first in electronic versions only. If you had Gladwell and Grisham and a bunch of big authors whose books were only available on e-readers, even at a price of $9.99, economically I think it would be worth their while. Then you follow with a printed book a few months later. Not to be mercenary about it, but if you dispensed with the shipping, with the production costs, you outsource editing, promotion, marketing, you could make a killing.

You say a literary center—but I have to ask, what’s at the center: writers, editors, shareholders in big companies?

My father always used to say, “Things aren’t like they used to be.” I used to call that geezer talk. But when I was between the ages of 10 and 40, there was a consensus about what mattered in terms of serious reading. I don’t feel that now. And I think I’m going to feel that less and less. I also think the blockbuster mentality is deleterious to literary culture—there is such a thing as too much fragmentation, and such a thing as too much concentration. For me, it was ideal in the 1960s, maybe because that’s when I was at my most enthusiastic. Then you had wonderful writers whose next work you knew you wanted to read. I guess people do want to read Dan Brown’s next book, but, well... I don’t know.

Some question whether future generations will continue to read, or maybe more to the point, whether they will continue to write, as if the next generation of Updikes might choose to express themselves through Twitter or YouTube videos or mashups instead. Is the future of literature really so challenged?

Well, it goes back to storytelling. We have always needed storytelling, and until we evolve into a different species, we always will need it. Nonfiction stories, novels, poetry. That is, unless the machines, from the outside, work their way in and change our brains into organs of complete impatience. Reading is quite recent, historically, and I suppose that narratives told for their own sake and for enlightenment may someday become obsolete. But that’s a long way away. It’s hard to imagine that people with long-form narrative and expository talent will not be in demand in one medium or another. I actually take some narrative comfort from knowing that last year was a good movie year. I’m not sure writers should think that way, but I do.