My enthusiasm for electronic outlining is based on my experience as a professional writer collaborating intensively on some twenty projects in technical communication, journalism, and book publishing  over the last ten years.

To show why I think that this software can help writers in the workplace and classroom, I need to go back a decade, to explain how I came to see outlining software as such a useful tool for collaboration, through my work in industry.

Working with one to five collaborators from 1984 through 1998, I used outlining software to create

• Five manuals and six online help systems for computer companies such as Apple, Claris, Epson, and GO
• Dozens of workshops for teams of professional writers at major hardware and software companies
• 12 mostly technical books with regular publishers.

My decision to use outlining software was somewhat "overdetermined," as Apple (1986), Bell (1975), and Tuman (1992), have suggested is so often the case with choice of tools. One outliner had been heavily funded by a company I worked for, so I'd tried it out, liked it, and recommended it.

My collaborators and I spent some 60% of the entire schedule developing the outline far beyond the initial table of contents, the point at which many teams stop outlining (Allen, Atkinson, Morgan, Moore, & Snow, 1987).

We worked together to flesh out the initial table of contents, putting in sections on new features as they arose, removing mention of options no longer part of the product, shifting procedures around as we came to understand them better, re-sequencing the explanations, and moving major sections forward and back.

1) During the first few months, the majority of our time was spent sitting together looking at the computer monitor, swapping the keyboard as one, then the other, got an idea. We argued about sequence, interpretation, emphasis, hierarchy, phrasing, and process until we reached agreement (not just acquiescence). We took the outline well past the initial document plan, so we could accommodate new understandings, new features, new marketing emphases. We also drove the outline down to the level of steps in procedures and explanations of individual commands. We were, in effect, researching and writing as we outlined.

2) We postponed doing any solo writing until more than half way through the project, because we wanted to keep our structure open to the latest news, and our own evolving ideas. We then took individual chapters home and fleshed them out. But unlike our experiences with similar writing, we now knew the subject inside out, and because we had really understood and agreed to the structure, we had almost no structural rethinking, reconsidering, or regrets to work through. The remaining writing went incredibly quickly, and our different modules, amazingly, dovetailed snugly, without the usual inconsistencies that show up when different writers draft different chapters, cooperatively.

3) When we got to the second and final drafts, we discovered that unlike every solo or team project I have witnessed in the computer industry, the structure held up under the scrutiny of two dozen reviewers; we had no last-minute structural changes to make, and so, even during the last week before production, we were able to knock off by midnight.

Such extended face-to-face collaboration goes well beyond the teamwork, reviewer feedback, informal chatting, email exchanges, chapter swapping, and enforced cooperation that are often considered collaboration in industry (Couture & Rymer, 1989; Davis, 1977; Duin, 1991; Duin and Hansen, 1994; Ede & Lunsford, 1986, 1990; Faigley & Miller, 1982).

We also went against a basic assumption of many computer-supported collaborative work applications, that electronic collaboration should take place with participants widely separated, at far ends of a network, in virtual communities (Barrett, 1988, 1989; Barrett & Paradis, 1989; Duin, 1991; Kiesler, Siegel, & McGuire, 1988; Mabrito, 1992; Olson & Atkins, 1990).

We were unusual in that we used electronics to intensify direct human conversation. We wanted to see how far we could take writing toward the improvisatory collaboration of jazz.

More common is a writing process in which each author develops a tentative table of contents to go into the group's document design, but retains control and ownership over his or her chapter, book, or online system, while he or she diplomatically conforms to a thousand agreed-upon formats, phrasings, and spellings, gets reviewed by many other folks in different fields, revises according to team decisions, responds diplomatically to editorial suggestions, adjusts personal aesthetics to a corporate style and layout, and, very occasionally, incorporates suggestions from members of the intended audience.

 As I have seen in working on many other documentation teams, as well as consulting with dozens more, all of these activities take writing well beyond the romantic idea of the individual poet scribbling alone in a garret.

These activities transform writing into a social process. But because each writer retains "ownership" of each module, the exchange of views often remains incomplete, despite a lot of nodding, and the resulting chapters retain individual differences in style, organization, and viewpoint.

Collaboration, then, may be thought of as existing along a continuum (compare Schneider, 1990), ranging from the most isolated author adjusting a line of iambic pentameter for an adored audience of one, through the give-and-take of regular technical and business writing, which I call cooperation, to the most intense form, in my opinion, the direct conversation of several people sitting around the same computer talking together as they try to make sense of a complex subject. At this more intense end of the spectrum, then, one loses all sense of personal ownership of a phrase, a sentence, a diagram; one can no longer harbor secret resentments and go home and "do it my way."

Such direct, conversational collaboration, we all concluded, worked best when we focused on questions of organization, allowing the details of phrasing to emerge in individual writing, based on our discussions of structure.

Electronic outlining software gave us a way to consider alternate structures more quickly, thoroughly, and thoughtfully than any other tool we tried (paper, yellow stickies, white board drawings, diagramming software). Why?

With a dedicated electronic outliner like More™, we were able to carry out many of the outlining activities that our teachers had encouraged in the past. In high school, we had tried those activities but given up after one or two outline drafts, because revising the outline on paper proved too tedious.

Now for the first time we could see the value of beating on structure over and over, to temper it, refine it, purify it, and, ultimately, to make it understandable and usable for our readers. And, even better, because we were working together as a team, we edited each other's ideas right away, arguing through disagreement, reaching a consensus that reflected our combined perspectives. The results were cleaner, less idiosyncratic, less personal than the tables of content we came up with when we worked solo.

My collaborators

I owe many of my ideas on collaboration to Henry Korman, my co-author in How to Communicate Technical Information (1993), and my partners: Elaine Pendergast, Lisa Price, Mick Renner, Adam Rochmes, and Linda Urban.

I have also learned enormously from collaborating on books and articles with Steve Anderson, Weifeng Bao, Suzanne Brown, Chuck Campbell, Marty Downey, David Gillette, Nancy Hindle, John Lahr, Subhasish Mazumdar, Tom Outler, Randy Scasny, Carlene Schnabel, and Zhengang Yao.

My ideas of collaboration also owe an enormous amount to Jack Jorgens, the Shakespearean scholar, Joel Katz, the photographer and designer, my fellow artists in the Westbroadway Gallery, a cooperative gallery in New York city, the many participants in the Association of Artist-Run Galleries, and my collaborators on the Wall project at Pleiades Gallery-Joellen Bard, Marilyn Belford, Ken Glickfeld, Jerry Herman, and E. S. Pearlman.

Caution

Although collaborative outlining worked well for me and other professional writers over more than ten years, I am not recommending it for everyone. 

Successful writers vary enormously in the amount of planning, exploration, drafting, and revision they do (Bridwell, 1980; Emig, 1971; Faigley & Witte, 1981; Flower & Hayes, 1981b; Harris, 1989; Witte, 1985, 1987). 

Still, the more complex the job, and the more professional the writer, the more likely some form of outlining will be useful.

• In 1972, McKee surveyed professional technical writers with an average of 12.2 years in industry, and found that 95% created some form of outline (topic, word, sentence) for projects of 3,000 words or more. 
•  Baker (1994), Hays (1982), McKee (1974/75), Plung (1982), and Wagner (1994) all urge various forms of outlining (electronic or not) on business, professional, and technical writers as excellent techniques already being practiced by their peers.

What I and my partners were trying to do, though, was to go farther, using outlining as a convivial tool for collaborative work. That's what I recommend, if you decide to get into electronic outlining.  See it as a way to carry out a conversation, preparing materials for a specific audience, working out the best structure possible, as you schmooze together.