(2002-04-02) d

Jon Udell's big piece on Instant Outlining. EMail is not a Context-preserving medium. Life is just too short to waste time looking for missing attachments, or trying to remember who was cc'd on which part of a discussion, or organizing inboxes by project, role, and priority. Instant outlining is not a solution to these problems. No technology, in and of itself, is a magic wand we can use to wave them away. But instant outlining is, perhaps, an environment within which we can finally begin to make some headway... When I turned in the first draft of my book, my editor, Tim OReilly, said: "This is great, but you ask too much from people." And he was right. I was advocating not just a communication tool, but a way of using it to optimize collaboration. That meant asking people to narrate their work, but also to think carefully about the attention demands they placed on their coworkers, and to label, structure, and layer their communications accordingly. Most people didn't want to do these things, and most people still don't... It's been clear to me for a long while that the only thing that might displace email would be some kind of persistent IM. That's exactly what instant outlining is... A few highly-motivated people will find they can improve their collaboration in new and powerful ways; most will still tend toward ill-considered and unstructured communication. But perhaps in this medium we can finally bootstrap software that encourages and supports best practices.

Dave Winer's [parallel](http://davenet.userland.com/2002/04/02/jonUdellOnInstant Outlining) article. Like many groups who depend on email for communication, we were frustrated and inefficient, messages were lost, as were opportunities. It was hard for me as the manager of this group to know what people were doing, when they hit milestones, or dead-ends, when they needed help from me, and if they were in synch with the rest of the group... I believe Instant Outlining is to Instant Messaging as the Spreadsheet is to a desktop calculator. A calculator can edit one number, a spreadsheet can express relationships between numbers. An Instant Messaging client can transmit a single idea, an Instant Outlining client can express relationships between ideas.