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I've spent about seven years learning to collaborate with other writers, and
I'd say go for it. Best way: sit down together and thrash out the outline
together. If you've got the outline, the other writer will have to wrestle
with it, then meet with you and argue out his different vision. Don't
postpone this, or assume someone else can follow your outline. They don't
think the way you do. If you don't argue this out early, his chapter will
not be what you dreamt. Get agreement early on structure. And-this is
critical-really make sure you agree on tone. Tone indicates your attitude
toward the reader, your expectation of the readers' abilities, interests, and
fears. If you don't reach real agreement on style before you both do much
writing, you will both be disappointed in each other's chapters.
By the way: I've written some of this up in a book I did with one of my
collaborators, Henry Korman: How to Communicate Technical Information, from
Benjamin Cummings (1993).