Here's an excerpt from a note I recently sent to a colleague of a colleague who asked for writing advice.
She was working in a field I normally don't help with and on a document type that's also outside my expertise. I free-associated a response that I thought might help her.
The essence of her question was: "How can I get started on a big writing project that intimidates me? I have a lot of knowledge, but I don't know how to channel my efforts. I feel lost."
Top three tips
1. Look for "turning points" in the content in front of you. Comb though your initial "brain dump" and look for new decisions, rejected options, shifts in perspective, forks in the road, or the place in your story where you didn't know what would happen next (or still don't know). Usually, that's where you'll find insights rather than a mere sequence of facts or observations. Pay the most attention to content at this point in your chronology, and dig deeper for more detail, facts and understanding of what's at stake and why it matters. Answer these questions: "Why did it matter?" and "How did I know that was true?"
2. Look for obstacles overcome and lessons learned. Show the journey from Point A to Point B, but not in chronological order. Start with the lesson learned or outcome achieved, and contrast it with the obstacles overcome, all in the same paragraph or -- when possible -- in the same sentence.
3. Make the first three words in each paragraph the most "to the point" or the most 'visual, memorable, active ..." The first three to five words are where skimmers' eyes will fall, and you may be able to lure them in and glue their eyes to the page if you deliver something good from the get-go.
4. Be messy. Dump your thoughts in a sloppy pile onto the page. Don't "write well." Just dump. Fragments. Ramblings. Lists. Brainstorm questions "the audience" might be asking themselves. Don't judge. Don't fix. Allow typos. Allow wrong vocabulary and tone. The first step is to generate what I delicately spell in make-believe French as "crappe." Write crap. Let it stay crap. Don't worry --- yet.
5. Step back from your brain-dump. Make a hard copy and add circles, arrows and notes in the margin as you begin to discern some order in the chaos. Then determine a structure -- as in three main points that back up your central premise.
6. Then look for holes, gaps, things you *wish* you knew. Reflect. Go get more info. Add.
7. Draft. Now and only now begin to smooth over your sentences and "write well." This is where you fix the typo and search for the most precise word. Then, after a break, delete words and shorten sentences.
8. For an ending, look at your beginning. Come full circle by picking up something from the start and repurposing it for use at the end. But spend time making it short, visual, emotional, catchy -- good stuff like that. Journalists use the term "kicker." In a great feature article that is likely to be read to the end, they sometimes use their second-best quotation as an ending. Something resonant and memorable that feels good to the ear. Notice, this is not like a conclusion in an essay; instead, move your conclusion to the intro ("get to the point fast") and let your ending instead be very sensory.
The big picture
9. Help others. I always advise looking at an organization's own long-term aspirations. Where does your organization want to be in the future, like in three to five years? How can you help it get there? I would keep those things in mind while doing the brain dump, and look for details and themes that dovetail with the organization's overarching goals.
10. Read current events. Spend time developing your own thoughts about data and current events in your field. Read a lot of articles and notice your response. Look for trends, contrasts and surprises. Repeat the arrows-and-circles process, paying most attention to insights that pop out, not necessarily the facts you gather.
Deepen, then forget. Those last two -- No. 9 and No. 10 -- can help you deepen your content. But don't dwell on your findings overly much so that you're writing *about* them. Just let them prime you, ready you, inspire you, coax you into exploring your own thoughts. Then "forget" about all of that and refocus on the question you've been asked.