Organize: Building Towards the Point
Deconstruct your source material into component ideas and zero in on the main point—the thesis that will guide your entire piece.
"For which of you, desiring to build a tower, does not first sit down and count the cost, whether he has enough to complete it?"
— Luke 14:28
Jeffery Deaver knows a thing or two about writing. With more than 40 mystery and crime books to his name and 50 million copies sold, Deaver stands as a titan of fiction authorship. His approach to writing is one of meticulous preparation.
"I spend eight months outlining and researching a novel before I begin to write a single word of the prose," he claims.
This quote underscores a fundamental truth about writing: the clearer your roadmap, the smoother the journey from conception to completion.
Outlining is indispensable. It compels the writer to crystallize the central point. It ensures a clear destination, compelling reasons to reach it, and the necessary "equipment" for the voyage.
Skeleton of Thought
In the realm of prompt engineering, using an outline to guide AI in stepwise fashion is called "skeleton of thought." Based on the "chain-of-thought" prompting method, the underlying principle is that AI performs better at smaller, sequential tasks, represented by the sections of a detailed outline.
For example, commanding AI to "Write an article based on this transcript" yields unpredictable results (at best). If, instead, you hold its hand through an outlining process before generating the article one section at a time, you retain control over both the intermediate steps and the final output.
A high-level outline functions as a special kind of prompt—a roadmap to navigate toward a more refined and cohesive piece of writing.
The Two Phases of Outlining
Because outlining is so crucial to great writing, I've broken this step into two phases:
Phase 1 (Organize): Deconstruct your source material into its component ideas and zero in on the main point
Phase 2 (Distill): Take the main point as the cornerstone for building a new outline out of the building blocks you assembled
Step 1: Map the Terrain (Timestamped Outline)
The first step of deconstruction is creating a territory map by breaking down the transcript into its constituent parts.
Paste or attach the transcript into Claude's chat box, along with this prompt:
"I'm sharing a transcript with you. Please create a timestamped outline breaking down the key topics, themes, and ideas discussed. Include approximate timestamps and descriptive headers for each segment."
This chronological summary provides you with a bird's-eye view of the flow of ideas, topics, and their interconnections. The timestamps and headers segment your content into manageable sections—like a table of contents.
Step 2: Cheat Sheet Outline
After completing your timestamped outline, prompt Claude to produce a "cheat sheet outline." Unlike the timestamped outline, which provides a chronological framework, the cheat sheet goes deeper—looking at the key themes, stylistic nuances, and most memorable phrases.
"Now create a 'cheat sheet' that organizes ideas not by when they were expressed but by their theme, substance, and relevance. Include: key themes, memorable phrases, supporting arguments, and unique insights."
Step 3: Organizing Additional Building Blocks
The cheat sheet is a kind of skeleton of your content, but it still contains mostly summary. We want to support this with the most important specific points, excerpted in full detail.
Additional building blocks to extract:
Source List: Compile all references made throughout the conversation
Anecdote Bank: Collect compelling stories and analogies
Visuals: Note any descriptive language or rhetorical devices
Timeline: Construct a timeline of key events or milestones
Step 4: Nailing the Point
Armed with your cheat sheet—enriched with condensed knowledge—you're ready to home in on "the point." This is the culmination of the divergent phase and the pivotal moment where you determine the key message.
"Based on everything we've discussed, suggest 3 different ways to characterize the main point or thesis of this content. What is the single biggest takeaway?"
After some iteration, paste this thesis statement at the top of your page, above the transcript, timestamped outline, and cheat sheet.
This statement will serve as the Archimedean point between the deconstruction and reconstruction phases—and the measuring stick by which you'll decide what makes it into your article and what gets left out.
This post is adapted from "Commanding the Page" (2023).