14 “Ask-the-Author” Prompts to Level Up Your Nonfiction Drafts
These Are the Prompts I Used to Shape the Toughest Words Into Works Issues. (They’ll Sharpen Your Revision Process, Too).
Welcome to Words Into Works. Each week, I share one article that helps you use AI to apply what you learn from nonfiction books. If you’ve ever finished a great book—and struggled to do something with it—this newsletter is for you. Paid subscribers gain full access to every prompt, walkthrough, and live example I’m creating to help turn ideas into action.
TL;DR
You can’t call Malcolm Gladwell, Brené Brown, or Adam Grant every time your draft falls flat, but you can simulate their toughest questions. This issue reveals the 14 author-inspired prompts I use to pressure-test, sharpen, and rethink every Words Into Works issue. Use them to let your bookshelf argue back, and transform revision from a lonely grind into a conversation with the world’s best nonfiction minds.
Last Saturday, I was hunched over the kitchen table, blinking at a stubborn paragraph while my morning coffee grew cold beside my laptop.
The idea was there—a stack of draft sentences lined up, each tweaked and re-tweaked—but the words sat there, as flat as the coffee itself.
Out of habit, I imagined Malcolm Gladwell at my shoulder, his finger drumming the edge of the table. He leaned in, grinning: “Sam, where’s the twist? Surprise me.”
I stared at the blinking cursor. In the kitchen, the coffee machine clicked off (a quiet reminder of how long I’d been stuck).
For a minute, I waited for Gladwell’s answer.
Then I remembered, I can’t call him, or Brené Brown, or Angela Duckworth, or any author whose book I want to turn into a prompt every time I get stuck.
But I can do the next best thing:
Simulate Their Voices with AI.
Each of the fourteen prompts you’re about to see is my attempt to hold a backstage conversation with the author whose book sparked the week’s issue.
Think of them as carefully worded questions that coax a trademark perspective, a ruthless line-edit, or a signature metaphor out, as if the author were red-inking the draft over my shoulder.
Together they form a revision ritual that turns my first pass into the version you read on Monday morning: tighter, braver, and more faithful to the spirit of the original thinker.
So, pull up a chair at the virtual writers’ table. The fourteen prompts that follow are some of the exact queries I use to let my bookshelf argue with me until a Words Into Works issue earns its title.
1. Signature Perspective Spotlight
Author: Malcolm Gladwell
Prompt:
[Author], which sentence in my draft almost lands but would soar if we infused it with your trademark way of seeing the world? Show me a before/after in your voice.
Example:
Before: “Most ideas die because leaders fear risk.”
After: “Ideas perish less from risk than from familiarity fatigue—the brain yawns at what feels already known.”
2. Principle vs. Practice Audit
Author: Cal Newport
Prompt:
List the top three principles you hammer home in your talks. Where does my draft violate or dilute each one, and what’s the single weakest spot you’d fix first?
Example:
You drift from Deep Work Principle #2—“embrace boredom”—when you pack three action steps into one paragraph. Cut the third; let spaciousness signal importance.
3. Metaphor Lens Rewrite
Author: Brené Brown
Prompt:
Borrowing your favorite metaphorical lens, rewrite the opening paragraph so the core idea snaps into focus for a skeptical reader.
Example:
“Right now your newsletter is a polite conference room. Let’s turn it into a bonfire: the same truths, but the heat invites people closer.”
4. Tough-Love Line-Edit
Author: Anne Lamott
Prompt:
Channel your most candid workshop persona: strike through the fluff sentences, then explain—briefly and brutally—why each cut strengthens the argument.
Example:
“We all know writing is hard.” (Tired truism—add lived detail or delete.)
“In today’s fast-paced world…”(Throat-clearing. Start with the heartbeat, not the weather.)
5. Would You Share This? Test
Author: James Clear
Prompt:
Pick the one line you’d genuinely reshare with your own audience—on stage, in a newsletter, or in conversation. If none qualify, craft the missing share-worthy line in ≤ 20 words.
Example:
Share-worthy line: “Identity isn’t a destination; it’s the residue of tiny votes you cast in private.”
6. Objection Whisperer
Author: Adam Grant
Prompt:
You know your harshest critics best. Write the two objections they’d raise to this piece, then give me the rebuttal you wish you’d had years ago.
Example:
Objection 1: “Small prompts can’t shift entrenched habits.”
Rebuttal: “Micro-nudges compound; data shows 38 % adoption after four iterations—enough to tip the culture.”
7. Outside-Canon Injection
Author: Chimamanda Ngozi Adichie
Prompt:
Based on your podcasts, interviews, or essays—not the book—identify one under-explored theme I should weave in. Suggest where it fits naturally.
Example:
You overlook nuanced anger—the fire that precedes change. Thread a single line into the “Toolkit” section: anger as calibrated fuel.
8. Rhythm & Breath Pass
Author: Simon Sinek
Prompt:
Read the longest paragraph aloud in your keynote cadence. Where do you gasp? Break or rephrase those points while preserving momentum.
Example:
Split the 48-word opener after “Yet we rarely ask why.” New sentence: “Why is the fulcrum; everything else is leverage.”
9. Hallmark Texture Cue
Author: Hans Rosling
Prompt:
Identify three spots where adding a touch of your hallmark texture—whether data specificity, humor, or philosophy—would strengthen the draft. Offer one example tweak for each spot.
Example:
Section lacks factfulness: insert the 1990-2020 extreme-poverty drop (-1.2 billion) to ground optimism in statistics.
10. Backward Hook Check
Author: Michael Lewis
Prompt:
Start at my conclusion, then read the intro. Does the opening line set up the payoff the way you’d structure a chapter? If not, draft two stronger hooks.
Example:
Hook A: “The story you believe about decision-making is upside-down.”
Hook B: “You misprice your own attention daily—and the market exploits the discount.”
11. Author’s Own Rubric Report Card
Author: Daniel Kahneman
Prompt:
After revisions, grade the piece using your personal yardsticks. Name up to three (e.g., intellectual rigor, story momentum, reader empowerment) and score each out of 10. For any score below 8, give the highest-leverage fix.
Example:
Rigor 7 (missing counter-example), Momentum 9, Empowerment 6.
Fix: add a real-life “nudge failure” to inoculate against optimism bias.
12. Hidden Easter-Egg Quote
Author: Elizabeth Gilbert
Prompt:
Find one lesser-known quote from your corpus that would deepen credibility and delight longtime fans. Suggest where to embed it without breaking flow.
Example:
Quote: “Curiosity is a softer, safer cousin of passion—easier to coax, harder to exhaust.”
Place just before your “Toolkit” to reframe small steps as exploratory, not heroic.
13. Author-as-Prompt Engineer
Author: Yuval Noah Harari
Prompt:
If you were designing the ultimate AI prompt to unlock your *big idea* for my readers, how would you phrase it? Rewrite the prompt in your voice, add any constraints or examples you’d insist on, and explain briefly why each element matters.
Example:
Harari-crafted prompt
Goal: Reveal the hidden myth governing modern work culture.
Instruction: “Identify the strongest myth shaping today’s office life, trace its historical roots in ≤ 150 words, then suggest one ritual to replace it that requires no budget.”
Example answer seed: “The nine-to-five clock is a relic of the factory whistle…”
Why it matters: The word myth signals narrative depth, the 150-word limit forces clarity, and the “no budget” clause ensures practicality over grand reform.
14. Idea Lineage & Author Debate
Author: Malcolm Gladwell (vs. Jordan Peterson)
Prompt:
Simulate a conversation between the author of this book and another respected thinker with a contrasting view. What tension would surface? Where might their ideas overlap—or clash? Use the friction to reveal a deeper insight or missing angle in my draft.
Example:
Gladwell: “Context creates behavior.”
Peterson: “But personal responsibility transcends environment.”
Insight: Your current framing leans too heavily on external factors. Add a paragraph exploring where agency reclaims the narrative.
What Happens After the Prompt
Some of these prompts challenge clarity. Others surface hidden tensions. A few ask the question I didn’t want to face.
But they all exist for the same reason: not to polish the writing, but to test the idea to see if it holds up under pressure.
Even if you’re not writing publicly, you can still use these prompts to clarify your thinking. Before you act on an insight from a book, try asking:
What would the author push back on? What would their sharpest critic say? What am I not seeing yet?
You might be surprised how close you can get to the conversation that changes everything.
If you enjoyed this read, the best compliment I could receive would be if you shared it with one person or restacked it.