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How to Use AI as a Sparring Partner to Improve Your Business Writing

Use AI between the first and final drafts to reflect your argument, expose weak logic and missing evidence, and test clearer structures without asking it to manufacture a point of view or replace the writer's final edit.

How to Use AI as a Sparring Partner to Improve Your Business Writing

Source episode · 23:42

How I AI: Hilary Gridley's Playbook for Scaling Yourself with Custom GPTs

with Claire Vo

Hilary begins with her own rough newsletter draft, asks AI to restate the argument so she can see whether it is clear, pushes it to make the point more compelling and challenge the logic, experiments with structure, then rewrites the final piece herself so it starts and ends in her voice.

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Before you start

What you need

  • A rough draft written by the author
  • The intended audience, decision, and desired reader response
  • Facts, quotes, examples, and links tied to sources
  • Voice examples and constraints that should survive editing
  • A clear distinction between confidential material and content approved for the model

What you’ll make

A revised piece with a sharper argument, explicit evidence and counterarguments, improved structure, verified factual material, and a final author pass that restores natural voice and deliberate nuance.

Tools used

Step by step

The workflow

Follow the sequence once, then adapt the prompts, checks, and handoffs to your own setup.

4 steps

Step01

Perform a 'Brain Dump' and Sanity Check

Write the first draft yourself, even if it is messy. Give the model the audience and desired response, then ask it to restate the argument, evidence, assumptions, and action without improving the prose.

Example prompt
Restate what this draft is arguing in plain language. Identify the central claim, supporting logic, evidence, assumptions, and requested reader action. Quote confusing passages and list questions a skeptical reader would ask. Do not rewrite yet. Draft: [text].
Step02

Make Your Argument More Compelling

Ask for ways to make the argument more compelling through specificity, evidence, consequence, sequence, and relevance, then choose only the suggestions that strengthen the point you actually believe.

Example prompt
Suggest ways to make this argument more compelling for [audience] by improving specificity, evidence, stakes, and sequence. Do not add facts. For each suggestion, explain the reader problem it solves and cite the affected passage.
Step03

Identify Blind Spots and Pressure-Test Your Logic

Pressure test the draft with counterarguments, alternative explanations, missing stakeholders, unsupported leaps, and evidence that would change the conclusion.

Example prompt
Challenge this draft as a thoughtful skeptic. Identify unsupported claims, hidden assumptions, strongest counterarguments, missing evidence, and conditions under which the recommendation would be wrong. Do not be agreeable and do not rewrite.
Step04

Restructure and Do the Final Polish

Choose a structure, revise in your own words, and use AI for a final clarity check. Verify facts, quotes, links, and commitments, read the piece aloud, and restore intentional personality or nuance the model removed.

Example prompt
Here is the latest draft of my article. The core argument is solid, but I'm not sure about the structure.

Suggest 2-3 alternative outlines for this piece. For each outline, briefly explain how it improves the flow or strengthens the main point for an audience of [describe your audience].

[paste your draft]

What good looks like

  • The model can restate the central claim, logic, evidence, and requested action without changing their meaning.
  • Critique identifies specific gaps, counterarguments, unsupported claims, and confusing passages rather than validating the draft.
  • No rewrite alters quotations, facts, links, commitments, or the author's intended position.
  • The author reads and rewrites the final text, checks every claim, and remains accountable for the message.

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After the steps

Runbook notes

How to recover when the loop fails and where human judgment helps.

Recover

If it goes sideways

The model praises the draft and reinforces an unsupported premise
Ask for the strongest counterargument, missing evidence, and conditions under which the claim is wrong.
Repeated rewrites replace the author's rhythm with generic business language
Request diagnosis and options first, then apply selected changes in the author's own words.
A clarity edit changes a number, quote, link, or commitment
Lock factual spans, compare them after each edit, and verify against primary sources.
Confidential business material is pasted into an unapproved model
Redact or generalize the draft, use an approved environment, and keep sensitive evidence in its source system.

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