Frictionless Outlining With ChatGPT (How I Prep Every Newsletter & Video)

Last week, I shared a deep-dive video breaking down how I run my $5M/year business:

• Our entire company operating system

• KPIs & how they connect

• The org chart of our 28-person team

• How we decide what to work on to keep growing

If you missed it, watch it here:

But here’s the part no one saw…

I didn’t sit down and “come up with ideas” for this video.

I followed a simple ChatGPT workflow that made the entire outlining process effortless.

How I Outlined This Video (And Every Other Piece Of Content I Create)

Before I write a newsletter or film a video, I never start from a blank page.

Instead, I follow a simple system that makes outlining effortless—so I know exactly what to say before I ever start writing or recording. This system saves me hours of second-guessing and makes content creation repeatable and scalable.

Let me walk you through how I use ChatGPT to do it.

Step 1: Ask “What Questions Can I Answer?”

Instead of forcing ideas, I let curiosity drive the outline.

For this video, I started with a few core ones:

• What is it?

• Who is it for?

• Who operates it?

• How is it different?

• How big is the team?

I always start with a brainstorm of "what questions can I answer for the reader?"

Then I feed my list of questions into ChatGPT and ask it to help me brainstorm more questions and organize them in the most coherent way for the viewer/reader.

For example:

This helps me instantly turn scattered thoughts into a structured outline.

Step 2: Reorder And Trim The List Of Questions For Maximum Clarity

Once I have ChatGPT’s outline, I edit and refine the list of questions:

• Rearranging them into a natural flow

• Keeping the most valuable, high-impact questions

• Identifying any missing angles (case studies, examples, stories, etc.)

Here's what came back to me from ChatGPT:

A handful of these would be extremely valuable for the reader/viewer, so I added them to my list.

Here's the final list of questions:

1. What is it?

2. Who is it for?

3. Why did you start it?

4. What inspired the idea?

5. How is it different from competitors?

6. What does success look like for customers?

7. How do people find out about it?

8. What is the marketing process?

9. What is the sales process?

10. Why that pricing structure?

11. What software stack does it use?

12. Who operates it / how big is the team?

13. What is your time involvement in it?

14. What’s the bottleneck to its growth?

15. What’s the most common feedback or testimonial you receive?

16. What challenges have you faced running it?

17. What are some mistakes you’ve made while running it?

18. What’s been the most surprising outcome?

19. What are some lessons you’ve learned from running it?

20. What metrics or KPIs do you focus on most?

21. What advice would you give someone wanting to build a similar business?

22. What makes you proud of this business?

23. What’s your long-term vision for this business?

With this list in hand, I have a clear roadmap before I even start creating.

Step 3: Write, Expand & Record

Once I have my list of questions, the writing becomes easy—I just answer them.

Each response is:

• Concise & clear

• Backed by examples, stories, or data

• Focused on value for the audience (tips, lessons, mistakes, etc.)

From here, I turn it into multiple content formats:

• Write the newsletter using a structured format (e.g. The 3X3 Method)

• Film a video walking through the outline, adding extra insights

• Send it as a combo email—giving my audience both written and visual content

For example:

Here's How I Operate A $6M / Year Coaching Business

How To Use This System for Yourself

This approach works for any type of content—newsletters, YouTube scripts, landing pages, and more.

Instead of asking, “What should I create today?”

Start by asking, “What questions can I answer for my audience?”

Then let ChatGPT help you structure your ideas, remove friction, and speed up your workflow.

Try it out this week with this simple prompt template:

I'm creating a [content type] breaking down [subject matter]. I want to answer valuable audience questions for each [component/section]. 

Here are my current questions:

{Insert your list of questions.}

Please help me:

Generate additional audience-focused questions specific to this [content type]. Organize all questions in the most logical sequence from the audience's perspective.

And if you found this helpful, hit reply and let me know.

Chat soon,

—Dickie & Cole

Co-Founders of Ship 30 For 30

Co-Founders of Premium Ghostwriting Academy

Co-Founders of Typeshare

Co-Founders of Write With AI

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