• How I AI
  • Posts
  • This is what happens when you ask AI the right question

This is what happens when you ask AI the right question

Asking questions about asking questions

This one’s a little meta.

But stick with me.

It’s worth it.

Today, I wanted to send an email that built on the last two emails I wrote about the AI bot-building workshop I attended.

I had already shared the main lessons I took away:

Both were based on me feeding the transcripts of all five days of the workshop into ChatGPT and asking what the meta lessons and patterns were.

Then I combined that with my notes and reflections to write those two emails.

But now I wanted to go deeper.

To turn those takeaways into future content ideas tied to my offers.

My initial instinct was to ask something generic like “Give me x content ideas drawing on these two emails.”

But instead, I did something a bit new:

I asked AI what question I should be asking.

I gave it the two emails and said:

“What’s the right question to pull more email content ideas related to my offers from these two emails?”

And here’s what it gave me:

“Where does my reader get stuck trying to apply each of these ideas, and how can I help them take the next step?”

That one question unlocks a whole new round of ideas.

But ChatGPT didn’t stop there.

It then gave me a full framework I can use on any piece of content to generate more useful, relevant follow-ups:

The 5-Part Idea Extraction Framework:

For every lesson, pattern, or principle you share, ask:

  1. What mindset shift is required?

  2. Where do most people get stuck trying to apply this?

  3. What’s one small action they can take today?

  4. How does this tie back to the result they want (list growth, sales, clarity)?

  5. How does this relate to my offer, tool, or product?

Then it gave me a prompt to re-use:

“Based on these emails, generate 10 content ideas that identify common struggles solopreneurs have when trying to apply these lessons. Focus on mindset gaps, workflow mistakes, and opportunities to use AI better. Each idea should tie back to using AI to grow a list, write better emails, or build smarter systems.”

And it worked beautifully.

Here’s what I got back:

Ten Content ideas pulled from just two emails:

  1. Why AI Feels Random (and How to Make It Predictable)

  2. The Real Reason Your AI Output Feels Off

  3. Don’t Save Time. Build a System.

  4. Your Prompts Are Assets—Start Treating Them Like It

  5. What a “Thinking Partner” AI Actually Looks Like

  6. Feeling Scattered with AI? Try Organizing by Project

  7. The 3 Hidden Bottlenecks in Every AI Workflow

  8. You’re Sitting on Gold (But You’re Not Feeding It to AI)

  9. Why You Still Feel Behind—Even with AI

  10. Stop Starting from Scratch: Build Your AI Library

Here’s the big takeaway:

You can do this with anything.

A blog post. A podcast transcript. A client case study. A sales page.

If you’ve already created something valuable, don’t let it be a one-and-done.

Drop it into ChatGPT.

Ask the right question (and if you don’t know the right question, ask AI to help you define it.)

Then let AI help you find the next five or ten or fifteen ideas hiding inside your last one.

That’s what I did this morning.

The whole process was so good, I decided to turn it into this email.

And to make it even easier:

I dictated my idea to turn this back-and-forth with ChatGPT into an email using Wispr, my new voice-to-text best friend.

Told ChatGPT what I wanted, how it should flow, and what to include.

It gave me the first draft. I cleaned it up, added some bits, hit send.

No blank page.

No overthinking.

Just a system that supports the habit I’m trying to build.

And that’s the point of all this.

Not just to write faster.

But to think more clearly.

And build something that compounds.

Nathan

When you’re ready, here’s how I can help

I build personalized AI Voice Bots that turn your own words and stories into ready‑to‑send drafts in seconds so you can hit Send on time and on brand.

I take only a few clients at a time. Even if we’re not a match, you’ll leave the call with some quick wins you can use immediately.

What did you think of today's edition?

Login or Subscribe to participate in polls.