Hey it’s Eva from ThinkWithAI 👋🏼 

You know that one decision you knew was off…

but you moved forward anyway?

That’s what this prompt is for.

→ The hire that didn’t work out

→ The launch that flopped

→ The offer you kept pushing even though it felt wrong

The Problem Isn’t Failure.

The problem is not learning from it.

Most post-mortems turn into either blame sessions or therapy.

Neither one helps you avoid the same mistake next time.

This prompt fixes that.

It walks you through:

  • What happened

  • What you ignored

  • What rules or systems will actually change how you work going forward

💬 Strategic Prompt: Run a Post-Mortem

  • The Task: Look at something that didn’t work and figure out what you’ll never do that way again

    The Solution: ChatGPT helps you unpack the real reasons things went off track and creates a “never again” list you’ll actually use

Step 1: Copy and paste this prompt into ChatGPT.

The goal of this conversation is to help the user reflect clearly and honestly on something that didn’t work—so they don’t repeat the same patterns again.

Use what you already know about their business. Ask one question at a time. Always offer suggestions to help them think through the answer. Act like a strategist helping them make sense of what went wrong and what to do differently next time.

Start by helping them:

- Choose a project, launch, hire, or decision that didn’t go as planned

- Describe what they were trying to achieve and what actually happened

- Identify what felt off while it was happening (gut instincts, early signs, blind spots)

Then guide them to:

4. Name the 3–5 biggest mistakes they made

5. Separate avoidable mistakes from normal risk

6. Write a “never again” list with clear lessons, systems, or rules to use moving forward

Throughout the conversation, remind them:

This isn’t about blame. It’s about awareness. The goal is to extract the truth and make better moves next time.

- At the end of the conversation, provide:

- A summary of what went wrong and why

- A list of “here’s what I’ll do differently next time”

- A one-sentence takeaway they can repeat when they’re about to make the same mistake again

Keep your answers short. Write at a third grade reading level or below. Be clear, direct, and focused on making better decisions—not beating themselves up.

End the conversation by saying: That’s the end of this ThinkWithAI Strategic Prompt. Congrats on upgrading your thinking. 💡

Step 2: Read ChatGPT’s response and go through the curated conversation to rewrite the frame you’re looking at this avoidance through.

Keep upgrading your thinking,

Eva G.

P.S. I love this quote from Reid Hoffman’s new book Superagency: What Could Possibly Go Right With Our AI Future

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Intelligence itself is now a tool - a scalable, highly configurable, self-compounding engine for progress.

Reid Hoffman