The million-dollar post-mortem: your dead online content

How a single failed content piece can teach you more than a dozen successes.

Oct 08, 2025

Welcome to today’s edition of ROBOTS ATE MY HOMEWORK. Today I realized I used to think digging up corpses was just for horror movies. Now I do it every quarter.

You know the first rule of the zombie apocalypse, right? The double-tap. Always secure the headshot. You don’t just wound the undead; you make sure they stay down for good.

In mood for something cool? 🧟‍♀️

And yet, what do we do with our dead content? We do the opposite.

For a long time, I was accidentally creating zombies. I’d take a post that failed, slap a new title on it, ask an AI to “make it better,” and push the shambling corpse back onto the internet, hoping it would do something other than groan and rot. It never did.

Your content graveyard is a goldmine of data. You just have to be willing to perform an autopsy.

Today, we’re going to cover:

The “Content Autopsy,” a step-by-step AI workflow I use for turning the worst-performing content into an invaluable strategic asset.
A powerful psychological concept that explains why some content connects and other content dies on arrival.
A one-shot prompt for a rapid-fire autopsy and the book I believe you must read to master the philosophy of failure.

🤖 ROBOT REPORT CARD

Every founder has a content graveyard. That one article you spent 20 hours on that got 12 clicks. The newsletter that had a 40% higher unsubscribe rate.

Good. These are your most valuable assets.

I’ve learned a successful post teaches you one replicable pattern. But a failed post reveals multiple failure points: mismatched search intent, weak hook, wrong format, poor distribution channel, misaligned audience expectations, and timing issues. Each failed post is a masterclass in what NOT to do across multiple dimensions.

I urge you to stop trying to replicate your wins and start interrogating your losses.

This is the AI-assisted “Content Autopsy.”

Step 1: Gather the evidence (pick a corpse)

Choose one piece of content that unequivocally failed. Not “did okay,” but bombed.

It must have had a clear goal (e.g., generate leads, earn subscribers, drive traffic) and it must have missed that goal by a mile. Grab the URL, the full text, and the analytics.

This part can feel a little uncomfortable. Your ego will want you to close the tab. Power through it. Trust me, it’s worth it.

Step 2: The “Three Perspectives” analysis

We will use an AI assistant to act as three different specialists, analyzing the same piece of content from three distinct perspectives.

This process delivers a truly multi-dimensional diagnosis. Shallow summaries are for interns; we’re looking for the root cause of death. (I developed this process because my initial, one-dimensional analyses were useless).

A. The search engine’s why: the SEO detective

This analysis focuses on search intent. Did you fail before anyone even read a word?

Prompt:

You are an SEO analyst. I’m going to give you a blog post and its target keyword. Your job is to analyze the mismatch between the content and the likely search intent for that keyword.

Based on the keyword, what are the top 3 things a searcher is most likely trying to accomplish? (e.g., learn a definition, find a how-to guide, compare products).

Does my content directly fulfill one of those primary intents in the first 200 words? Be brutally honest.

Where is the biggest mismatch between the promise of the keyword and the payoff of my content?

Target Keyword: [Insert your target keyword] 

Content Text: [Paste the full text of your article]

B. The reader’s why: the impatient audience

This analysis focuses on the human experience. The hook, the promise, the flow.

Prompt:

You are a skeptical, busy reader who is an expert in [your audience’s field]. You have 30 seconds before you click away. I gave you this article to read.

Read only the headline and the first two paragraphs. What promise did you think this article was making?

Now, skim the rest of the article. Did it keep that promise, or did it bait-and-switch you?

What was the single most confusing sentence or boring paragraph that made you want to leave? Quote it.

Article Text: [Paste the full text of your article]

C. The strategist’s why: the CEO

This analysis is about the business case. Was this the right mission, even if the execution was flawed?

Prompt:

You are a marketing strategist with a limited budget.

This content was for an audience of [describe your audience] and the goal was to [state your content’s goal]. Was this the right FORMAT (e.g., blog post, webinar, video) to achieve that goal for that audience?

Was this the right CHANNEL (e.g., Google search, LinkedIn, newsletter) to distribute this format?

Propose one alternative strategy. A different format or channel that would have been a better bet for the same core idea.

Content Idea: [Briefly describe the core idea of your content]

Step 3: Cross-reference with a winner

Now, take your most successful piece of content - one that crushed its goal - and run it through the exact same “Three Whys” prompts.

Put the answers side-by-side ⬇️

Create a two-column document or spreadsheet. Label one column ‘Failed Post Analysis’ and the other ‘Successful Post Analysis.’ Under each, paste the three AI responses. Then, highlight the differences: Where did the failed post miss search intent? What made the winner’s hook work?

I promise, the patterns will be blindingly obvious. You will see a winning post that perfectly matches search intent, has a killer opening hook, and uses the right format for the job.

You will see a failed post that is trying to be a scholarly article when the reader just wanted a checklist.

Step 4: Formulate the “Resurrection Hypothesis”

Your autopsy is complete. Now you have a diagnosis. Use it to form a hypothesis.

“The original post failed because it was a long, academic blog post that mismatched search intent (The Search Engine’s Why) and had a boring intro (The Reader’s Why). We believe a short, tactical video script based on the same core idea, distributed on LinkedIn (The Strategist’s Why), will succeed.”

This autopsy reveals WHAT failed. But understanding WHY requires a deeper psychological lens.

💡 A NEW CONCEPT FOR YOU

I came across a really cool psychological phenomenon called “experience-taking.”

And it changed how I think about content.

Research shows that when we get deeply absorbed in a story, we can unconsciously adopt the traits, beliefs, and behaviors of the characters we’re reading about. In essence, a great story gives you an identity to try on for size.

This is the secret job of your content.

Your audience approaches your content with two goals. The surface goal is to learn something - how to do X. But the deeper, more powerful goal is to feel like the kind of person who is an expert at X.

When a piece of my content fails, I can almost always trace it back to this. My failed blog post likely just presented information.

My successful one probably did something more. It offered the reader a chance to “experience-take.” It made them feel smarter, more capable, or more insightful while they were reading it.

It let them try on the identity of the person who has already solved the problem.

When your content autopsy reveals a “Reader’s Why” failure, the root cause is often a failure of experience-taking. You gave them a manual when they wanted to feel like a magician.

Found this autopsy useful? The ultimate ‘thank you’ is sharing it with someone else who needs it.

✨ ONE MORE THING...

To truly master this, you need a philosophy that embraces rigorous learning from mistakes. The bible for this is Matthew Syed’s book, “Black Box Thinking.”

I don’t consider myself a business book ‘guru,’ but this one is non-negotiable. He argues that the single greatest predictor of success in any field, from aviation to business, is having a system to investigate failures without shame or ego. Your content autopsy is your black box.

You can also find a community of people who live this philosophy. The newsletter Failory, for instance, is a treasure of stories from founders who dissect their failed startups to extract the lessons.

They celebrate the autopsy.

Now it’s your turn. What’s one content zombie still shuffling around on your site right now that you know you need to put out of its misery?