Happy Saturday!

Wait, you're sending this newsletter out on a Saturday morning? I haven't even had my coffee yet!

Well, hear me out: I got a reply to my last newsletter about Mel Robbins from someone just starting to outline her book. She wrote: "These new newsletters you're sending are super deep and awesome. But I feel like it's more of a weekend-read kinda thing."

Data point of one (thanks, Mom, for reading). So I just decided to try sending this new one on a Saturday morning to kick off your weekend reads (let me know if you approve or would rather see this during the week).

Either way, trust me, this topic was a major unlock for my last two book projects:

Don't Outline.

After I signed my publishing deal with Taylor & Francis for my first book about fifteen years ago, the acquiring editor sent me a to-do list, and the first item on the list was "Send Detailed Outline." Gulp. I kinda had some ideas, but a month later, I had skimmed a dozen 'peer' books, had gotten myself turned around in knots, regretted the entire idea of writing the book, and drafted (and deleted) a half dozen emails to the editor seeing if I could get out of my contract.

Many people believe that writing great thought leadership content starts with a perfect outline. After six weeks of struggling to organize and structure enough content that could fill each 4,000 to 6,000-word chapter for my book, I shipped something off and waited for the reply. My editor bluntly told me, “This reads like you're trying to write a 5th-grade essay.” Her advice?

“Don't outline yet. First, gather all your content, then figure out how to organize it.”

That single insight changed everything for me.

Now, I teach authors to focus on content gathering first. I call it 'content inventory-ing'--building an unorganized, unstructured list of all the stuff in your head into a document or spreadsheet. Once you have the right content—stories, data, research, and lessons—writing not only becomes easier but also more impactful. This approach doesn’t just improve books and articles; it makes repurposing content for social media, reels, and email newsletters a breeze.

I've learned how to reverse-engineer my content for a nonfiction book. When you study authors like Adam Grant, Brene Brown, Simon Sinek, Mel Robbins, or James Clear, their writing is 60-80% storytelling and anecdotes. It’s the personal, relatable content that captures attention and builds trust. The other 20-40%? It's what I call the contribution: research, data, experts, narrative, and teachings to ensure your content is persuasive and actionable.

That’s where my 9-Point Thought Leadership Writing Checklist comes in (aka don't outline yet). Too many 'stuck' authors will tell me they've got a pretty solid outline already... and I tell them that's probably why they are stuck.

Here's how you can leverage this:

First, Make Your Writing a Math Problem

For my writing purists among you, you'll hate this advice. But for almost everyone else, what I'll teach you here is a relief if you're writing a nonfiction book.

Book chapters and long-form thought leadership writing (long-form articles, ebooks, course materials, etc.) can be broken down into math problems. (This math is based on my own analysis of hundreds of beloved nonfiction books as well as helping nearly 3,000 first-time authors).

-- Your typical chapter will be 4,000 to 6,000 words.

-- Stories, anecdotes, or case studies will be 60-80%. And you'll typically have 2-4 of them.

-- To make it simple, for a 4,000-word chapter, assume you'll need 2,500 words of stories; for a 6,000-word chapter, assume you'll have 4,500 words of stories.

-- That means you'll probably need 3 stories in each chapter, and they'll each average about 800 to 1,500 words.

-- The rest? We call this the contribution -- research, teaching, experts, data, narrative, and quotes. You'll have 1,000 to 1,500 words of this.

If the typical nonfiction book has 10-15 chapters, you can begin to back your way into the content you need to gather. A dozen personal stories, a dozen from people you interview, and a dozen stories that have been shared in books, podcasts, or online.

To make it even easier, I break the content down into nine things you'll need in (nearly) every chapter:

The 9-Point Thought Leadership Writing Checklist

In the beginning, I don't try to become overly rigid on the checklist. It's a loose guide to help me gather. I know I'll likely need about a dozen over each of these for my book, so I start gathering more of a rough list of ideas.

But as I go along and start grouping content into themes that could become chapters, I often paste this at the bottom of the document to check off each item before I really start organizing.

1. Hook – Grab Attention Immediately
   • Your opening should subvert expectations and engage curiosity. Examples include provocative questions, surprising statistics, or personal challenges.
   • Example: “Most people think outlining is the first step to great writing. I used to think so too—until I learned a better way.”
2. Personal Story – Build Connection Through Authenticity
   • Share relatable experiences that reveal vulnerability and tie into your message.
   • Example: “When I first tried writing my book, I had no idea where to start, and my editor’s feedback was humbling.”
3. Primary Interview Information – Firsthand Credibility
   • Insights from experts that you have directly interviewed. These establish authority and credibility.
   • Example: “I spoke with bestselling author Jane Doe, who emphasized that gathering content first transformed her writing process.”
4. Secondary Interview – Supporting External Voices
   • Incorporate insights from interviews conducted by others, adding broader perspectives.
   • Example: “Research from Harvard Business Review reinforces this concept with interviews from top CEOs.”
5. Teaching/Lesson – Clear, Actionable Takeaways
   • Ensure your content delivers a clear lesson that readers can immediately apply.
   • Example: “If you gather these 9 components first, you’ll avoid writer’s block and have a roadmap for compelling content.”
6. Thematic Narrative – Tie It All Together
   • A unifying story or theme that runs through your writing to keep it cohesive and engaging.
   • Example: “Throughout my journey as a writer, I’ve learned that great content starts with gathering, not structuring.”
7. Research/Data – Supporting Evidence
   • Add statistics, studies, and empirical data to bolster your argument.
   • Example: “Studies show that structured content planning increases engagement by 47%.”
8. External Research – Context and Background
   • Leverage existing reports, case studies, or academic sources to provide depth.
   • Example: “In his book Deep Work, Cal Newport highlights the importance of preparation in thought leadership.”
9. Quotes – Reinforce Your Argument
   • Use relevant quotes from reputable sources to lend additional authority.
   • Example: “As Stephen King says, ‘The scariest moment is always just before you start.’”

Wait, is this like my Chapter Outline?

No, no. This would be pretty boring if you just wrote chapters in this way. The next step is developing your chapter template -- which is a rough structure of how you'll use these elements to convey or teach something. For example, you can see how James Clear structures these components in his Clear Principles framework and how Mel Robbins organizes them in her Positive Vulnerability framework.

These are the components of the chapter, and you'll typically arrange and organize them in a way that aligns with your voice, style, and tone.

Components are your building blocks; your chapter template is the way you put them together.

If you like James Clear's approach, then you can easily use the structure I break down for your writing.

Don't start with the outline; start with the components and then apply them to your outline. It'll make the writing way less painful, and you'll have a much better starting point.

Prompt to Evaluate Thought Leadership Writing:

Let's say you've written a chapter or chapters, and wanted to see how you've done to capture and include all the relevant components. Copy and paste this into ChatGPT or your favorite GenAI tool and analyze your content against the checklist:

“I’m working on a thought leadership piece, and I want to ensure it includes all the key components that make it compelling. Please analyze my content and provide feedback based on the following criteria:

1. Hook: Does it grab attention and set expectations?
2. Personal Story: Is there a relatable, authentic personal story?
3. Primary Interview: Are there firsthand insights included?
4. Secondary Interview: Are supporting external perspectives present?
5. Teaching/Lesson: Is there a clear takeaway for the reader?
6. Thematic Narrative: Is there a consistent, engaging storyline?
7. Research/Data: Are there relevant statistics or studies cited?
8. External Research: Does the content provide broader context?
9. Quotes: Are relevant quotes used effectively?

Additional considerations: - Does the writing align with my target audience, goals, and aims? (e.g., business leaders, aspiring entrepreneurs, industry experts) - Is the content structured to be easily repurposed for social media and video content? - Are storytelling elements making up 60-80% of the content?

Here is my content: [Insert Your Content Here]. Please analyze and suggest areas for improvement.”

By using this prompt, you’ll gain actionable insights to refine your writing and ensure it aligns with the best thought leadership practices.

What's Coming Next?

I hope you're enjoying these, and honestly, send me any thoughts, feedback, or authors to break down (or you can just say hi like my mom does)!

Next up in my "Write Like a Thought Leader" series, I'll be breaking down the writings and chapters of:

​Russell Brunson. Russell is the founder of Click Funnels and one of my favorite digital entrepreneurs who has used his writing to build immense trust among his clients and customers. This is an awesome style for all entrepreneurs and business owners.

​Barbara Minto's Pyramid Principles. Barbara is really the "OG" of thought leadership writing, and her approaches have become the standard in consulting and professional services firms. For anyone aiming to use their writing to do consulting or appeal to professional services clientele, this approach is terrific.

Lastly, I did a few updates to my personal website this week (https://erickoester.com/). Take a peek, and I'd love any feedback!

Write On!

Eric
​