Your table of contents is the menu of your book. Test it before you write a chapter.
From Charlie Hoehn
A while back, I worked on a book with 20 chapters spread across five parts. We kept refining the Table of Contents until it felt perfect, landing on 12 chapters over three parts. Same material. Just a much clearer path.
When you’ve spent years getting good at something, you have a lot to say about it. A bloated Table of Contents is common in the beginning, because every piece of it feels important. But past ~12 chapters, a book starts to feel like inundation rather than what the reader needs.
The longer an oversized structure stays in place, the harder it is to untangle once chapters are written around it. So before any of our authors record a word, we spend time getting one page right. Measure twice, cut once.
Do you want to eat here or not?
I think of the Table of Contents as the menu of the book.
Picture a typical diner where the menu runs on for several pages, each item blending into the next. Nothing really stands out. You have to ask the waiter “What’s good here?” because it’s impossible to tell.
Compare that to a five-star Michelin restaurant where the menu is on a tiny card. There are just a few items listed, but everything on it makes you think “Hell yes, this all looks awesome.” That is the feeling you want to evoke in your reader when they open your book and land on the Table of Contents.
Everybody wants to hole up in a cave and write, and I understand the pull, because writing feels like progress. But if you’ve got hard-won expertise and a book you keep pushing to next quarter, the most useful thing you can do this week is one page and a handful of phone calls, no writing required. Here’s how I’d approach it.
I like to start by drawing a line. On one side is your reader as they are today, with the problem that made them pick up your book. On the other side is that same reader, completely transformed. Then I ask a simple question: how do I take this one reader from zero to hero, and what are the exact steps?
The big milestones show up first, and there tend to be two to four of them. Each milestone becomes a part of your book, and the chapters become the steps inside each part.
With the milestones in place, aim for about 12 chapters, and make every title work like a click-worthy headline. When you’re looking at a menu, it shouldn’t require explanation. It should be an impulse.
A good way to check yours is to read the titles in order, out loud, the way you’d read a menu to a friend across the table. If a title needs you to explain it, that’s the one to rework.
It’s natural to save your strongest material for later, the way you might build to a big finish in a keynote. The trouble with a book is that not every reader makes it to the end, so it’s worth asking: what percentage of your readers are even getting to that?
Find the chapter you’d most want every reader to see. If it’s sitting in the back half, move it up.
This is the step that turns a good Table of Contents into one you can trust. Before you write a chapter, take it to the people you’re writing for.
Talk to about five people. These can be 10 to 15 minute Zoom calls or conversations in person, and three is the bare minimum. Live is the most helpful, and it doesn’t have to be one on one, since a small group works too. Here’s the whole ask:
Every chapter title needs to be a hell yes. As you go, write down their words along with their answers, because the way someone describes a chapter back to you often tells you more than the rating. Rework anything that lands as a meh or a no, and keep the conversations going until every chapter is hitting three hell yeses.
Surveys can help too, but it’s easy for someone to rattle through a survey without you ever understanding where they’re coming from. The signal is in the conversation.
Before writing The AI-Driven Leader, Geoff Woods pulled 20 CEOs together and walked them through his Table of Contents. One of them said, “Wow, you’re talking about how to create disruptive results without disrupting your organization.” Geoff wrote that down, and it went into the book. By the time the book was done, he’d tested it with well over 200 people.
He kept working the structure the whole way through. Below is his table of contents during one of our calls, with his own note on the right suggesting chapter 7 move up to chapter 4.
You don’t need 200 conversations to get the benefit. Five short calls will tell you more than another month working on it alone.
In our process, the Table of Contents comes right after we’re clear on who the book is for and what it promises, and before a single chapter gets recorded. Everything that follows is built on that one page, so it’s worth getting right first.
Once every chapter is a hell yes, you have a book people already want to read, and that opens up a bigger question.
What if those same people paid for it before it was even out? That’s where we’ll pick up next time.
If you’re sitting with a book idea or a draft Table of Contents and want a second set of eyes on it, book a call with my co-founder Miles.
And if you know someone with a book in them, feel free to send this along.
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