David Barnes @ Packt

When a reader looks down the chapter listing of any how to book, this is what they are secretly hoping to see:

1. How this book will make your life incredibly brilliantly amazing
   
2. The first essential steps to a more amazing life
3. Make your life more amazing right now
4. Steps to an even more amazing life
5. Becoming amazingly amazing
   
6. Avoid the pitfalls of an amazing life
   
7. Becoming brilliantly amazing
8. Living a brilliantly incredibly amazing existence
   
9. Final tips for an amazing life

Cheesy self help books like The Secret make no bones about it -- its TOC and selling points are a thinly veiled paraphrase of the outline above.

For a technical book you can't get away with anything so tacky.

Even so, your reader's subconscious mind is trying to translate your book's outline into something like this one. If it can't then you're in trouble. Your reader's subconscious mind won't like the book. And that means your reader won't like the book.

That's why each chapter title in your book should use language the reader can understand, and should make it very clear that they are progressing towards their goal. Your reader has already decided that learning the topic of your book is the key to a better life... so every chapter title should show significant progress to that aim.

Example: "The Order Processing System" -- miserable title. No sign of a better life there. Just more computer drudgery.
"Fulfilling your incoming orders" -- compelling title. The wording of the title implies progress and success. "I've launched my site, and I'm getting orders."

Amazingly amazing.

When you plan a book or a chapter it's dangerous to think in bullets.

Bullets encourage you to think of each topic as a separate item, with no relationship to each other:

Making tea:

• Teabags
• Tea pot
• Milk
• Sugar
• The importance of boiling water
• Loose leaf?

If you plan a chapter that way, you'll end up with a mini-essay on each topic. "Now lets talk about teabags. Teabags are very important. They work by putting dried tea in a porous paper packet". But readers usually learn more from understanding the connection between ideas than we do from the ideas themselves. It's bringing ideas together that gives readers understanding.

We use the word "coherent" to mean "understandable". The origin of the word has to do with "all the bits stick together well" -- the cohere. They connect.

Instead of outlining your book in bullets, why not try to describe each chapter in a paragraph? That way, you can see if there is a logical connection between each idea... and you can start to see those connections right from the start:

First of all we'll look at teabags, which are the most common way of making tea today. We'll see how to use teabags with a teapot and also with a mug. Once the tea is made, people like to take it in different ways -- so we'll look at adding milk and sugar, the most popular ways to take tea. We'll see why it's so important to use boiling water when you make tea, and wrap up the chapter with an advanced tea making technique -- loose leaf.

Now somebody who doesn't know much about tea will understand the progression of ideas in the chapter, and even if they don't know about they ideas themselves they do all connect together in a clear way. it can also reveal gaps in the progression that aren't obvious in bullet form (what about lemon? should we cover making tea in the mug?)

Form a plan that brings ideas together instead of tearing them apart with a barrage of bullets.

Over at JeremyKrames.com...

Excellent point about outlines, the highlight for me:

* The outline or table of contents: Even if the book is just an idea, you should be able to put together a rough outline. Each and every chapter title is an opportunity to make the book sound compelling. If you are having problems here (or with the preface or description above) go directly to Amazon.com and search “Inside the Book” of business bestsellers such asGood to Great (Collins/Collins), Now Discover Your Strenths (Buckingham & Clifton/S&S), orFree Lunch (Johnston/Portfolio). All of these have cool chapter titles and intros that could inspire you to come up with some great ones on your own.

Maybe business books aren't the best place to look for help with computer book writing. Instead, check out some best selling Missing Manual, Dummies, or Head First TOCs (not to mention Packt's own) and take inspiration from them.

From Book Proposal Secrets, via @davidmoldawar.