You probably won’t get it right the first time.

I’m not trying to be negative here, so hear me out. Every once in a while I get a proposal where the author just absolutely nails it, but the majority of the time the first draft outline is a great start that needs some fine tuning to get it ready for the shelf.

I look at the book proposal process as a collaborative effort with the author. If I believe in your book idea and you as an author, then I am going to take the time to help you develop your ideas into something that I think has the best chance of success.

An exercise I like to suggest to authors who are bogged down in the outline is to forget that it’s a book. We will worry about turning it into a book a little later, but for now imagine you are creating something other than a book outline. How would you think about your outline differently if I told you were:

• Drafting a presentation for SxSW, Microsoft TechEd or TED (insert the most appropriate conference here)
• Writing the script or talking points for a podcast or video
• Preparing a series of blog posts on a subject

Sometimes thinking about content as just a book is limiting. As publishers move to providing content in a variety of formats – not just books – I think it’s important to open our thinking up a bit during the proposal process. Not everything will necessarily end up in the book per se, but the ideas that don’t may make for great supporting materials, or interesting marketing and promotional angles.

Thinking beyond the book allows you to be a bit more creative with your ideas. Couple that with an editor who is willing to work with you to develop those ideas into a great book is a winning combination.

(Photo credit: Massdistraction)

1. Details
2. Structure
3. Did I mention details?

A great outline might tell me a few key things about an prospective author:

• They understand the topic of the book in a deep and detailed way and are able to communicate that understanding to readers
• They are committed to their book enough to have carefully thought it out to certain level of detail
• They are able to organize their thoughts

The more detail you can get into your draft outline the better. (read that sentence again – I am looking for details.) I almost always work with a potential author to further develop outlines for books I want to publish, but the further along you are with the first draft the faster I can get a proposal approved. Therefore its good for everyone when your proposal includes a detailed, well conceived outline. Here is a list of items I look for in a tech book outline:

1. Each chapter title is “active” and accurately describes what we are doing, discovering or learning in the chapter. We should be building, creating, programming, developing, understanding etc.
2. Each chapter has an estimated page count
3. Each chapter has at least 2 levels of headings and should clearly be broken into main headings, and then into subheadings where possible. A third level of detail gets you bonus points.
4. The outline should flow either chronologically or in increasing difficulty of topic. The flow of the book should be logical.
5. Chapters are grouped logically into Parts
6. Bonus if you include a short descriptive paragraph with each chapter that indicates what will be covered in the chapter and what the reader will learn
7. Are series elements included? For instance, all Wrox Beginning books use 3 mandatory elements in each chapter – “Try it Out,” “How it Works,” and “Exercises.” If you are submitting a proposal for that series, I expect you to know this either because you read the series guidelines I sent you, or you are already familiar with the series through your research.

In addition, there are a few tips to pass along:

• Don’t use the Microsoft Word outline feature. I know it is technically correct, but we editors like to see things like Chapters and Parts
• Parts have more than one Chapter
• Chapters have more than 1 subheading

And last but not least, don’t forget the details.