Each book chapter should answer a question. Which kind of questions are best?

I’ve written about the reader question method of organizing a nonfiction book, with one question for each chapter. Now let’s go deeper. Which questions make for the best chapters?

A recap of the reader question method

As I describe in an earlier post, the reader question method is ideal for an advice or how-to book. Each chapter answers a question the reader wants to know about. For example, take a book I edited about the future of transportation, Transportation Transformation by Evangelos Simoudis. The chapters answer these questions:

1. What’s the future of consumer transportation?
2. What’s the current state of consumer transportation?
3. What’s the future for carmakers?
4. What’s the future for mobility services like Uber?
5. What will the new value chains look like?
6. How will municipal governments — cities — participate in this future?
7. What is the value of data in the new value chains?
8. What are the business models for the new value chains?
9. What risks will we face on the way to this future?
10. How should you think about this future?

Which kinds of questions make for good chapters?

To use this method to plan your book, start by brainstorming a set of questions. These should be questions that your reader wants to know about. You can’t even start this exercise until you’ve got a clear idea of your audience.

You can probably come up with dozens of questions. But which ones make good chapters?

Let’s examine what this might look like in a book about the post-COVID future of work.

There are three basic kinds of questions. At the start (and end) of the book, you’ll have some big open-ended questions.

• What will work look like in the future?
• Why are the changes in how we work important to managers and executives?
• How will changes in work change what is important to companies?

The second kind of questions are big definitional questions.

• What is “work anywhere” and why is it important?
• What are the main elements of the new way of working?

The third type of question involves big buckets of more detailed information.

• What technologies must companies master to enable this new way of working?
• How will this change the way you hire and manage workers?
• What does this mean for fully digital companies?
• What does this mean for companies with a significant bricks-and-mortar component?
• What can individual workers do to better prepare themselves for the new way of working?

It’s not a coincidence that I used the word “big” in describing all three types of questions. A chapter isn’t worth doing unless it answers a big question.

What kinds of questions don’t work well?

As you write these questions, you’ll probably reject some.

Some are too small and detailed for a full chapter.

• What is the future of work for insurance companies?
• How will the future of work affect accounting departments?

Others are too centered on the author’s knowledge, as compared to the reader’s challenges:

• What are some companies that I’ve worked with who have dealt with this problem?
• Can I share how I built a fully remote cloud-based infrastructure for the future of work?
• How do I run my small consultancy in a fully remote way?

Some have answers that are too simple to support a whole chapter:

• Will work be different in the future?
• Will we use videoconferencing a lot?
• Will air travel for business return to the way it was?

And some are too likely to become obsolete quickly:

• How do the top three teleconferencing vendors compare?
• How should companies deal with vaccination rules and mask mandates?
• Who are the top experts in remote work?

How to build a table of contents out of questions

To structure your book appropriately, consider the reader’s journey. First, they want to know why your topic matters (which is why the best books of this kind start with a “scare the crap out of you” chapter). Then they’d like to know a little more about why your solution is the right one for this problem. Then they’re likely to ask about details — for example, steps to follow, ways to collaborate around the solution, or elements that will require further planning.

If you can imagine having a conversation with a potential reader that starts with the big question and broadens out into elements of the solution, then you can build the book around the reader’s questions that would be part of that conversation.

What about the questions you can’t answer?

Ideally, you’ll have a case study and a framework for discussing each of the questions. But you may have questions that you can’t answer right now.

You could ignore those questions or sweep them under the rug and hope no one notices.

But in the best books of this kind, the author does hard work — research — to find the answers to those tough questions.

That kind of research may take you out of your comfort zone. But if you can’t answer those questions — or at least address them in some way — then your book won’t really be complete.