Questions to Ask When Writing a Book

Turning a top-down search for answers into the bottom-up discovery of questions


The nameless authors at First Round Review interviewed Tim Urban of Wait But Why about getting complex ideas across to his readers. They distilled that interview (which I haven't listened to) into an article.

When I read the piece it occurred to me that the questions raised could form a good template for helping me clarify issues related to writing a book. Or, more specifically, for me confronted with writing a book-length treatment of my post, 10 Work Skills for the Postnormal Era.

So I decided to dig into this interview and break it into a series of questions that I could answer to help me triangulate on the book-writing process. (Also, this is the sort of constructive procrastination that I am attracted to.)

Different Sorts of Complexity

Urban's technique involves answering (and reanswering) several kinds of questions.

The first question deals with complexity, since he's generally dealing with complex subjects. He believes that there are different types of complexity, which he defines by the activities needed to make sense of them. His big three:

  1. Gathering sort of complexity
  2. Dusting sort of complexity, but which I call Insight
  3. Pattern matching or pattern resisting sort of complexity.

Gathering — an issue that needs to be tackled by collating information, exhaustively. And, once that time and energy is expended, writing about the topic is relatively straightforward. So, this is a front-loaded practice, where the barrier is learning the subject matter, what he calls 'classic complexity'. It's not like learning the difference between tying a granny knot and a square knot in your shoelaces, which takes two minutes. This is like trying to understand machine learning, which takes hours or days of reading.

Insight — an issue that needs to be understood through analogy, or metaphor, the application of a general rule in a specific case: deductive reasoning. For example, Urban mentions the cook versus chef concept: a cook follows recipes, but a chef invents new ones. Once this general principle is learned, you can recognize it popping up all over. And of course, people already know what chefs and cooks are, so using the analogy in other settings make them immediately understandable.

Patterns — This involves and builds on the prior two approaches. You are gathering information and digging for insights, hoping to find patterns in the mix. You have to evaluate if a pattern you think is present is in fact there, and if so, is it fundamental to the issue in a way that will help understanding it by making the complexity simpler.

So, one of the first questions for a writer faced with a complex topic is 'what kind of complexity is it?', which really means 'what kind of approach can I productively take to attempt to make this complex issue understandable?'.

And this isn't just for the central theme of the book, a question to be asked once: it's recursive. So, if someone were writing a chapter about climate change, as the author gathers more information about the various causes and impacts of climate change, each of those has to be subjected to the same questioning as well. So you'd have to ask 'what sort of complex is methane production?' which would lead you to 'agricultural methane production (cows farting, etc.)' and 'melting permafrost', each of which need to be explored.

(My additional two cents is that it might be helpful when gathering facts and looking for patterns and insights to use tools, like bookmarking and annotation aids (I use Dynalist), and mind mapping tools (like Mindmeister) to link things together visually.)

Who Are You Cutting Through the Complexity For?

Are you trying to connect the dots for PhDs in their area of specialization? Not likely. But where are you pitching?

Urban's scale is based on familiarity with the complex issue in question:

10 - Is world’s leading expert on the idea.

9 - Can ask expert questions and generate new information/data on the idea.

8 - Can answer expert questions and reconcile contradictory thoughts about the idea.

7 - Can answer any layman’s question and forms independent thoughts on the idea.

6 - Can answer any layman’s question and forms intelligent opinions on the idea.

5 - Knows about the idea, and can discern inaccurate statements about the idea.

4 - Knows about the idea, and can explain what’s been learned in one’s own words.

3 - Heard of the idea, and recites what others have said about it.

2 - Heard of the idea, but doesn’t know anything about it.

1 - Never heard of the idea.

Where do you fall on the scale? Where does your target audience fall?

For example, I have a serious grounding in network theory (my MS in computer science, and grounding in discrete math) so if I am approaching something like an explanation of Mark Granovetter's Strength of Weak Ties I am at least an eight. However, most people — even those who follow my work — are likely down in the middle of the range, at best. In other cases, I might be a seven talking to sixes.

The important thing is to think about where you and the reader are starting from, and where you want to take them. And then to get them to get involved in the narrative around the idea being pursued so they are in on the hunt, too.

Urban believes there are a bazillion sites and books that try to take readers from a one to a three, but as he says

the people who want to get to a six are an underserved audience in my opinion. I know that because I'm one of those people.

Lastly, we want to help the reader by leaving them with concrete application of the idea, like knowing exactly how to tie a square knot in their shoelaces, or how to create more weak ties in their company and why that's good.

Find The Narrator

Urban maintains that finding the right protagonist in the narrative may be the hardest part. Many writers write without reference to themselves, like journalists relating a new story and trying to stay out of the camera frame. But sometimes you have to be the reporter at the scene talking to the camera. Or describe the inventor of some new gizmo, and use his words to get its charm across.

Here are some questions that can help, and should be asked for the book as a whole and for every complex idea you are introducing:

Who is taking the reader by the hand?

Is it me or a a storytelling character?

Is the narrator behind the scenes?

Where can/should they start?

What's the game you're playing?

What voice are you using? Which emotions?

Is their job to show or to tell?

To some extent, part of this is 'finding your voice' as a writer, but some is the scaffolding of exposition, like a writer of fiction employing dialogue to develop two characters' relationship, or a movie director choosing a particular series of camera angles and cuts to denote tension.

In the case of trying to explain Granovetter's Strength of Weak Ties, I might relate an insight that occurred to me when I first learned about weak ties, where I am personalizing the transition from a five or six to an eight, and how that allowed me to understand something about the world.

Or, I might use someone else as the story teller, like Everett Harper, who wrote about weak ties as the pivot in his efforts to diversify a Silicon Valley startup.

Or I might fictionalize a character, Bette, who is weakly linked to a large number of acquaintances at work, and why that may be better preparing her to respond to major challenges than her previous job where she had a smaller number of more strong relationships.

The important thing is to pick a narrative angle, and voice, one that can reach the reader and help them move from a minimal understanding of social networks to a deeper appreciation of Granovetter's contribution (he's on the unofficial Nobel for Economics list).

Bringing it Together

Clearly, these approaches have to be balanced, but first the questions should be asked, and the writer has to at least try to answer them.

I'm not starting my book from scratch. I wrote a wildly popular post — 10 Work Skills for a Postnormal Era — and will be using that as the skeleton of the book I'm writing.

I plan to start with an annotation of that post, retrospectively applying Urban's lenses to what I did, and attempting to project what I need to do, chapter by chapter, to simplify the complex ideas, to target the reader, and to find the narrator. And after I synthesize that that exercise reveals, that, I can try to build the new version, one triangulation at a time.

In some cases, I will need to return to the gathering stage, in others, I may choose alternative analogies or models to make the complex less so. And in the original post, aside from a few quotes, there is really only one narrator.

Finally, it's essential to build on understanding with concrete takeaways, because knowledge should be grounded to demonstrate its value.