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Questorming: exploring the unknown unknowns

Nominally, questorming is brainstorming with questions. In other words, it's a group technique designed to help a group of people to come up with creative solutions to a topic.

However, I've found it much, much more useful than that. One of the great uses for questorming is in Hypothesis Driven Development, where you explore a startup via questions, but there are many other uses for it. You can use it in any situation where you're trying to explore an unknown topic, by which I mean a topic where you think you know a thing or two, but you don't know what the boundaries of your knowledge are - i.e. a topic rife with unknown unknowns.

If Lean Startup is a method for developing a startup in conditions of extreme uncertainty, questorming is a method for exploring a topic in conditions of extreme uncertainty. It gives you a solid starting point which you can leverage into a fuller understanding of a topic that was previously a black box. It's like bootstrapping for your mind.

I've used questorming for everything from exploring statup ideas to drafting a book's table of content (the book didn't get written, but the TOC was solid!). Questorming is very easy to apply once you know about the technique, so I hope this will be useful to others too.

How to apply questorming

As the saying goes, asking the right questions is half the battle. This is what questorming focuses on: questions. The objective of the game is to ask as many questions as possible, in a free-flowing, unscripted way, about the topic. Much like with brainstorming, there are no bad questions in the initial phase - anything goes. As the storm of questions grows, it provides a map of your current understanding of the topic, and some clear next steps for deepening that understanding.

Here's an example. I might want to know more about how to write a book. For such a common topic, I could probably just find some texts on the topic which would teach me the basics, but many other topics (for example, any startup idea) don't have volumes written about them, so for those there is often no source other than your own current understanding.

We start with a simple question:

  • How can I write a book?

And free-flow from there:

  • How can I not write a book?
  • Are there activities that will increase the chances of me writing a book?
  • Are there things that I absolutely must do to write a book?
  • Are there things that, if I do them, will guarantee I don't write a book?
  • What are all those things?
  • Do I need anyone else's help to write a book?
  • Is it possible to write a book without any help from anyone?
  • What are all the key things that need to happen before a book is ready?
  • What does it mean for a book to be ready?
  • Is a book ready when I decide it's ready, or are there other factors?
  • What are clear signs that a book is not ready?
  • Are there some books that can never be ready?
  • Can I do something to make sure that my book will some day be ready?
  • What could I do to ensure that my book will never be ready?
  • Is a book's readiness entirely driven by its content, or is there an external readiness too?
  • What does the external readiness consist of?
  • Is it ready externally when enough people know about it?
  • Are there different stages of internal/external readiness?
  • Does the external readiness help validate the internal readiness?
  • Are they related?
  • Can they be used to push each other forward?
  • Why do I want the book to be ready?
  • What do I want out of it?
  • How does that relate to whether it's ready?
  • Who am I writing this book for?
  • Do they have any impact on whether it's ready?
  • Can I find out if it's ready from the perspective of its audience, before actually publishing it?
  • Do I even need to publish a book?
  • Are there ways to publish a book so that it can be improved iteratively?
  • Are those ways better or worse than traditional ways? Why?
  • Are there benefits to publishing a book in the traditional way, vs a more modern approach?
  • Which is better to match what I want out of this book?

Obviously I could go on... this is an exercise that ends when you decide it's over. For the purpose of illustrating questorming, I think this does the trick. Not all the questions are useful, of course, but on the whole, they provide a good starting point.

Within a few minutes of simply asking questions, I've identified several key actions to take the activity of writing a book to the next level:

  • Finding out what sorts of things people do to get their books finished
  • Thinking about what I actually would want out of a book
  • Figuring out who I know that can advise or help with this
  • Thinking through what I actually mean by a book being ready, and finding out what the industry means by this, and comparing the two
  • In particular, exploring the interplay between a book's content and its market (perhaps in a startup-like fashion, where content is validated in some way before being developed)
  • Defining my audience for this book
  • Exploring traditional vs electronic publishing, and deciding which one suits me better

Of course, these concerns and starting point are deeply related to my own concerns and my knowledge of book writing - and that's exactly as it should be. They provide a map of what I know about the topic, and some next steps about how to expand that knowledge.

In my experience, no subject is safe from questorming. You can always use questorming to expand your knowledge of a topic, no matter how little or how much you know about it. That, in my opinion, makes it an incredibly valuable tool when operating in situations where there is often no authoritative source to tell you what to learn or think about next.


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Designer, Architect, Developer
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