The 365 Best Business Books Of All-Time: A More Beautiful Question

Steve Cunningham
3 min readJan 5, 2018

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Great questions are the heart of everything — but especially innovation and creativity. And so, great questioners are at the heart of all innovation and creativity.

As Warren Berger — the author of A More Beautiful Question points out, great questioners are very comfortable with their own ignorance. In fact, it’s one of the things that drives almost all scientists towards new discoveries. As Stuart Fierstein — the author of the book Ignorance — puts it:

“One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking. Answers, on the other hand, often end the process.”

So how do we ask great questions?

My Key Takeaway/Principle

Open and close questions to challenge your assumptions.

The first thing we need to do in order to ask great questions is to get comfortable with not having the answers.

As Paul Bennet, the creative director at renowned design firm IDEO says, “I position myself relentlessly as an idiot at IDEO…being comfortable with not knowing — that’s the first part of being able to question.”

One of the benefits of doing this is that it allows you to ask naive questions. And that allows you to bring clarity to otherwise complex issues by forcing the person you are asking questions to simplify their thinking down to its very essence.

Once you are able to let go and ask seemingly naive questions, you’ll start to generate a lot of questions about the world around you.

One technique for becoming an ever better questioner is to “open and close” your questions. The example Berger gives in the book is “why is my father-in-law difficult to get along with?” This is an open-ended question without a clear answer.

However, when you close that question, you end up with “Is my father-in-law difficult to get along with?”, which forces you to confront the assumption of the original question. This process works both ways — you should close your open questions, and open your closed questions. You’ll start to see the world from completely new perspectives if you do.

Questions to ask yourself

  • How can I use the principle of opening/closing questions in the next week?
  • What assumptions am I making in my day-to-day decision making that I need to challenge?

What else is covered in this book?

The power in asking great questions comes to life in a 3-step process — asking why, what if, and how. It sounds simple, but the devil is in the details. Learn more about those details in this book.

This year (2018) I’m reading and summarizing the top 365 business books of all-time. You can get the full list of books, and links to my reviews of each book, by clicking here.

Happy learning!

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Steve Cunningham

Founder/CEO, www.readitfor.me. This year (2018) I’m reading and summarizing the 365 best business books of all-time, and posting my thoughts here daily.