This is an interesting and inspiring book that is also flawed in such a way that I wonder how much of it is actually valuable. So that’s a problem.

First, the good stuff:

• Berger tells a good story and the way he spreads out some of these stories throughout the book is really skillful, as it keeps you reading even when you might be less inclined to read something this fawning of business leaders.
• The chapter that critiques the educational system is particularly effective, in revealing a deep flaw in how industrialized education fails to encourage kids to think for themselves. This is probably the best part of the book.
• I will say the section on questions for your life is also pretty valuable, albeit brief. This type of approach is, in my opinion, a much better approach than reading self-help books. I have employed it myself for years, in some sense, and I can say that asking yourself provocative questions is a much better way to figure out why you’re unhappy than being told what’s wrong by some guru.

So, for this type of thing the book is pretty valuable, but there are a couple of major problems that keep me from really wanting to recommend it.

So, as I noted before, Berger can be fawning. His day job seems to be a business magazine writer and there is a degree of “business profile of the week/month” to his writing about some of these people. The people in this book are presented as successes, not as people. That’s a problem for me.

I read this book four years after it was published and already some of the companies profiled in the book haven’t had the greatest success. That’s because this book is pure survivor bias – by looking only at people who have successfully asked these questions, we don’t know what happens to those who ask similar questions but who are not successful. Certainly that story is also worth telling (though it would completely undermine the claims in this book, which is why I bring it up).

And that brings me to a related point. When friends and family are getting rid of books, I like to raid the book piles and pick out ones that look interesting. That’s how I got this book. I got it from my boss when he was throwing out some books. (I don’t know why he threw out this one, as should become clear shortly.) I don’t know what came first: my boss’s innate desire to ask questions or this book, but it’s clear to me that this book made a profound impact on him. Reading this book, I recognized things he’d quoted verbatim, stories he’d told me and especially the way he asks questions about what we’re doing at a business. That stuff is for the good.

But the problem is that my boss was never taught what a good answer looks like. He didn’t get the critical thinking education I did. And so he believes that asking questions is the best way to approach everything, even settled things. He is a climate change denier and he believes in so many conspiracies that I wouldn’t want to try to itemize them for fear of leaving some out. Now, this book didn’t cause the conspiratorial thinking in his mind, but it did encourage it. And I think a fundamental flaw of the book is that it fails to address the “I’m just asking questions” moment we’re in, where people think they’re being smart and thinking outside-of-the-box, but they really just don’t know how to construct a good theory (i.e. answer). (I’m not blaming these people, I’m just observing that there are a lot of people in our society who think that “just asking questions” is the only way to think about the world.)

In promoting unlimited question-asking in business and your own life, this book is inadvertently promoting question-asking in areas where people just don’t have the basic knowledge to actually ask good questions, and especially understand the answers. I’m not sure what Berger could have done here to deal with this part of the issue, but I feel like it’s a little irresponsible to spend hundreds of pages talking about the importance of questions while essentially assuming that these questions will always lead to good answers. Because they often don’t.

But there’s still lots to value here. And if you’re aware enough to realize that this book isn’t actually telling you that you need to “question everything” in order to make your life better or do your job better or innovate more, then it’s worthwhile. Just don’t read this and decide that the world’s climate can’t be changing due to human behaviour because we haven’t asked “cui bono?”

6/10