The Ten Best Decision Making Books of All Time

The Ten Best Business Decision Making Books Ever Written

Gaining insight into how the editors of AskTheManager.com chose the Ten Best Decision Making Books Ever can itself be a lesson in decision making. While the list of qualified books on this subject is quite long, we decided early on to exclude any and all that read like an encyclopedia, dictionary or college textbook. While many of these types of books do provide useful decision making information, we decided we wouldn’t feel right sending our readers in search of dull or boring reads.  

And just as we did with our popular Ten Best Leadership Books Ever, we struggled more with where to place each of the Top Ten on our list than we did deciding which titles actually made our Top Ten. After several heated discussions and lots of backroom deal making, we decided on the following order for the terrific tomes topping our list of The Ten Best Business Decision Making Books Ever Written:

10. Predictably Irrational: The Hidden Forces That Shape Our Decisions; by Dan Ariely – A mostly fun read that details why we decide what we decide and when, Predictably Irrational immediately grabs your attention through a very strong and entertaining start. While this tome won’t necessarily turn you into a top decision maker overnight, it does offer insight into some of the most common and odd choices we make. From a purely social or behavioral economics standpoint, this book is nowhere near the read of Freakonomics, though its explanation and application of these economic principles detailing why people make irrational decisions easily earns it a spot on our Top Ten.

9. How We Decide; by Jonah Lehrer – Very much like Number 10 on our list, How We Decide introduces the reader to many concepts surrounding behavioral psychology and economics, and how these affect our decision making. Also like Number 10, this tome is loaded with entertaining information that will stimulate your thoughts about how we think and make decisions in response to the complex situations we face. While slightly more enjoyable than Predictably Irrational, this book still falls a little short at helping the reader uncover clear rules for making better decisions; and although both are very, very good and deserve their mention on this list, you only need to read one (you make the decision).

8. The 7 Habits of Highly Effective People; by Stephen R. Covey – Number One on our list of the Ten Best Leadership Books of All Time, Covey’s coverage of Habit 2: Begin with the End in Mind, earns him the right to crack this Top Ten list, as well. While not a primer on avoiding analysis paralysis or helping teams makes better decisions, the chapters covering Habit 2 in this book do provide a great lesson for anyone who’s known for making bad decisions. The best part about this title is it also provides the reader with a clear plan of attack for making and executing better decisions.

7. Blunder: Why Smart People Make Bad Decisions; by Zachary Shore – Using examples of some of the biggest blunders in history, Shore provides an entertaining, historical and hard-hitting examination of bad decisions. Probably due to Shore’s fantastic ability to tell a story, we fear we may have been too easily swayed by style and not substance in including this title in our Top Ten. That said, Shore provides enough practical thought (and some very concise causation theories) to carry this read.

6. Smart Choices: A Practical Guide to Making Better Decisions; by John S. Hammond, Ralph L. Keeney, and Howard Raiffa – One of the truest books ever to its title, Smart Choices is indeed a practical guide to making better decisions. Unlike some of the novel-like reads on this list, this book clearly outlines steps readers can take when faced with both minor and major decisions in their work and personal lives – and because the authors do so without sounding like academicians, it was an easy decision to add this to our Top Ten list. 

5. Why We Make Mistakes: How We Look Without Seeing, Forget Things in Seconds, and Are All Pretty Sure We Are Way Above Average; by Joseph T. Hallinan – As much as a title this long may make you want to skip to the last page just see how it ends, we advise against this because you’d miss a great read. Although Why We Make Mistakes takes us in a slightly different direction than many of the books on this list, it strikes a cord with us by proving that we are flawed and that internal changes aren’t enough to repair these flaws. (If nothing else, this read provides a classic example as to why so many books published in the last two years made this list: We are just now becoming aware of how we make decisions and what we can do to improve them.)

4. Sway: The Irresistible Pull of Irrational Behavior; by Ori Brafman and Rom Brafman – Probably the quickest 224 pages you’ll ever read, Brothers Brafman deliver some very compelling arguments regarding our innate irrationality. Though very similar in content to Predictably Irrational, Sway stands on its own by never bogging the reader down in too much detail (while delivering enjoyable detailed analysis throughout). Overall, Sway does an excellent job of showing us how to make better decisions by understanding the irrational forces that want to sway us otherwise.

3. The Goal: A Process of Ongoing Improvement; by Eliyahu M. Goldratt and Jeff Cox – A business classroom classic that was originally published in 1984 as part organizational management and part production operations management; this novel was one of the very first to use fiction to illustrate a business point. While the decision making lessons delivered here are often veiled in other concepts, the fictional factory turnaround that is engineered by the book’s protagonist provides a step-by-step plan for managers in crisis to follow when faced with difficult decisions. A must read for anyone in business. (Editor’s Note: We’re often asked which book would rank at Number 11 on our list of the best leadership books ever, and The Goal is clearly the favorite for that spot.)

2. Overcoming the Five Dysfunctions of a Team: A Field Guide for Leaders, Managers, and Facilitators; by Patrick M. Lencioni – It’s one thing to rant about what’s wrong, it’s quite another to detail how to make things right. In Overcoming the Five Dysfunctions of a Team, the master at team dynamics Lencioni offers specific, practical advice for overcoming the five dysfunctions he details in his earlier book. And while many will argue this is strictly a book about leadership or team dynamics, we say then you’ve never really read it. Among other things, Lencioni’s advice expertly helps teams become more effective by making better decisions. Clearly the best book for improving team decision making and effectiveness ever published; earning it our Number 2 spot.

1. Blink: The Power of Thinking Without Thinking; by Malcolm Gladwell – You either love this book or you hate it; there is no middle ground with Blink. By naming this the Best Decision Making Book Ever, we know we’ve probably lost half our readership – of course, had we not named it Number One, we would have lost the other half. (Because we read Blink, we went with our gut and named it Number One.) On a serious note, Blink is one of those “must reads” for anyone in business… end of story. Not only because it explains the power and accuracy of first impressions, but because it also provides data and examples to prove that over-thinking our problems is often the problem. Analysis paralysis and self doubt are the greatest enemies of management decision making today and Gladwell cuts to the quick better than anyone ever has (or likely ever will). Read Blink, it will be the best decision you ever made.

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On the bubble: Tipping Point; Freakonomics; Execution; and Gut Feelings.

Never even in the consideration set: Nudge and The Paradox of Choice.