Decision making is an acquired skill and one that I have worked to improve throughout my life. Here are eight books that shaped my thinking on decision-making:
The Seven Habits of Highly Effective People, by Steven Covey. This is not a book about decision making, but it does talk about defining your values. You cannot make effective decisions without defining your values. There will always be trade-offs. Values help you determine which trade-offs are acceptable and which ones aren’t.
Thinking Fast and Slow, by Daniel Kahneman. This book summarizes in a fun, readable way Kahneman and Amos Tversky’s ground-breaking work which showed the many ways that our biases cloud our reason. By knowing these biases, we can account for them and make better decisions.
The Effective Executive by Peter Drucker. Drucker was the Aristotle of business management and an exceptionally clear thinker. This book stretches the gamut from management, to time management, to decision-making. This is an important and useful book.
Principles by Ray Dalio. Dalio founded Bridgewater Associates in 1975 and grew it into the largest hedge fund in the world. He sets out in outline form and text his process for making decisions. He has a lucid thought process that breaks every process down into its component parts, takes risk into account, and judges the credibility of sources of information. His emphasis on radical truth and radical transparency give a modern nod to the Stoic writings of Marcus Aurelius.
Thinking in Bets by Annie Duke. Duke translates her experience as a poker player, cognitive psychologist, and corporate advisor into helping us think about risk constructively and make better decisions.
The Black Swan by Nassim Nicholas Taleb. With sardonic wit, erudition, and mathematics somehow rolled together into a fascinating and very readable narrative, Taleb discusses the disproportionate impact of extreme events and how to avoid their consequences.
Decisive by Dan and Chip Heath. Dan and Chip Heath do a great job of making otherwise dry topics easily understandable, memorable and readable. Decisive sets out their framework on decision-making.
Leadership in Turbulent Times by Dorothy Kearns Goodwin. This study of the leadership styles of Lincoln, the two Roosevelts, and Lindon Johnson includes examples and analyses of the decision-making process of these great leaders.