A defense-contractor CEO once sat across from Edmund Wakefield about to bet a quarter of his company's annual revenue on a single foreign contract. He had a deck, spreadsheets, and the backing of two vice presidents. What he did not have was anyone in the room who had ever lost money on a deal like it, and he had never asked, in writing, what failure would look like. They sat for ninety minutes. He changed one termination clause. Two years later that clause saved the company. He didn't need a new mental model. He needed someone to make him slow down.
Most decision-making books teach you to admire cognitive biases and name them in alphabetical order. This one teaches you to work around them. Drawing on twelve years as an intelligence analyst and two decades advising founders, CEOs, and agency directors, Wakefield delivers a working kit for better thinking under pressure: a few diagnostics for what kind of decision you face, a few exercises that pull you out of your own head, and a few habits that compound over a career. You will learn the difference between reversible and irreversible decisions, when to decide fast and when to slow down, and why "producing" documents is not "deciding." Every chapter ends with a three-minute exercise you can run this week.
Inside this decision-making book:
- The two mental modes you already misuse — When to trust the quick read and when the slow walk-through should override it, illustrated by a bank president whose gut caught a bad loan the numbers approved
- The premortem — How to imagine failure before it happens, the exact move that saved the defense contractor a quarter of his revenue
- Reversible vs. irreversible decisions — Why speed is a virtue for cheap-to-reverse calls and a disaster for the ones you cannot undo
- The biases most likely to trip you up at work — Plus the outside view, decision journals that compound over years, and deciding under uncertainty with probabilities you do not have
- The hardest people decisions — Hiring, firing, and promoting, and how to stop laundering a decision through a committee that exists only to share the blame
- Recovering from a bad decision — How to stop doubling down, plus building decision hygiene into your week and teaching others to decide well
- Decisions under time pressure — The five-minute discipline for when the information will always be bad and the question itself is unclear
This is not a survey of behavioral economics and it does not promise transformation. It is the small set of moves that separates a competent decision-maker from one who just sounds competent: the pause before, the structure during, the accounting after. Practiced over a career, these habits give you steadier hands when the stakes are real and better judgment when time is short.
For readers of Annie Duke's Thinking in Bets and Chip and Dan Heath's Decisive.