Day 51 of The 100 Day Project: Thinking in Bets—How Great Leaders Make Smarter Decisions

Learn how Thinking in Bets by Annie Duke helps leaders improve decision-making through probabilistic thinking and better habits.

In business and in life, you rarely get to make decisions with all the information you'd like. So you do the best you can with the information you have. The world is uncertain, complex, and full of hidden variables. Thinking in Bets by Annie Duke invites you to approach this uncertainty the way a professional poker player would: with curiosity, humility, and a commitment to continuous learning.

Decisions Are Bets on the Future

Every decision you make is essentially a bet. It’s a prediction about the future with incomplete information. Yet you often judge decisions solely by their outcomes. When things go well, you pat ourselves on the back for our brilliance. When they go poorly, you blame luck, others, or yourself without truly analyzing the process that led you there.

Annie Duke challenges this thinking. Instead of evaluating decisions by whether they turn out well, she urges you to assess the quality of the decision-making process. This shift in mindset, away from results and toward process, is the first step toward becoming a more effective and resilient leader.

Life Is Poker, Not Chess

One of Duke’s most memorable insights is that life is more like poker than chess. Chess is a game of complete information. If you know the rules and practice, you can become excellent. But poker, and real life, is full of unknowns. You don't get to see all the cards. You're often reacting to other people’s hidden motives, random variables, and changing environments.

This is where many people fall into the trap of "resulting," equating a good outcome with a good decision, or a bad outcome with a poor decision. In poker, and in leadership, you can make all the right moves and still lose. Separating the influence of skill and luck is important for growth and accountability.

Biases That Distort Our Thinking

Duke highlights several cognitive biases that get in the way of making sound decisions:

Resulting: Judging a decision by its outcome rather than its reasoning.
Hindsight Bias: Believing you “knew it all along” after the fact.
Motivated Reasoning: Processing information to support your existing beliefs.
Binary Bias: Reducing complex issues to black-and-white answers.
Blind-Spot Bias: Noticing bias in others while being blind to your own.

These patterns don’t just limit your thinking. They actively reinforce poor decision habits. Leaders who want to grow must learn to recognize and challenge these biases daily.

The Power of “I Don’t Know”

Admitting uncertainty is often seen as weakness. But Duke reframes it as strength. The phrase “I don’t know” opens the door to better information, more inclusive discussion, and higher-quality decisions. When you acknowledge your knowledge gaps, you give yourself the chance to fill them. This is the essence of calibration, updating your beliefs as you receive new evidence.

By avoiding all-or-nothing thinking and allowing for shades of gray, you train yourself to think probabilistically. This shift helps you avoid extremes, improves long-term outcomes, and strengthens your leadership credibility.

Use Scenario Planning to Improve Your Odds

One of the most practical strategies in Thinking in Bets is scenario planning, particularly backcasting and premortems. These tools let you imagine future success or failure and reverse-engineer the path to (or away from) that outcome.

Backcasting: Start from a successful outcome and work backward. What decisions and events led there?
Premortem: Imagine a failure. What went wrong? What could you have done differently?

Both tools help teams avoid overly optimistic plans and spot potential roadblocks in advance. These mental models also support a growth-oriented leadership style that values thoughtful preparation over wishful thinking.

Build Better Decision-Making Habits

Duke compares improved decision-making to compound interest. The earlier and more consistently you practice it, the better your long-term results. Here are some practices to implement now:

Ask yourself “Wanna bet?” when forming an opinion to test the strength of your conviction.
Create a decision journal to track what you knew, what you guessed, and what you learned.
Develop a truth-seeking group—people who hold you accountable to reasoning and not just agreement.
Use Ulysses contracts to protect your future self from impulsive decisions, by creating structure and barriers that keep you aligned with your long-term goals.

Conclusion: Thinking in Bets in the Leadership Arena

Great leaders aren’t the ones who get every decision right. They’re the ones who improve the quality of their decisions. Thinking in Bets teaches you to embrace uncertainty, separate skill from luck, and continually refine our thinking through better habits and frameworks.

When outcomes are unpredictable, betting wisely on your ideas, your team, and your future becomes the ultimate leadership skill.

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Categories: : Cognitive bias and thinking tools, Decision-making strategies, Leadership development