Strategic Thinking & Decision Making
Strategy isn’t just a plan—it’s a mindset. The best leaders are those who think long-term, frame problems clearly, and make decisions under uncertainty with confidence and clarity. In a world of noise and speed, strategic thinking is a competitive advantage.
This pathway curates five key readings to sharpen your thinking, enhance your foresight, and help you make better decisions—personally, professionally, and organizationally.
Included Summaries
-
Good Strategy Bad Strategy – Richard Rumelt (how to diagnose and design strategy)
Rumelt’s book is a masterclass in clarity. It explains how to spot weak strategy and how to craft powerful ones through clear diagnosis, guiding policies, and coherent actions. -
Thinking in Bets – Annie Duke (decision making under uncertainty)
A former poker pro, Duke teaches how to separate decision quality from outcomes, helping leaders navigate complex environments by thinking probabilistically. -
Superforecasting – Philip Tetlock & Dan Gardner (predictive skill and analytical thinking)
This book presents evidence on how ordinary people can make extraordinarily accurate predictions by being open-minded, evidence-driven, and reflective. -
The Art of Thinking Clearly – Rolf Dobelli (cognitive biases and logical traps)
Dobelli catalogues dozens of mental mistakes we all make—from confirmation bias to sunk cost fallacies—helping readers improve their judgment and awareness. -
Playing to Win – Lafley & Martin (strategy as choice and execution)
This practical guide defines strategy as making choices, not plans. It emphasizes where to play and how to win—crucial for leaders aligning vision with action.
Reflection & Application
Strategic thinking is not about guessing the future—it’s about being prepared to meet it with intention and adaptability.
Key Takeaways:
- Good Strategy Bad Strategy offers a clear template for diagnosing and building powerful strategies.
- Thinking in Bets teaches how to improve judgment by embracing uncertainty and probability.
- Superforecasting provides tools to improve foresight through precision and humility.
- The Art of Thinking Clearly identifies mental pitfalls that cloud judgment.
- Playing to Win emphasizes clarity in strategic choice and alignment.
Applying the Insights
To improve your strategic acumen:
- Run a strategy review using Rumelt’s kernel: What’s the diagnosis? Policy? Action?
- Use decision journaling as Annie Duke recommends to track how and why you made key choices.
- Create a forecast calibration workshop with your team to test assumptions.
- Audit recent decisions for cognitive bias using Dobelli’s checklist.
- Align your OKRs with strategic choices from Playing to Win—are they coherent?
Thinking strategically isn’t a talent—it’s a practice. These readings will help you slow down, think deeper, and act smarter.
“The essence of strategy is choosing what not to do.” – Michael Porter