Senior executives rarely fail because they lack intelligence.
They fail because they rely on intuition precisely when intuition is least reliable.
At senior levels, experience becomes a double-edged sword. It speeds up judgment, but it also hardens assumptions. The higher you go, the fewer people challenge your thinking, the faster decisions are expected, and the more dangerous unchecked intuition becomes.
How Not to Be Wrong by Jordan Ellenberg is not a book about being perfect. It is about building thinking systems that reduce error, expose blind spots, and protect leaders from the subtle mistakes that quietly derail strategy, talent decisions, and credibility at the top.
What follows is not a chapter-by-chapter summary.
It is a translation of the book’s core ideas into executive judgment: how smart leaders actually go wrong, and what to do differently.
The Law of Small Numbers
How Senior Leaders See Patterns That Don’t Exist
This is one of the most common and most expensive errors I see at senior levels.
Executives draw strong conclusions from weak signals.
“This market is slowing.”
“That leader isn’t ready.”
“This strategy isn’t working.”
Often, they are reacting to noise, not patterns. Small samples create the illusion of certainty. Once a senior leader labels something a trend, the organization aligns around it, often too early.
This is how it shows up:
- High-potential leaders get written off prematurely
- Promising strategies are abandoned before they mature
- Short-term volatility is mistaken for structural decline
Executive behavior shift
Before acting, slow the decision down and ask:
- What would this data look like if the opposite were true?
- What is the base rate for this situation?
- How often have we seen similar fluctuations before?
This discipline does not slow execution.
It prevents overreaction, which is far more costly.
Survivorship Bias
Why Leadership Teams Keep Learning the Wrong Lessons
Most executive teams study success.
- Top performers
- Winning strategies
- Deals that closed
Very few systematically study failure.
That is a problem.
The leaders who left, the deals that collapsed, and the strategies that quietly died contain the real learning. Ignoring them creates an overly optimistic view of reality, especially at the top.
Boards rarely call this out directly.
They do notice when leadership teams repeat the same mistakes with different slides.
Executive behavior shift
Make failure visible:
- Who did not make it, and why?
- What decisions looked reasonable at the time but failed?
- What data is missing because the “losers” disappeared?
This builds strategic realism, a trait every board values.
Linear Thinking in a Nonlinear World
When More Effort Makes Things Worse
Senior leaders are trained to believe:
- More resources lead to more results
- More pressure leads to more performance
- More meetings lead to more alignment
Many systems do not work that way.
Organizations are nonlinear. Doubling effort often produces diminishing returns or unintended damage. Burnout, complexity, and fragility live here.
This is how it shows up:
- Transformations stall
- Teams become busy but ineffective
- Motion gets confused with progress
Executive behavior shift
Shift from force to leverage:
- Where is effort no longer paying off?
- What small change could unlock disproportionate impact?
- What system effects are being ignored?
This is the difference between execution and leadership.
The Danger of “Obvious” Explanations
Confidence Can Hide Bad Thinking
Executives are rewarded for certainty.
Clarity is praised. Speed is celebrated.
But many “obvious” explanations collapse under scrutiny.
The danger is not lack of intelligence. It is premature certainty. The faster a conclusion feels right, the less likely it is to be tested. This is how groupthink forms, especially in high-trust senior teams.
Executive behavior shift
Create space for doubt:
- Delay your first conclusion
- Test at least one alternative explanation
- Ask, “What else could be true?”
This single habit protects decision quality under pressure.
Intuition vs. Expectation
Why Gut Feel Fails in Complex Decisions
Intuition works in familiar, stable environments. Senior leadership is neither.
Complex systems demand expectation-based thinking grounded in probability, not preference.
Hope feels good.
Probability feels cold.
Only one leads to better decisions.
Executive behavior shift
Before committing, ask:
- What outcome should I reasonably expect?
- What is the most likely scenario, not the most attractive?
- What is the cost if I am wrong?
This is how disciplined leaders protect both the organization and their credibility.
Asking the Right Question
Most Strategic Errors Start Here
Many leadership teams solve the wrong problem brilliantly.
They start with:
“How do we fix this?”
Instead of:
“What is actually broken?”
The framing determines the solution.
Executive behavior shift
Practice reframing:
- Instead of “How do we grow?” ask “Where are we leaking value?”
- Instead of “How do we speed up?” ask “What should we stop doing?”
- Instead of “Why is this not working?” ask “What assumption is failing?”
Better questions lead to better strategy.
Expected Value Thinking
How Elite Decision-Makers Actually Choose
Expected value thinking forces clarity:
- Probability
- Impact
- Long-term consequences
This is how experienced investors, strategists, and top executives evaluate risk.
Executive behavior shift
Apply expected value to:
- Talent bets
- Strategic initiatives
- Capital allocation
- Risk decisions
Ask:
- What is the upside?
- What is the downside?
- How likely is each?
This reduces emotional, political, and reactive decision-making.
The Real Mindset Shift
From Certainty to Calibration
The most important insight in How Not to Be Wrong is this:
Being less wrong matters more than being right.
The best leaders do not cling to certainty.
They update their thinking as new information emerges.
At senior levels, this requires humility, not insecurity.
Executive behavior shift
Adopt:
- Continuous updating
- Curiosity over confidence
- Evidence over instinct
- Flexibility over ego
This is what modern executive leadership looks like.
Practical Actions for Senior Leaders
Daily
- Challenge your first conclusion
- Ask for the base rate
- Identify what data might be missing
Weekly
- Review one decision and identify the assumption behind it
- Test one belief that feels “obvious”
Monthly
- Conduct a failure review
- Revisit a past decision with new evidence
Quarterly
- Reassess priorities using expected value
- Recalibrate stakeholder assumptions
These habits compound quietly and powerfully.
Bottom Line
Senior executives do not need more intelligence.
They need better thinking systems.
How Not to Be Wrong offers a disciplined way of seeing the world that reduces blind spots, sharpens judgment, and improves leadership impact.
The leaders who rise are not the ones who know the most.
They are the ones who think most clearly, especially when it matters most.