Smart People Make The Worst Business Decisions

Written by

Graeme Crawford

Why intelligence works against founders

Why intelligence works against founders

Why intelligence works against founders

Your biggest business risk isn't market volatility, it's you.

That's what Glen Hellman, one of Inc. Magazine's top executive coaches for 2026, told me during our recent conversation. After watching brilliant minds sabotage themselves for decades, he's discovered something shocking: the smarter you are, the worse your business decisions become.

Here's why this matters to you as a CEO, and what you can do about it:

  • Intelligence creates analysis paralysis

  • Smart people gather too much data and can't feed it to the part of their brain that actually makes decisions

  • Your reptilian brain (where decisions happen) can't process abstractions—it needs simple, binary choices

Let me share the frameworks that can save you from yourself.

3 Ways Smart CEOs Make Terrible Decisions (And How to Fix Them)

To scale past $10M, you need to outsmart your own intelligence.

Glen's research reveals a brutal truth: while "dumb folks" naturally make binary choices, smart people try to process everything at once and fail spectacularly.

1. The Menu Problem: Too Much Data, Too Little Action

The Problem: You're the CEO staring at a 20-page analytics report, trying to process every metric simultaneously. Sound familiar?

What's Really Happening: Your cerebellum (language processing) can handle complexity, but your reptilian brain (decision-making) operates on simple yes/no logic. When you overload it with data, it shuts down.

The Fix: Create decision rubrics on paper. List 5-8 factors that matter, weight them by importance, then score each option. Glen's rule: "If you can say it in 15 words, try to say it in 10. If you can say it in 10, try 7, then 5."

2. The Perfect Decision Trap

The Problem: You're waiting for 100% certainty before launching that new product line or expanding into a new market.

What's Really Happening: Your third-grade perfectionist is running your boardroom. That pattern of seeking approval through flawless execution doesn't serve you at $15M+ revenue.

The Fix: Aim for 80% good solutions and move fast. Glen uses the flight simulator analogy: "Low-risk failures are learning experiences. Small failures prevent big ones when the stakes are higher."

This is exactly what separates the companies that scale from those that stall. The businesses I work with that break through the $20M barrier? They test fast, fail cheap, and iterate based on real market feedback. The ones stuck at $10M? They're still perfecting their "strategy" in conference rooms.

3. Correlation vs. Causation Confusion

The Problem: Your iPhone adoption data perfectly correlates with World War II veteran deaths. Did the iPhone cause veteran deaths? (Hopefully not.)

What's Really Happening: Too much data finds meaningless correlations. Smart people get seduced by complex relationships that don't drive business outcomes.

The Fix: Focus on 5-8 key factors maximum. Glen's favorite question: "What if it wasn't everybody else's fault—whose fault would it be?" Force accountability while keeping analysis simple.

I see this constantly with growth-stage companies. They'll track 47 different metrics across 12 dashboards, then wonder why they can't make quick decisions. The companies that breakthrough? They focus obsessively on 3-5 leading indicators that actually predict revenue growth.

The Entrepreneur's Dice: Why Luck Matters More Than You Think

Here's Glen's most powerful framework: Success is a six-sided die.

  • If you're not smart and don't work hard: You get one throw at rolling a six

  • If you're smart: You get a four-sided die (better odds)

  • If you work hard: You get to throw twice

  • If you're both smart AND work hard: You get the best chance, but luck still matters

The worst outcome? Rolling a six on your first try and thinking it was all skill. These people never learn from failure because they've never failed.

In his career, Glen had three major wins - one IPO and two successful sales. But he hasrolled the dice 30+ times, meaning he’s had plenty of snake eyes. Those failures taught him more than any success ever did. The key is not fearing the bad rolls but learning from them to improve your odds next time.

That's it.

Here's what you learned today:

  • Your intelligence can work against you if you don't structure decisions properly

  • Simple rubrics beat complex analysis every time

  • 80% solutions executed quickly outperform 100% solutions delivered late

  • Success includes luck. Stay humble and keep learning

The data doesn't lie: many businesses still base decisions on gut feel rather than structured analysis. But the companies that combine smart frameworks with fast execution? They're the ones scaling past their competitors.

PS...If you're enjoying this, please consider sending it to a friend. They'll thank you for helping them avoid expensive data mistakes.

Whenever you are ready, we can help you with a ​free data infrastructure assessment​ to identify your highest-impact opportunities. Get in touch! Listen to the Scale Your Business Data podcast every week on: ​YouTube​ ​Spotify​ ​Apple

Your biggest business risk isn't market volatility, it's you.

That's what Glen Hellman, one of Inc. Magazine's top executive coaches for 2026, told me during our recent conversation. After watching brilliant minds sabotage themselves for decades, he's discovered something shocking: the smarter you are, the worse your business decisions become.

Here's why this matters to you as a CEO, and what you can do about it:

  • Intelligence creates analysis paralysis

  • Smart people gather too much data and can't feed it to the part of their brain that actually makes decisions

  • Your reptilian brain (where decisions happen) can't process abstractions—it needs simple, binary choices

Let me share the frameworks that can save you from yourself.

3 Ways Smart CEOs Make Terrible Decisions (And How to Fix Them)

To scale past $10M, you need to outsmart your own intelligence.

Glen's research reveals a brutal truth: while "dumb folks" naturally make binary choices, smart people try to process everything at once and fail spectacularly.

1. The Menu Problem: Too Much Data, Too Little Action

The Problem: You're the CEO staring at a 20-page analytics report, trying to process every metric simultaneously. Sound familiar?

What's Really Happening: Your cerebellum (language processing) can handle complexity, but your reptilian brain (decision-making) operates on simple yes/no logic. When you overload it with data, it shuts down.

The Fix: Create decision rubrics on paper. List 5-8 factors that matter, weight them by importance, then score each option. Glen's rule: "If you can say it in 15 words, try to say it in 10. If you can say it in 10, try 7, then 5."

2. The Perfect Decision Trap

The Problem: You're waiting for 100% certainty before launching that new product line or expanding into a new market.

What's Really Happening: Your third-grade perfectionist is running your boardroom. That pattern of seeking approval through flawless execution doesn't serve you at $15M+ revenue.

The Fix: Aim for 80% good solutions and move fast. Glen uses the flight simulator analogy: "Low-risk failures are learning experiences. Small failures prevent big ones when the stakes are higher."

This is exactly what separates the companies that scale from those that stall. The businesses I work with that break through the $20M barrier? They test fast, fail cheap, and iterate based on real market feedback. The ones stuck at $10M? They're still perfecting their "strategy" in conference rooms.

3. Correlation vs. Causation Confusion

The Problem: Your iPhone adoption data perfectly correlates with World War II veteran deaths. Did the iPhone cause veteran deaths? (Hopefully not.)

What's Really Happening: Too much data finds meaningless correlations. Smart people get seduced by complex relationships that don't drive business outcomes.

The Fix: Focus on 5-8 key factors maximum. Glen's favorite question: "What if it wasn't everybody else's fault—whose fault would it be?" Force accountability while keeping analysis simple.

I see this constantly with growth-stage companies. They'll track 47 different metrics across 12 dashboards, then wonder why they can't make quick decisions. The companies that breakthrough? They focus obsessively on 3-5 leading indicators that actually predict revenue growth.

The Entrepreneur's Dice: Why Luck Matters More Than You Think

Here's Glen's most powerful framework: Success is a six-sided die.

  • If you're not smart and don't work hard: You get one throw at rolling a six

  • If you're smart: You get a four-sided die (better odds)

  • If you work hard: You get to throw twice

  • If you're both smart AND work hard: You get the best chance, but luck still matters

The worst outcome? Rolling a six on your first try and thinking it was all skill. These people never learn from failure because they've never failed.

In his career, Glen had three major wins - one IPO and two successful sales. But he hasrolled the dice 30+ times, meaning he’s had plenty of snake eyes. Those failures taught him more than any success ever did. The key is not fearing the bad rolls but learning from them to improve your odds next time.

That's it.

Here's what you learned today:

  • Your intelligence can work against you if you don't structure decisions properly

  • Simple rubrics beat complex analysis every time

  • 80% solutions executed quickly outperform 100% solutions delivered late

  • Success includes luck. Stay humble and keep learning

The data doesn't lie: many businesses still base decisions on gut feel rather than structured analysis. But the companies that combine smart frameworks with fast execution? They're the ones scaling past their competitors.

PS...If you're enjoying this, please consider sending it to a friend. They'll thank you for helping them avoid expensive data mistakes.

Whenever you are ready, we can help you with a ​free data infrastructure assessment​ to identify your highest-impact opportunities. Get in touch! Listen to the Scale Your Business Data podcast every week on: ​YouTube​ ​Spotify​ ​Apple

Your biggest business risk isn't market volatility, it's you.

That's what Glen Hellman, one of Inc. Magazine's top executive coaches for 2026, told me during our recent conversation. After watching brilliant minds sabotage themselves for decades, he's discovered something shocking: the smarter you are, the worse your business decisions become.

Here's why this matters to you as a CEO, and what you can do about it:

  • Intelligence creates analysis paralysis

  • Smart people gather too much data and can't feed it to the part of their brain that actually makes decisions

  • Your reptilian brain (where decisions happen) can't process abstractions—it needs simple, binary choices

Let me share the frameworks that can save you from yourself.

3 Ways Smart CEOs Make Terrible Decisions (And How to Fix Them)

To scale past $10M, you need to outsmart your own intelligence.

Glen's research reveals a brutal truth: while "dumb folks" naturally make binary choices, smart people try to process everything at once and fail spectacularly.

1. The Menu Problem: Too Much Data, Too Little Action

The Problem: You're the CEO staring at a 20-page analytics report, trying to process every metric simultaneously. Sound familiar?

What's Really Happening: Your cerebellum (language processing) can handle complexity, but your reptilian brain (decision-making) operates on simple yes/no logic. When you overload it with data, it shuts down.

The Fix: Create decision rubrics on paper. List 5-8 factors that matter, weight them by importance, then score each option. Glen's rule: "If you can say it in 15 words, try to say it in 10. If you can say it in 10, try 7, then 5."

2. The Perfect Decision Trap

The Problem: You're waiting for 100% certainty before launching that new product line or expanding into a new market.

What's Really Happening: Your third-grade perfectionist is running your boardroom. That pattern of seeking approval through flawless execution doesn't serve you at $15M+ revenue.

The Fix: Aim for 80% good solutions and move fast. Glen uses the flight simulator analogy: "Low-risk failures are learning experiences. Small failures prevent big ones when the stakes are higher."

This is exactly what separates the companies that scale from those that stall. The businesses I work with that break through the $20M barrier? They test fast, fail cheap, and iterate based on real market feedback. The ones stuck at $10M? They're still perfecting their "strategy" in conference rooms.

3. Correlation vs. Causation Confusion

The Problem: Your iPhone adoption data perfectly correlates with World War II veteran deaths. Did the iPhone cause veteran deaths? (Hopefully not.)

What's Really Happening: Too much data finds meaningless correlations. Smart people get seduced by complex relationships that don't drive business outcomes.

The Fix: Focus on 5-8 key factors maximum. Glen's favorite question: "What if it wasn't everybody else's fault—whose fault would it be?" Force accountability while keeping analysis simple.

I see this constantly with growth-stage companies. They'll track 47 different metrics across 12 dashboards, then wonder why they can't make quick decisions. The companies that breakthrough? They focus obsessively on 3-5 leading indicators that actually predict revenue growth.

The Entrepreneur's Dice: Why Luck Matters More Than You Think

Here's Glen's most powerful framework: Success is a six-sided die.

  • If you're not smart and don't work hard: You get one throw at rolling a six

  • If you're smart: You get a four-sided die (better odds)

  • If you work hard: You get to throw twice

  • If you're both smart AND work hard: You get the best chance, but luck still matters

The worst outcome? Rolling a six on your first try and thinking it was all skill. These people never learn from failure because they've never failed.

In his career, Glen had three major wins - one IPO and two successful sales. But he hasrolled the dice 30+ times, meaning he’s had plenty of snake eyes. Those failures taught him more than any success ever did. The key is not fearing the bad rolls but learning from them to improve your odds next time.

That's it.

Here's what you learned today:

  • Your intelligence can work against you if you don't structure decisions properly

  • Simple rubrics beat complex analysis every time

  • 80% solutions executed quickly outperform 100% solutions delivered late

  • Success includes luck. Stay humble and keep learning

The data doesn't lie: many businesses still base decisions on gut feel rather than structured analysis. But the companies that combine smart frameworks with fast execution? They're the ones scaling past their competitors.

PS...If you're enjoying this, please consider sending it to a friend. They'll thank you for helping them avoid expensive data mistakes.

Whenever you are ready, we can help you with a ​free data infrastructure assessment​ to identify your highest-impact opportunities. Get in touch! Listen to the Scale Your Business Data podcast every week on: ​YouTube​ ​Spotify​ ​Apple

Get your free data maturity assessment today!

If you want to achieve ground-breaking growth with Enterprise-grade business intelligence as a key part of your success, then you're in the right place.

Get your free data maturity assessment today!

If you want to achieve ground-breaking growth with Enterprise-grade business intelligence as a key part of your success, then you're in the right place.

Get your free data maturity assessment today!

If you want to achieve ground-breaking growth with Enterprise-grade business intelligence as a key part of your success, then you're in the right place.