198: Why Smart Leaders Make Bad Decisions — and How to Stop | Rob Duboff

Winning decisions aren’t made by spreadsheets—they’re forged in the imperfect art of judgment, humility, and learning from mistakes. 

In this episode, Damon sits down with Rob Duboff, co-founder of Hawk Partners and longtime instructor of decision-making at Harvard Extension School, for a masterclass on the mysteries of effective leadership and organizational success. Rob pulls back the curtain on why most choices in business and life aren’t neatly solvable puzzles, but open-ended mysteries—shaped by bias, culture, and a willingness to challenge the status quo. The pair break down why healthy conflict fuels great companies, how AI is transforming decision-making, and the science behind trusting your gut. Learn tools for fighting confirmation bias, the value of decision journals, and why the best leaders never stop learning. 

From boardrooms to everyday life, this episode gives you the playbook for making better choices, building healthier teams, and turning failures into breakthroughs. 

In this episode, you’ll learn: 

• Why most decisions in life and business are “mysteries”—not puzzles with a single answer—and how to navigate them 
• The impact of behavioral economics and cognitive biases like confirmation bias and anchoring on leaders’ choices 
• How to use “decision journals,” healthy dissent, and pilot tests to strengthen decision quality and organizational culture 
• Strategies for integrating AI as a thought partner (not thought leader) in decision-making—without abdicating human judgment 
• The secret to building a thriving culture: hiring for values, fostering autonomy, and leveraging healthy friction among co-founders 
• Why decision-making and financial literacy should be taught in high school—and how lifelong learning is the real leadership edge 

 

Timestamps: 

00:01 – The myth of the immortal corporation & why openness fuels lasting businesses 

00:58 – Meet Rob Duboff: co-founder, strategist, and Harvard decision-making instructor 

01:18 – Decisions as mysteries vs. puzzles 

02:53 – The trouble with “spreadsheet” decision-making and the power of personal judgment 

04:21 – Why everyone needs decision-making courses 

05:41 – What’s changed in decision-making over the last decade 

07:22 – Kahneman, Tversky, and the rise of behavioral economics 

10:01 – The danger of overconfidence and the pitfalls of memory 

11:26 – How marketers use behavioral insights to shape peak experiences 

12:06 – Yes-men, open conflict, and organizational survival 

13:15 – Preparing for AI disruption in business strategy 

16:30 – Using AI as a thought partner, not decision-maker 

19:09 – How AI can help bust confirmation bias 

22:14 – Anchoring, priming, and what System 1 thinking means for leaders 

23:03 – Gut vs. data: blending intuition with facts for big decisions 

26:31 – Learning from bad decisions: The power of decision journals 

33:27 – How healthy conflict builds stronger companies 

39:38 – Using pilot tests to de-risk organizational and hiring choices 

43:44 – Hiring for culture: questions and signals that matter 

46:27 – Why values and curiosity outweigh fancy degrees 

51:42 – Why decision-making should be a required high school course 

55:10 – The power of single-minded brand focus in a noisy world 

56:47 – How to connect with Rob Duboff and join the conversation 

 

About Rob Duboff 

Rob Duboff is the co-founder of Hawk Partners, a premier marketing strategy and research consultancy, and a longtime faculty member at Harvard University Extension School, where...