198: Why Smart Leaders Make Bad Decisions — and How to Stop | Rob Duboff
Release Date:
July 31, 2025
Release Date: July 31
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.
What 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
In This Episode:
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
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 he teaches decision-making to executive and graduate students. Over a career spanning multiple decades, Rob has been a thought leader in marketing strategy, a trusted advisor to Fortune 500 clients, and an early advocate of integrating behavioral economics into business practice. Passionate about building healthy organizational cultures, he’s helped companies turn the science (and art) of decision-making into a competitive edge.
