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

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Written By damon lembi

Rob Duboff, Co-founder of Hawk Partners and instructor at Harvard Extension School, brings decades of strategy expertise and a behavioral economics lens to this powerful episode on the art—and science—of better decision-making. In this episode, host Damon Lembi and Rob unpack how real leadership decisions are made in the gray areas—through experience, judgment, and a willingness to learn from failure.

Read the full breakdown of Rob Duboff’s episode on Learnit.

Key Leadership Lessons from Rob Duboff’s Journey:

  • Most decisions are mysteries, not puzzles—treat them accordingly. Rob challenges the myth that leaders can spreadsheet their way to the best answer. Instead, great decisions come from curiosity, dissent, and iterative learning.

  • Use tools like decision journals and pilot tests to reduce bias. Whether you're facing confirmation bias or anchoring, techniques like documenting your reasoning or testing ideas on a small scale can improve both clarity and outcomes.

  • AI is a tool, not a replacement for human judgment. Rob shares how forward-thinking leaders are using AI as a thought partner—while keeping humans at the helm of nuance, ethics, and culture.

Connect with Rob Duboff:

Rob has advised Fortune 500 leaders and pioneered the integration of behavioral economics in marketing and strategy. His decision-making frameworks have helped organizations de-risk bold moves and cultivate healthier cultures.

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