Coburn Ventures Podcast

#232: Unlocking Questions for Management with Bob Gilbreath

Jun 26, 2025
Bob Gilbreath, a seasoned investor and marketing expert known for his work with iconic brands at P&G, shares invaluable insights on effective management. He discusses the art of asking the right questions to improve decision-making and leadership dynamics. The conversation emphasizes balancing optimism with skepticism to better assess potential leaders. Gilbreath also delves into understanding intrinsic motivations behind entrepreneurial decisions and highlights the importance of vulnerability and honest feedback in cultivating a strong organizational culture.
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INSIGHT

Positive Regard With A Default No

  • Bob balances positive regard with a default 'no' to avoid naive optimism and to dig deeper in meetings.
  • This mindset helps him stay open while maintaining a high bar for founders and hires.
INSIGHT

Self-Management Predicts Success

  • The key trait Bob seeks is self-management under challenge—can leaders stay composed and solve creatively?
  • That capability predicts a founder's ability to inspire teams through uncertainty.
ADVICE

Ask Why They Took The Risk

  • Ask founders why they took the risk to start the company to reveal internal versus external motivation.
  • Prioritize intrinsically motivated founders over those driven mainly by external rewards.
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