May 28, 2025

Jeff Oak: Embracing Failure, Empowering Leaders

26 minutes

Want to know the real secret weapon CEOs use to grow, lead with purpose, and overcome blind spots? You’ll find the answer in this empowering episode.
In this episode of Legacy Leaders, Stan and Katie Beth sit down with Jeff Oak, Vistage Chair, executive coach, and host of the Taking Care of Your Business podcast. Together, they explore the power of peer advisory groups, the vital role of trust, accountability, and vulnerability in leadership, and how leaders can confront their blind spots to unlock their full potential. Jeff draws from decades of experience stewarding culture at billion-dollar organizations and coaching CEOs to dive deep into the inner challenges leaders face, offering practical guidance to help them succeed with both excellence and humility. This episode is a must-listen for executives, entrepreneurs, and leadership teamsseeking to lead more authentically, grow with intention, and leave a lasting legacy.

Key Takeaways:

🔑 Trust as a Foundation: Jeff explains how trust, rooted in vulnerability, is essential for real leadership growth and team performance.

👥 The Power of Peers: Peer advisory groups create safe, honest environments where CEOs can confront blind spots and gain unfiltered feedback.

🧠 Accountability Without Fear: Accountability should be about promise-keeping, not punishment—and works best when paired with psychological safety.

🛑 Avoiding Leadership Pitfalls: Leaders must be conscious of how power dynamics and imposter syndrome can both sabotage trust and performance.

🔍 Blind Spot Awareness: Continuous feedback from trusted peers is the most reliable way to uncover and work through the things leaders can't see themselves.

“Without trust, there is no growth. Trust is built on vulnerability.”

“The truth will set you free, but usually it’ll make you miserable first.”

“I hope my legacy is empowering people to reach their highest potential—in their values, their purpose, and their leadership.”

Quotes from Jeff Oak:

🔗 Conclusion: Leadership is not about having all the answers—it's about creating the conditions for growth, truth, and transformation. Jeff Oak shows us how.

Connect With Jeff:

Website: www.vistage.com/legacy (this will be a dedicated Welcome Page for your listeners)
LinkedIn: https://www.linkedin.com/in/jeffoak/
Facebook: https://www.facebook.com/profile.php?id=100082981682259
YouTube: https://www.youtube.com/channel/UCVrMnz4DiVi2NfnCLy3smDw

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By Stan Miller & Katie Beth Hand

22 ratings